vinblastine   Click here for help

GtoPdb Ligand ID: 6851

Synonyms: 29060-LE | Velban® | Velbe® | vincaleucoblastin | vincaleukoblastine
Approved drug PDB Ligand
vinblastine is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: A pan tubulin inhibitor. A chemical analogue of vincristine (from Catharanthus roseus, also known as Vinca rosea). There is some ambiguity surrounding the exact stereochemistry of vinblastine. The chirality shown here corresponds to the PubChem entry linked to in the table above. However, bioactivity data for the compound is also listed against CID 241903, and some of the links in the table above refer to this chiral specification or others. Marketed formulations contain vinblastine sulfate (PubChem CID 5388983).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 154.1
Molecular weight 810.42
XLogP 4.73
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc2N(C)C3C4(c2cc1C1(CC2CN(CCc5c1[nH]c1c5cccc1)CC(C2)(O)CC)C(=O)OC)CCN1C4C(C(C3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
Isomeric SMILES COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
InChI InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
InChI Key JXLYSJRDGCGARV-CFWMRBGOSA-N
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
tubulin beta class I Primary target of this compound Hs Inhibitor Inhibition 9.0 pIC50 -
pIC50 9.0 (IC50 1x10-9 M)