1.0 2016-09-30 22:42:44 UTC 2020-05-21 16:28:39 UTC BMDB0001220 BMDB01220 Prostaglandin E2 Prostaglandin e2, also known as dinoprostone or PGE2, 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 E2 is considered to be an eicosanoid lipid molecule. Prostaglandin e2 is a drug which is used for the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage. Prostaglandin e2 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Prostaglandin e2 exists in all living organisms, ranging from bacteria to humans. (15S)-Prostaglandin e2 (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate (e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid (Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid Dinoproston Dinoprostona Dinoprostone Dinoprostonum PGE2 Prepidil Propess Prostin e2 Cervidil (5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate (5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate (5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oate (5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid (5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate (5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid (5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate (5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid (5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoate (5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid (5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoate (5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid (e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate (Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate (-)-Prostaglandin e2 (5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoate (5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acid 5-trans-PGE2 Glandin L-Prostaglandin e2 Minprositin e2 Minprostin e2 Prostaglandin e Prostaglandin e2alpha Prostarmon e Prostin e2, Prostaglandin Prepidil gel alpha, Prostaglandin e2 e2 alpha, Prostaglandin e2alpha, Prostaglandin alpha, PGE2 Prostenon Gel, prepidil PGE2 alpha PGE2alpha Prostaglandin e2 alpha C20H32O5 352.4651 352.224974134 (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid dinoprostone 363-24-6 CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 XEYBRNLFEZDVAW-ARSRFYASSA-N This compound 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 Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty acid 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 Unsaturated fatty acid Aliphatic homomonocyclic compounds Prostaglandins Prostaglandins prostaglandins E Solid melting_point 67 °C logp 2.82 HANSCH,C ET AL. (1995) logp 3.31 ALOGPS logs -3.90 ALOGPS logp 3.23 ChemAxon pka_strongest_acidic 4.3 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid ChemAxon average_mass 352.4651 ChemAxon mono_mass 352.224974134 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O ChemAxon formula C20H32O5 ChemAxon inchi InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 ChemAxon inchikey XEYBRNLFEZDVAW-ARSRFYASSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 99.44 ChemAxon polarizability 41 ChemAxon rotatable_bond_count 12 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 Arachidonic Acid Metabolism SMP0087220 Succinate Signalling During Inflammation SMP0120886 Specdb::NmrTwoD 1605 Specdb::MsMs 6304 Specdb::MsMs 6305 Specdb::MsMs 6306 Specdb::MsMs 6307 Specdb::MsMs 6308 Specdb::MsMs 6309 Specdb::MsMs 6310 Specdb::MsMs 6311 Specdb::MsMs 6312 Specdb::MsMs 258636 Specdb::MsMs 258637 Specdb::MsMs 258638 Specdb::MsMs 278574 Specdb::MsMs 278575 Specdb::MsMs 278576 Specdb::MsMs 435539 Specdb::MsMs 435540 Specdb::MsMs 435541 Specdb::MsMs 435542 Specdb::MsMs 435543 Specdb::MsMs 435544 Specdb::MsMs 435545 Specdb::MsMs 435546 Specdb::MsMs 435547 Specdb::MsMs 440666 Specdb::CMs 2128 Specdb::CMs 14843 Specdb::CMs 31295 Specdb::CMs 37981 Specdb::CMs 130882 Specdb::CMs 138616 Specdb::NmrOneD 1664 Brain 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 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 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Raw milk, by GC-TOF/MS Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 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 Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 C00584 DB00917 4444059 FDB022498 15551 5280360 5Z13E-15S-1115-DIHYDROXY-9-OXOPROS Prostaglandin_E2 35424 6089 Corey, Elias J.; Weinshenker, Ned M.; Schaaf, Thomas K.; Huber, Willy. Stereo-controlled synthesis of dl-prostaglandins F2a and E2. Journal of the American Chemical Society (1969), 91(20), 5675-7. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. 29197344 BMDBP00528 15-hydroxyprostaglandin dehydrogenase [NAD(+)] Q309F3 HPGD Enzyme BMDBP00602 Carbonyl reductase [NADPH] 1 Q3SZD7 CBR1 Enzyme BMDBP01608 Prostaglandin E2 receptor EP4 subtype Q8MJ08 PTGER4 Enzyme BMDBP01609 Prostaglandin E receptor 4, subtype EP4 Q1JPJ5 PTGER4 Enzyme BMDBP01610 Prostaglandin E2 receptor EP3 subtype P34979 PTGER3 Enzyme BMDBP01611 EP2 receptor Q8MJ09 Enzyme BMDBP01612 Prostaglandin E2 receptor EP1 Q95M52 ep1 Enzyme BMDBP01613 Prostaglandin E2 receptor EP4 Q95M50 ep4 Enzyme BMDBP01614 Prostaglandin E2 receptor EP2 Q95M51 ep2 Enzyme BMDBP03190 Prostaglandin E synthase Q95L14 PTGES Enzyme