(1S,2R,5S,9S,10S,11S,15R)-2,15-dimethyl-14-[(2R)-6-(2H3)methyl(6,7,7,7-2H4)heptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5,9-diol

• ChemBase ID: 170345
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• SMILES: C1[C@@H](CC2=C[C@H]([C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1[C@@H](CCCC(C)C)C)C)O)O
• Canonical SMILES: CC(CCC[C@H](C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](O)C=C2[C@]1(C)CC[C@@H](C2)O)C)C
• InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21?,22+,23+,24-,25+,26+,27-/m1/s1
• InChIKey: OYXZMSRRJOYLLO-OCFRJRHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,9S,10S,11S,15R)-2,15-dimethyl-14-[(2R)-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5,9-diol
• IUPAC Traditional name: (1S,2R,5S,9S,10S,11S,15R)-2,15-dimethyl-14-[(2R)-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5,9-diol
• Synonyms: (3β,7α)-Cholest-5-ene-3,7-diol-d7; 7α-Hydroxycholest-5-en-3βol-d7; 7α-Hydroxy Cholesterol-d7

Database IDs

• PubChem SID: 164226255
• PubChem CID: 71748932

CALCULATED PROPERTIES

• Acid pKa: 18.204233
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.9600315
• LogD (pH = 7.4): 5.9600315
• Log P: 5.9600315
• Molar Refractivity: 122.055 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 174-178°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H917992

Secondary metabolite of Cholesterol. A representative lot was: 84%d7; 14% d6; 1% d5 with no detectable d0.

REFERENCES

• Notaro, G., et al.: J. Nat. Prod., 55, 1588 (1992)
• Aydogmus, Z., et al.: Nat. Prod. Res., 18, 43 (1992)
• Mao, S., et al.: J. Nat. Prod ., 69, 1209 (1992)
• Shoji, T., et al.: J. Agric. Food Chem., 54, 884 (1992)