Combretastatin A1
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Basic information
- CAS
109971-63-3- Standard SMILES
COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)c(O)c1O- InChIKey
YUSYSJSHVJULID-WAYWQWQTSA-N- Molecular formula
- C18H20O6
- Average molar mass
- 332.3 g/mol
- Monoisotopic mass
- 332.12598835
Overview
Combretastatin A-1 has been reported in Combretum afrum and Combretum kraussii with data available.
Names & identifiers
- Preferred name
- Combretastatin A1
- IUPAC
- 3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol
- English name
- COMBRETASTATIN A1
- Molecular formula
- C18H20O6
- Molecular weight
- 332.35
Names & synonyms
Combretastatin A-1Combretastatin A1109971-63-3NSC-600032OXi45002222ATS339NSC 6000323-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diolDTXSID7010288421,2-Benzenediol, 3-methoxy-6-(2-(3,4,5-trimethoxyphenyl)ethenyl)-, (Z)-3-methoxy-6-((Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)benzene-1,2-diolRefChem:127576
Show more names
(Z)-3',4,4',5'-Tetramethoxystilbene-2,3-diol(Z)-3,4,4',5-Tetramethoxy-2',3'-dihydroxystilbene3-Methoxy-6-[(Z)-3,4,5-trimethoxystyryl]-1,2-benzenediol3-methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol1,2-Benzenediol, 3-methoxy-6-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-Combretastatin A1( 3-Methoxy-6-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-benzene-1,2-diol )
DTXCID8015144781,2-Benzenediol, 3-methoxy-6-((Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-CHEMBL36255(Z)-3-METHOXY-6-(3,4,5-TRIMETHOXYSTYRYL)BENZENE-1,2-DIOL3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]benzene-1,2-diolUNII-2222ATS339combretastatins A-1orb1693389
Database identifiers
- CAS
109971-63-3- PubChem CID
- 5458993
- DTXSID
DTXSID701028842- ChEMBL
CHEMBL36255- UNII
- 2222ATS339
- Nikkaji
- J435.579B
Properties
Computed structural propertiesFilling in
- XLogP
- 3.4
- Topological polar surface area
- 77.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 387
Physicochemical properties
- Melting point
- 113 · 113-115 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
- Boiling point
- 528.4 · 528.4±50.0 °C(Predicted)
- Density
- 1.251 · 1.251±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 5 mg/ml; · DMF: 5 mg/ml; DMSO: 5 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 3 mg/ml
- form
- A crystalline solid
- pka
- 8.89 · 8.89±0.45(Predicted)
- color
- White to off-white
- FDA UNII
- 2222 ATS339 · 2222ATS339
Chemistry & industry
Applications
UsesCombretastatin A-1 is a microtubule polymerization inhibitor that binds to the colchicine-binding site of tubulin. Combretastatin A-1 inhibits the Wnt/β-catenin pathway through tubulin depolymerization mediated AKT deactivation. Combretastatin A-1 exhibits anti-tumor and anti-vascular effects[1][2][3].
Related reactions
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Compound notes
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