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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:08 UTC

Update Date

2022-09-22 17:43:49 UTC

HMDB ID

HMDB0002752

Secondary Accession Numbers

HMDB0062524
HMDB02752
HMDB62524

Metabolite Identification

Common Name

Prostaglandin A2

Description

Produced by the seminal vesicles, prostaglandins are a group of lipid compounds that are derived enzymatically from fatty acids. Technically hormones, the prostanoid class of fatty acid derivatives is a subclass of 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 signaling pathways. Prostaglandin A is a cyclopentenone and is an endogenous metabolite derived from arachidonic acid. It exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. There is also an increase in DNA content preceeding the G0/G1 peak (indicative of apoptotic body formation) mediated by changes in expression levels of Bax and Bcl-2.

Structure

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

HMDB0002752
     RDKit          3D
Prostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -5.4908    2.2869    2.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.1926    1.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.5538    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    0.4877   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    0.1881   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7229   -0.8974   -1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4781   -2.0478   -1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785   -1.1811   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -1.9518   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102   -2.2736   -0.1979 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9341   -3.7371   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354   -3.9193   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.6394   -2.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -2.3585   -3.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.6353   -1.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0545   -1.6352   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -0.9934   -1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.0991   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5874    0.7844   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    2.2041   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    2.8422    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    2.2097    2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920    1.2108    1.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3934    2.7520    3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    3.2978    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5825    2.1571    2.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    2.2391    3.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8973    1.0558    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886    0.2449    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2218    1.6967    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    2.5441    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8621    0.7908   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.4377   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9805   -0.0879    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    1.1281   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887   -0.5784   -2.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108   -2.1974   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295   -0.7178   -1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895   -2.4134    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -1.9823    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -4.5021    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -4.8800   -2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.6299   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572   -2.7199   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.2013    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8660   -1.4815   -2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    0.5341   -2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084    0.9384    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    0.2656    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069    2.7876   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    2.2200   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884    2.8135    1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    3.9431    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672    2.6316    3.8774 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 11 41  1  0
 12 42  1  0
 15 43  1  6
 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


  Mrv1652311161700512D          

 24 24  0  0  0  0            999 V2000
 2499.7539 2502.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.4700 2503.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.2944 2503.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.0084 2502.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7224 2503.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.4365 2502.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.1505 2503.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.8645 2502.6378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.1505 2503.8735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1226 2501.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.8367 2501.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5507 2501.7211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2503.2646 2501.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9788 2501.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.6928 2501.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.4068 2501.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.1208 2501.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5507 2502.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2890 2501.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7372 2501.8028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2499.0692 2501.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3244 2500.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1501 2500.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.4052 2501.3174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 21 19  2  0  0  0  0
 24 10  1  1  0  0  0
 20  1  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002752

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\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+/t16-,17-,18+/m0/s1

