(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

• ChemBase ID: 109423
• Molecular Formular: C19H32O2
• Molecular Mass: 292.45618
• Monoisotopic Mass: 292.24023026
• SMILES: O[C@@H]1CC[C@]2([C@@H](CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@H]23)C1)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: CBMYJHIOYJEBSB-KHOSGYARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol; (1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: 5α-androstane-3α,17β-diol
• Synonyms: ANDROSTAN-3α, 17β-DIOL; Hombreol; 3α-Androstanediol; 5α-Androstane-3α,17β-diol; ANDROSTAN-3β, 17β-DIOL; 3α,17β-二羟基-5α-雄甾烷; 二氢雄甾酮; 5α-雄甾烷-3α,17β-二醇

Database IDs

• CAS Number: 1852-53-5
• EC Number: 217-447-4
• MDL Number: MFCD00003676
• PubChem SID: 24278236; 162094822
• PubChem CID: 15818
• Chemspider ID: 15039
• Wikipedia Title: 3α-Androstanediol

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.2037566
• LogD (pH = 7.4): 3.2037568
• Log P: 3.2037568
• Molar Refractivity: 84.6312 cm^3
• Polarizability: 34.047752 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: BV8044310
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

DETAILS

MP Biomedicals - 05214000

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05211000

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A7755

Biochem/physiol Actions
Dihydroandrosterone is a testosterone metabolite; affects sperm maturation and survival.
Application
5α-Androstane-3α,17β-diol (dihydroandrosterone) is a testosterone metabolite. Dihyroandrosterone inhibited the cell growth of seven cancer cell lines while showing weak toxicity on normal cell lines.