15-dehydroprostaglandin A1
Basic information
- CAS
61600-67-7- Standard SMILES
CCCCCC(=O)/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O- InChIKey
YKXHFAJZOFTAOC-DTXSUPOZSA-N- Molecular formula
- C20H30O4
- Average molar mass
- 334.4 g/mol
- Monoisotopic mass
- 334.21440943
Overview
15-dehydroprostaglandin A1 is a member of the class of prostaglandins A obtained by oxidation of the 15-hydroxy group of prostaglandin A1 to the corresponding ketone. It has a role as an Escherichia coli metabolite and a human metabolite. It is functionally related to a prostaglandin A1. It is a conjugate acid of a 15-dehydroprostaglandin A1(1-).
Names & identifiers
- Preferred name
- 15-dehydroprostaglandin A1
- IUPAC
- 7-[(1R,5S)-2-oxo-5-[(E)-3-oxooct-1-enyl]cyclopent-3-en-1-yl]heptanoic acid
- English name
- 15-keto Prostaglandin A1
- Molecular formula
- C20H30O4
- Molecular weight
- 334.45
Names & synonyms
61600-67-715-keto Prostaglandin A115-dehydroprostaglandin A115-Keto-PGA17-[(1R,5S)-2-oxo-5-[(E)-3-oxooct-1-enyl]cyclopent-3-en-1-yl]heptanoic acid(13E)-9,15-dioxoprosta-10,13-dien-1-oic acid15-ketoProstaglandinA1orb1693939CHEBI:85552DTXSID601348005AKOS040755121PD018719
Show more names
15-keto PGA1Prosta-10,13-dien-1-oic acid, 9,15-dioxo-, (13E)- (9CI)
HY-137024CS-0135891T36209Q271586387-((1R,5S)-2-Oxo-5-((E)-3-oxooct-1-en-1-yl)cyclopent-3-en-1-yl)heptanoic acid
Database identifiers
- CAS
61600-67-7- PubChem CID
- 90659869
- DTXSID
DTXSID601348005- ChEBI
CHEBI:85552
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 71.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 13
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 476
Physicochemical properties
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 50 mg/ml; · DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS (pH 7.2): 1 mg/ml
Chemistry & industry
Applications
DescriptionProstaglandin A1 (PGA1) was first isolated as a dehydration product of the PGE1 compounds found in human semen. 15-keto PGA1 is a metabolite of PGA1, produced by 15-hydroxy PG dehydrogenase. It can be produced from PGA1 in pig lung, trachea, aorta, and pulmonary artery tissue preparations. 15-keto PGA1, given at a concentration of 6 μM, causes vasoconstriction of rabbit lung that is comparable to that induced by angiotensin II.
Uses15-keto PGA1 is a metabolite of PGA1 (P838545), produced by 15-hydroxy PG dehydrogenase.
Additional notes
DefinitionChEBI: 15-dehydroprostaglandin A1 is a member of the class of prostaglandins A obtained by oxidation of the 15-hydroxy group of prostaglandin A1 to the corresponding ketone. It has a role as an Escherichia coli metabolite and a human metabolite. It is functionally related to a prostaglandin A1. It is a conjugate acid of a 15-dehydroprostaglandin A1(1-).
Related reactions
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Compound notes
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