1.0 2016-09-30 22:46:02 UTC 2020-05-11 20:44:46 UTC BMDB0001442 BMDB01442 Prostaglandin E1 (11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid Alprostadil Alprostadilum Befar Caverject Edex Muse PGE-1 PGE1 Prostin VR Prostin VR pediatric (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 (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)-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-enoic acid (13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate (13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid 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 11Α,15α-dihydroxy-9-oxo-13-trans-prostenoate 11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid Abbott brand OF alprostadil Minprog Paladin brand OF alprostadil Prostaglandin e1alpha Schwarz pharma brand OF alprostadil Astra brand OF alprostadil Hoyer brand OF alprostadil Sugiran Allphar brand OF alprostadil AstraZeneca brand OF alprostadil lipo PGE1 Viridal lipo-PGE1 Vasaprostan Janssen brand OF alprostadil PGE1alpha Pharmacia brand 1 OF alprostadil Prostavasin Prostine VR Pharmacia brand 2 OF alprostadil Prostaglandin e1 Schwarz brand OF alprostadil Vivus brand OF alprostadil Prink Vitaros Caverject impulse U-10136prostin U-10136alprostadil (+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate (+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid (-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate (-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid (-)-Prostaglandin e1 (13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate (13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid (13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate (13E)-(15S)-11-alpha,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) 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid Alprostadil prostoglandin e1 Alprostadil(usan) L-Prostaglandin e1 C20H34O5 354.487 354.240624195 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid alprostadil 745-65-3 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O 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)/b13-12+/t15-,16+,17+,19+/m0/s1 GMVPRGQOIOIIMI-DWKJAMRDSA-N 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. Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Prostaglandins and related compounds Carboxylic acids Cyclic alcohols and derivatives Cyclic ketones Cyclopentanols Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty alcohol Hydrocarbon derivative Hydroxy fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Aliphatic homomonocyclic compounds Prostaglandins Prostaglandins prostaglandins E Solid logp 3.59 ChemAxon pka_strongest_acidic 4.35 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid ChemAxon average_mass 354.487 ChemAxon mono_mass 354.240624195 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O ChemAxon formula C20H34O5 ChemAxon 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)/b13-12+/t15-,16+,17+,19+/m0/s1 ChemAxon inchikey GMVPRGQOIOIIMI-DWKJAMRDSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 98.32 ChemAxon polarizability 42.13 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 150409 Specdb::MsMs 50532 Specdb::MsMs 50533 Specdb::MsMs 50534 Specdb::MsMs 145797 Specdb::MsMs 145798 Specdb::MsMs 145799 Specdb::MsMs 2245518 Specdb::MsMs 2375753 Specdb::MsMs 2375754 Specdb::MsMs 2375755 Specdb::MsMs 2559996 Specdb::MsMs 2559997 Specdb::MsMs 2559998 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C04741 4444306 5280723 15544 Prostaglandin_E1 Liang, Yong-tao; Wei, Feng-ping; Li, Gui-ying; Wang, En-si. Chemoenzymic synthesis of prostaglandin E1. Jilin Daxue Ziran Kexue Xuebao (2001), (2), 77-80.