CHEBI:480999 - vinorelbine

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ChEBI Name vinorelbine
ChEBI ID CHEBI:480999
Definition A vinca alkaloid with a norvinblastine skeleton.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB3469220, eMolecules:36500497, eMolecules:36754948, Selleckchem:vinorelbine-navelbine, ZINC000085536958
Download Molfile XML SDF
Formula C45H54N4O8
Net Charge 0
Average Mass 778.93230
Monoisotopic Mass 778.39416
InChI InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1
InChIKey GBABOYUKABKIAF-IELIFDKJSA-N
SMILES CCC1=C[C@@H]2CN(C1)Cc1c([nH]c3ccccc13)[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N(C)[C@@H]1[C@]22CCN3CC=C[C@](CC)([C@@H]23)[C@@H](OC(C)=O)[C@]1(O)C(=O)OC
Roles Classification
Biological Role(s): 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): photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vinorelbine (CHEBI:480999) has role antineoplastic agent (CHEBI:35610)
vinorelbine (CHEBI:480999) has role photosensitizing agent (CHEBI:47868)
vinorelbine (CHEBI:480999) is a acetate ester (CHEBI:47622)
vinorelbine (CHEBI:480999) is a methyl ester (CHEBI:25248)
vinorelbine (CHEBI:480999) is a organic heteropentacyclic compound (CHEBI:38164)
vinorelbine (CHEBI:480999) is a organic heterotetracyclic compound (CHEBI:38163)
vinorelbine (CHEBI:480999) is a ring assembly (CHEBI:36820)
vinorelbine (CHEBI:480999) is a vinca alkaloid (CHEBI:27288)
Incoming vinflunine (CHEBI:90241) has functional parent vinorelbine (CHEBI:480999)
vinorelbine D-tartrate (CHEBI:53750) has part vinorelbine (CHEBI:480999)
vinorelbine L-tartrate (CHEBI:32296) has part vinorelbine (CHEBI:480999)
IUPAC Name
methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
INNs Sources
vinorelbina DrugBank
vinorelbine KEGG DRUG
vinorelbinum DrugBank
Synonym Source
Nor-5'-anhydrovinblastine ChemIDplus
Manual Xrefs Databases
2827 DrugCentral
D08680 KEGG DRUG
DB00361 DrugBank
JP8031096 Patent
US4307100 Patent
View more database links
Registry Numbers Types Sources
71486-22-1 CAS Registry Number KEGG DRUG
71486-22-1 CAS Registry Number ChemIDplus
71486-22-1 CAS Registry Number DrugBank
9035861 Beilstein Registry Number Beilstein
Last Modified
22 February 2017