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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001139

Secondary Accession Numbers

HMDB01139

Metabolite Identification

Common Name

Prostaglandin F2a

Description

Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins. It is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. It is used in medicine to induce labor and as an abortifacient. PGF2a binds to the Prostaglandin F2 receptor (PTGFR) which is a member of the G-protein coupled receptor family. PGF2-alpha mediates luteolysis. Luteolysis is the structural and functional degradation of the corpus luteum (CL) that occurs at the end of the luteal phase of both the estrous and menstrual cycles in the absence of pregnancy. PGF2 may also be involved in modulating intraocular pressure and smooth muscle contraction in the uterus and gastrointestinal tract sphincters. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787 ). Prostaglandins 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

HMDB0001139
     RDKit          3D
Prostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -7.0185   -0.2319    2.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    0.1151    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1625   -1.1481    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6597   -0.8145   -1.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4458    0.0463   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307   -0.5346   -0.4306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3722   -0.8195    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.4393   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.0025   -1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962    0.8792   -1.3311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    2.3204   -1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6511    3.1026   -2.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    2.6739    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8908    1.3284    0.8118 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6564    1.3543    1.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.5122   -0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5975    1.0012   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    0.7453   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.0422    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -0.1127    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -1.5296    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -2.2505   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458   -1.6482   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -0.6816   -1.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443   -2.1251   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6548    0.5166    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569   -1.2482    2.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238   -0.2780    2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3331    0.6666    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079    0.7373    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1308   -1.7034    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439   -1.7670    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5368   -1.7535   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4931   -0.2669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371    0.2871   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    1.0389   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -1.4600   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.5912    1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.4666   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -1.0972   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.6682   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    2.6631   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    4.0239   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1387    3.1763    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149    3.2503    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    0.8866    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.6037    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -0.5580   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    2.1143   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    0.5787   -2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763    1.1919   -0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.4536    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2411    0.4221    0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    0.3881    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4078   -2.0814    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0304   -1.5277    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036   -3.3290    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9103   -2.2244   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9563   -1.6986   -0.8507 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  1
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  1
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END


  Mrv0541 02231218572D          

 25 25  0  0  1  0            999 V2000
   24.7199  -20.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0695  -18.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -16.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3589  -20.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8005  -18.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9499  -19.1606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6174  -18.6756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2049  -19.9452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2848  -19.1606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.0299  -19.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1653  -18.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -17.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5522  -19.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3318  -17.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3318  -16.6131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7675  -19.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0463  -16.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0463  -15.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1544  -19.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -14.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3698  -19.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -14.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7567  -20.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4753  -13.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9720  -19.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  6  0  0  0
 15  3  1  1  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  6  0  0  0
  7  9  1  0  0  0  0
  7 12  1  1  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001139

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
PXGPLTODNUVGFL-UAAPODJFSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.70056243906626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.6110544173333317

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964334215405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294048784039

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263153076120291

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
100.47070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-trans-PGF2α

