(1S,2S,5S,7S,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol

• ChemBase ID: 153145
• Molecular Formular: C19H32O
• Molecular Mass: 276.45678
• Monoisotopic Mass: 276.24531564
• SMILES: C[C@@]12CCC[C@H]1[C@@H]1CC[C@H]3C[C@H](CC[C@@]3([C@H]1CC2)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2)C)C
• InChI: InChI=1S/C19H32O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h13-17,20H,3-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: DJTOLSNIKJIDFF-LOVVWNRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,7S,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• IUPAC Traditional name: 5a-androstan-3b-ol
• Synonyms: (3β,5α)-Androstan-3-ol; NSC 50887; 5α-Androstan-3β-ol; 3β-Hydroxy-5α-androstane; 5α-Androstan-3β-ol

Database IDs

• CAS Number: 1224-92-6
• EC Number: 214-952-1
• MDL Number: MFCD00067608
• PubChem SID: 162247285
• PubChem CID: 92877

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.434568
• LogD (pH = 7.4): 4.434568
• Log P: 4.434568
• Molar Refractivity: 83.1157 cm^3
• Polarizability: 33.44575 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble14 mg/mL at ≤60 °C; H2O: insoluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C19H32O

DETAILS

Sigma Aldrich - A2480

Biochem/physiol Actions
mCAR (constitutive androstane receptor) inverse agonist; testosterone metabolite.

Toronto Research Chemicals - A637360

An Androstane metabolite.

REFERENCES

• Weusten, J., et al.: J. Steroid Biochem., 32, 689 (1989)
• Choi, H., et al.: J. Biol. Chem., 272, 23565 (1989)