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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-29 08:32:00 UTC

Update Date

2022-11-30 19:03:54 UTC

HMDB ID

HMDB0011128

Secondary Accession Numbers

HMDB11128

Metabolite Identification

Common Name

LysoPC(0:0/18:0)

Description

LysoPC(0:0/18:0) or LPC(0:0/18:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types.LysoPC(0:0/18:0) has been shown to be protective against lethal sepsis in experimental animals by various mechanisms, including stimulation of neutrophils to eliminate invading pathogens through a peroxide-dependent reaction. LPL-R's are members of the G protein-coupled receptor (GPR) family of integral membrane proteins. Lysophosphatidylcholines (LPCs) specifically bind to GPR119, GPR40, GPR55 and GPR4. binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins. Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin (PMID: 32599910 ). In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood. Hypoalbuminemia with albumin concentrations of <20 g/L are typical of patients with sepsis, burns or serious trauma (PMID: 26557421 ). Such low levels of albumin often lead to LPC levels that are 50-80 % lower than that seen in healthy individuals (PMID: 27501420 ). Decreased levels of LPC have been observed in a number of other inflammatory conditions beyond sepsis, including rheumatoid arthritis, diabetes, schizophrenia, polycystic ovary syndrome, Alzheimer’s disease, pulmonary arterial hypertension, aging, asthma and liver cirrhosis, where they were associated with increased mortality risk (PMID: 32599910 ). LPCs have a number of protective or anti-inflammatory effects. Higher levels of LPC induce cyclooxygenase-2 and endothelial nitric oxide synthase (eNOS) expression in endothelial cells, both of which can have vasoprotective effects either via production of prostacyclin or nitric oxide (PMID: 32599910 ). LPCs have been shown to elicit a number of effects on the innate immune system and effectively serve as dual-activity ligand molecules. In particular, LPCs directly activate toll-like receptor (TLR) 4 and TLR-2-1 receptors in the absence of classical TLR ligands. However, LPCs can also inhibit TLR-mediated signaling in the presence of classical TLR ligands, thereby acting as anti-inflammatory molecules (PMID: 32599910 ). Low levels of LPC during a bacterial or viral infection with TLR-mediated signalling can lead to opposing (inflammatory vs. anti-inflammatory) effects and immune dysregulation.

Structure

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

PC(0:0/18:0)
  Mrv1652303192020102D          

 36 35  0  0  0  0            999 V2000
   -3.8021    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2007    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7943   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5084   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9366   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6508   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3649   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0790   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7931   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5072   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2214   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9355   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6496   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
 10 18  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
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2   5  -1  14   1
M  END

HMDB0011128
     RDKit          3D
LysoPC(0:0/18:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
   10.3290   -0.2559   -3.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782   -0.8902   -3.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8887   -1.4904   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0643   -0.3886   -1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9686   -1.0347    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220   -0.0680    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0783    1.0231    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739    0.4556    1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7297    1.6330    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642    1.1881    1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0243    0.4205    2.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763    0.0208    3.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914   -0.8389    1.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -1.2615    1.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.0952    2.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1157    0.8094    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    1.9598    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.4568    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3566    2.3115    1.3413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883    0.1759    0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.2595    0.9561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4499   -1.2578    2.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8167   -1.5873    2.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951   -0.7386   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330    0.3598   -1.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -0.1730   -2.7209 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3583   -0.9996   -3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7602    1.2096   -3.6198 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.7890   -1.0466   -2.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8939   -0.2145   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1065   -1.0214   -1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2925   -0.2488   -1.6779 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.4787   -1.0314   -2.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5083    0.1890   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3164    0.9297   -2.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3054    0.7428   -3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6178   -0.1333   -4.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0747   -0.9024   -3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630   -0.1429   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8294   -1.6754   -4.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8484   -1.8610   -1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5897   -2.3200   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0347    0.0730   -1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2593    0.3526   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0311   -1.5926    0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7908   -1.7677    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0385   -0.6137    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1101    0.4417    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251    1.6778    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2689    1.6558    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364   -0.1696    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.1618    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7952    2.2166    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383    2.3313    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0557    0.5698    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6534    2.1062    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.5167    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.9778    3.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    0.9830    3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -0.5399    3.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -0.2546    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -1.7560    1.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -1.8104    2.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -1.9652    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024   -0.4377    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.5174    2.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    0.1896   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    1.1612    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099    2.6388    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0095    2.5317   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8220    0.6553    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.7953    3.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8221   -2.1580    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -1.6262    2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459   -1.0322   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863   -1.6167   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0641    0.4249   -3.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6691    0.4701   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2836   -1.7481   -2.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8977   -1.5541   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2451   -2.0844   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6826   -0.9472   -3.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3505   -0.6702   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5627   -0.6302    0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5178    0.6905   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7833    0.9860   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5123    1.6377   -2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1872    0.5954   -3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3309    1.3941   -2.4899 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  1
 22 72  1  0
 22 73  1  0
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  0
 34 85  1  0
 34 86  1  0
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

