7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
PubChem CID: 149351
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| Compound Synonyms | 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid, Kaishi, Prestwick0_001018, Prestwick1_001018, CBiol_001943, KBioGR_000208, KBioSS_000208, SPBio_003046, SCHEMBL2962928, CHEBI:92915, KBio2_000208, KBio2_002776, KBio2_005344, KBio3_000415, KBio3_000416, GMVPRGQOIOIIMI-DODZYUBVSA-N, Bio1_000229, Bio1_000718, Bio1_001207, Bio2_000208, Bio2_000688, AKOS032960372, PD009728, BRD-K48099440-001-01-7, Q27164659 |
|---|---|
| Topological Polar Surface Area | 94.8 |
| Hydrogen Bond Donor Count | 3.0 |
| Heavy Atom Count | 25.0 |
| Description | Prostaglandin E1 (PGE1) is a potent endogenous vasodilator agent that increases peripheral blood flow. It inhibits platelet aggregation and has many other biological effects such as bronchodilation, mediation of inflammation, and various protective functions. The protective action of PGE1 has been shown on both experimental animal models of liver injury and patients with fulminant viral hepatitis. PGE1-treated cirrhotic rats had less hepatosplenomegaly, lower serum alanine aminotransferase levels, and portal pressures and higher arterial pressure than placebo-treated cirrhotic rats. Mechanisms of hepatic cytopotection of PGE1: inhibitory effects on T-cell mediated cytotoxicity, enhance DNA synthesis of injured liver after partial hepatectomy by stimulating cyclic AMP production and increasing ATP level in hepatic tissue, and could accelerate the recovery of mitochondrial respiratory functio n after reperfusion, stabilization of membrane microviscosity. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). (PMID: 11819590, 16986207) 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 signaling pathways. [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 432.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 4.0 |
| Enzyme Uniprot Id | P16152 |
| Iupac Name | 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid |
| Prediction Hob | 0.0 |
| Class | Fatty Acyls |
| Xlogp | 3.2 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Eicosanoids |
| Molecular Formula | C20H34O5 |
| Prediction Swissadme | 0.0 |
| Inchi Key | GMVPRGQOIOIIMI-DODZYUBVSA-N |
| Fcsp3 | 0.8 |
| Logs | -3.148 |
| Rotatable Bond Count | 13.0 |
| State | Solid |
| Logd | 1.946 |
| Synonyms | (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate, (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid, (-)-Prostaglandin E1, (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate, (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid, (11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate, (11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid, (11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate, (11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid, (11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate, (11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid, (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate, (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoic acid, (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoate, (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoic acid, (13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate, (13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid, (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate, (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acid, (13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoate, (13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acid, 11,15-Dihydroxy-9-oxoprost-13-en-1-oate, 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid, 11,15-dihydroxy-9-oxoprost-13-en-1-oic acid (ACD/Name 4.0), 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate, 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid, 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate, 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid, 11α,15α-dihydroxy-9-oxo-13-trans-prostenoate, 11α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid, 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate, 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid, Alprostadil, Alprostadil Prostoglandin E1, Alprostadil(usan), Alprostadilum, Befar, Befar (TN), Caverject, EDEX, l-Prostaglandin E1, MUSE, PGE-1, PGE1, Prink, Prink (TN), prostaglandin E1, Prostin VR |
| Substituent Name | Prostaglandin skeleton, Long-chain fatty acid, Hydroxy fatty acid, Fatty alcohol, Carbocyclic fatty acid, Cyclopentanol, Cyclic alcohol, Cyclic ketone, Secondary alcohol, Ketone, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Alcohol, Aliphatic homomonocyclic compound |
| Compound Name | 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 354.241 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 354.241 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 354.5 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 4.0 |
| Total Bond Stereocenter Count | 1.0 |
| Esol | -3.1958194 |
| Inchi | InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1 |
| Smiles | CCCCC[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O |
| Nring | 1.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Aleurites Cordata (Plant) Rel Props:Source_db:cmaup_ingredients