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001139
     RDKit          3D
Prostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -7.0185   -0.2319    2.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    0.1151    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1625   -1.1481    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6597   -0.8145   -1.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4458    0.0463   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307   -0.5346   -0.4306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3722   -0.8195    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.4393   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.0025   -1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962    0.8792   -1.3311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    2.3204   -1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6511    3.1026   -2.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    2.6739    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8908    1.3284    0.8118 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6564    1.3543    1.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.5122   -0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5975    1.0012   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    0.7453   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.0422    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -0.1127    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -1.5296    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -2.2505   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458   -1.6482   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -0.6816   -1.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443   -2.1251   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6548    0.5166    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569   -1.2482    2.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238   -0.2780    2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3331    0.6666    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079    0.7373    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1308   -1.7034    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439   -1.7670    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5368   -1.7535   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4931   -0.2669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371    0.2871   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    1.0389   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -1.4600   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.5912    1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.4666   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -1.0972   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.6682   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    2.6631   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    4.0239   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1387    3.1763    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149    3.2503    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    0.8866    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.6037    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -0.5580   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    2.1143   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    0.5787   -2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763    1.1919   -0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.4536    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2411    0.4221    0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    0.3881    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4078   -2.0814    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0304   -1.5277    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036   -3.3290    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9103   -2.2244   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9563   -1.6986   -0.8507 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  1
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  1
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      46.144 -38.477   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.530 -35.290   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.819 -30.241   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      36.137 -37.985   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      36.961 -35.448   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      46.573 -35.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.819 -34.861   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.049 -37.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.065 -35.766   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      48.589 -37.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.109 -35.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.819 -33.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.964 -36.321   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.153 -32.551   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      49.153 -31.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.499 -35.845   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.486 -30.241   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.486 -28.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.355 -36.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      51.820 -27.931   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.890 -36.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.820 -26.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.746 -37.430   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      53.154 -25.621   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.281 -36.954   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    7    8   11                                                  
CONECT    7    6    9   12                                                  
CONECT    8    1    6   10                                                  
CONECT    9    2    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   15                                                       
CONECT   15    3   14   17                                                  
CONECT   16   13   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22                                                            
CONECT   25    4    5   23                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0001139
HETATM    1  C1  UNL     1      -7.018  -0.232   2.430  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.514   0.115   1.045  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.162  -1.148   0.292  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.660  -0.814  -1.086  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.446   0.046  -1.103  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.231  -0.535  -0.431  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.372  -0.819   0.896  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.103   0.439  -0.681  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.933  -0.003  -1.072  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.196   0.879  -1.331  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.054   2.320  -1.105  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.651   3.103  -2.076  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.602   2.674   0.217  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.891   1.328   0.812  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.656   1.354   1.923  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.377   0.512  -0.364  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.597   1.001  -1.030  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.893   0.745  -0.424  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.118   0.042   0.658  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.522  -0.113   1.139  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.971  -1.530   1.214  1.00  0.00           C  
HETATM   22  C19 UNL     1       5.955  -2.250  -0.092  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.846  -1.648  -1.083  1.00  0.00           C  
HETATM   24  O4  UNL     1       6.511  -0.682  -1.804  1.00  0.00           O  
HETATM   25  O5  UNL     1       8.144  -2.125  -1.284  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.655   0.517   3.164  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.657  -1.248   2.686  1.00  0.00           H  
HETATM   28  H3  UNL     1      -8.124  -0.278   2.436  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.333   0.667   0.526  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.608   0.737   1.173  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.131  -1.703   0.154  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.444  -1.767   0.835  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.537  -1.754  -1.676  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.493  -0.267  -1.618  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.237   0.287  -2.182  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.713   1.039  -0.662  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.980  -1.460  -1.017  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.881  -1.591   1.231  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.377   1.467  -0.500  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.872  -1.097  -1.187  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.608   0.668  -2.361  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.096   2.663  -1.100  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.330   4.024  -1.947  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.139   3.176   0.906  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.515   3.250   0.110  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.098   0.887   1.083  1.00  0.00           H  
HETATM   47  H22 UNL     1       1.452   0.604   2.553  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.409  -0.558  -0.181  1.00  0.00           H  
HETATM   49  H24 UNL     1       2.511   2.114  -1.233  1.00  0.00           H  
HETATM   50  H25 UNL     1       2.585   0.579  -2.087  1.00  0.00           H  
HETATM   51  H26 UNL     1       4.776   1.192  -0.915  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.349  -0.454   1.209  1.00  0.00           H  
HETATM   53  H28 UNL     1       6.241   0.422   0.457  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.651   0.388   2.140  1.00  0.00           H  
HETATM   55  H30 UNL     1       5.408  -2.081   1.997  1.00  0.00           H  
HETATM   56  H31 UNL     1       7.030  -1.528   1.578  1.00  0.00           H  
HETATM   57  H32 UNL     1       6.204  -3.329   0.111  1.00  0.00           H  
HETATM   58  H33 UNL     1       4.910  -2.224  -0.494  1.00  0.00           H  
HETATM   59  H34 UNL     1       8.956  -1.699  -0.851  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   16   41
CONECT   11   12   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   16   46
CONECT   15   47
CONECT   16   17   48
CONECT   17   18   49   50
CONECT   18   19   19   51
CONECT   19   20   52
CONECT   20   21   53   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   24   25
CONECT   25   59
END

HMDB0001139
     RDKit          3D
Prostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
   -7.0185   -0.2319    2.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    0.1151    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1625   -1.1481    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6597   -0.8145   -1.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4458    0.0463   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2307   -0.5346   -0.4306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3722   -0.8195    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    0.4393   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.0025   -1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962    0.8792   -1.3311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    2.3204   -1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6511    3.1026   -2.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    2.6739    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8908    1.3284    0.8118 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6564    1.3543    1.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.5122   -0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5975    1.0012   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    0.7453   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.0422    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223   -0.1127    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -1.5296    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -2.2505   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8458   -1.6482   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -0.6816   -1.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443   -2.1251   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6548    0.5166    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569   -1.2482    2.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238   -0.2780    2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3331    0.6666    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079    0.7373    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1308   -1.7034    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439   -1.7670    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5368   -1.7535   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4931   -0.2669   -1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371    0.2871   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    1.0389   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -1.4600   -1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.5912    1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.4666   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -1.0972   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.6682   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    2.6631   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    4.0239   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1387    3.1763    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149    3.2503    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982    0.8866    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.6037    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092   -0.5580   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    2.1143   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    0.5787   -2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763    1.1919   -0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.4536    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2411    0.4221    0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    0.3881    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4078   -2.0814    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0304   -1.5277    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036   -3.3290    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9103   -2.2244   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9563   -1.6986   -0.8507 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  1
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  1
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Prostaglandin F2a	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oate	HMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acid	HMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate	HMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid	HMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oate	HMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acid	HMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate	HMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid	HMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oate	HMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acid	HMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oate	HMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acid	HMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate	HMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid	HMDB
9a,11a-PGF2	HMDB
9a,11a-PGF2a	HMDB
Amoglandin	HMDB
Cyclosin	HMDB
Dinifertin	HMDB
Dinoprost	HMDB
Enzaprost	HMDB
Enzaprost F	HMDB
F2a Isoprostane	HMDB
Glandin N	HMDB
L-PGF2-alpha	HMDB
L-Prostaglandin F2-alpha	HMDB
Panacelan	HMDB
PGF2a	HMDB
Prostaglandin F2	HMDB
Prostamate	HMDB
Prostarmon F	HMDB
Prostin F 2 alpha	HMDB
Protamodin	HMDB
9alpha,11beta PGF2	HMDB
9alpha,11beta-PGF2	HMDB
Estrofan	HMDB
F2 alpha, Prostaglandin	HMDB
F2alpha, Prostaglandin	HMDB
PGF2	HMDB
PGF2 alpha	HMDB
PGF2alpha	HMDB
Prostaglandin F2 alpha	HMDB
Prostaglandin F2alpha	HMDB
alpha, PGF2	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

