(1S,2S,5S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-one

• ChemBase ID: 105367
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: O=C1[C@]2(CC[C@H]3[C@H]([C@@H]2CC1)CC[C@H]1C[C@@H](O)CC[C@]31C)C
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1
• InChIKey: QGXBDMJGAMFCBF-LUJOEAJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one; (1S,2S,5S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
• IUPAC Traditional name: aetiocholanolone
• Synonyms: (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one; 3β-Hydroxy-5α-androstan-17-one; 3β-Hydroxyetioallocholan-17-one; 5α-Androstan-3β-ol-17-one; Epi-androsterone; trans-Androsterone; (3β,5α)-3-Ηydroxyandrostan-17-one; 3-Epiandrosterone; 3β-Androsterone; 3β-Hydroxy-17-oxo-5α-androstane; NSC 93996; d-Epiandrosterone; iso-Androsterone; 5α-Androstan-3β-ol-17-one; Isoandrosterone; trans-Androsterone; 3β-Hydroxyetioallocholan-17-one; 3β-Hydroxy-5α-androstan-17-one; EPIANDROSTERONE

Database IDs

• CAS Number: 481-29-8
• EC Number: 207-563-3
• MDL Number: MFCD00064134
• Beilstein Number: 1884007
• PubChem SID: 24894509; 162093595; 24846613
• PubChem CID: 441302

CALCULATED PROPERTIES

• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.7672846
• LogD (pH = 7.4): 3.7672846
• Log P: 3.7672846
• Molar Refractivity: 83.8089 cm^3
• Polarizability: 33.49998 Å^3

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 172-174 °C; 173-174°C
• Optical Rotation: [α]20/D +95±5°, c = 1% in methanol

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: human ... HSD17B3(3293)

Product Information

• Purity: ≥97.0% (TLC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C19H30O2

DETAILS

MP Biomedicals - 02159923

Crystalline

Sigma Aldrich - 10360

Other Notes
Sales restrictions may apply

Toronto Research Chemicals - E578000

A steroid hormone that is present in normal human urine as a minor constituent , it is a less active 3β-isomer of the androgen Androsterone (A635535). Controlled Substance.

REFERENCES

• Marchand, M., et al.: Eur. J. Biochem., 184, 455 (1989)
• Dardonville, C., et al.: Bioorg. Med. Chem., 11, 3205 (1989)
• Fumarola, L., et al.: Res. Microbiol., 155, 224 (1989)
• Albert, M., et al.: J. Biol. Chem., 280, 28306 (1989)