vinorelbine   Click here for help

GtoPdb Ligand ID: 7105

Synonyms: Navelbine®
Approved drug
vinorelbine is an approved drug (FDA (1994))
Compound class: Synthetic organic
Comment: Vinorelbine is an anti-mitotic chemotherapy drug.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 133.87
Molecular weight 778.39
XLogP 4.82
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CCC1=CC2CN(C1)Cc1c3ccccc3[nH]c1C(C2)(C(=O)OC)c1cc2c(cc1OC)N(C1C32CCN2C3C(CC)(C=CC2)C(C1(O)C(=O)OC)OC(=O)C)C
Isomeric SMILES CCC1=C[C@@H]2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@H]([C@]1(O)C(=O)OC)OC(=O)C)C
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
InChI Key GBABOYUKABKIAF-IELIFDKJSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1994))
Approved drug? Yes. FDA (1994)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
International Nonproprietary Names Click here for help
INN number INN
6054 vinorelbine
Synonyms Click here for help
Navelbine®
Database Links Click here for help
CAS Registry No. 71486-22-1
ChEBI CHEBI:480999
ChEMBL Ligand CHEMBL553025
DrugBank Ligand DB00361
DrugCentral Ligand 2827
GtoPdb PubChem SID 178103682
PubChem CID 5311497
Search Google for chemical match using the InChIKey GBABOYUKABKIAF-IELIFDKJSA-N
Search Google for chemicals with the same backbone GBABOYUKABKIAF
Search PubMed clinical trials vinorelbine
Search PubMed titles vinorelbine
Search PubMed titles/abstracts vinorelbine
UniChem Compound Search for chemical match using the InChIKey GBABOYUKABKIAF-IELIFDKJSA-N
UniChem Connectivity Search for chemical match using the InChIKey GBABOYUKABKIAF-IELIFDKJSA-N
Wikipedia Vinorelbine