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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 15:29:01 UTC

Update Date

2021-09-23 15:29:02 UTC

HMDB ID

HMDB0302203

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prostaglandin A-2

Description

Prostaglandin a-2, also known as pga2 or medullin, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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. Prostaglandin a-2 is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Prostaglandin a-2 can be found in soft-necked garlic, which makes prostaglandin a-2 a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302203
     RDKit          3D
Prostaglandin A-2
 54 54  0  0  0  0  0  0  0  0999 V2000
    5.7579    2.0742   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    1.1813    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4583   -0.2555    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0835   -0.8371   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -0.7639    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212   -1.3326    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640   -2.6838    0.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -0.5833    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -1.0763   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2811   -0.2661   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675   -0.8809   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -0.5418   -3.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    0.3184   -2.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638    1.1008   -2.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.0413   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -1.1082   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315   -0.6379   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.6357    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.1717    1.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    0.3012    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    0.7672    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    1.9000    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    2.2815    1.9836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2009    2.5640    2.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309    2.0386   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    3.1216   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7010    1.8208   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    1.5383    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    1.3727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9815   -0.2691   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0698   -0.8868    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588   -1.8998   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6195   -0.2405   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2758    0.3180    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022   -1.2682    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.2701    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -2.6937   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657    0.4158   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -2.0672   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979    0.7079   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -1.5108   -3.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -0.8692   -4.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209    0.9219   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.4632    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -1.9692   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8790   -0.2709   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055   -0.9944    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9632    0.6144    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337   -1.0063    2.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9675   -0.4814   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3307    1.2018   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8063   -0.0854    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7758    1.0720   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7863    3.3473    1.6584 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END


  Mrv0541 02241223392D          

 24 24  0  0  0  0            999 V2000
   -3.0095    0.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095   -0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2243   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3497   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643    1.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768    1.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799   -1.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1 21  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 22  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302203

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)\C=C\C1C=CC(=O)C1C\C=C\CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4+,14-12+

> <INCHI_KEY>
MYHXHCUNDDAEOZ-BMZFSJBMSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38172167071295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-7-{2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.375950963666667

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.746753582730975

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4020347457496705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5972353190575

