1.0 2016-09-30 22:48:00 UTC 2020-06-04 20:42:59 UTC BMDB0001830 BMDB01830 Progesterone Progesterone, also known as gesterol or corlutin, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, progesterone is considered to be a steroid lipid molecule. Progesterone is a drug which is used for progesterone supplementation or replacement as part of an assisted reproductive technology (art) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. also used for the reduction of the incidence of endometrial hyperplasia and the attendant risk of endometrial carcinoma in postmenopausal women receiving estrogen replacement therapy, as well as treatment of abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology such as fibroids or uterine cancer. Progesterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Progesterone exists in all living organisms, ranging from bacteria to humans. Progesterone participates in a number of enzymatic reactions, within cattle. In particular, Progesterone can be converted into deoxycorticosterone; which is mediated by the enzyme steroid 21-hydroxylase. In addition, Progesterone can be biosynthesized from pregnenolone; which is mediated by the enzyme 3-beta-HSD 1. In cattle, progesterone is involved in the metabolic pathway called the steroidogenesis pathway. Progesterone is a potentially toxic compound. (S)-4-Pregnene-3,20-dione (S)-Pregn-4-en-3,20-dione (S)-Progesterone 17alpha-Progesterone 4-Pregnene-3,20-dione Agolutin Akrolutin Corpus luteum hormone Crinone Delta(4)-Pregnene-3,20-dione Gelbkoerperhormon Luteohormone Progesteron Prometrium 17a-Progesterone 17Α-progesterone Δ(4)-pregnene-3,20-dione 3,20-Pregnene-4 4-Pregnen-3,20-dione beta-Progesterone Bio-luton CIDR Colprosterone Corlutin Corlutina Corluvite Corporin Crinone progesterone gel Curretab Cyclogest Cyclogesterin D4-Pregnene-3,20-dione Delalutin Duraprogen Estima Flavolutan Fologenon Gesterol Gesterol 100 Gesterol 50 Gestiron Gestone Gestormone Gestron Glanducorpin Gynlutin Gynoluton Gynolutone Hormoflaveine Hormoluton Hydroxyprogesterone caproate Hydroxyprogesterone caproic acid Lingusorbs Lipo-lutin Lucorteum Lucorteum sol Lugesteron Luteal hormone Luteocrin normale Luteodyn Luteogan Luteol Luteopur Luteosan Luteostab Luteovis Luteum Lutex Lutidon Lutociclina Lutocuclin m Lutocyclin Lutocyclin m Lutocylin Lutocylol Lutoform Lutogyl Lutren Lutromone Membrettes Methylpregnone MPA Nalutron Percutacrine Percutacrine luteinique Piaponon Pranone Pregn-4-en-3,20-dione Pregn-4-ene-3,20-dione Pregnene-3,20-dione Pregnenedione Primolut Prochieve Progeffik Progekan Progestan Progestasert Progesterol Progesteronum Progestin Progestogel Progestol Progeston Progestone Progestosol Progestron Progestronol Projestaject Prolets Prolidon Prolutin Proluton Prolutone Prontogest Protormone Syngesterone Syngestrets Synovex S Syntolutan Utrogest Utrogestan Vitarrine Progesterone, (13 alpha,17 alpha)-(+-)-isomer Progesterone, (17 alpha)-isomer Progesterone, (9 beta,10 alpha)-isomer C21H30O2 314.4617 314.224580204 (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 57-83-0 [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 RJKFOVLPORLFTN-LEKSSAKUSA-N belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Pregnane steroids Gluco/mineralocorticoids, progestogins and derivatives 20-oxosteroids 3-oxo delta-4-steroids Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides 20-oxosteroid 3-oxo-delta-4-steroid 3-oxosteroid Aliphatic homopolycyclic compound Carbonyl group Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Aliphatic homopolycyclic compounds 20-oxo steroid 3-oxo Delta(4)-steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives C21-steroid hormone Pregnane and derivatives [Fig] Progestagens Solid melting_point 121 °C water_solubility 0.00881 mg/mL at 25 °C YALKOWSKY,SH & DANNENFELSER,RM (1992) logp 3.87 HANSCH,C ET AL. (1995) logp 3.58 ALOGPS logs -4.76 ALOGPS logp 4.15 ChemAxon pka_strongest_acidic 18.92 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 314.4617 ChemAxon mono_mass 314.224580204 ChemAxon smiles [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 ChemAxon inchikey RJKFOVLPORLFTN-LEKSSAKUSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 92.71 ChemAxon polarizability 37.26 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Steroidogenesis SMP0087238 Specdb::NmrTwoD 1686 Specdb::MsMs 1684 Specdb::MsMs 1685 Specdb::MsMs 1686 Specdb::MsMs 5444 Specdb::MsMs 5445 Specdb::MsMs 258768 Specdb::MsMs 258769 Specdb::MsMs 258770 Specdb::MsMs 278706 Specdb::MsMs 278707 Specdb::MsMs 278708 Specdb::MsMs 374461 Specdb::MsMs 374700 Specdb::MsMs 374962 Specdb::MsMs 440850 Specdb::MsMs 440851 Specdb::MsMs 440852 Specdb::MsMs 440853 Specdb::MsMs 440854 Specdb::MsMs 440855 Specdb::MsMs 444006 Specdb::MsMs 444007 Specdb::MsMs 444008 Specdb::MsMs 444009 Specdb::MsMs 444010 Specdb::CMs 2212 Specdb::CMs 2217 Specdb::CMs 22446 Specdb::CMs 27515 Specdb::CMs 28722 Specdb::CMs 29898 Specdb::CMs 31351 Specdb::CMs 31352 Specdb::CMs 31900 Specdb::CMs 153226 Specdb::EiMs 469 Specdb::NmrOneD 1746 Specdb::NmrOneD 2490 Specdb::NmrOneD 3186 Adipose Tissue 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 Blood 0.0922 uM Detected by HPLC-MS/MS in Holstein cows. Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21. 21172370 Blood 0.000594 uM Detected by HPLC-MS/MS Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21. 21172370 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 Milk 0.0541 - 0.143 uM Raw milk. range during estrous cycle Narendran R, Hacker RR, Smith VG, Lun A: Estrogen and progesterone concentrations in bovine milk during the estrous cycle. Theriogenology. 1979 Jul;12(1):19-25. 16725427 Milk 0.0312 uM Raw whole milk Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. 18214159 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 Ovary 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 Prostate Tissue 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 Testis 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 C00410 DB00396 FDB001871 5994 5773 17026 PROGESTERONE C00034649 34898 Progesterone 402 Vasquez, L.; Alarcon, J.; Zunza, H.; Becerra, J.; Silva, M. Chemical-microbiological synthesis of progesterone. Boletin de la Sociedad Chilena de Quimica (2001), 46(1), 29-31. Narendran R, Hacker RR, Smith VG, Lun A: Estrogen and progesterone concentrations in bovine milk during the estrous cycle. Theriogenology. 1979 Jul;12(1):19-25. 16725427 Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. 18214159 BMDBP00010 Cytochrome P450 11B1, mitochondrial P15150 CYP11B1 Enzyme BMDBP00040 Steroid 17-alpha-hydroxylase/17,20 lyase P05185 CYP17A1 Enzyme BMDBP00060 Steroid 21-hydroxylase P00191 CYP21 Enzyme BMDBP00551 Prostaglandin E synthase 3 Q3ZBF7 PTGES3 Enzyme BMDBP01473 Membrane-associated progesterone receptor component 1 Q17QC0 PGRMC1 Enzyme BMDBP01624 Progesterone receptor O18972 Enzyme BMDBP01625 Progesterone receptor Q8MIL9 Enzyme BMDBP01626 Progestin and adipoQ receptor family member 6 Q2KHW1 PAQR6 Enzyme BMDBP01627 Progesterone receptor Q690N0 PGR Enzyme BMDBP01628 Progestin and adipoQ receptor family member 9 Q0II88 PAQR9 Enzyme BMDBP01629 Prostaglandin F2-alpha receptor P37289 PTGFR Enzyme BMDBP01630 Progesterone receptor Q863K6 pr Enzyme BMDBP01631 Transforming growth factor beta-1-induced transcript 1 protein Q3MHZ4 TGFB1I1 Enzyme BMDBP01632 Progestin and adipoQ receptor family member 7 Q2T9S9 PAQR7 Enzyme