methyl N-[(1E,5R)-5-[(3S)-3-[(2E,4E)-2,5-dimethylocta-2,4-dienoyl]-2,4-dioxo-3,4-dihydro-2H-pyran-6-yl]hexylidene]carbamate

• ChemBase ID: 5890
• Molecular Formular: C23H31NO6
• Molecular Mass: 417.49534
• Monoisotopic Mass: 417.21513772
• SMILES: O1C(=O)[C@@H](C(=O)C=C1[C@H](C)CCC/C=N/C(=O)OC)C(=O)/C(=C/C=C(\C)/CCC)/C
• Canonical SMILES: CCC/C(=C/C=C(/C(=O)[C@H]1C(=O)OC(=CC1=O)[C@@H](CCC/C=N/C(=O)OC)C)\C)/C
• InChI: InChI=1S/C23H31NO6/c1-6-9-15(2)11-12-17(4)21(26)20-18(25)14-19(30-22(20)27)16(3)10-7-8-13-24-23(28)29-5/h11-14,16,20H,6-10H2,1-5H3/b15-11+,17-12+,24-13+/t16-,20+/m1/s1
• InChIKey: LTDLIPXLSBMTFP-HQCMHGIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[(1E,5R)-5-[(3S)-3-[(2E,4E)-2,5-dimethylocta-2,4-dienoyl]-2,4-dioxo-3,4-dihydro-2H-pyran-6-yl]hexylidene]carbamate
• IUPAC Traditional name: methyl N-[(1E,5R)-5-[(5S)-5-[(2E,4E)-2,5-dimethylocta-2,4-dienoyl]-4,6-dioxo-5H-pyran-2-yl]hexylidene]carbamate
• Synonyms: methyl [(1E,5R)-5-{(3S)-3-[(2E,4E)-2,5-dimethylocta-2,4-dienoyl]-2,4-dioxo-3,4-dihydro-2H-pyran-6-yl}hexylidene]carbamate

Database IDs

• PubChem SID: 99444737; 160969317
• PubChem CID: 46937136

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.9816562
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.4465904
• LogD (pH = 7.4): 2.4450293
• Log P: 4.544198
• Molar Refractivity: 116.4001 cm^3
• Polarizability: 44.066162 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.39
• LOG S: -5.38
• Solubility (Water): 1.73e-03 g/l

DETAILS

DrugBank - DB08266

Drug information: experimental