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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-07-12 23:05:07 UTC

HMDB ID

HMDB0001085

Secondary Accession Numbers

HMDB0005072
HMDB01085
HMDB05072

Metabolite Identification

Common Name

Leukotriene B4

Description

Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted in human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before omega-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. The term leukotriene was coined to indicate the presence of three conjugated double bonds within the 20-carbon structure of arachidonic acid as well as the fact that these compounds were derived from leucocytes such as PMNNs or transformed mast cells. Interestingly, most of the cells known to express 5-LO are of myeloid origin, which includes neutrophils, eosinophils, mast cells, macrophages, basophils, and monocytes. Leukotriene biosynthesis begins with the specific oxidation of arachidonic acid by a free radical mechanism as a consequence of interaction with 5-LO. The first enzymatic step involves the abstraction of a hydrogen atom from C-7 of arachidonate followed by the addition of molecular oxygen to form 5-HpETE (5-hydroperoxyeicosatetraenoic acid). A second enzymatic step is also catalyzed by 5-LO and involves removal of a hydrogen atom from C-10, resulting in the formation of the conjugated triene epoxide LTA4. LTA4 must then be released by 5-LO and encounter either LTA4-H (LTA4 hydrolase) or LTC4-S [LTC4 (leukotriene C4) synthase]. LTA4-H can stereospecifically add water to C-12 while retaining a specific double-bond geometry, leading to LTB4 [leukotriene B4, 5(S),12(R)-dihydroxy-6,8,10,14-(Z,E,E,Z)-eicosatetraenoic acid]. If LTA4 encounters LTC4-S, then the reactive epoxide is opened at C-6 by the thiol anion of glutathione to form the product LTC4 [5(S)-hydroxy-6(R)-S-glutathyionyl-7,9,11,14- (E,E,Z,Z)-eicosatetraenoic acid], essentially a glutathionyl adduct of oxidized arachidonic acid. Both of these terminal leukotrienes are biologically active in that specific GPCRs recognize these chemical structures and receptor recognition initiates complex intracellular signalling cascades. In order for these molecules to serve as lipid mediators, however, they must be released from the biosynthetic cell into the extracellular milieu so that they can encounter the corresponding GPCRs. Surprising features of this cascade include the recognition of the assembly of critical enzymes at the perinuclear region of the cell and even localization of 5-LO within the nucleus of some cells. Under some situations, the budding phagosome has been found to assemble these proteins. Non-enzymatic proteins such as FLAP are now known as critical partners of this protein-machine assembly. An unexpected pathway of leukotriene biosynthesis involves the transfer of the chemically reactive intermediate, LTA4, from the biosynthetic cell followed by conversion into LTB4 or LTC4 by other cells that do not express 5-LO (PMID: 17623009 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv1652303192023122D          

 24 23  0  0  0  0            999 V2000
10001.736610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.561910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.277010004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.991810004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422410004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910004.4998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.851710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.565210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.392310004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.105910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.821610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.537210004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.250810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.968610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710004.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.306710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.591810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.877010004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.445010004.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001085

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

> <INCHI_KEY>
VNYSSYRCGWBHLG-AMOLWHMGSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.514010035725704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
4.125548676999999

