progesterone   Click here for help

GtoPdb Ligand ID: 2377

Synonyms: Prometrium® | Utrogestan®
Approved drug PDB Ligand
progesterone is an approved drug (FDA (1959))
Compound class: Metabolite
Comment: Progesterone is an endogenous steroid and progestogen sex hormone. It is the major progestogen and is required for the production of other endogenous steroids, including the sex hormones and corticosteroids.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 34.14
Molecular weight 314.22
XLogP 4.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1CCC2(C(=C1)CCC1C2CCC2(C1CCC2C(=O)C)C)C
Isomeric SMILES O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
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
InChI Key RJKFOVLPORLFTN-LEKSSAKUSA-N
References
1. Edwards JP, Zhi L, Pooley CL, Tegley CM, West SJ, Wang MW, Gottardis MM, Pathirana C, Schrader WT, Jones TK. (1998)
Preparation, resolution, and biological evaluation of 5-aryl-1, 2-dihydro-5H-chromeno[3,4-f]quinolines: potent, orally active, nonsteroidal progesterone receptor agonists.
J Med Chem, 41 (15): 2779-85. [PMID:9667968]
2. Lishko PV, Botchkina IL, Kirichok Y. (2011)
Progesterone activates the principal Ca2+ channel of human sperm.
Nature, 471 (7338): 387-91. [PMID:21412339]
3. Majeed Y, Amer MS, Agarwal AK, McKeown L, Porter KE, O'Regan DJ, Naylor J, Fishwick CW, Muraki K, Beech DJ. (2011)
Stereo-selective inhibition of transient receptor potential TRPC5 cation channels by neuroactive steroids.
Br J Pharmacol, 162 (7): 1509-20. [PMID:21108630]
4. Maksay G, Laube B, Betz H. (2001)
Subunit-specific modulation of glycine receptors by neurosteroids.
Neuropharmacology, 41 (3): 369-76. [PMID:11522328]
5. Rupprecht R, Reul JM, van Steensel B, Spengler D, Söder M, Berning B, Holsboer F, Damm K. (1993)
Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands.
Eur J Pharmacol, 247 (2): 145-54. [PMID:8282004]
6. Strünker T, Goodwin N, Brenker C, Kashikar ND, Weyand I, Seifert R, Kaupp UB. (2011)
The CatSper channel mediates progesterone-induced Ca2+ influx in human sperm.
Nature, 471 (7338): 382-6. [PMID:21412338]
7. Zhi L, Tegley CM, Kallel EA, Marschke KB, Mais DE, Gottardis MM, Jones TK. (1998)
5-Aryl-1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal human progesterone receptor agonists.
J Med Chem, 41 (3): 291-302. [PMID:9464360]