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Chemistry

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Also known as: (-)-combretastatin, (r)-(-)-combretastatin, 82855-09-2, Combretastatin, (-)-, 7o62j06f18, Nsc-348103
Molecular Formula
C18H22O6
Molecular Weight
334.4  g/mol
InChI Key
LGZKGOGODCLQHG-CYBMUJFWSA-N
FDA UNII
7O62J06F18

Combretastatin
Combretastatin is a stilbenoid phenol, originally isolated from the bark of the African bush willow tree Combretum caffrum, with vascular disrupting and antineoplastic activities. Combretastatin targets and binds to the colchicine-binding site of tubulin, thereby impairs the polymerization of tubulin dimers and prevents the formation of microtubules in the endothelial cells of tumor. As a result, this may eventually lead to a destruction of the tumor vasculature, disruption of tumor blood flow and tumor cell necrosis.
1 2D Structure

Combretastatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[(2R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
2.1.2 InChI
InChI=1S/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3/t13-/m1/s1
2.1.3 InChI Key
LGZKGOGODCLQHG-CYBMUJFWSA-N
2.1.4 Canonical SMILES
COC1=C(C=C(C=C1)CC(C2=CC(=C(C(=C2)OC)OC)OC)O)O
2.1.5 Isomeric SMILES
COC1=C(C=C(C=C1)C[C@H](C2=CC(=C(C(=C2)OC)OC)OC)O)O
2.2 Other Identifiers
2.2.1 UNII
7O62J06F18
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-hydroxy-4-methoxy-alpha-(3,4,5-trimethoxyphenyl)benzeneethanol

2. Nsc 348103

3. Nsc-348103

2.3.2 Depositor-Supplied Synonyms

1. (-)-combretastatin

2. (r)-(-)-combretastatin

3. 82855-09-2

4. Combretastatin, (-)-

5. 7o62j06f18

6. Nsc-348103

7. 3-hydroxy-4-methoxy-alpha-(3,4,5-trimethoxyphenyl)benzeneethanol

8. Unii-7o62j06f18

9. Nsc 348103

10. Combretastatin [mi]

11. Schembl19955

12. Chembl246600

13. Dtxsid80897571

14. Zinc1607492

15. Db12596

16. Q5150954

17. 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol

18. Benzeneethanol, 3-hydroxy-4-methoxy-alpha-(3,4,5-trimethoxyphenyl)-, (r)-

19. Benzeneethanol, 3-hydroxy-4-methoxy-.alpha.-(3,4,5-trimethoxyphenyl)-, (r)-

20. Benzeneethanol, 3-hydroxy-4-methoxy-alpha-(3,4,5-trimethoxyphenyl)-, (alphar)-

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 334.4 g/mol
Molecular Formula C18H22O6
XLogP32.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass334.14163842 g/mol
Monoisotopic Mass334.14163842 g/mol
Topological Polar Surface Area77.4 Ų
Heavy Atom Count24
Formal Charge0
Complexity351
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)


Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)


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