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720820347637158

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725928205

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749373349576958

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
102.985

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leukotriene B4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8669.9088674.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.4498674.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.7848675.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.1188674.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8675.4528675.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8676.7888674.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8678.1208675.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8679.4578674.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8680.7888675.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8682.3328675.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8683.6648674.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8685.0008675.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.3368674.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.6688675.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8689.0088674.298   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8678.1208676.607   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8668.5748675.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.2398674.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9058675.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.5708674.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.2368675.066   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8661.8978674.298   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8663.2368676.607   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8668.5748676.607   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    1   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0001085
HETATM    1  C1  UNL     1       8.859   0.147   0.883  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.915  -0.336  -0.195  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.170   0.836  -0.745  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.195   0.525  -1.826  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.110  -0.453  -1.346  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.370   0.106  -0.227  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.082   0.319  -0.259  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.250   0.023  -1.413  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.160  -0.992  -1.122  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.673  -2.204  -0.705  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.281  -0.495  -0.049  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.962  -0.122  -0.299  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.807   0.359   0.752  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.052   0.733   0.496  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.932   1.221   1.524  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.168   1.584   1.265  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.781   1.538  -0.038  1.00  0.00           C  
HETATM   18  O2  UNL     1      -4.952   2.254  -0.945  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.234   0.286  -0.645  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.267  -0.572  -0.051  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.112  -1.250   1.234  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.945  -0.506   2.467  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.936  -0.712   3.233  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.861   0.460   2.882  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.850  -0.537   1.756  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.566   1.175   1.172  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.904   0.213   0.487  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.534  -0.804  -0.994  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.253  -1.102   0.266  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.629   1.366   0.071  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.917   1.564  -1.124  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.670   1.431  -2.134  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.746   0.043  -2.668  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.659  -1.371  -0.962  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.581  -0.762  -2.231  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.971   0.350   0.686  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.644   0.749   0.664  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.719  -0.196  -2.358  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.657   0.979  -1.614  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.562  -1.140  -2.033  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.390  -2.053  -0.061  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.676  -0.443   0.952  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.342  -0.183  -1.317  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.423   0.420   1.783  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.365   0.663  -0.518  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.564   1.293   2.555  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.736   1.979   2.145  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.706   2.215   0.014  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.295   2.139  -1.861  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.346  -0.381  -0.941  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.602   0.574  -1.713  1.00  0.00           H  
HETATM   52  H28 UNL     1      -8.271   0.006  -0.046  1.00  0.00           H  
HETATM   53  H29 UNL     1      -7.544  -1.385  -0.830  1.00  0.00           H  
HETATM   54  H30 UNL     1      -6.249  -1.999   1.155  1.00  0.00           H  
HETATM   55  H31 UNL     1      -7.993  -1.974   1.339  1.00  0.00           H  
HETATM   56  H32 UNL     1      -7.546   1.186   3.490  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   14   44
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   19   48
CONECT   18   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	ChEBI
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acid	ChEBI
5,12-Dihete	ChEBI
5,12-Hete	ChEBI
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	ChEBI
LTB4	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Kegg
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate	Kegg
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate	Generator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Generator
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoate	Generator
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid	Generator
5,12 HETE	HMDB
5,12 DiHETE	HMDB
Leukotriene b-4	HMDB
Leukotrienes b	HMDB
b-4, Leukotriene	HMDB
Leukotriene b 4	HMDB
Leukotriene b	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid	HMDB
Leukotriene b4 ethanol solution	HMDB
(+)-Leukotriene b4	HMDB
(5S,12R)-Leukotriene b4	HMDB
5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acid	HMDB
Leucotriene b4	HMDB
cis-Leukotriene b4	HMDB
Leukotriene B4	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

leukotriene B4

CAS Registry Number

71160-24-2

SMILES

CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

InChI Key

VNYSSYRCGWBHLG-AMOLWHMGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15647 )
leukotriene (CHEBI:15647 )
dihydroxy monocarboxylic acid (CHEBI:15647 )
polyunsaturated fatty acid (CHEBI:15647 )
hydroxy fatty acid (CHEBI:15647 )
Leukotrienes (C02165 )
Leukotrienes (LMFA03020001 )

Ontology

Not Available

Leukocyte (HMDB: HMDB0001085)

Hematocyte

Platelet (HMDB: HMDB0001085)

Tissue

Epithelium

Epidermis (HMDB: HMDB0001085)

Biofluid or Excreta

Non-excretory biofluid

Cerebrospinal Fluid (CSF) (PMID: 11166796)
Blood (PMID: 10543508)

Excreta

Urine (PMID: 11166796)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001085)

Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Other bread

Other bread (FooDB: FOOD00269)

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Fruit vegetable

Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)
Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)

Onion-family vegetable

Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)
Leek (FooDB: FOOD00007)

Tuber

Stalk vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)
Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)

Cabbage

Shoot vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Drupe

Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)
Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)

Tropical fruit

Pome

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)
Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)

Berry

Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)

Other fruit

Jujube (FooDB: FOOD00388)
Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruits (FooDB: FOOD00871)