> <INCHI_KEY>
MYHXHCUNDDAEOZ-FOSBLDSVSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.65998139808427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2S)-2-[(1E,3S)-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>
99.08989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin A2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002752
     RDKit          3D
Prostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -5.4908    2.2869    2.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.1926    1.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.5538    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    0.4877   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    0.1881   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7229   -0.8974   -1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4781   -2.0478   -1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785   -1.1811   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -1.9518   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102   -2.2736   -0.1979 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9341   -3.7371   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354   -3.9193   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.6394   -2.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -2.3585   -3.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.6353   -1.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0545   -1.6352   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -0.9934   -1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.0991   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5874    0.7844   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    2.2041   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    2.8422    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    2.2097    2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920    1.2108    1.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3934    2.7520    3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    3.2978    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5825    2.1571    2.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    2.2391    3.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8973    1.0558    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886    0.2449    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2218    1.6967    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    2.5441    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8621    0.7908   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.4377   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9805   -0.0879    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    1.1281   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887   -0.5784   -2.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108   -2.1974   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295   -0.7178   -1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895   -2.4134    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -1.9823    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -4.5021    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -4.8800   -2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.6299   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572   -2.7199   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.2013    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8660   -1.4815   -2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    0.5341   -2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084    0.9384    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    0.2656    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069    2.7876   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    2.2200   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884    2.8135    1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    3.9431    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672    2.6316    3.8774 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 11 41  1  0
 12 42  1  0
 15 43  1  6
 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                                 16-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-17         0                                  
HETATM    1  C   UNK     0    4666.2074671.591   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4667.5444672.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4669.0834672.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4670.4164671.591   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4671.7484672.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4673.0814671.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4674.4144672.358   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4675.7474671.591   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4674.4144673.897   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4668.7624669.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4670.0954669.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4671.4284669.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4672.7614669.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4674.0944669.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4675.4274669.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4676.7594669.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4678.0924669.108   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    4671.4284671.418   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    4663.4734669.585   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    4666.1764670.032   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4664.9294669.126   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4665.4064667.660   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    4666.9474667.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    4667.4234669.126   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   24                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
CONECT   19   21                                                            
CONECT   20   21   24    1                                                  
CONECT   21   20   22   19                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   20   23   10                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0002752
HETATM    1  C1  UNL     1      -5.491   2.287   2.722  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.969   1.193   1.814  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.136   1.554   0.358  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.630   0.488  -0.553  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.160   0.188  -0.371  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.723  -0.897  -1.329  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.478  -2.048  -1.057  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.278  -1.181  -1.240  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.716  -1.952  -0.341  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.710  -2.274  -0.198  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.934  -3.737  -0.417  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.435  -3.919  -1.615  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.597  -2.639  -2.304  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.706  -2.359  -3.505  1.00  0.00           O  
HETATM   15  C13 UNL     1       1.608  -1.635  -1.200  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.054  -1.635  -0.657  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.860  -0.993  -1.704  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.552   0.099  -1.499  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.587   0.784  -0.208  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.059   2.204  -0.289  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.120   2.842   1.050  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.328   2.210   2.106  1.00  0.00           C  
HETATM   23  O3  UNL     1       2.592   1.211   1.945  1.00  0.00           O  
HETATM   24  O4  UNL     1       3.393   2.752   3.381  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.280   3.298   2.280  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.583   2.157   2.873  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.975   2.239   3.689  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.897   1.056   2.083  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.489   0.245   2.052  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.222   1.697   0.194  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.663   2.544   0.185  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.862   0.791  -1.594  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.207  -0.438  -0.345  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.980  -0.088   0.682  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.605   1.128  -0.565  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.989  -0.578  -2.348  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.411  -2.197  -0.083  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.629  -0.718  -1.974  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.389  -2.413   0.393  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.031  -1.982   0.828  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.711  -4.502   0.307  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.705  -4.880  -2.065  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.327  -0.630  -1.500  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.357  -2.720  -0.508  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.055  -1.201   0.327  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.866  -1.482  -2.711  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.141   0.534  -2.337  1.00  0.00           H  
HETATM   48  H24 UNL     1       5.708   0.938   0.002  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.231   0.266   0.663  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.707   2.788  -0.974  1.00  0.00           H  
HETATM   51  H27 UNL     1       3.038   2.220  -0.719  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.188   2.813   1.399  1.00  0.00           H  
HETATM   53  H29 UNL     1       3.892   3.943   1.001  1.00  0.00           H  
HETATM   54  H30 UNL     1       4.267   2.632   3.877  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

