(10S)-10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one

• ChemBase ID: 133871
• Molecular Formular: C19H21NO5
• Molecular Mass: 343.37374
• Monoisotopic Mass: 343.14197278
• SMILES: COc1cc2c(c(c1OC)OC)c1ccc(c(=O)cc1[C@H](CC2)N)O
• Canonical SMILES: COc1c(OC)c(OC)cc2c1c1ccc(c(=O)cc1[C@H](CC2)N)O
• InChI: InChI=1S/C19H21NO5/c1-23-16-8-10-4-6-13(20)12-9-15(22)14(21)7-5-11(12)17(10)19(25-3)18(16)24-2/h5,7-9,13H,4,6,20H2,1-3H3,(H,21,22)/t13-/m0/s1
• InChIKey: IRVWPZRYDQROLU-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one; (10S)-10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
• IUPAC Traditional name: (10S)-10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one; (10S)-10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
• Synonyms: (7S)-7-Amino-6,7-dihydro-10-hydroxy-1,2,3-trimethoxy-benzo[a]heptalen-9(5H)-one; NSC 36796; Trimethylcolchicinic Acid; N-Deacetyl Colchiceine; Trimethylcolchicinic acid; Trimethylcolchicinate; 三甲基秋水仙酸

Database IDs

• CAS Number: 3482-37-9
• EC Number: 222-464-5
• MDL Number: MFCD00082296
• PubChem SID: 162228148; 24900490
• PubChem CID: 453131

CALCULATED PROPERTIES

• Acid pKa: 9.3816805
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.4502466
• LogD (pH = 7.4): -0.4569272
• Log P: 1.316512
• Molar Refractivity: 97.1806 cm^3
• Polarizability: 36.339672 Å^3
• Polar Surface Area: 91.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Yellow-green Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Storage Temperature: -20°C

Pharmacology Properties

• Mechanism of Action: Inhibitor of microtubule polymerization by binding to tubulin

Product Information

• Biological Source: Alkaloid from the above-ground parts of Merendera robusta (Liliaceae)
• Application(s): Cytostatic

DETAILS

Toronto Research Chemicals - D198900

An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pa

REFERENCES

• Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
• Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
• Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
• Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
• Jordan, A., et al.: Med. Res. Rev