Nut

Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)
Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)

Herbs and Spices (FooDB: FOOD00866)

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Lentil

Lentils (FooDB: FOOD00098)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Soy

Soy product

Other soy product (FooDB: FOOD00271)

Soy bean (FooDB: FOOD00085)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0001085)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Industrial application

Pharmaceutical industry

Biomarker

Meningitis (HMDB: HMDB0001085)
Glutathione Synthetase Deficiency (HMDB: HMDB0001085)
Hydrocephalus (HMDB: HMDB0001085)
Hypertension (HMDB: HMDB0001085)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	187.435	30932474
[M-H]-	Not Available	187.435	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001866

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	5.46	ALOGPS
logP	4.13	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	39.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.024	31661259
DarkChem	[M-H]-	187.386	31661259
AllCCS	[M+H]+	190.774	32859911
AllCCS	[M-H]-	187.881	32859911
DeepCCS	[M+H]+	197.18	30932474
DeepCCS	[M-H]-	194.589	30932474
DeepCCS	[M-2H]-	229.114	30932474
DeepCCS	[M+Na]+	204.456	30932474
AllCCS	[M+H]+	190.8	32859911
AllCCS	[M+H-H2O]+	188.0	32859911
AllCCS	[M+NH4]+	193.4	32859911
AllCCS	[M+Na]+	194.1	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	191.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene B4	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	4605.7	Standard polar	33892256
Leukotriene B4	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2645.4	Standard non polar	33892256
Leukotriene B4	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2873.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene B4,1TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3003.9	Semi standard non polar	33892256
Leukotriene B4,1TMS,isomer #2	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	2997.2	Semi standard non polar	33892256
Leukotriene B4,1TMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	2902.7	Semi standard non polar	33892256
Leukotriene B4,2TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3062.5	Semi standard non polar	33892256
Leukotriene B4,2TMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2960.7	Semi standard non polar	33892256
Leukotriene B4,2TMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2958.3	Semi standard non polar	33892256
Leukotriene B4,3TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3003.4	Semi standard non polar	33892256
Leukotriene B4,1TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3251.3	Semi standard non polar	33892256
Leukotriene B4,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3244.7	Semi standard non polar	33892256
Leukotriene B4,1TBDMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3148.3	Semi standard non polar	33892256
Leukotriene B4,2TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3518.0	Semi standard non polar	33892256
Leukotriene B4,2TBDMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3449.6	Semi standard non polar	33892256
Leukotriene B4,2TBDMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3444.0	Semi standard non polar	33892256
Leukotriene B4,3TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3735.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-7896000000-60973fb1d8ff05c73e4e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 GC-MS (3 TMS) - 70eV, Positive	splash10-01rl-9113530000-205b0d713aeb42a9afc2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-000i-0419000000-061132d646cd5dd85a1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-00ks-0829000000-7da7ab59ee0d4812767b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0002-0933000000-3fb381ce0f3609a90222	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udj-0931000000-ccfdaa3226146fe9edc3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udj-1940000000-ef988be204f5c54f4b21	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0r00-1910000000-e16cc958487f06dc4287	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0006-6900000000-a356f0334bf220eb54cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-052f-9700000000-66a6a217eba63b4874d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0a4l-7900000000-aeb350579ea4a84117d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QQ , negative-QTOF	splash10-000i-0619000000-dc49d3f4ab097db18f18	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 10V, Positive-QTOF	splash10-0gb9-0019000000-39d0f0947681f1f7fc37	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 20V, Positive-QTOF	splash10-0v4i-5498000000-4599d3006831091f926c	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 40V, Positive-QTOF	splash10-052f-9450000000-b6647dcbb40f3175983d	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 10V, Negative-QTOF	splash10-00kr-0029000000-d2d2e17f68f90518361e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 20V, Negative-QTOF	splash10-014r-2269000000-1a60fcc2f712b3beea2a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 40V, Negative-QTOF	splash10-0a4l-9340000000-edfb4e3fd8a8f4667ead	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 10V, Negative-QTOF	splash10-000i-0009000000-74962f74765b30de04ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 20V, Negative-QTOF	splash10-00kr-3659000000-98607094f1fa036e16e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 40V, Negative-QTOF	splash10-052f-5191000000-91a6c7d4dfff9bd70967	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 10V, Positive-QTOF	splash10-0uxr-0019000000-bbfb0bde6a04ea9b05bc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 20V, Positive-QTOF	splash10-0udi-3439000000-d8140c418a63ad2159a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 40V, Positive-QTOF	splash10-0ar0-9320000000-afb563cb7a2b51e02836	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Epidermis
Leukocyte
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000037 +/- 0.000007 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.0309 +/- 0.00178 uM	Infant (0-1 year old)	Not Specified	Normal	9820300	details
Blood	Detected and Quantified	0.000296 +/- 0.000292 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.00009686 +/- 0.0000062 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00011 +/- 0.00006 uM	Children (1-13 years old)	Both	Normal	11166796	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000115 +/- 0.00005710 uM	Not Specified	Not Specified	Normal	15243994	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00363 +/- 0.000480 uM	Children (1-13 years old)	Not Specified	Normal	8703223	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000115 +/- 0.00005706 uM	Infant (0-1 year old)	Not Specified	Normal	9820300	details
Urine	Detected and Quantified	0 - 0.000005 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	11166796	details
Urine	Detected and Quantified	0.00003 +/- 0.000014 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	11166796	details
Urine	Detected and Quantified	<0.000000005 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	9820300	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.082 uM	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	9820300	details
Blood	Detected and Quantified	0.00015 +/- 0.00005 uM	Infant (0-1 year old)	Both	Postoperative pulmonary hypertension	10543508	details
Blood	Detected and Quantified	0.00016 +/- 0.00006 uM	Infant (0-1 year old)	Both	Postoperative pulmonary hypertension	10543508	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00477 +/- 0.000813 uM	Children (1-13 years old)	Not Specified	Aseptic meningitis	8703223	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000177 uM	Adult (>18 years old)	Male	glutathione synthetase deficiency, acute metabolic crisis	15243994	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.000149 uM	Not Specified	Not Specified	closed head injury	2835791	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.000149 uM	Not Specified	Not Specified	gunshot wound	2835791	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.000595 uM	Not Specified	Not Specified	hydrocephalus	2835791	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.000297 uM	Not Specified	Not Specified	meningitis	2835791	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00014 +/- 0.00002 uM	Children (1-13 years old)	Both	Sjögren-Larsson syndrome	11166796	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0002 uM	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	9820300	details
Urine	Detected and Quantified	<0.000000005 umol/mmol creatinine	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	9820300	details