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
99.08989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-7-{2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302203
     RDKit          3D
Prostaglandin A-2
 54 54  0  0  0  0  0  0  0  0999 V2000
    5.7579    2.0742   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    1.1813    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4583   -0.2555    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0835   -0.8371   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -0.7639    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212   -1.3326    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640   -2.6838    0.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -0.5833    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -1.0763   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2811   -0.2661   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675   -0.8809   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -0.5418   -3.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    0.3184   -2.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638    1.1008   -2.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.0413   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -1.1082   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315   -0.6379   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.6357    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.1717    1.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    0.3012    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    0.7672    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    1.9000    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    2.2815    1.9836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2009    2.5640    2.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309    2.0386   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    3.1216   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7010    1.8208   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    1.5383    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    1.3727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9815   -0.2691   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0698   -0.8868    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588   -1.8998   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6195   -0.2405   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2758    0.3180    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022   -1.2682    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.2701    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -2.6937   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657    0.4158   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -2.0672   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979    0.7079   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -1.5108   -3.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -0.8692   -4.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209    0.9219   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.4632    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -1.9692   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8790   -0.2709   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055   -0.9944    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9632    0.6144    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337   -1.0063    2.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9675   -0.4814   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3307    1.2018   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8063   -0.0854    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7758    1.0720   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7863    3.3473    1.6584 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.618   1.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.523   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.618  -1.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.152  -0.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.157   0.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.823   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.488   0.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.154   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.180   0.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.515   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.849   0.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.183   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.518   0.771   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.818  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.483  -0.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.149  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.185  -0.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.519  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.854  -0.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.188  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.093   2.718   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.183   3.083   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.149  -3.083   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.523  -0.769   0.000  0.00  0.00           C+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12                                                            
CONECT   14    4   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   24                                                       
CONECT   21    1                                                            
CONECT   22   12                                                            
CONECT   23   16                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0302203
HETATM    1  C1  UNL     1       5.758   2.074  -0.436  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.438   1.181   0.581  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.458  -0.256   0.146  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.083  -0.837  -0.074  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.317  -0.764   1.203  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.921  -1.333   1.095  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.064  -2.684   0.720  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.127  -0.583   0.111  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.024  -1.076  -0.432  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.281  -0.266  -1.411  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.167  -0.881  -2.729  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.991  -0.542  -3.260  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.734   0.318  -2.344  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.664   1.101  -2.612  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.122   0.041  -1.017  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.856  -1.108  -0.403  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.232  -0.638  -0.068  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.725  -0.636   1.146  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.096  -0.172   1.508  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.870   0.301   0.322  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.249   0.767   0.681  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.283   1.900   1.626  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.442   2.281   1.984  1.00  0.00           O  
HETATM   24  O4  UNL     1      -6.201   2.564   2.142  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.331   2.039  -1.386  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.875   3.122  -0.048  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.701   1.821  -0.584  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.495   1.538   0.663  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.985   1.373   1.557  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.981  -0.269  -0.846  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.070  -0.887   0.832  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.259  -1.900  -0.407  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.619  -0.240  -0.894  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.276   0.318   1.502  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.902  -1.268   1.997  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.480  -1.270   2.121  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.117  -2.694  -0.285  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.466   0.416  -0.178  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.712  -2.067  -0.129  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.798   0.708  -1.543  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.912  -1.511  -3.193  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.330  -0.869  -4.251  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.221   0.922  -0.353  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.407  -1.463   0.548  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.949  -1.969  -1.096  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.879  -0.271  -0.867  1.00  0.00           H  
HETATM   47  H23 UNL     1      -3.105  -0.994   1.960  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.963   0.614   2.273  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.634  -1.006   2.002  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.968  -0.481  -0.442  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.331   1.202  -0.088  1.00  0.00           H  
HETATM   52  H28 UNL     1      -7.806  -0.085   1.150  1.00  0.00           H  
HETATM   53  H29 UNL     1      -7.776   1.072  -0.257  1.00  0.00           H  
HETATM   54  H30 UNL     1      -5.786   3.347   1.658  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   15   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   15
CONECT   15   16   43
CONECT   16   17   44   45
CONECT   17   18   18   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   54
END

HMDB0302203
     RDKit          3D
Prostaglandin A-2
 54 54  0  0  0  0  0  0  0  0999 V2000
    5.7579    2.0742   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    1.1813    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4583   -0.2555    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0835   -0.8371   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -0.7639    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212   -1.3326    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640   -2.6838    0.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -0.5833    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -1.0763   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2811   -0.2661   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675   -0.8809   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -0.5418   -3.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    0.3184   -2.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638    1.1008   -2.6121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.0413   -1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559   -1.1082   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315   -0.6379   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.6357    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.1717    1.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    0.3012    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    0.7672    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    1.9000    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    2.2815    1.9836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2009    2.5640    2.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309    2.0386   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    3.1216   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7010    1.8208   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    1.5383    0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    1.3727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9815   -0.2691   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0698   -0.8868    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588   -1.8998   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6195   -0.2405   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2758    0.3180    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022   -1.2682    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.2701    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -2.6937   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657    0.4158   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -2.0672   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979    0.7079   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -1.5108   -3.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -0.8692   -4.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209    0.9219   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073   -1.4632    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -1.9692   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8790   -0.2709   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055   -0.9944    1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9632    0.6144    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337   -1.0063    2.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9675   -0.4814   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3307    1.2018   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8063   -0.0854    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7758    1.0720   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7863    3.3473    1.6584 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5E)-7-{2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoate	Generator
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5, 10,13-triene-1-Oic acid	MeSH
Medullin	MeSH
Prostaglandin a2	MeSH
(Z)-7-((1R,2S)-2-((e)-(3S)-3-Hydroxyoct-1-enyl)-5-oxocyclopent-3-enyl)hept-5-enoic acid	MeSH
PGA2	MeSH