5-trans-PGF2α

CAS Registry Number

551-11-1

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

PXGPLTODNUVGFL-UAAPODJFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Prostaglandins (LMFA03010077 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	30 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	4.39	BODOR,H & HUANG,M (1992)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.11	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	41.7 Å³	ChemAxon
Number of Rings	1	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]+	188.473	31661259
DarkChem	[M-H]-	191.162	31661259
AllCCS	[M+H]+	194.252	32859911
AllCCS	[M-H]-	191.78	32859911
DeepCCS	[M+H]+	198.172	30932474
DeepCCS	[M-H]-	195.776	30932474
DeepCCS	[M-2H]-	229.008	30932474
DeepCCS	[M+Na]+	204.085	30932474
AllCCS	[M+H]+	194.3	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.4	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	193.1	32859911
AllCCS	[M+HCOO]-	194.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	4461.2	Standard polar	33892256
Prostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	2708.1	Standard non polar	33892256
Prostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	2924.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin F2a,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2883.7	Semi standard non polar	33892256
Prostaglandin F2a,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O	2784.6	Semi standard non polar	33892256
Prostaglandin F2a,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	2765.8	Semi standard non polar	33892256
Prostaglandin F2a,1TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2816.1	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2755.7	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2746.0	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2827.9	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	2750.7	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #5	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2762.8	Semi standard non polar	33892256
Prostaglandin F2a,2TMS,isomer #6	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2742.2	Semi standard non polar	33892256
Prostaglandin F2a,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2718.1	Semi standard non polar	33892256
Prostaglandin F2a,3TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2744.9	Semi standard non polar	33892256
Prostaglandin F2a,3TMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2730.6	Semi standard non polar	33892256
Prostaglandin F2a,3TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2713.7	Semi standard non polar	33892256
Prostaglandin F2a,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2746.0	Semi standard non polar	33892256
Prostaglandin F2a,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3139.4	Semi standard non polar	33892256
Prostaglandin F2a,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O	2997.0	Semi standard non polar	33892256
Prostaglandin F2a,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	2980.6	Semi standard non polar	33892256
Prostaglandin F2a,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3080.5	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3245.1	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3232.7	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3363.9	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	3197.2	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3243.4	Semi standard non polar	33892256
Prostaglandin F2a,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3227.3	Semi standard non polar	33892256
Prostaglandin F2a,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3429.7	Semi standard non polar	33892256
Prostaglandin F2a,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3490.6	Semi standard non polar	33892256
Prostaglandin F2a,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3479.2	Semi standard non polar	33892256
Prostaglandin F2a,3TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3432.6	Semi standard non polar	33892256
Prostaglandin F2a,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3625.0	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 - Prostaglandin F2a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-6489000000-bf681ff653e664e9cde0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin F2a GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9300188000-0fc1fbcf7464fb00c07e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin F2a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin F2a 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 - Prostaglandin F2a LC-ESI-QQ , negative-QTOF	splash10-0udi-0009000000-cd642664d59adb85ae59	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Positive-QTOF	splash10-014r-0019000000-3c46ffbee46021b80901	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Positive-QTOF	splash10-01bi-2297000000-9fe530991fdc645e26f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Positive-QTOF	splash10-0103-9170000000-0fa33343bc482bd6f5a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Negative-QTOF	splash10-0udr-0009000000-a337fc1b13431013f06a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Negative-QTOF	splash10-000i-1039000000-40b895b35529c4a81763	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Negative-QTOF	splash10-0a4i-9631000000-8dc66a223446641955e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Negative-QTOF	splash10-0udi-0009000000-4f29fd22c6b0dfe3ac77	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Negative-QTOF	splash10-0udr-0098000000-06ede09931efe0fba78e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Negative-QTOF	splash10-00el-9182000000-f1a4c9aba7f705d2868d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 10V, Positive-QTOF	splash10-014r-0019000000-ece58dc4c35634d7fe3f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 20V, Positive-QTOF	splash10-014i-9255000000-c6aef7e365cba872a558	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin F2a 40V, Positive-QTOF	splash10-05mo-9300000000-552900f74505f7605b0b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Placenta
Platelet
Testis

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	0.000053 +/- 0.000012 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000371 +/- 0.000144 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.00033 +/- 0.000018 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000248 +/- 0.00013 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	7.340e-05 +/- 8.469e-06 uM	Adult (>18 years old)	Both	Normal	6593432	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00007340 +/- 0.000008469 uM	Adult (>18 years old)	Both	Normal	6593432	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002 (0.0-0.004) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00091 +/- 0.00008 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Urine	Detected and Quantified	0.00013 +/- 0.00020 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	24817352	details
Urine	Detected and Quantified	0.00021 +/- 0.000053 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.00031 +/- 0.00012 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.0000924 (0.0000588-0.000126) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	489926	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0010 +/- 0.0002 uM	Adult (>18 years old)	Both	Cardiac arrest	7634804	details
Blood	Detected and Quantified	0.0005 +/- 0.0001 uM	Adult (>18 years old)	Both	Cardiac arrest	7634804	details
Blood	Detected and Quantified	0.0016 +/- 0.0004 uM	Adult (>18 years old)	Both	Cardiac arrest	7634804	details
Blood	Detected and Quantified	0.0007 +/- 0.0001 uM	Adult (>18 years old)	Both	Cardiac arrest	7634804	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000545 0.0000(4799 uM	Not Specified	Not Specified	HIV-Seropositive, Dementia	7910004	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000500 (0.000452-0.000545) uM	Not Specified	Not Specified	HIV-Seropositive (Neurologically normal)	7910004	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details

Associated Disorders and Diseases

Disease References

Cardiac arrest
Strohmenger HU, Lindner KH, Keller A, Lindner IM, Bothner U, Georgieff M: Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55. [PubMed:7634804 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022448

