(9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2(7),3,5,12,14-hexaen-9-ol

• ChemBase ID: 153253
• Molecular Formular: C24H32O7
• Molecular Mass: 432.50668
• Monoisotopic Mass: 432.21480336
• SMILES: C[C@H]1Cc2cc(c(c(c2c2c(cc(c(c2OC)OC)OC)C[C@]1(C)O)OC)OC)OC
• Canonical SMILES: COc1c(OC)cc2c(c1OC)c1c(cc(c(c1OC)OC)OC)C[C@@H]([C@@](C2)(C)O)C
• InChI: InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1
• InChIKey: YEFOAORQXAOVJQ-RZFZLAGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^2,^7]hexadeca-1(16),2(7),3,5,12,14-hexaen-9-ol; (9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^2,^7]hexadeca-1(12),2,4,6,13,15-hexaen-9-ol
• IUPAC Traditional name: (9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^2,^7]hexadeca-1(16),2(7),3,5,12,14-hexaen-9-ol; (9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^2,^7]hexadeca-1(12),2,4,6,13,15-hexaen-9-ol
• Synonyms: (+)-Schizandrin; Schisandrin; Schisandrine; Wuweizi alcohol A; Wuweizichun A; Schizandrin; Schisandrol A; Schizandrol A

Database IDs

• CAS Number: 7432-28-2
• MDL Number: MFCD00905761
• PubChem SID: 162247392
• PubChem CID: 3001664

CALCULATED PROPERTIES

• Acid pKa: 14.6397295
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 3.3855288
• LogD (pH = 7.4): 3.3855288
• Log P: 3.3855288
• Molar Refractivity: 118.2349 cm^3
• Polarizability: 47.169952 Å^3
• Polar Surface Area: 75.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥13 mg/mL
• Apperance: Powder; white to tan powder
• Optical Rotation: [α]/D 75 to 85° in methanol

Safety Information

• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H32O7

DETAILS

Sigma Aldrich - SML0054

Biochem/physiol Actions
Schizandrin is a natural product with several biological properties involved with antioxidant and anti-inflammatory activities. It reduces the formation of ROS, inhibits the mitochondrial pathway of the apoptotic process and oxidative stress. Schizandrin has been reported to have hepatoprotective, antitumor, antiviral, and antiamnesic effects, and has neuroprotective activity against glutamate induced neurotoxicity.