pentarane A

{{Short description|Chemical compound}}

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| IUPAC_name = (4aR,4bS,6aS,6bS,10aR,11aS,11bR)-6b-Acetyl-4a,6a-dimethyl-4,4b,5,6,7,8,9,10,10a,11,11a,11b,12,13-tetradecahydro-3H-indeno[2,1-a]phenanthren-2-one

| image = Pentarane A.svg

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| CAS_number = 38522-51-9

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| PubChem = 189105

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| ChemSpiderID = 164309

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| UNII = UMG87A58PN

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| C=25 | H=36 | O=2

| SMILES = CC(=O)[C@@]12CCCC[C@@H]1C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C

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| StdInChI = 1S/C25H36O2/c1-16(26)25-11-5-4-6-18(25)15-22-20-8-7-17-14-19(27)9-12-23(17,2)21(20)10-13-24(22,25)3/h14,18,20-22H,4-13,15H2,1-3H3/t18-,20-,21+,22+,23+,24+,25+/m1/s1

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| StdInChIKey = QRVBGQLTPQQFJY-IEHCJHDVSA-N

| synonyms = D'6-Pentarane; Pregna-D'6-pentarane; 16α,17α-Cyclohexanoprogesterone; 16α,17α-Tetramethylenepregn-4-ene-3,20-dione; 17α-Acetyl-16β,24-cyclo-21-norchol-4-en-3-one

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Pentarane A, also known as D'6-pentarane or pregna-D'6-pentarane, as well as 16α,17α-cyclohexanoprogesterone, 16α,17α-tetramethylenepregn-4-ene-3,20-dione, or 17α-acetyl-16β,24-cyclo-21-norchol-4-en-3-one, is a steroidal progestin that was developed by the Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences and was never marketed.{{cite journal | vauthors = Kamernitzky AV, Levina IS, Kulikova LE, Ignatov VN, Korkhov VV, Nikitina GV, Terekhina AI | title = Pregna-D'-pentaranes - a new class of active gestagenes | journal = Journal of Steroid Biochemistry | volume = 16 | issue = 1 | pages = 61–67 | date = January 1982 | pmid = 7062740 | doi = 10.1016/0022-4731(82)90144-3 }}{{cite journal | vauthors = Bhakta A, Herman M, Levina IS, Moudgil VK | title = Interaction of cycloalkanoprogesterones with mammalian progesterone receptor: binding of pregna-D'-pentaranes in the calf uterine cytosol | journal = Molecular and Cellular Biochemistry | volume = 125 | issue = 2 | pages = 153–161 | date = August 1993 | pmid = 8283970 | doi = 10.1007/BF00936444 | s2cid = 20319611 }} The 6α-methylated analogue of pentarane A is known as mecigestone or as pentarane B.