HMDB0002752
     RDKit          3D
Prostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -5.4908    2.2869    2.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    1.1926    1.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361    1.5538    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    0.4877   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    0.1881   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7229   -0.8974   -1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4781   -2.0478   -1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785   -1.1811   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -1.9518   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102   -2.2736   -0.1979 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9341   -3.7371   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354   -3.9193   -1.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -2.6394   -2.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -2.3585   -3.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.6353   -1.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0545   -1.6352   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -0.9934   -1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.0991   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5874    0.7844   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    2.2041   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    2.8422    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    2.2097    2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920    1.2108    1.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3934    2.7520    3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    3.2978    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5825    2.1571    2.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    2.2391    3.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8973    1.0558    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886    0.2449    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2218    1.6967    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    2.5441    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8621    0.7908   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.4377   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9805   -0.0879    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    1.1281   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887   -0.5784   -2.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108   -2.1974   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295   -0.7178   -1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895   -2.4134    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -1.9823    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -4.5021    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -4.8800   -2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266   -0.6299   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572   -2.7199   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.2013    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8660   -1.4815   -2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    0.5341   -2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084    0.9384    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    0.2656    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069    2.7876   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    2.2200   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884    2.8135    1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    3.9431    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672    2.6316    3.8774 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 11 41  1  0
 12 42  1  0
 15 43  1  6
 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
(15S)-PGA2	ChEBI
(15S)-Prostaglandin a2	ChEBI
5,6-cis-PGA2	ChEBI
Medullin	ChEBI
PGA2	ChEBI
7-[2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl]-5-heptenoic acid	HMDB
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,10,13-trien-1-Oic acid	HMDB
(+)-Prostaglandin a2	HMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate	HMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid	HMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate	HMDB
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid	HMDB
15(S)-Prostaglandin a2	HMDB
15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate	HMDB
15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid	HMDB
15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate	HMDB
15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid	HMDB
NSC 165561	HMDB
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5, 10,13-triene-1-Oic acid	HMDB
(Z)-7-((1R,2S)-2-((e)-(3S)-3-Hydroxyoct-1-enyl)-5-oxocyclopent-3-enyl)hept-5-enoic acid	HMDB
Prostaglandin A2	HMDB

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

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

Traditional Name

prostaglandin A2

CAS Registry Number

13345-50-1

SMILES

CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\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+/t16-,17-,18+/m0/s1

InChI Key

MYHXHCUNDDAEOZ-FOSBLDSVSA-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

prostaglandins A (CHEBI:27820 )
Prostaglandins (C05953 )
Prostaglandins (LMFA03010035 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062524)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0062524)