Associated Disorders and Diseases

Disease References

Cardiopulmonary bypass
Pearl JM, Manning PB, McNamara JL, Saucier MM, Thomas DW: Effect of modified ultrafiltration on plasma thromboxane B2, leukotriene B4, and endothelin-1 in infants undergoing cardiopulmonary bypass. Ann Thorac Surg. 1999 Oct;68(4):1369-75. [PubMed:10543508 ]
Leukotriene C4-Synthesis Deficiency
Mayatepek E, Flock B: Leukotriene C4-synthesis deficiency: a new inborn error of metabolism linked to a fatal developmental syndrome. Lancet. 1998 Nov 7;352(9139):1514-7. [PubMed:9820300 ]
Sjögren-Larsson syndrome
Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [PubMed:11166796 ]
Aseptic meningitis
Matsuo M, Hamasaki Y, Masuyama T, Ohta M, Miyazaki S: Leukotriene B4 and C4 in cerebrospinal fluid from children with meningitis and febrile seizures. Pediatr Neurol. 1996 Feb;14(2):121-4. [PubMed:8703223 ]
Glutathione synthetase deficiency
Mayatepek E, Meissner T, Grobe H: Acute metabolic crisis with extreme deficiency of glutathione in combination with decreased levels of leukotriene C4 in a patient with glutathione synthetase deficiency. J Inherit Metab Dis. 2004;27(2):297-9. [PubMed:15243994 ]
Hydrocephalus
Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Meningitis
Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]

Associated OMIM IDs

614037 (Leukotriene C4-Synthesis Deficiency)
270200 (Sjögren-Larsson syndrome)
266130 (Glutathione synthetase deficiency)