PC(0:0/18:0)
  Mrv1652303192020102D          

 36 35  0  0  0  0            999 V2000
   -3.8021    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6132    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2007    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3277    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.3649   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0790   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7931   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5072   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2214   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9355   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6496   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
 10 18  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
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2   5  -1  14   1
M  END
> <DATABASE_ID>
HMDB0011128

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](CO)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1

> <INCHI_KEY>
IQGPMZRCLCCXAG-RUZDIDTESA-N

> <FORMULA>
C26H54NO7P

> <MOLECULAR_WEIGHT>
523.6832

> <EXACT_MASS>
523.363789599

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
62.3322692018541

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.081879806861589

> <ALOGPS_LOGS>
-6.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579258211672176

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550617598182955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758125699806

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
151.47570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011128
     RDKit          3D
LysoPC(0:0/18:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
   10.3290   -0.2559   -3.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782   -0.8902   -3.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5897   -2.3200   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0347    0.0730   -1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0385   -0.6137    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1101    0.4417    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251    1.6778    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2689    1.6558    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364   -0.1696    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.1618    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7952    2.2166    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383    2.3313    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0557    0.5698    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6534    2.1062    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.5167    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.9778    3.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    0.9830    3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -0.5399    3.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -0.2546    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -1.7560    1.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -1.8104    2.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -1.9652    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024   -0.4377    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.5174    2.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    0.1896   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    1.1612    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099    2.6388    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2083   -1.6262    2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2863   -1.6167   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0641    0.4249   -3.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6691    0.4701   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2836   -1.7481   -2.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8977   -1.5541   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.5627   -0.6302    0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5178    0.6905   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7833    0.9860   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5123    1.6377   -2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1872    0.5954   -3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  1
 22 72  1  0
 22 73  1  0
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  0
 34 85  1  0
 34 86  1  0
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PC(0:0/18:0)                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O-1
HETATM    6  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -3.677  -0.664   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0      -5.217  -0.664   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.544   2.211   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.878   1.441   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       4.108   0.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.112   3.054   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.212   0.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.551  -1.434   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.551  -2.874   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.217  -1.434   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.883  -1.434   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.549  -1.434   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -17.215  -1.434   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -18.548  -0.662   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -19.881  -1.434   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.214  -0.662   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -22.547  -1.434   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -23.880  -0.662   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -25.214  -1.434   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -26.547  -0.662   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -27.880  -1.434   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -29.213  -0.662   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    8                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7    1                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7    2                                                       
CONECT    9    7                                                            
CONECT   10    7   18                                                       
CONECT   11   12    3                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

