(2R,3S,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),4,11(18),12,14-pentaen-6-one

• ChemBase ID: 126814
• Molecular Formular: C20H20N2O3
• Molecular Mass: 336.3844
• Monoisotopic Mass: 336.14739251
• SMILES: CC(=O)C1=C(O)[C@H]2N(C1=O)C(C)(C)[C@@H]1Cc3cccc4[nH]cc(c34)[C@H]21
• Canonical SMILES: CC(=O)C1=C(O)[C@H]2N(C1=O)C([C@H]1[C@@H]2c2c[nH]c3c2c(C1)ccc3)(C)C
• InChI: InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1
• InChIKey: SZINUGQCTHLQAZ-DQYPLSBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^2,^9.0^3,^7.0^1^5,^1^8]octadeca-1(17),4,11(18),12,14-pentaen-6-one
• IUPAC Traditional name: cyclopiazonic acid
• Synonyms: Cyclopiazonic acid

Database IDs

• CAS Number: 18172-33-3
• PubChem SID: 162221141
• PubChem CID: 65261; 54682463
• CHEBI ID: 22450
• CHEMBL: 480627
• Chemspider ID: 21106432
• Wikipedia Title: Cyclopiazonic_acid

CALCULATED PROPERTIES

• Acid pKa: -0.45829082
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.1651261
• LogD (pH = 7.4): -1.7397176
• Log P: 1.7741741
• Molar Refractivity: 94.6425 cm^3
• Polarizability: 37.09527 Å^3
• Polar Surface Area: 73.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true