(1S,14S)-9,20,21,25-tetramethoxy-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),9,11,18,20,22(33),24,26,31,35-dodecaene

• ChemBase ID: 73023
• Molecular Formular: C38H42N2O6
• Molecular Mass: 622.74988
• Monoisotopic Mass: 622.30428707
• SMILES: c1c2c3c(c(c1OC)OC)Oc1c(cc4c(c1)[C@H](Cc1ccc(Oc5c(ccc(C[C@@H]3N(CC2)C)c5)OC)cc1)N(CC4)C)OC
• Canonical SMILES: COc1c(OC)cc2c3c1Oc1cc4c(cc1OC)CCN([C@H]4Cc1ccc(Oc4cc(C[C@@H]3N(CC2)C)ccc4OC)cc1)C
• InChI: InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1
• InChIKey: WVTKBKWTSCPRNU-KYJUHHDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,14S)-9,20,21,25-tetramethoxy-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),9,11,18,20,22(33),24,26,31,35-dodecaene; (1S,14S)-9,20,21,25-tetramethoxy-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-dodecaene; (1S,14S)-9,20,21,25-tetramethoxy-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-dodecaene
• IUPAC Traditional name: (1S,14S)-9,20,21,25-tetramethoxy-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),9,11,18,20,22(33),24,26,31,35-dodecaene; (1S,14S)-9,20,21,25-tetramethoxy-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-dodecaene; (1S,14S)-9,20,21,25-tetramethoxy-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-dodecaene
• Synonyms: Fanchinine; Hanfangchin A; NSC 77037; S; S-(+)-Tetrandrine; Tetrandrine(Fanchinine); (1β)-6,6′,7,12-Tetramethoxy-2,2′-dimethylberbaman; Tetrandrine; (S,S)-(+)-Tetrandrine; (1S,14S)-9,20,21,25-tetramethoxy-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-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-do decaene; 倒地拱素; 汉防己甲素; (S,S)-(+)-粉防己碱

Database IDs

• CAS Number: 518-34-3
• MDL Number: MFCD08689909
• Beilstein Number: 877811
• PubChem SID: 24900066; 162037943; 24862548
• PubChem CID: 73078

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.2245115
• LogD (pH = 7.4): 4.760781
• Log P: 6.4782624
• Molar Refractivity: 180.1146 cm^3
• Polarizability: 69.61369 Å^3
• Polar Surface Area: 61.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid
• Melting Point: 219-222 °C; 219-222 °C(lit.)
• Optical Rotation: [α]20/D +283±5°, c = 1% in chloroform; [α]20/D +285°, c = 1 in chloroform

Safety Information

• Storage Condition: -20°C
• RTECS: XE9350000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: calcium channel

Product Information

• Purity: ≥90%; ≥96.0% (CH); 98%
• Grade: analytical standard, for drug analysis; purum
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C38H42N2O6

DETAILS

Selleck Chemicals - S2403

Research Area: Cancer
Biological Activity:
Tetrandrine (Fanchinine; Hanfangchin A) is a calcium channel blocker with an IC50 of 38.23± 25.77 μM. Tetrandrine (Fanchinine; Hanfangchin A) has anti-inflammatory, immunologic and antiallergenic effects. Tetrandrine (Fanchinine; Hanfangchin A) inhibits the degranulation of mast cells. Tetrandrinehas a "Quinidine like" anti-arrhythmic effect. Tetrandrine (Fanchinine; Hanfangchin A) has been isolated from Stephania tetandra and other Chinese and Japanese Herbs. Tetrandrine (Fanchinine; Hanfangchin A) increased populations of both apoptotic sub-G1 and G1 phase. Tetrandrine-induced growth inhibition was associated with induction of Cdk inhibitor p21, inhibition of cyclin D1 and activation of caspase-3. Tetrandrine (Fanchinine; Hanfangchin A) also affected the expression patterns of cytoskeletons including distribution of F-actin and expression level of microtubule. [1][2][3]References on Tetrandrine(Fanchinine)[2] Int J Oncol., 2002 Dec, 21(6):1239-44.[3] http://en.wikipedia.org/wiki/Tetrandrine, , [1] Cancer Letters, 2008, 268:166–175

Sigma Aldrich - 365629

Packaging
500 mg in glass bottle

Sigma Aldrich - T2695

Application
Analgesic, antipyretic
Packaging
1 g in poly bottle

REFERENCES

• Lee JH et al. Int J Oncol. 2002 Dec;21(6):1239-44.