henatinib   Click here for help

GtoPdb Ligand ID: 9930

Synonyms: compound 25 [PMID: 21028894]
Compound class: Synthetic organic
Comment: Henatinib is a kinase inhibitor with some selectivity for VEGFR2 (KDR). Discovery was reported by Cho et al. (2010), the same article that disclosed famitinib [1]. The name henatinib is linked to the structure of 'compound 25' in the article by Gu et al. (2010) that describes a method for detecting and quantifying henatinib maleate in rat plasma [2].
Henatinib is a 'pseudo' INN, that takes the form of an INN for a kinase inhibitor, but has not been submitted to the World Health Organisation for ratification.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 97.9
Molecular weight 468.22
XLogP 1.03
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC(CN1CCCc2c(C1=O)c(C)c([nH]2)C=C1C(=O)Nc2c1cc(F)cc2)CN1CCOCC1
Isomeric SMILES O[C@@H](CN1CCCc2c(C1=O)c(C)c([nH]2)/C=C/1\C(=O)Nc2c1cc(F)cc2)CN1CCOCC1
InChI InChI=1S/C25H29FN4O4/c1-15-22(12-19-18-11-16(26)4-5-20(18)28-24(19)32)27-21-3-2-6-30(25(33)23(15)21)14-17(31)13-29-7-9-34-10-8-29/h4-5,11-12,17,27,31H,2-3,6-10,13-14H2,1H3,(H,28,32)/b19-12-/t17-/m1/s1
Bioactivity Comments
Henatinib is not selective for VEGFR2 (KDR) compared to PDGFRβ and c-KIT [1]. It inhibits HUVEC cell growth with an IC50 of 26 nM in vitro, and exhibits antitumour efficacy in mice bearing human HT-29 colon tumour xenografts.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
KIT proto-oncogene, receptor tyrosine kinase Hs Inhibitor Inhibition 8.1 pIC50 - 1
pIC50 8.1 (IC50 8x10-9 M) [1]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 8.0 pIC50 - 1
pIC50 8.0 (IC50 1.1x10-8 M) [1]
kinase insert domain receptor Hs Inhibitor Inhibition 7.6 pIC50 - 1
pIC50 7.6 (IC50 2.7x10-8 M) [1]