(1R,3R,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

• ChemBase ID: 3137
• Molecular Formular: C40H56O4
• Molecular Mass: 600.87024
• Monoisotopic Mass: 600.41786027
• SMILES: C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@]12O[C@@]1(C)C[C@H](O)CC2(C)C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@H](O)CC2(C)C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@@]12O[C@@]2(C)C[C@@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@@H](CC1(C)C)O)\C
• InChI: InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37-,38+,39+,40-/m1/s1
• InChIKey: SZCBXWMUOPQSOX-PSXNNQPNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• IUPAC Traditional name: (1R,3R,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R,6S)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• Synonyms: Violaxanthin

Database IDs

• PubChem SID: 46505440; 160966581
• PubChem CID: 46936684

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.838654
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 7.257461
• LogD (pH = 7.4): 7.257461
• Log P: 7.257461
• Molar Refractivity: 192.327 cm^3
• Polarizability: 71.99721 Å^3
• Polar Surface Area: 65.52 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 8.33
• LOG S: -6.02
• Solubility (Water): 5.68e-04 g/l

DETAILS

DrugBank - DB03460

Drug information: experimental