COMPND    HMDB0011128
HETATM    1  C1  UNL     1      10.329  -0.256  -3.623  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.978  -0.890  -3.482  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.889  -1.490  -2.074  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.064  -0.389  -1.050  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.969  -1.035   0.308  1.00  0.00           C  
HETATM    6  C6  UNL     1       9.122  -0.068   1.437  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.078   1.023   1.446  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.674   0.456   1.563  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.730   1.633   1.566  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.264   1.188   1.673  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.024   0.420   2.928  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.576   0.021   3.017  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.191  -0.839   1.855  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.756  -1.261   1.989  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.156  -0.095   2.036  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.116   0.809   0.838  1.00  0.00           C  
HETATM   17  C17 UNL     1      -1.077   1.960   0.958  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.458   1.457   1.051  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.357   2.312   1.341  1.00  0.00           O  
HETATM   20  O2  UNL     1      -2.888   0.176   0.859  1.00  0.00           O  
HETATM   21  C19 UNL     1      -4.214  -0.260   0.956  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.450  -1.258   2.068  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.817  -1.587   2.026  1.00  0.00           O  
HETATM   24  C21 UNL     1      -4.795  -0.739  -0.355  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.733   0.360  -1.236  1.00  0.00           O  
HETATM   26  P1  UNL     1      -5.394  -0.173  -2.721  1.00  0.00           P  
HETATM   27  O5  UNL     1      -4.358  -1.000  -3.411  1.00  0.00           O  
HETATM   28  O6  UNL     1      -5.760   1.210  -3.620  1.00  0.00           O1-
HETATM   29  O7  UNL     1      -6.789  -1.047  -2.347  1.00  0.00           O  
HETATM   30  C22 UNL     1      -7.894  -0.214  -2.189  1.00  0.00           C  
HETATM   31  C23 UNL     1      -9.107  -1.021  -1.859  1.00  0.00           C  
HETATM   32  N1  UNL     1     -10.292  -0.249  -1.678  1.00  0.00           N1+
HETATM   33  C24 UNL     1     -11.479  -1.031  -2.052  1.00  0.00           C  
HETATM   34  C25 UNL     1     -10.508   0.189  -0.317  1.00  0.00           C  
HETATM   35  C26 UNL     1     -10.316   0.930  -2.527  1.00  0.00           C  
HETATM   36  H1  UNL     1      10.305   0.743  -3.134  1.00  0.00           H  
HETATM   37  H2  UNL     1      10.618  -0.133  -4.685  1.00  0.00           H  
HETATM   38  H3  UNL     1      11.075  -0.902  -3.077  1.00  0.00           H  
HETATM   39  H4  UNL     1       8.163  -0.143  -3.572  1.00  0.00           H  
HETATM   40  H5  UNL     1       8.829  -1.675  -4.239  1.00  0.00           H  
HETATM   41  H6  UNL     1       7.848  -1.861  -1.973  1.00  0.00           H  
HETATM   42  H7  UNL     1       9.590  -2.320  -1.946  1.00  0.00           H  
HETATM   43  H8  UNL     1      10.035   0.073  -1.225  1.00  0.00           H  
HETATM   44  H9  UNL     1       8.259   0.353  -1.215  1.00  0.00           H  
HETATM   45  H10 UNL     1       8.031  -1.593   0.423  1.00  0.00           H  
HETATM   46  H11 UNL     1       9.791  -1.768   0.379  1.00  0.00           H  
HETATM   47  H12 UNL     1       9.038  -0.614   2.386  1.00  0.00           H  
HETATM   48  H13 UNL     1      10.110   0.442   1.432  1.00  0.00           H  
HETATM   49  H14 UNL     1       8.125   1.678   0.561  1.00  0.00           H  
HETATM   50  H15 UNL     1       8.269   1.656   2.335  1.00  0.00           H  
