(1S,14S)-9,19,20,21,25-pentamethoxy-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),9,11,18,20,22(33),24,26,31,35-dodecaene

• ChemBase ID: 179842
• Molecular Formular: C39H44N2O7
• Molecular Mass: 652.77586
• Monoisotopic Mass: 652.31485176
• SMILES: c12c3c(c(c(c1CCN([C@H]2Cc1cc(Oc2ccc(C[C@H]4c5cc(O3)c(cc5CCN4C)OC)cc2)c(cc1)OC)C)OC)OC)OC
• Canonical SMILES: COc1ccc2cc1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1cc(Oc1c4[C@H](C2)N(C)CCc4c(c(c1OC)OC)OC)c(OC)c3
• InChI: InChI=1S/C39H44N2O7/c1-40-16-14-25-21-32(43-4)34-22-28(25)29(40)18-23-8-11-26(12-9-23)47-33-20-24(10-13-31(33)42-3)19-30-35-27(15-17-41(30)2)36(44-5)38(45-6)39(46-7)37(35)48-34/h8-13,20-22,29-30H,14-19H2,1-7H3/t29-,30-/m0/s1
• InChIKey: FUZMQNZACIFDBL-KYJUHHDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,14S)-9,19,20,21,25-pentamethoxy-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)-9,19,20,21,25-pentamethoxy-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: Hernandezine

Database IDs

• CAS Number: 6681-13-6
• PubChem SID: 164235752
• PubChem CID: 72343

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.12924
• LogD (pH = 7.4): 4.658131
• Log P: 6.3205914
• Molar Refractivity: 186.5778 cm^3
• Polarizability: 72.13038 Å^3
• Polar Surface Area: 71.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Calcium antagonist; Inhibitor of conditioned avoidance reactions in exptl. animals

Product Information

• Biological Source: Alkaloid from Thalictrum hernandezii, Thalictrum fendleri, Thalictrum podocarpum, Thalictrum rochebrunianum and other Thalictrum spp. (Ranunculaceae)
• Application(s): Antiseptic; Shows strong antiinflammatory activity; Weak antineoplastic agent

REFERENCES

• Padilla, J. et al., Tetrahedron, 1962, 18, 427, (isol, uv, ir, pmr, struct)
• Battersby, A.R. et al., J.C.S., 1965, 2239, (ord)
• Shamma, M. et al., Tetrahedron, 1967, 23, 2887, (Hernandezine, Thalidezine, isol, uv, ms, pmr, struct)
• Baldas, J. et al., J.C.S. Perkin 1, 1972, 592, (ms)
• Cava, M.P. et al., Tet. Lett., 1974, 4259, (cd)