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

(5E)-7-{2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid

Traditional Name

(5E)-7-{2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(O)\C=C\C1C=CC(=O)C1C\C=C\CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4+,14-12+

InChI Key

MYHXHCUNDDAEOZ-BMZFSJBMSA-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
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Soft-necked garlic (FooDB: FOOD00850)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	4.08	ALOGPS
logP	4.38	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	99.09 m³·mol⁻¹	ChemAxon
Polarizability	39.38 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
AllCCS	[M+H]+	188.006	32859911
AllCCS	[M+H-H2O]+	185.158	32859911
AllCCS	[M+Na]+	191.393	32859911
AllCCS	[M+NH4]+	190.638	32859911
AllCCS	[M-H]-	187.945	32859911
AllCCS	[M+Na-2H]-	189.217	32859911
AllCCS	[M+HCOO]-	190.768	32859911
DeepCCS	[M+H]+	192.254	30932474
DeepCCS	[M-H]-	189.896	30932474
DeepCCS	[M-2H]-	222.782	30932474
DeepCCS	[M+Na]+	198.347	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin A-2,3TMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2872.4	Semi standard non polar	33892256
Prostaglandin A-2,3TMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2745.3	Standard non polar	33892256
Prostaglandin A-2,3TMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3007.2	Standard polar	33892256
Prostaglandin A-2,3TBDMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3620.7	Semi standard non polar	33892256
Prostaglandin A-2,3TBDMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3273.2	Standard non polar	33892256
Prostaglandin A-2,3TBDMS,isomer #1	CCCCCC(/C=C/C1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3185.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 10V, Positive-QTOF	splash10-014r-0169000000-f26b81feab4f77f98b82	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 20V, Positive-QTOF	splash10-06ds-3192000000-01d9dc5671274fbf26f7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 40V, Positive-QTOF	splash10-0q2l-9210000000-cb4772681f5b53caa276	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 10V, Negative-QTOF	splash10-001i-0029000000-497bcadaa1837d846315	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 20V, Negative-QTOF	splash10-00lr-2269000000-b993645cd03bd237f17f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 40V, Negative-QTOF	splash10-0a4i-9430000000-bbab6fcb5b00d95e5da3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 10V, Positive-QTOF	splash10-00kb-0096000000-0512adf664dfc92e309b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 20V, Positive-QTOF	splash10-015a-6592000000-19736467f3757c7e2399	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 40V, Positive-QTOF	splash10-069u-9410000000-58ab2d3e8090e7cf4fdb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 10V, Negative-QTOF	splash10-014i-0049000000-81a3f3dd4586250ad9d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 20V, Negative-QTOF	splash10-00m0-0894000000-add76968bc35e889a4d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A-2 40V, Negative-QTOF	splash10-05mo-9850000000-b9e815d2e66be565edc3	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB003669

KNApSAcK ID

Not Available

Chemspider ID

4510251

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5353901

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Prostaglandin A-2 (HMDB0302203)

MOL for HMDB0302203 (Prostaglandin A-2)

3D MOL for HMDB0302203 (Prostaglandin A-2)

3D SDF for HMDB0302203 (Prostaglandin A-2)

3D-SDF for HMDB0302203 (Prostaglandin A-2)

PDB for HMDB0302203 (Prostaglandin A-2)

3D PDB for HMDB0302203 (Prostaglandin A-2)

SMILES for HMDB0302203 (Prostaglandin A-2)

INCHI for HMDB0302203 (Prostaglandin A-2)

Structure for HMDB0302203 (Prostaglandin A-2)

3D Structure for HMDB0302203 (Prostaglandin A-2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra