(1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen-9-ol dihydrochloride

• ChemBase ID: 119607
• Molecular Formular: C37H42Cl2N2O6
• Molecular Mass: 681.64518
• Monoisotopic Mass: 680.24199243
• SMILES: c12c3[C@H](N(CCc3cc(c2OC)OC)C)Cc2cc(Oc3ccc(C[C@H]4c5cc(O1)c(cc5CCN4C)OC)cc3)c(cc2)O.Cl.Cl
• Canonical SMILES: COc1c(OC)cc2c3c1Oc1cc4c(cc1OC)CCN([C@H]4Cc1ccc(Oc4cc(C[C@H]3N(CC2)C)ccc4O)cc1)C.Cl.Cl
• InChI: InChI=1S/C37H40N2O6.2ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33;;/h6-11,18-21,28-29,40H,12-17H2,1-5H3;2*1H/t28-,29+;;/m0../s1
• InChIKey: USRXDYNDPPUBSG-KKXMJGKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^3,^6.1^8,^1^2.1^1^4,^1^8.0^2^7,^3^1.0^2^2,^3^3]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen-9-ol dihydrochloride; (1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^3,^6.1^8,^1^2.1^1^4,^1^8.0^2^7,^3^1.0^2^2,^3^3]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaen-9-ol dihydrochloride
• IUPAC Traditional name: (+)-berbamine dihydrochloride; (1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^3,^6.1^8,^1^2.1^1^4,^1^8.0^2^7,^3^1.0^2^2,^3^3]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaen-9-ol dihydrochloride
• Synonyms: berbenine; Berbamine dihydrochloride; (1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecae n-9-ol dihydrochloride; 盐酸小檗胺; 小檗胺 二盐酸盐

Database IDs

• CAS Number: 6078-17-7
• MDL Number: MFCD11982910
• PubChem SID: 162107692; 24878760
• PubChem CID: 16217067

CALCULATED PROPERTIES

• Acid pKa: 8.936118
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0888311
• LogD (pH = 7.4): 4.5986533
• Log P: 5.7211514
• Molar Refractivity: 175.6323 cm^3
• Polarizability: 67.69852 Å^3
• Polar Surface Area: 72.86 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 250-253 °C(lit.)
• Optical Rotation: [α]20/D +116°, c = 1% in ethanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Salt Data: 2 HCl
• Empirical Formula (Hill Notation): C37H40N2O6 ·2HCl

DETAILS

Sigma Aldrich - 547190

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Preparation of and anti-leukemia active berbamine derivatives1