External Links

DrugBank ID

DB12961

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leukotriene_B4

METLIN ID

Not Available

PubChem Compound

5280492

PDB ID

Not Available

ChEBI ID

15647

Food Biomarker Ontology

Not Available

VMH ID

LEUKTRB4

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Han, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
Emingil G, Coker I, Atilla G, Huseyinov A: Levels of leukotriene B4 and platelet activating factor in gingival crevicular fluid in renal transplant patients receiving cyclosporine A. J Periodontol. 2000 Jan;71(1):50-7. [PubMed:10695938 ]
Ahmadzadeh N, Shingu M, Nobunaga M, Tawara T: Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids. Inflammation. 1991 Dec;15(6):497-503. [PubMed:1661709 ]
Lambiase A, Bonini S, Rasi G, Coassin M, Bruscolini A, Bonini S: Montelukast, a leukotriene receptor antagonist, in vernal keratoconjunctivitis associated with asthma. Arch Ophthalmol. 2003 May;121(5):615-20. [PubMed:12742837 ]
Nathan H, Naveh N, Meyer E: Levels of prostaglandin E2 and leukotriene B4 in tears of vernal conjunctivitis patients during a therapeutic trial with indomethacin. Doc Ophthalmol. 1994;85(3):247-57. [PubMed:7924852 ]
Yanagisawa Y, Nagai T: [The relationship between serum leukotriene B4 and smoking]. Nihon Eiseigaku Zasshi. 1993 Aug;48(3):698-706. [PubMed:8397308 ]
Iversen L, Fogh K, Ziboh VA, Kristensen P, Schmedes A, Kragballe K: Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. J Invest Dermatol. 1993 Mar;100(3):293-8. [PubMed:8382716 ]
Mancuso P, Nana-Sinkam P, Peters-Golden M: Leukotriene B4 augments neutrophil phagocytosis of Klebsiella pneumoniae. Infect Immun. 2001 Apr;69(4):2011-6. [PubMed:11254552 ]
Mozalevskii AF, Travianko TD, Iakovlev AA, Smirnova EA, Novikova NP, Sapa IIu: [Content of arachidonic acid metabolites in blood and saliva of children with bronchial asthma]. Ukr Biokhim Zh (1978). 1997 Sep-Dec;69(5-6):162-8. [PubMed:9606840 ]
Shindo K, Koide K, Fukumura M: Enhancement of leukotriene B4 release in stimulated asthmatic neutrophils by platelet activating factor. Thorax. 1997 Dec;52(12):1024-9. [PubMed:9516893 ]
Sieunarine K, Lawrence-Brown MM, Goodman MA, Prendergast FJ, Rocchetta S: Plasma levels of the lipid mediators, leukotriene B4 and lyso platelet-activating factor, in intraoperative salvaged blood. Vox Sang. 1992;63(3):168-71. [PubMed:1333134 ]
Blackburn WD Jr, Heck LW, Loose LD, Eskra JD, Carty TJ: Inhibition of 5-lipoxygenase product formation and polymorphonuclear cell degranulation by tenidap sodium in patients with rheumatoid arthritis. Arthritis Rheum. 1991 Feb;34(2):204-10. [PubMed:1847289 ]
Soyombo O, Spur BW, Soh C, Lee TH: Structure/activity relationship of leukotriene B4 and its structural analogues in chemotactic, lysosomal-enzyme release and receptor-binding assays. Eur J Biochem. 1993 Nov 15;218(1):59-66. [PubMed:8243477 ]
Garcia-Pastor P, Randazzo A, Gomez-Paloma L, Alcaraz MJ, Paya M: Effects of petrosaspongiolide M, a novel phospholipase A2 inhibitor, on acute and chronic inflammation. J Pharmacol Exp Ther. 1999 Apr;289(1):166-72. [PubMed:10087000 ]
Nieminen MM, Moilanen EK, Koskinen MO, Karvonen JI, Tuomisto L, Metsa-Ketela TJ, Vapaatalo H: Inhaled budesonide fails to inhibit the PAF-induced increase in plasma leukotriene B4 in man. Br J Clin Pharmacol. 1992 Jun;33(6):645-52. [PubMed:1327049 ]
Seyger MM, van Pelt JP, van den Born J, Latijnhouwers MA, de Jong EM: Epicutaneous application of leukotriene B4 induces patterns of tenascin and a heparan sulfate proteoglycan epitope that are typical for psoriatic lesions. Arch Dermatol Res. 1997 May;289(6):331-6. [PubMed:9209678 ]
Berry KA, Borgeat P, Gosselin J, Flamand L, Murphy RC: Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem. 2003 Jul 4;278(27):24449-60. Epub 2003 Apr 22. [PubMed:12709426 ]
Pacheco Y, Hosni R, Chabannes B, Gormand F, Moliere P, Grosclaude M, Piperno D, Lagarde M, Perrin-Fayolle M: Leukotriene B4 level in stimulated blood neutrophils and alveolar macrophages from healthy and asthmatic subjects. Effect of beta-2 agonist therapy. Eur J Clin Invest. 1992 Nov;22(11):732-9. [PubMed:1335872 ]
Bentancur AG, Naveh N, Lancri J, Selah BA, Livneh A: Urine leukotriene B4 in familial Mediterranean fever. Clin Exp Rheumatol. 2004 Jul-Aug;22(4 Suppl 34):S56-8. [PubMed:15515787 ]
Fogh J, Poulsen LK, Bisgaard H: A specific assay for leukotriene B4 in human whole blood. J Pharmacol Toxicol Methods. 1992 Dec;28(4):185-90. [PubMed:1338371 ]
Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]

