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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:10:56 UTC

Update Date

2022-09-22 18:34:45 UTC

HMDB ID

HMDB0341285

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid

Description

Prostaglandin A3, also known as PGA3, 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. Thus, prostaglandin A3 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Prostaglandin A3.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309092222492D          

 33 33  0  0  1  0            999 V2000
   -2.0820   -2.2658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -1.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236   -0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -1.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -1.7559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -0.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -0.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3412   -0.9489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4434   -0.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    1.2171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865    0.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    0.3679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    1.7269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5991    1.2078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185    3.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254    2.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    3.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4036    2.5118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462    0.0927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7130    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

  Mrv1652309092222492D          

 33 33  0  0  1  0            999 V2000
   -2.0820   -2.2658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -1.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236   -0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -1.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -1.7559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -0.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -0.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3412   -0.9489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4434   -0.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    1.2171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865    0.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    0.3679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    1.7269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5991    1.2078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185    3.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254    2.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    3.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4036    2.5118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462    0.0927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7130    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341285

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/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/h3-4,6-7,12-18,21H,2,5,8-11H2,1H3,(H,23,24)/b6-3-,7-4-,14-12+/t16-,17-,18+/m0/s1

> <INCHI_KEY>
KSIRMUMXJFWKAC-FHJHOUOTSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.61571757489038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2S)-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid

> <JCHEM_LOGP>
4.0140293069999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.65885057015222

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.402034708903253

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6356715565721287

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
100.20649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin A3

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0      -3.886  -4.229   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -3.566  -2.723   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.711  -1.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.175  -2.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.102  -2.247   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      -0.957  -3.278   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0      -1.781  -0.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.317  -0.265   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -0.637  -1.771   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0       0.828  -1.295   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.003   1.241   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -1.141   2.272   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       1.468   1.717   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.612   0.687   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.788   3.224   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.985   2.254   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       0.758   4.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.528   5.702   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.034   5.382   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.179   6.412   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.195   3.850   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       4.487   4.689   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       4.529   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.529   1.540   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       3.820   0.173   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       5.862   0.770   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       5.862  -0.770   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       7.196   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.530   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.863   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.197   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.531   1.540   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.197  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PGA3	ChEBI

Chemical Formula

C₂₀H₂₈O₄

Average Molecular Weight

332.44

Monoisotopic Molecular Weight

332.198759382

IUPAC Name

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

Traditional Name

prostaglandin A3

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H28O4/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/h3-4,6-7,12-18,21H,2,5,8-11H2,1H3,(H,23,24)/b6-3-,7-4-,14-12+/t16-,17-,18+/m0/s1

InChI Key

KSIRMUMXJFWKAC-FHJHOUOTSA-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 (LMFA03010140 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.01	ChemAxon
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	11	ChemAxon
Refractivity	100.21 m³·mol⁻¹	ChemAxon
Polarizability	37.62 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 Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4446236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283112

PDB ID

Not Available

ChEBI ID

134510

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for 9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid (HMDB0341285)

MOL for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

3D MOL for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

3D SDF for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

3D-SDF for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

PDB for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

3D PDB for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

SMILES for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

INCHI for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

Structure for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

3D Structure for HMDB0341285 (9-Oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid)

Predicted Kovats Retention Indices