HETATM   51  H16 UNL     1       6.436  -0.170   0.690  1.00  0.00           H  
HETATM   52  H17 UNL     1       6.588  -0.162   2.467  1.00  0.00           H  
HETATM   53  H18 UNL     1       5.795   2.217   0.643  1.00  0.00           H  
HETATM   54  H19 UNL     1       5.938   2.331   2.405  1.00  0.00           H  
HETATM   55  H20 UNL     1       4.056   0.570   0.773  1.00  0.00           H  
HETATM   56  H21 UNL     1       3.653   2.106   1.596  1.00  0.00           H  
HETATM   57  H22 UNL     1       4.645  -0.517   2.896  1.00  0.00           H  
HETATM   58  H23 UNL     1       4.268   0.978   3.841  1.00  0.00           H  
HETATM   59  H24 UNL     1       2.001   0.983   3.030  1.00  0.00           H  
HETATM   60  H25 UNL     1       2.437  -0.540   3.966  1.00  0.00           H  
HETATM   61  H26 UNL     1       2.259  -0.255   0.916  1.00  0.00           H  
HETATM   62  H27 UNL     1       2.833  -1.756   1.805  1.00  0.00           H  
HETATM   63  H28 UNL     1       0.631  -1.810   2.960  1.00  0.00           H  
HETATM   64  H29 UNL     1       0.538  -1.965   1.153  1.00  0.00           H  
HETATM   65  H30 UNL     1      -1.202  -0.438   2.256  1.00  0.00           H  
HETATM   66  H31 UNL     1       0.095   0.517   2.947  1.00  0.00           H  
HETATM   67  H32 UNL     1      -0.491   0.190  -0.029  1.00  0.00           H  
HETATM   68  H33 UNL     1       0.914   1.161   0.605  1.00  0.00           H  
HETATM   69  H34 UNL     1      -0.810   2.639   1.794  1.00  0.00           H  
HETATM   70  H35 UNL     1      -1.010   2.532  -0.001  1.00  0.00           H  
HETATM   71  H36 UNL     1      -4.822   0.655   1.224  1.00  0.00           H  
HETATM   72  H37 UNL     1      -4.275  -0.795   3.061  1.00  0.00           H  
HETATM   73  H38 UNL     1      -3.822  -2.158   1.964  1.00  0.00           H  
HETATM   74  H39 UNL     1      -6.208  -1.626   2.918  1.00  0.00           H  
HETATM   75  H40 UNL     1      -5.846  -1.032  -0.156  1.00  0.00           H  
HETATM   76  H41 UNL     1      -4.286  -1.617  -0.764  1.00  0.00           H  
HETATM   77  H42 UNL     1      -8.064   0.425  -3.080  1.00  0.00           H  
HETATM   78  H43 UNL     1      -7.669   0.470  -1.346  1.00  0.00           H  
HETATM   79  H44 UNL     1      -9.284  -1.748  -2.688  1.00  0.00           H  
HETATM   80  H45 UNL     1      -8.898  -1.554  -0.892  1.00  0.00           H  
HETATM   81  H46 UNL     1     -11.245  -2.084  -1.846  1.00  0.00           H  
HETATM   82  H47 UNL     1     -11.683  -0.947  -3.145  1.00  0.00           H  
HETATM   83  H48 UNL     1     -12.351  -0.670  -1.471  1.00  0.00           H  
HETATM   84  H49 UNL     1     -10.563  -0.630   0.404  1.00  0.00           H  
HETATM   85  H50 UNL     1     -11.518   0.691  -0.307  1.00  0.00           H  
HETATM   86  H51 UNL     1      -9.783   0.986  -0.021  1.00  0.00           H  
HETATM   87  H52 UNL     1      -9.512   1.638  -2.314  1.00  0.00           H  
HETATM   88  H53 UNL     1     -10.187   0.595  -3.593  1.00  0.00           H  
HETATM   89  H54 UNL     1     -11.331   1.394  -2.490  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   39   40
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6   45   46
CONECT    6    7   47   48
CONECT    7    8   49   50
CONECT    8    9   51   52
CONECT    9   10   53   54
CONECT   10   11   55   56
CONECT   11   12   57   58
CONECT   12   13   59   60
CONECT   13   14   61   62
CONECT   14   15   63   64
CONECT   15   16   65   66
CONECT   16   17   67   68
CONECT   17   18   69   70
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   24   71
CONECT   22   23   72   73
CONECT   23   74
CONECT   24   25   75   76
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   29   30
CONECT   30   31   77   78
CONECT   31   32   79   80
CONECT   32   33   34   35
CONECT   33   81   82   83
CONECT   34   84   85   86
CONECT   35   87   88   89
END

HMDB0011128
     RDKit          3D
LysoPC(0:0/18:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
   10.3290   -0.2559   -3.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782   -0.8902   -3.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8887   -1.4904   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0643   -0.3886   -1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9686   -1.0347    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220   -0.0680    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0783    1.0231    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739    0.4556    1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7297    1.6330    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642    1.1881    1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0243    0.4205    2.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763    0.0208    3.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914   -0.8389    1.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -1.2615    1.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.0952    2.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1157    0.8094    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    1.9598    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.4568    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3566    2.3115    1.3413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883    0.1759    0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -0.2595    0.9561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4499   -1.2578    2.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8167   -1.5873    2.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951   -0.7386   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330    0.3598   -1.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -0.1730   -2.7209 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3583   -0.9996   -3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7602    1.2096   -3.6198 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.7890   -1.0466   -2.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8939   -0.2145   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1065   -1.0214   -1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2925   -0.2488   -1.6779 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.4787   -1.0314   -2.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5083    0.1890   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3164    0.9297   -2.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3054    0.7428   -3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6178   -0.1333   -4.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0747   -0.9024   -3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630   -0.1429   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8294   -1.6754   -4.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8484   -1.8610   -1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5897   -2.3200   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0347    0.0730   -1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2593    0.3526   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0311   -1.5926    0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7908   -1.7677    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0385   -0.6137    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1101    0.4417    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251    1.6778    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2689    1.6558    2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364   -0.1696    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.1618    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7952    2.2166    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383    2.3313    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0557    0.5698    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6534    2.1062    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -0.5167    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.9778    3.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    0.9830    3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -0.5399    3.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -0.2546    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329   -1.7560    1.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -1.8104    2.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -1.9652    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024   -0.4377    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.5174    2.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    0.1896   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9140    1.1612    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099    2.6388    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0095    2.5317   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8220    0.6553    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.7953    3.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8221   -2.1580    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -1.6262    2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459   -1.0322   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863   -1.6167   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0641    0.4249   -3.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6691    0.4701   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2836   -1.7481   -2.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8977   -1.5541   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2451   -2.0844   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6826   -0.9472   -3.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3505   -0.6702   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5627   -0.6302    0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5178    0.6905   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7833    0.9860   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5123    1.6377   -2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1872    0.5954   -3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3309    1.3941   -2.4899 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  1
 22 72  1  0
 22 73  1  0
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  0
 34 85  1  0
 34 86  1  0
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	HMDB
2-Octadecanoyl-sn-glycero-3-phosphocholine	HMDB
2-Stearoyllysophosphatidylcholine	HMDB
LPC (18:0)	HMDB
PC(0:0/18:0)	HMDB
Stearoyl lysophosphatidylcholine	HMDB
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	HMDB
1-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphocholine	HMDB
1-Hydroxy-2-stearoyl-sn-glycero-3-phosphocholine	HMDB
Lysophosphatidylcholine	HMDB
2-Stearoyl-glycero-3-phosphocholine	HMDB
LysoPC(18:0)	HMDB
LPC(0:0/18:0)	HMDB
Lysophosphatidylcholine(0:0/18:0)	HMDB
LyPC(0:0/18:0)	HMDB
Lysophosphatidylcholine(18:0)	HMDB
LPC(18:0)	HMDB
LyPC(18:0)	HMDB
2-Octadecanoyl-glycero-3-phosphocholine	HMDB
2-Octadecanoylglycerophosphocholine	HMDB
2-Stearoylglycerophosphocholine	HMDB
LysoPC(0:0/18:0)	Lipid Annotator

Chemical Formula

C₂₆H₅₄NO₇P

Average Molecular Weight

523.6832

Monoisotopic Molecular Weight

523.363789599

IUPAC Name

(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

4421-58-3

SMILES

CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1

InChI Key

IQGPMZRCLCCXAG-RUZDIDTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

2-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

2-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-acyl-sn-glycero-3-phosphocholine (CHEBI:76076 )
lysophosphatidylcholine 18:0 (CHEBI:76076 )
Monoacylglycerophosphocholines (LMGP01050076 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Alzheimer's Disease (PMID: 30845751)

Renal system and urinary system

Renal disorder

Renal failure (PMID: 30845751)
Renal cell carcinoma (PMID: 26162894)

Cancer

Ovarian cancer (PMID: 30845751)
Colorectal cancer (PMID: 26162894)

Digestive system disorder

Gastrointestinal disorder

Stomach cancer (PMID: 26162894)

Organoleptic effect

Touch

Smooth (HMDB: HMDB0011128)

Disposition

Biological location

Cell membrane (HMDB: HMDB0011128)
Intracellular membrane (HMDB: HMDB0011128)

Biofluid or Excreta

Blood (HMDB: HMDB0011128)

Cellular substructure

Cell

All cells and tissues (HMDB: HMDB0011128)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011128)

Source

Endogenous

Endogenous (HMDB: HMDB0011128)

Animal

Animal (HMDB: HMDB0011128)

Exogenous

Food

Food (HMDB: HMDB0011128)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)
Cell signaling (HMDB: HMDB0011128)

Biochemical pathway

Signaling pathway

Apoptosis (PMID: 30845751)

Glycerophospholipid metabolism (HMDB: HMDB0011128)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0011128)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0011128)

Role

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00022 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.08	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	151.48 m³·mol⁻¹	ChemAxon
Polarizability	62.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	238.531	30932474
DeepCCS	[M-H]-	235.959	30932474
DeepCCS	[M-2H]-	269.521	30932474
DeepCCS	[M+Na]+	246.029	30932474
AllCCS	[M+H]+	240.7	32859911
AllCCS	[M+H-H2O]+	239.5	32859911
AllCCS	[M+NH4]+	241.8	32859911
AllCCS	[M+Na]+	242.1	32859911
AllCCS	[M-H]-	234.5	32859911
AllCCS	[M+Na-2H]-	237.0	32859911
AllCCS	[M+HCOO]-	239.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(0:0/18:0)	CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3426.0	Standard polar	33892256
LysoPC(0:0/18:0)	CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3216.9	Standard non polar	33892256
LysoPC(0:0/18:0)	CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3500.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(0:0/18:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C	3484.5	Semi standard non polar	33892256
LysoPC(0:0/18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C(C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C	3709.3	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 - LysoPC(0:0/18:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fek-9550100000-80d62412107a36847bc7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(0:0/18:0) GC-MS (1 TMS) - 70eV, Positive	splash10-008a-9721020000-9b41f1bf1e3d5e7cf26c	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOF	splash10-0fc0-0900060000-e99379bc4ac53cc77147	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOF	splash10-0ul0-0900050000-23f28f5f047f20928b27	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOF	splash10-0ul0-0900050000-bfd773fc6fa74017c0dc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Positive-QTOF	splash10-000i-9071130000-2c3354f59d1c3ced0f44	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOF	splash10-00n3-8292010000-d0e88a09c384d49429af	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Positive-QTOF	splash10-002r-9130000000-de498d2cd72d4ce9e8ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Negative-QTOF	splash10-00e9-0070290000-bdddd2700d06c482f6d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Negative-QTOF	splash10-014r-2370920000-8d3fcd824e1c0856f606	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Negative-QTOF	splash10-00o0-6290000000-dabf6a0ad90d8af67ae6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Positive-QTOF	splash10-00di-1100090000-3808cd3b9510a0dec128	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOF	splash10-001i-2910020000-6397418d2fe7e18b74e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Positive-QTOF	splash10-00dr-6900000000-b110314336110b417795	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Negative-QTOF	splash10-00di-0000090000-c3d13afe335d8b212b66	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Negative-QTOF	splash10-0089-0090160000-c2b2361f52a0743ec66a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Negative-QTOF	splash10-003r-8290200000-f73f39a5b22cf648489f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027907

KNApSAcK ID

Not Available

Chemspider ID

24766523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779491

PDB ID

Not Available

ChEBI ID

76076

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Enzyme Details

2. Eosinophil lysophospholipase

General function:: Involved in sugar binding
Specific function:: May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:: CLC
Uniprot ID:: Q05315
Molecular weight:: 16452.785

Enzyme Details

3. Platelet-activating factor acetylhydrolase

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Modulates the action of platelet-activating factor (PAF) by hydrolyzing the sn-2 ester bond to yield the biologically inactive lyso-PAF. Has a specificity for substrates with a short residue at the sn-2 position. It is inactive against long-chain phospholipids.
Gene Name:: PLA2G7
Uniprot ID:: Q13093
Molecular weight:: 50076.99

