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

• ChemBase ID: 170352
• Molecular Formular: C29H48O3
• Molecular Mass: 444.68962
• Monoisotopic Mass: 444.3603454
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)CO)CC[C@]1([C@H]3CCC1[C@@H](CCCC(C)C)C)C)OC(=O)C
• Canonical SMILES: OC[C@]12CC[C@H](CC1=CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2[C@@H](CCCC(C)C)C)C)OC(=O)C
• InChI: InChI=1S/C29H48O3/c1-19(2)7-6-8-20(3)25-11-12-26-24-10-9-22-17-23(32-21(4)31)13-16-29(22,18-30)27(24)14-15-28(25,26)5/h9,19-20,23-27,30H,6-8,10-18H2,1-5H3/t20-,23-,24+,25?,26+,27+,28-,29-/m1/s1
• InChIKey: ZUYKAEVLUWUNMD-FXDZCWCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,10S,11S,15R)-2-(hydroxymethyl)-15-methyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• IUPAC Traditional name: (1S,2S,5R,10S,11S,15R)-2-(hydroxymethyl)-15-methyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• Synonyms: (3β)-Cholest-5-ene-3,19-diol 3-Acetate; 3β-Acetoxycholest-5-en-19-ol; 19-Hydroxycholesterol 3-Acetate; 19-Hydroxycholesterol Acetate; NSC 123342; 19-Hydroxy Cholesteryl 3-Acetate

Database IDs

• CAS Number: 750-59-4
• PubChem SID: 164226262
• PubChem CID: 71748937

CALCULATED PROPERTIES

• Rotatable Bonds: 8
• Lipinski's Rule of Five: false
• Acid pKa: 19.126312
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.273243
• LogD (pH = 7.4): 6.2732434
• Log P: 6.2732434
• Molar Refractivity: 131.5427 cm^3
• Polarizability: 52.377945 Å^3
• Polar Surface Area: 46.53 Å^2

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 121-123°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H918070

A C-19 functionalized cholesterol derivative and popular substrate for steroid biotransformations.

REFERENCES

• Mathai, M., et al.: Steroids, 59, 244 (1994)
• Madyastha, K., et al.: App. Environ. Microbiol., 60, 1500 (1994)