14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-13-carbonitrile

• ChemBase ID: 104547
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: CC(=O)C1C(CC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C#N
• Canonical SMILES: N#CC1CC2C(C1C(=O)C)(C)CCC1C2CC=C2C1(C)CCC(C2)O
• InChI: InChI=1S/C22H31NO2/c1-13(24)20-14(12-23)10-19-17-5-4-15-11-16(25)6-8-21(15,2)18(17)7-9-22(19,20)3/h4,14,16-20,25H,5-11H2,1-3H3
• InChIKey: VSBHRRMYCDQLJF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-13-carbonitrile
• IUPAC Traditional name: pregnenolone 16 α-carbonitrile
• Synonyms: Pregnenolone-16α-carbonitrile; 5-PREGNEN-3β-OL-20-ONE-16α-CARBONITRILE

Database IDs

• CAS Number: 1434-54-4
• PubChem SID: 162093064
• PubChem CID: 5225515

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8620517
• LogD (pH = 7.4): 2.8620517
• Log P: 2.8620517
• Molar Refractivity: 98.9759 cm^3
• Polarizability: 38.625042 Å^3
• Polar Surface Area: 61.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: TU4536500

DETAILS

MP Biomedicals - 02156362

(Pregnenolone-16α-carbonitrile) Activates the transcription of the PCN1 gene and induces cytochrome P-450 activity.

REFERENCES

• Hardwick, J.P., et al., J. Biol. Chem. , 258 : 10182 (1983).
• Watkins, P.B., et al., Proc. Natl. Acad. Sci. USA, 82: 6310 (1985).
• Gonzalez, F.J., et al., Mol. Cell. Biol., 6: 2969 (1986).