Enzyme Details

4. Platelet-activating factor acetylhydrolase IB subunit gamma

General function:: Involved in hydrolase activity
Specific function:: Inactivates paf by removing the acetyl group at the sn-2 position. This is a catalytic subunit. Plays an important role during the development of brain.
Gene Name:: PAFAH1B3
Uniprot ID:: Q15102
Molecular weight:: 25734.13

Enzyme Details

5. Platelet-activating factor acetylhydrolase IB subunit beta

General function:: Involved in hydrolase activity
Specific function:: Inactivates PAF by removing the acetyl group at the sn-2 position. This is a catalytic subunit.
Gene Name:: PAFAH1B2
Uniprot ID:: P68402
Molecular weight:: 22733.715

Enzyme Details

6. Platelet-activating factor acetylhydrolase 2, cytoplasmic

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Has a marked selectivity for phospholipids with short acyl chains at the sn-2 position. May share a common physiologic function with the plasma-type enzyme.
Gene Name:: PAFAH2
Uniprot ID:: Q99487
Molecular weight:: 44035.255

Enzyme Details

7. Free fatty acid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:: FFAR1
Uniprot ID:: O14842
Molecular weight:: 31456.6

Enzyme Details

8. Lysophospholipid acyltransferase 5

General function:: Involved in 1-acylglycerophosphocholine O-acyltransfera
Specific function:: Acyltransferase which mediates the conversion of lysophosphatidylcholine (1-acyl-sn-glycero-3-phosphocholine or LPC) into phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine or PC) (LPCAT activity). Catalyzes also the conversion of lysophosphatidylserine (1-acyl-2-hydroxy-sn-glycero-3-phospho-L-serine or LPS) into phosphatidylserine (1,2-diacyl-sn-glycero-3-phospho-L-serine or PS) (LPSAT activity). Has also weak lysophosphatidylethanolamine acyltransferase activity (LPEAT activity). Favors polyunsaturated fatty acyl-CoAs as acyl donors compared to saturated fatty acyl-CoAs. Seems to be the major enzyme contributing to LPCAT activity in the liver. Lysophospholipid acyltransferases (LPLATs) catalyze the reacylation step of the phospholipid remodeling pathway also known as the Lands cycle.
Gene Name:: LPCAT3
Uniprot ID:: Q6P1A2
Molecular weight:: 56034.48

Enzyme Details

9. Lysophosphatidylcholine acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:: LPCAT1
Uniprot ID:: Q8NF37
Molecular weight:: 59150.675

Enzyme Details

10. Lysophosphatidylcholine acyltransferase 2

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-dependent. Involved in platelet-activating factor (PAF) biosynthesis by catalyzing the conversion of the PAF precursor, 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) into 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF). Also converts lyso-PAF to 1-alkyl-phosphatidylcholine (PC), a major component of cell membranes and a PAF precursor. Under resting conditions, acyltransferase activity is preferred. Upon acute inflammatory stimulus, acetyltransferase activity is enhanced and PAF synthesis increases (By similarity).
Gene Name:: LPCAT2
Uniprot ID:: Q7L5N7
Molecular weight:: 60207.295

Only showing the first 10 proteins. There are 15 proteins in total.

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Showing metabocard for LysoPC(0:0/18:0) (HMDB0011128)

MOL for HMDB0011128 (LysoPC(0:0/18:0))

3D MOL for HMDB0011128 (LysoPC(0:0/18:0))

3D SDF for HMDB0011128 (LysoPC(0:0/18:0))

3D-SDF for HMDB0011128 (LysoPC(0:0/18:0))

PDB for HMDB0011128 (LysoPC(0:0/18:0))

3D PDB for HMDB0011128 (LysoPC(0:0/18:0))

SMILES for HMDB0011128 (LysoPC(0:0/18:0))

INCHI for HMDB0011128 (LysoPC(0:0/18:0))

Structure for HMDB0011128 (LysoPC(0:0/18:0))

3D Structure for HMDB0011128 (LysoPC(0:0/18:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes