vincristine   

GtoPdb Ligand ID: 6785

Synonyms: 22-oxovincaleukoblastine | kyocristine | leurocristine sulfate | NSC-67574 | Oncovin®
vincristine is an approved drug (FDA (1963))
Comment: A pan tubulin inhibitor, isolated from Catharanthus roseus (the Madagascar periwinkle, formerly Vinca rosea). Marketed formulations contain vincristine sulfate (PubChem CID 249332).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 171.17
Molecular weight 824.4
XLogP 3.56
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=CN1c2cc(OC)c(cc2C23C1C(O)(C(=O)OC)C(OC(=O)C)C1(C3N(CC2)CC=C1)CC)C1(CC2CN(CCc3c1[nH]c1c3cccc1)CC(C2)(O)CC)C(=O)OC
Isomeric SMILES O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC
InChI InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
InChI Key OGWKCGZFUXNPDA-XQKSVPLYSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (1963))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names
INN number INN
1440 vincristine
Synonyms
22-oxovincaleukoblastine | kyocristine | leurocristine sulfate | NSC-67574 | Oncovin®
Database Links
CAS Registry No. 57-22-7
ChEBI CHEBI:28445
ChEMBL Ligand CHEMBL90555
DrugBank Ligand DB00541
GtoPdb PubChem SID 178103391
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PubChem CID 5978
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