(1S,2R,6R,8S,11S,12S,15S,16S)-4-isocyano-2,6,15,16-tetramethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-5,15-diol

• ChemBase ID: 168106
• Molecular Formular: C22H31NO3
• Molecular Mass: 357.48644
• Monoisotopic Mass: 357.23039386
• SMILES: C1(=C([C@@]2([C@]3([C@](C1)([C@@H]1[C@@H](CC3)[C@H]3[C@](CC1)([C@](CC3)(O)C)C)C)O2)C)O)[N+]#[C-]
• Canonical SMILES: [C-]#[N+]C1=C(O)[C@@]2([C@]3([C@@](C1)(C)[C@H]1CC[C@]4([C@H]([C@@H]1CC3)CC[C@]4(C)O)C)O2)C
• InChI: InChI=1S/C22H31NO3/c1-18-9-7-15-13(14(18)8-10-20(18,3)25)6-11-22-19(15,2)12-16(23-5)17(24)21(22,4)26-22/h13-15,24-25H,6-12H2,1-4H3/t13-,14-,15-,18-,19+,20-,21+,22-/m0/s1
• InChIKey: QBEXHJRIQYMCMI-KMMJEOBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6R,8S,11S,12S,15S,16S)-4-isocyano-2,6,15,16-tetramethyl-7-oxapentacyclo[9.7.0.0^2,^8.0^6,^8.0^1^2,^1^6]octadec-4-ene-5,15-diol
• IUPAC Traditional name: (1S,2R,6R,8S,11S,12S,15S,16S)-4-isocyano-2,6,15,16-tetramethyl-7-oxapentacyclo[9.7.0.0^2,^8.0^6,^8.0^1^2,^1^6]octadec-4-ene-5,15-diol
• Synonyms: (4α,5α,17β)-4,5-Epoxy-3,17-dihydroxy-4,17-dimethylandrost-2-ene-2-carbonitrile; Win 32729; Epostane

Database IDs

• CAS Number: 80471-63-2
• PubChem SID: 162262238
• PubChem CID: 46781475

CALCULATED PROPERTIES

• Acid pKa: 0.42743537
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.1133645
• LogD (pH = 7.4): -3.1239486
• Log P: 0.13619538
• Molar Refractivity: 109.7691 cm^3
• Polarizability: 39.62196 Å^3
• Polar Surface Area: 57.35 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; Pyridine
• Apperance: White to Off-White Solid
• Melting Point: 98-102°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E588850

3β-Hydroxysteroid dehydrogenase inhibitor; a derivative of trilostane. Interceptive.

REFERENCES

• Creange, J.E., et al.: Contraception, 24, 289 (1981)
• Christiansen, R.G., et al.: J. Med. Chem., 27, 928 (1981)
• Han, Z., et al.: J. Biol. Chem., 272, 13432 (1981)
• Du, C., et al.: Cell, 102, 33 (1981)