N-[(10S,12R,16S)-3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl]acetamide

• ChemBase ID: 172429
• Molecular Formular: C22H25NO6
• Molecular Mass: 399.437
• Monoisotopic Mass: 399.16818753
• SMILES: C12=C([C@H]3[C@@H]1C=C(C3=O)OC)[C@H](CCc1c2c(c(c(c1)OC)OC)OC)NC(=O)C
• Canonical SMILES: COC1=C[C@H]2[C@@H](C1=O)C1=C2c2c(CC[C@@H]1NC(=O)C)cc(c(c2OC)OC)OC
• InChI: InChI=1S/C22H25NO6/c1-10(24)23-13-7-6-11-8-15(27-3)21(28-4)22(29-5)16(11)17-12-9-14(26-2)20(25)18(12)19(13)17/h8-9,12-13,18H,6-7H2,1-5H3,(H,23,24)/t12-,13+,18-/m1/s1
• InChIKey: VKPVZFOUXUQJMW-FHSNZYRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S,12R,16S)-3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0^2,^7.0^1^2,^1^6]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl]acetamide
• IUPAC Traditional name: N-[(10S,12R,16S)-3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0^2,^7.0^1^2,^1^6]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl]acetamide
• Synonyms: N-[(7S,7bR,10aS)-5,6,7,7b,8,10a-Hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]acetamide; β-Lumicolchicine; (-)-β-Lumicolchicine; Lumicolchicine; NSC 221661; NSC 56233; β-Lumi-(-)-colchicine; β-Lumi (-)-Colchicine

Database IDs

• CAS Number: 6901-13-9
• PubChem SID: 164228339
• PubChem CID: 244898

CALCULATED PROPERTIES

• Acid pKa: 6.545579
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.8643262
• LogD (pH = 7.4): 0.0038371473
• Log P: 0.90164053
• Molar Refractivity: 108.4012 cm^3
• Polarizability: 41.236774 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 177-180°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L474300

An analog of Colchicine (C640000), β-lumicolchicine, does not bind tubulin or disrupt microtubules. A GABAA receptor chloride channel.

REFERENCES

• Andreu, J., et al.: Biochemistry, 37, 8356 (1998)
• Weiner, J., et al.: J. Pharmacol. Exp. Ther., 284, 95 (1998)
• Hong, G., et al.: J. Pharm. Sci., 88, 147 (1998)