KNApSAcK ID

Not Available

Chemspider ID

4446204

KEGG Compound ID

C00639

BioCyc ID

Not Available

BiGG ID

35568

Wikipedia Link

Prostaglandin F2alpha

METLIN ID

6032

PubChem Compound

5283078

PDB ID

Not Available

ChEBI ID

15553

Food Biomarker Ontology

Not Available

VMH ID

PROSTGF2

MarkerDB ID

MDB00000302

Good Scents ID

Not Available

References

Synthesis Reference

Chen, Shaoqing; Janda, Kim D. Total synthesis of naturally occurring prostaglandin F2a on a non-crosslinked polystyrene support. Tetrahedron Letters (1998), 39(23), 3943-3946.

Material Safety Data Sheet (MSDS)

Not Available

General References

Grinsted J, Byskov AG: Meiosis-inducing and meiosis-preventing substances in human male reproductive organs. Fertil Steril. 1981 Feb;35(2):199-204. [PubMed:7202743 ]
Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. [PubMed:2403792 ]
Carr BR, Milburn J Jr, Wright EE, Simpson ER: Adenylate cyclase activity in neocortex and fetal zone membrane fractions of the human fetal adrenal gland. J Clin Endocrinol Metab. 1985 Apr;60(4):718-22. [PubMed:2982905 ]
Negrel R, Gaillard D, Ailhaud G: Prostacyclin as a potent effector of adipose-cell differentiation. Biochem J. 1989 Jan 15;257(2):399-405. [PubMed:2539085 ]
Hammarstrom S, Hamberg M, Samuelsson B, Duell EA, Stawiski M, Voorhees JJ: Increased concentrations of nonesterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2, and prostaglandin F2alpha in epidermis of psoriasis. Proc Natl Acad Sci U S A. 1975 Dec;72(12):5130-4. [PubMed:1061097 ]
Steele GL, Leung PC: Intragonadal signalling mechanisms in the control of steroid hormone production. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):515-22. [PubMed:1562522 ]
Ciabattoni G, Pugliese F, Spaldi M, Cinotti GA, Patrono C: Radioimmunoassay measurement of prostaglandins E2 and F2alpha in human urine. J Endocrinol Invest. 1979 Apr-Jun;2(2):173-82. [PubMed:489926 ]
Davi G, Chiarelli F, Santilli F, Pomilio M, Vigneri S, Falco A, Basili S, Ciabattoni G, Patrono C: Enhanced lipid peroxidation and platelet activation in the early phase of type 1 diabetes mellitus: role of interleukin-6 and disease duration. Circulation. 2003 Jul 1;107(25):3199-203. Epub 2003 Jun 16. [PubMed:12810609 ]
Komoto J, Yamada T, Watanabe K, Woodward DF, Takusagawa F: Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost. Biochemistry. 2006 Feb 21;45(7):1987-96. [PubMed:16475787 ]

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

Reactions

Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Ion	details

Enzyme Details

2. Carbonyl reductase [NADPH] 3

General function:: Involved in oxidoreductase activity
Specific function:: Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:: CBR3
Uniprot ID:: O75828
Molecular weight:: 30849.97

Reactions

Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Ion	details

Enzyme Details

3. 15-hydroxyprostaglandin dehydrogenase [NAD(+)]

General function:: Involved in oxidoreductase activity
Specific function:: Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:: HPGD
Uniprot ID:: P15428
Molecular weight:: 28977.105

Showing metabocard for Prostaglandin F2a (HMDB0001139)

MOL for HMDB0001139 (Prostaglandin F2a)

3D MOL for HMDB0001139 (Prostaglandin F2a)

3D SDF for HMDB0001139 (Prostaglandin F2a)

3D-SDF for HMDB0001139 (Prostaglandin F2a)

PDB for HMDB0001139 (Prostaglandin F2a)

3D PDB for HMDB0001139 (Prostaglandin F2a)

SMILES for HMDB0001139 (Prostaglandin F2a)

INCHI for HMDB0001139 (Prostaglandin F2a)

Structure for HMDB0001139 (Prostaglandin F2a)

3D Structure for HMDB0001139 (Prostaglandin F2a)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions