(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-one

• ChemBase ID: 140159
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CCC(=O)C2)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CCC(=O)C2)C)C
• InChI: InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: GGCLNOIGPMGLDB-GYKMGIIDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-one
• IUPAC Traditional name: oxidized cholesterol
• Synonyms: 3-Keto-5-cholestene; 5-Cholesten-3-one; Cholest-5-en-3-one; Δ5-Cholesten-3-one; 3-Oxocholest-5-ene; 5-Cholestenone; NSC 118979; 3-Keto Cholesterol; 胆甾-5-烯-3-酮; 5-胆甾烯-3-酮

Database IDs

• CAS Number: 601-54-7
• EC Number: 210-004-6
• MDL Number: MFCD00009940
• PubChem SID: 162234403; 24892964
• PubChem CID: 9908107

CALCULATED PROPERTIES

• Acid pKa: 16.227856
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.3203897
• LogD (pH = 7.4): 7.3203897
• Log P: 7.3203897
• Molar Refractivity: 119.5884 cm^3
• Polarizability: 47.426888 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 104-106°C; 125-127 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C27H44O

DETAILS

Sigma Aldrich - C75004

Packaging
500 mg in glass bottle

Toronto Research Chemicals - K185030

A metabolite of Cholesterol.

REFERENCES

• Kieslich, K., et al.: J. Basic. Microbiol., 25, 461 (1985)
• Wakeham, S., et al.: Nature, 342, 787 (1985)
• Pollegioni, L., et al.: Eur. J. Biochem., 264, 140 (1985)
• Kniemeyer, O., et al.: J. Biol. Chem., 276, 21381 (1985)