Enzymes

Enzyme Details

1. Leukotriene-B(4) omega-hydroxylase 1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP4F2
Uniprot ID:: P78329
Molecular weight:: 59852.825

Reactions

Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

2. Leukotriene-B(4) omega-hydroxylase 2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:: CYP4F3
Uniprot ID:: Q08477
Molecular weight:: 59846.085

Reactions

Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

3. Leukotriene A-4 hydrolase

General function:: Involved in binding
Specific function:: Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name:: LTA4H
Uniprot ID:: P09960
Molecular weight:: 69284.64

Reactions

Leukotriene A4 + Water → Leukotriene B4	details

Enzyme Details

4. Cytochrome P450 4F11

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Not Available
Gene Name:: CYP4F11
Uniprot ID:: Q9HBI6
Molecular weight:: 60145.165

Reactions

Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

5. Cytochrome P450 4F8

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
Gene Name:: CYP4F8
Uniprot ID:: P98187
Molecular weight:: 59993.995

Reactions

Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

6. Leukotriene B4 receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y receptor involved in the regulation of cardiac muscle contraction through modulation of L-type calcium currents. Is a receptor for leukotriene B4, a potent chemoattractant involved in inflammation and immune response
Gene Name:: LTB4R
Uniprot ID:: Q15722
Molecular weight:: 37556.9

Enzyme Details

7. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Enzyme Details

8. Leukotriene B4 receptor 2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Low-affinity receptor for leukotrienes including leukotriene B4. Mediates chemotaxis of granulocytes and macrophages. The response is mediated via G-proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTB4 > 12-epi-LTB4 > LTB5 > LTB3
Gene Name:: LTB4R2
Uniprot ID:: Q9NPC1
Molecular weight:: 41524.3

Enzyme Details

9. Cytochrome P450 4F22

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4F22
Uniprot ID:: Q6NT55
Molecular weight:: Not Available

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Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Showing metabocard for Leukotriene B4 (HMDB0001085)

MOL for HMDB0001085 (Leukotriene B4)

3D MOL for HMDB0001085 (Leukotriene B4)

3D SDF for HMDB0001085 (Leukotriene B4)

3D-SDF for HMDB0001085 (Leukotriene B4)

PDB for HMDB0001085 (Leukotriene B4)

3D PDB for HMDB0001085 (Leukotriene B4)

SMILES for HMDB0001085 (Leukotriene B4)

INCHI for HMDB0001085 (Leukotriene B4)

Structure for HMDB0001085 (Leukotriene B4)

3D Structure for HMDB0001085 (Leukotriene B4)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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