Role

Not Available

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	0.021 g/L	ALOGPS
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	38.66 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
DeepCCS	[M+H]+	192.474	30932474
DeepCCS	[M-H]-	189.871	30932474
DeepCCS	[M-2H]-	224.406	30932474
DeepCCS	[M+Na]+	199.635	30932474
AllCCS	[M+H]+	188.0	32859911
AllCCS	[M+H-H2O]+	185.2	32859911
AllCCS	[M+NH4]+	190.6	32859911
AllCCS	[M+Na]+	191.4	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	189.2	32859911
AllCCS	[M+HCOO]-	190.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	6.82 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5765 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.86 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2772.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	272.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	675.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	478.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1543.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	525.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1470.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	420.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin A2	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	4422.2	Standard polar	33892256
Prostaglandin A2	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2544.3	Standard non polar	33892256
Prostaglandin A2	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2765.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin A2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2804.7	Semi standard non polar	33892256
Prostaglandin A2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2715.9	Semi standard non polar	33892256
Prostaglandin A2,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O	2832.9	Semi standard non polar	33892256
Prostaglandin A2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2783.5	Semi standard non polar	33892256
Prostaglandin A2,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2906.9	Semi standard non polar	33892256
Prostaglandin A2,2TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C	2824.2	Semi standard non polar	33892256
Prostaglandin A2,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2897.0	Semi standard non polar	33892256
Prostaglandin A2,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2722.7	Standard non polar	33892256
Prostaglandin A2,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2989.0	Standard polar	33892256
Prostaglandin A2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3046.3	Semi standard non polar	33892256
Prostaglandin A2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2957.7	Semi standard non polar	33892256
Prostaglandin A2,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O	3083.2	Semi standard non polar	33892256
Prostaglandin A2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3263.6	Semi standard non polar	33892256
Prostaglandin A2,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3368.1	Semi standard non polar	33892256
Prostaglandin A2,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3307.7	Semi standard non polar	33892256
Prostaglandin A2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=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	3597.9	Semi standard non polar	33892256
Prostaglandin A2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=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	3229.7	Standard non polar	33892256
Prostaglandin A2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=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	3170.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Prostaglandin A2 GC-MS (1 MEOX; 2 TMS)	splash10-0059-4920000000-710b83c9a85f25a1d16c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Prostaglandin A2 GC-MS (1 MEOX; 2 TMS)	splash10-0059-4910000000-db2352d8228dc4eb9a18	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-02bo-6293000000-822f7d0eecbf0f64639b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A2 GC-MS (2 TMS) - 70eV, Positive	splash10-0209-9313300000-440ddaf4dbe3670c7d28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A2 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 10V, Positive-QTOF	splash10-014j-0169000000-4a6959ca7f335a56a955	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 20V, Positive-QTOF	splash10-06ds-3192000000-3ab10f6f0529d4cee7b9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 40V, Positive-QTOF	splash10-0l0j-9120000000-0ee0572914cf0adba33b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 10V, Negative-QTOF	splash10-001i-0019000000-17f7af2365a9dd00dcd6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 20V, Negative-QTOF	splash10-0159-2159000000-c7485c819c912f1819ce	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 40V, Negative-QTOF	splash10-0a4i-9430000000-9a1157c44c3655697519	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 10V, Positive-QTOF	splash10-00kb-0095000000-52912cbc0a9bfa893684	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 20V, Positive-QTOF	splash10-015a-6592000000-19736467f3757c7e2399	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 40V, Positive-QTOF	splash10-069u-9410000000-58ab2d3e8090e7cf4fdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 10V, Negative-QTOF	splash10-014i-0049000000-81a3f3dd4586250ad9d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 20V, Negative-QTOF	splash10-00m0-0894000000-add76968bc35e889a4d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A2 40V, Negative-QTOF	splash10-05mo-9850000000-b9e815d2e66be565edc3	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	0.0000448 +/- 0.000496 uM	Adult (>18 years old)	Both	Normal	1153801	details
Blood	Detected and Quantified	0.0010 +/- 0.0002 uM	Adult (>18 years old)	Male	Normal	948620	details
Blood	Detected and Quantified	0.0000747 +/- 0.000254 uM	Adult (>18 years old)	Both	Normal	1153801	details
Blood	Detected and Quantified	0.0008 +/- 0.0002 uM	Adult (>18 years old)	Male	Normal	948620	details
Blood	Detected and Quantified	0.000167 +/- 0.000401 uM	Adult (>18 years old)	Not Specified	Normal	1153801	details
Blood	Detected and Quantified	0.0019 +/- 0.0004 uM	Adult (>18 years old)	Male	Normal	948620	details
Blood	Detected and Quantified	0.0027 +/- 0.0008 uM	Adult (>18 years old)	Male	Normal	948620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB023060

KNApSAcK ID

Not Available

Chemspider ID

4444403

KEGG Compound ID

C05953

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280880

PDB ID

Not Available

ChEBI ID

27820

Food Biomarker Ontology

Not Available

VMH ID

HC02203

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Grieco, Paul A.; Abood, Norman. Facile retro Diels-Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2. Journal of the Chemical Society, Chemical Communications (1990), (5), 410-12.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Prostaglandin A2 (HMDB0002752)

MOL for HMDB0002752 (Prostaglandin A2)

3D MOL for HMDB0002752 (Prostaglandin A2)

3D SDF for HMDB0002752 (Prostaglandin A2)

3D-SDF for HMDB0002752 (Prostaglandin A2)

PDB for HMDB0002752 (Prostaglandin A2)

3D PDB for HMDB0002752 (Prostaglandin A2)

SMILES for HMDB0002752 (Prostaglandin A2)

INCHI for HMDB0002752 (Prostaglandin A2)

Structure for HMDB0002752 (Prostaglandin A2)

3D Structure for HMDB0002752 (Prostaglandin A2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra