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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:01 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002656

Secondary Accession Numbers

HMDB02656

Metabolite Identification

Common Name

Prostaglandin A1

Description

Prostaglandin A1 (PGA1, a prostaglandin characterized by a cyclopentenone structure) has a fundamental structure common to punaglandin and clavulone, the antitumor eicosanoids discovered in marine organisms such as corals. It is well established that PGA1, which exert potent antiviral activity in several DNA and RNA virus models, induce heat shock protein (hsp)70 syntheses through cycloheximide sensitive activation of heat shock transcription factor. Antitumor prostaglandins are actively incorporated through cell membrane and control gene expression. P53 (protein 53, is a transcription factor that regulates the cell cycle and functions as a tumor suppressor) independent expression of p21 (also known as cyclin-dependent kinase inhibitor 1A or CDKN1A, is a human gene on chromosome 6 (location 6p21.2), that encodes a cyclin-dependent kinase) and gadd 45 (growth arrest and DNA-damage-inducible, alpha 45, a major breast cancer (BRCA1) target is the DNA damage-responsive gene GADD45) activation of peroxisome proliferative activated receptor gamma (PPARgamma) are involved in antitumor mechanism of these prostaglandins. At the low concentration, these prostaglandins exhibit physiological or pathological activity such as osteoblast calcification, promotion of colon cancer cell proliferation. One of the mechanisms of anti-cancer activity of prostaglandins, has been believed to be that these prostaglandins might have p53 like effect in cells lacking p53. (PMID: 7988663 , 11104898 )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

HMDB0002656
     RDKit          3D
Prostaglandin A1
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.0601   -1.4823   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5702   -0.1596   -1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5008    0.1268    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2026    0.2279    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3966   -1.0164    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982   -0.8675    1.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3885   -0.5859    2.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.1351    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688   -0.1340    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0322    0.7798   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5886    2.0971   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    3.0473   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.3910    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268    2.8415   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    1.1862    0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1245    0.1087    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -0.3531   -0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -1.4394    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -1.0570    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886    0.1183    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795   -0.2064   -1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007    1.0045   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046    2.0070   -1.9878 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3949    1.1137   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8130   -1.9174   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0462   -2.2337   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1215   -1.3421   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0948    0.6643   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6623   -0.0756   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288    1.1150    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1875   -0.6078    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3483    0.5316    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734    1.0744    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128   -1.1966   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -1.8827    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -1.8671    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4614    0.4052    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.0822    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5777   -1.0821    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3425   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    2.3455   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209    4.0974   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.4608    1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377    0.3266    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.7896    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674   -0.7998   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650    0.5084   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -2.3237    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -1.7582   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.7253    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061   -1.9370    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    0.4295    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865    0.9578    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.4124   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -1.0277   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8673    0.7030   -0.6504 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  1  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  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv0541 02231219342D          

 24 24  0  0  1  0            999 V2000
   25.2892  -13.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0307  -17.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4723  -16.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3917  -17.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0036  -13.6307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.7181  -13.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7181  -12.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4393  -16.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8262  -16.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4327  -11.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2240  -16.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0416  -16.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4327  -11.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8371  -15.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4285  -17.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1471  -10.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6217  -16.1782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2892  -15.6933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6438  -16.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0036  -14.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2892  -14.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8767  -16.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9566  -16.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7017  -16.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  2 19  1  0  0  0  0
  3 19  2  0  0  0  0
  4 22  2  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 14  1  6  0  0  0
 15 19  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  1  0  0  0
 18 23  1  0  0  0  0
 20 21  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002656

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1

> <INCHI_KEY>
BGKHCLZFGPIKKU-LDDQNKHRSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.10607487396389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.737872620333333

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.74675363107826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.45154130592671

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5972323838202795

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
97.97329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin A1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002656
     RDKit          3D
Prostaglandin A1
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.0601   -1.4823   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5702   -0.1596   -1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5008    0.1268    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2026    0.2279    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3966   -1.0164    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982   -0.8675    1.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3885   -0.5859    2.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.1351    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688   -0.1340    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0322    0.7798   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5886    2.0971   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    3.0473   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.3910    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268    2.8415   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    1.1862    0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1245    0.1087    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -0.3531   -0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -1.4394    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -1.0570    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886    0.1183    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795   -0.2064   -1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007    1.0045   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046    2.0070   -1.9878 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3949    1.1137   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8130   -1.9174   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0462   -2.2337   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1215   -1.3421   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0948    0.6643   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6623   -0.0756   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288    1.1150    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1875   -0.6078    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3483    0.5316    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734    1.0744    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128   -1.1966   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -1.8827    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -1.8671    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4614    0.4052    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.0822    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5777   -1.0821    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3425   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    2.3455   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209    4.0974   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.4608    1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377    0.3266    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.7896    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674   -0.7998   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650    0.5084   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -2.3237    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -1.7582   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.7253    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061   -1.9370    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    0.4295    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865    0.9578    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.4124   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -1.0277   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8673    0.7030   -0.6504 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  1  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  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 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      47.207 -24.674   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.524 -32.418   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.348 -29.881   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      45.531 -32.910   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      48.540 -25.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.874 -24.674   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.874 -23.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.887 -30.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.742 -31.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.208 -22.364   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.351 -30.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.278 -30.833   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.208 -20.824   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.496 -29.723   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.133 -31.863   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.541 -20.054   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.961 -30.199   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      47.207 -29.294   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.668 -31.387   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      48.540 -26.984   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      47.207 -27.754   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.437 -31.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      48.452 -30.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.977 -31.664   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   22                                                            
CONECT    5    1    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   19                                                       
CONECT   16   13                                                            
CONECT   17   14   18   22                                                  
CONECT   18   17   21   23                                                  
CONECT   19    2    3   15                                                  
CONECT   20    5   21                                                       
CONECT   21   18   20                                                       
CONECT   22    4   17   24                                                  
CONECT   23   18   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0002656
HETATM    1  C1  UNL     1      -6.060  -1.482  -1.908  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.570  -0.160  -1.424  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.501   0.127   0.012  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.203   0.228   0.707  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.397  -1.016   0.648  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.098  -0.868   1.446  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.388  -0.586   2.755  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.254   0.135   0.773  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.969  -0.134   0.590  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.032   0.780  -0.064  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.589   2.097  -0.439  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.357   3.047  -0.331  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.600   2.391   0.126  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.727   2.842  -0.103  1.00  0.00           O  
HETATM   15  C13 UNL     1       1.115   1.186   0.848  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.125   0.109   1.011  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.800  -0.353  -0.234  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.815  -1.439   0.008  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.931  -1.057   0.917  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.689   0.118   0.334  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.280  -0.206  -1.017  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.001   1.005  -1.497  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.405   2.007  -1.988  1.00  0.00           O  
HETATM   24  O4  UNL     1       8.395   1.114  -1.436  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.813  -1.917  -2.669  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.046  -2.234  -1.124  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.122  -1.342  -2.479  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.095   0.664  -2.036  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.662  -0.076  -1.736  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.029   1.115   0.183  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.187  -0.608   0.541  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.348   0.532   1.799  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.573   1.074   0.319  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.113  -1.197  -0.433  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.979  -1.883   0.971  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.598  -1.867   1.326  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.461   0.405   2.847  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.598   1.082   0.417  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.578  -1.082   0.940  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.425   0.342  -0.990  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.586   2.345  -0.764  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.221   4.097  -0.545  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.679   1.461   1.834  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.838   0.327   1.840  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.554  -0.790   1.403  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.067  -0.800  -0.965  1.00  0.00           H  
HETATM   47  H23 UNL     1       3.265   0.508  -0.750  1.00  0.00           H  
HETATM   48  H24 UNL     1       3.297  -2.324   0.473  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.206  -1.758  -0.978  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.572  -0.725   1.916  1.00  0.00           H  
HETATM   51  H27 UNL     1       5.606  -1.937   1.070  1.00  0.00           H  
HETATM   52  H28 UNL     1       6.521   0.429   0.995  1.00  0.00           H  
HETATM   53  H29 UNL     1       4.987   0.958   0.244  1.00  0.00           H  
HETATM   54  H30 UNL     1       5.501  -0.412  -1.784  1.00  0.00           H  
HETATM   55  H31 UNL     1       7.008  -1.028  -0.951  1.00  0.00           H  
HETATM   56  H32 UNL     1       8.867   0.703  -0.650  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   46   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0002656
     RDKit          3D
Prostaglandin A1
 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.0601   -1.4823   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5702   -0.1596   -1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5008    0.1268    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2026    0.2279    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3966   -1.0164    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982   -0.8675    1.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3885   -0.5859    2.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.1351    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9688   -0.1340    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0322    0.7798   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5886    2.0971   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    3.0473   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.3910    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268    2.8415   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145    1.1862    0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1245    0.1087    1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -0.3531   -0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -1.4394    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -1.0570    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886    0.1183    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795   -0.2064   -1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007    1.0045   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046    2.0070   -1.9878 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3949    1.1137   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8130   -1.9174   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0462   -2.2337   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1215   -1.3421   -2.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0948    0.6643   -2.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6623   -0.0756   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288    1.1150    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1875   -0.6078    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3483    0.5316    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734    1.0744    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128   -1.1966   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9794   -1.8827    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -1.8671    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4614    0.4052    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.0822    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5777   -1.0821    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3425   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    2.3455   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209    4.0974   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.4608    1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377    0.3266    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.7896    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674   -0.7998   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650    0.5084   -0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -2.3237    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -1.7582   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.7253    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061   -1.9370    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214    0.4295    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865    0.9578    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.4124   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -1.0277   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8673    0.7030   -0.6504 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  1  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  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoate	ChEBI
PGA1	ChEBI
(13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoic acid	Generator
(13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-Oate	HMDB
(13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-Oic acid	HMDB
15-Hydroxy-9-oxoprosta-10,13-dienoate	HMDB
15-Hydroxy-9-oxoprosta-10,13-dienoic acid	HMDB
15a-Hydroxy-9-ketoprosta-10,13-dienoate	HMDB
15a-Hydroxy-9-ketoprosta-10,13-dienoic acid	HMDB
15a-Hydroxy-9-oxo-10,13E-prostadienoate	HMDB
15a-Hydroxy-9-oxo-10,13E-prostadienoic acid	HMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate	HMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid	HMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoate	HMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoic acid	HMDB
Prostaglandin e1-217	HMDB
Prostaglandin a1, (13E,15R)-(+-)-isomer	MeSH, HMDB
Prostaglandin a1, (13E,15R)-isomer	MeSH, HMDB
Prostaglandin a1, (13E,15S)-(+-)-isomer	MeSH, HMDB
Prostaglandin a1, (8beta,12alpha,13E,15S)-isomer	MeSH, HMDB
Prostaglandin a1	MeSH

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

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

Traditional Name

prostaglandin A1

CAS Registry Number

14152-28-4

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1

InChI Key

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins A (CHEBI:15545 )
Prostaglandins (LMFA03010005 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1159043)

Cellular substructure

Cell

Hematocyte

Platelet (HMDB: HMDB0002656)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002656)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002656)

Source

Endogenous

Endogenous (HMDB: HMDB0002656)

Animal

Animal (HMDB: HMDB0002656)

Exogenous

Food

Food (HMDB: HMDB0002656)

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)

Exogenous (HMDB: HMDB0002656)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002656)

Modulator

Immunomodulator (HMDB: HMDB0002656)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002656)

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	0.015 g/L	ALOGPS
logP	4.21	ALOGPS
logP	4.74	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.45	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	13	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	40.11 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]+	191.36	30932474
DeepCCS	[M-H]-	188.964	30932474
DeepCCS	[M-2H]-	222.954	30932474
DeepCCS	[M+Na]+	198.167	30932474
AllCCS	[M+H]+	189.2	32859911
AllCCS	[M+H-H2O]+	186.4	32859911
AllCCS	[M+NH4]+	191.7	32859911
AllCCS	[M+Na]+	192.5	32859911
AllCCS	[M-H]-	189.1	32859911
AllCCS	[M+Na-2H]-	190.4	32859911
AllCCS	[M+HCOO]-	191.9	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. Predicted by Afia on May 17, 2022.	8.2 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0771 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2797.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	701.5 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	540.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1590.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	524.5 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	1550.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	291.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	313.3 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin A1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O	4357.3	Standard polar	33892256
Prostaglandin A1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O	2548.3	Standard non polar	33892256
Prostaglandin A1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O	2743.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin A1,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O)O[Si](C)(C)C	2801.9	Semi standard non polar	33892256
Prostaglandin A1,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O[Si](C)(C)C	2711.2	Semi standard non polar	33892256
Prostaglandin A1,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O	2866.4	Semi standard non polar	33892256
Prostaglandin A1,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2788.2	Semi standard non polar	33892256
Prostaglandin A1,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O)O[Si](C)(C)C	2927.0	Semi standard non polar	33892256
Prostaglandin A1,2TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C	2841.4	Semi standard non polar	33892256
Prostaglandin A1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2941.2	Semi standard non polar	33892256
Prostaglandin A1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2755.6	Standard non polar	33892256
Prostaglandin A1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3073.2	Standard polar	33892256
Prostaglandin A1,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3050.1	Semi standard non polar	33892256
Prostaglandin A1,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2975.2	Semi standard non polar	33892256
Prostaglandin A1,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O	3108.0	Semi standard non polar	33892256
Prostaglandin A1,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3316.6	Semi standard non polar	33892256
Prostaglandin A1,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3395.4	Semi standard non polar	33892256
Prostaglandin A1,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3315.4	Semi standard non polar	33892256
Prostaglandin A1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3642.2	Semi standard non polar	33892256
Prostaglandin A1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3227.2	Standard non polar	33892256
Prostaglandin A1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3267.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A1 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0673-4092000000-6874868660d1be2cc397	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A1 GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9103300000-0b8807822e2ae6a44c8e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin A1 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 A1 10V, Positive-QTOF	splash10-0gb9-0029000000-ef612f000f40cf5fb612	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 20V, Positive-QTOF	splash10-0l6u-3194000000-1d504119f0ddf6f99cfc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 40V, Positive-QTOF	splash10-05tv-9120000000-04e28ba462f08d52e16b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 10V, Negative-QTOF	splash10-000i-0019000000-af954838d61275b1a6b2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 20V, Negative-QTOF	splash10-014r-2159000000-3d6b28690c12cfabfbb1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 40V, Negative-QTOF	splash10-0a4i-9540000000-0657404cf2ca8a295d26	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 10V, Positive-QTOF	splash10-0uxr-0019000000-943865bd4f76ac81c5b5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 20V, Positive-QTOF	splash10-0uxr-8978000000-1b9129ec137ac84e784f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 40V, Positive-QTOF	splash10-05qc-9500000000-74f6b19254976131ff01	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 10V, Negative-QTOF	splash10-014r-0029000000-eee5cd4fa1c96d9b3408	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 20V, Negative-QTOF	splash10-00kr-0597000000-eae1be9c15781533cefc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin A1 40V, Negative-QTOF	splash10-05oa-5940000000-1dadced25493924491cc	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000074 +/- 0.000048 uM	Adult (>18 years old)	Both	Normal	1159043	details

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

FDB023040

KNApSAcK ID

Not Available

Chemspider ID

4445196

KEGG Compound ID

C04685

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prostaglandin-A1 Delta-isomerase

METLIN ID

407

PubChem Compound

5281912

PDB ID

Not Available

ChEBI ID

15545

Food Biomarker Ontology

Not Available

VMH ID

HC02202

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Pike, John E.; Lincoln, F. H.; Schneider, William Paul. Prostanoic acid chemistry. Journal of Organic Chemistry (1969), 34(11), 3552-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sasaki H, Fukushima M: Prostaglandins in the treatment of cancer. Anticancer Drugs. 1994 Apr;5(2):131-8. [PubMed:8049495 ]
Gueriguian FL: Prostaglandin-macromolecule interactions. I. Noncovalent binding of prostaglandins A1, E1, F2alpha, and E2 by human and bovine serum albumins. J Pharmacol Exp Ther. 1976 May;197(2):391-401. [PubMed:944773 ]
Montgomery RG, Patel NC, Lee JG: A comparison of the diuretic effects of prostaglandin A1, sodium ethacrynate, and placebo. Int J Clin Pharmacol Biopharm. 1975 Jul;12(1-2):102-8. [PubMed:1165130 ]
Aitokallio-Tallberg A, Viinikka L, Ylikorkala O: Urinary 6-keto-prostaglandin F1a in patients with gynaecological tumours. Cancer Lett. 1987 Feb;34(2):201-6. [PubMed:3545443 ]
Zhu Y, Gu ZL, Liang ZQ, Zhang HL, Qin ZH: Prostaglandin A1 inhibits increases in intracellular calcium concentration, TXA(2) production and platelet activation. Acta Pharmacol Sin. 2006 May;27(5):549-54. [PubMed:16626509 ]
Santoro MG: Heat shock proteins and virus replication: hsp70s as mediators of the antiviral effects of prostaglandins. Experientia. 1994 Nov 30;50(11-12):1039-47. [PubMed:7988663 ]
Fukushima S, Kishimoto S, Takeuchi Y, Fukushima M: Preparation and evaluation of o/w type emulsions containing antitumor prostaglandin. Adv Drug Deliv Rev. 2000 Dec 6;45(1):65-75. [PubMed:11104898 ]

Showing metabocard for Prostaglandin A1 (HMDB0002656)

MOL for HMDB0002656 (Prostaglandin A1)

3D MOL for HMDB0002656 (Prostaglandin A1)

3D SDF for HMDB0002656 (Prostaglandin A1)

3D-SDF for HMDB0002656 (Prostaglandin A1)

PDB for HMDB0002656 (Prostaglandin A1)

3D PDB for HMDB0002656 (Prostaglandin A1)

SMILES for HMDB0002656 (Prostaglandin A1)

INCHI for HMDB0002656 (Prostaglandin A1)

Structure for HMDB0002656 (Prostaglandin A1)

3D Structure for HMDB0002656 (Prostaglandin A1)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra