(1S,2R,5S,10S,11S,13R,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-13-carbonitrile

• ChemBase ID: 129098
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: CC(=O)[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)O)C)C)C#N
• Canonical SMILES: N#C[C@@H]1C[C@@H]2[C@]([C@H]1C(=O)C)(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](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/t14-,16-,17+,18-,19-,20-,21-,22-/m0/s1
• InChIKey: VSBHRRMYCDQLJF-ZDNYCOCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,13R,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-13-carbonitrile
• IUPAC Traditional name: pregnenolone carbonitrile
• Synonyms: Pregnenolone carbonitrile; Pregnenolone-16α-carbonitrile; 5-Pregnen-3β-ol-20-one-16α-carbonitrile

Database IDs

• CAS Number: 1434-54-4
• MDL Number: MFCD00079212
• PubChem SID: 24898113; 162223397
• PubChem CID: 15032
• CHEMBL: 1400945
• Wikipedia Title: Pregnenolone_carbonitrile

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

Physical Property

• Flash Point: >199.4 °F; >93 °C

Safety Information

• RTECS: TU4536500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%
• Empirical Formula (Hill Notation): C22H31NO2

DETAILS

Sigma Aldrich - P0543

Biochem/physiol Actions
Pregnenolone-16α-carbonitrile (PCN) is a glucocorticoid receptor antagonist and a PXR (pregnane X receptor) activator.