(1S,2R,3S,5R,11R,12S,15R,16S)-15-[(1,2-13C2,2H3)acetyl]-9-chloro-15-hydroxy-2-(2H3)methyl-16-methyl(5,7-2H2)pentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one

• ChemBase ID: 165314
• Molecular Formular: C22H27ClO3
• Molecular Mass: 376.88628968
• Monoisotopic Mass: 376.17158208
• SMILES: [C@H]12[C@H](C(=O)C=C3[C@@]1([C@@H]1[C@@H](C=C3Cl)[C@H]3[C@](CC1)([C@@](CC3)(O)[13C](=O)[13CH3])C)C)C2
• Canonical SMILES: O=C1C=C2C(=C[C@@H]3[C@@H]([C@@]2([C@@H]2[C@H]1C2)C)CC[C@]1([C@H]3CC[C@]1(O)[13C](=O)[13CH3])C)Cl
• InChI: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13?,14-,15-,16-,20-,21+,22-/m0/s1/i1+1,11+1
• InChIKey: DUSHUSLJJMDGTE-PEVATUOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3S,5R,11R,12S,15R,16S)-15-[(1,2-^1^3C₂,^2H₃)acetyl]-9-chloro-15-hydroxy-2-(^2H₃)methyl-16-methyl(5,7-^2H₂)pentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-6-one
• IUPAC Traditional name: (1S,2R,3S,5R,11R,12S,15R,16S)-15-[(1,2-^1^3C₂,^2H₃)acetyl]-9-chloro-15-hydroxy-2-(^2H₃)methyl-16-methyl(5,7-^2H₂)pentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-6-one
• Synonyms: 6-Chloro-6-dehydro-17α-hydroxy-1,2α-methyleneprogesterone-13C2,d8; 6-Chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione-13C2,d8; 1,2α-Methylene-6-chloro-6-17α-hydroxyprogesterone-13C2,d8; (1β,2β)-6-Chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione-13C2,d8; Cyproterone-13C2,d8

Database IDs

• PubChem SID: 162259447
• PubChem CID: 71315141

CALCULATED PROPERTIES

• Acid pKa: 12.6991005
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1977315
• LogD (pH = 7.4): 3.1977293
• Log P: 3.1977315
• Molar Refractivity: 102.658 cm^3
• Polarizability: 39.72794 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C989093

Labelled Cyproterone (C989090). An antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsex

REFERENCES

• Gracia, T., et al.: Toxicol. App. Pharmacol., 225, 142 (2007)
• Ahlin, G., et al.: J. Med. Chem., 51, 5932 (2007)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2007)
• Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2007)