CHEBI:28445 - vincristine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name vincristine
ChEBI ID CHEBI:28445
Definition A vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:27289, CHEBI:9987
Supplier Information ChemicalBook:CB62129873, ChemicalBook:CB0271682, eMolecules:485113, ZINC000001532521
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C46H56N4O10
Net Charge 0
Average Mass 824.95780
Monoisotopic Mass 824.39964
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
InChIKey OGWKCGZFUXNPDA-XQKSVPLYSA-N
SMILES [H][C@@]12N3CC[C@@]11c4cc(c(OC)cc4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@@H]2C[N@](CCc3c1[nH]c1ccccc31)C[C@](O)(CC)C2)C(=O)OC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
tubulin modulator
Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules.
microtubule-destabilising agent
Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
drug
Any substance which when absorbed into a living organism may modify one or more of its functions. The term is generally accepted for a substance taken for a therapeutic purpose, but is also commonly used for abused substances.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vincristine (CHEBI:28445) has parent hydride vincaleukoblastine (CHEBI:27375)
vincristine (CHEBI:28445) has role antineoplastic agent (CHEBI:35610)
vincristine (CHEBI:28445) has role drug (CHEBI:23888)
vincristine (CHEBI:28445) has role microtubule-destabilising agent (CHEBI:61951)
vincristine (CHEBI:28445) has role plant metabolite (CHEBI:76924)
vincristine (CHEBI:28445) has role tubulin modulator (CHEBI:60832)
vincristine (CHEBI:28445) is a acetate ester (CHEBI:47622)
vincristine (CHEBI:28445) is a formamides (CHEBI:24079)
vincristine (CHEBI:28445) is a methyl ester (CHEBI:25248)
vincristine (CHEBI:28445) is a organic heteropentacyclic compound (CHEBI:38164)
vincristine (CHEBI:28445) is a organic heterotetracyclic compound (CHEBI:38163)
vincristine (CHEBI:28445) is a tertiary alcohol (CHEBI:26878)
vincristine (CHEBI:28445) is a tertiary amino compound (CHEBI:50996)
vincristine (CHEBI:28445) is a vinca alkaloid (CHEBI:27288)
vincristine (CHEBI:28445) is conjugate base of vincristine(2+) (CHEBI:143658)
Incoming vincristine(2+) (CHEBI:143658) is conjugate acid of vincristine (CHEBI:28445)
IUPAC Name
22-oxovincaleukoblastine
Synonyms Sources
(+)-Vincristine DrugCentral
22-oxo-vincaleukoblastine DrugCentral
22-Oxovincaleukoblastine KEGG COMPOUND
leucristine DrugCentral
leurocristine ChemIDplus
oncovin DrugCentral
vincristin DrugCentral
Vincristine KEGG COMPOUND
vinkristin DrugCentral
Manual Xrefs Databases
2825 DrugCentral
C00001783 KNApSAcK
C07204 KEGG COMPOUND
CPD-19894 MetaCyc
D08679 KEGG DRUG
DB00541 DrugBank
HMDB0014681 HMDB
Vincristine Wikipedia
View more database links
Registry Numbers Types Sources
4779289 Beilstein Registry Number Beilstein
57-22-7 CAS Registry Number KEGG COMPOUND
57-22-7 CAS Registry Number ChemIDplus
Citations Types Sources
18520608 PubMed citation Europe PMC
30277559 PubMed citation Europe PMC
30429697 PubMed citation Europe PMC
30599272 PubMed citation Europe PMC
30604513 PubMed citation Europe PMC
30657998 PubMed citation Europe PMC
31048222 PubMed citation Europe PMC
31161774 PubMed citation Europe PMC
31214762 PubMed citation Europe PMC
31296986 PubMed citation Europe PMC
Last Modified
09 August 2019