(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one

• ChemBase ID: 147648
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1Cc1c3c(c(cc1)OC)O)OC
• Canonical SMILES: COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(cc4)OC
• InChI: InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
• InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5,11-tetraen-13-one
• IUPAC Traditional name: sinomenine
• Synonyms: Sinomenine; 青藤碱

Database IDs

• CAS Number: 115-53-7
• EC Number: 204-094-6
• MDL Number: MFCD00134303
• PubChem SID: 162241835; 24862546
• PubChem CID: 5459308

CALCULATED PROPERTIES

• Acid pKa: 9.832212
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.1205362
• LogD (pH = 7.4): 0.6472067
• Log P: 1.4476779
• Molar Refractivity: 92.9974 cm^3
• Polarizability: 35.338394 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180 °C (dec.)(lit.)

Safety Information

• RTECS: QD2170000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H311-H315-H319-H330-H335
• GHS Precautionary statements: P260-P280-P284-P305 + P351 + P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Impurities: 0.3 mol chloroform of crystallization
• Empirical Formula (Hill Notation): C19H23NO4 · 0.3CHCl3

DETAILS

Sigma Aldrich - 365602

Packaging
100 mg in glass bottle