carotegrast   Click here for help

GtoPdb Ligand ID: 10511

Synonyms: HCA2969
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Carotegrast (HCA2969) is the active metabolite of carotegrast methyl [1,4]. It acts as an antagonist of α4 integrin-mediated transmigration of leukocytes to sites of inflammation. The chemical structure of carotegrast is claimed as example 108 in EA Pharma patent US20110065918A1 which claims phenylalanine derivatives as α4 integrin antagonists for use as clinical therapeutics [2].
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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 113.12
Molecular weight 554.11
XLogP 6.12
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CN(c1ccc2c(c1)c(=O)n(c(=O)n2C)c1ccc(cc1)CC(C(=O)O)NC(=O)c1c(Cl)cccc1Cl)C
Isomeric SMILES CN(c1ccc2c(c1)c(=O)n(c(=O)n2C)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(Cl)cccc1Cl)C
InChI InChI=1S/C27H24Cl2N4O5/c1-31(2)17-11-12-22-18(14-17)25(35)33(27(38)32(22)3)16-9-7-15(8-10-16)13-21(26(36)37)30-24(34)23-19(28)5-4-6-20(23)29/h4-12,14,21H,13H2,1-3H3,(H,30,34)(H,36,37)/t21-/m0/s1
InChI Key YQKBOUPIOWUMTE-NRFANRHFSA-N
Classification Click here for help
Compound class Synthetic organic
Prodrug carotegrast methyl
IUPAC Name Click here for help
(2S)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[6-(dimethylamino)-1-methyl-2,4-dioxoquinazolin-3-yl]phenyl]propanoic acid
International Nonproprietary Names Click here for help
INN number INN
9224 carotegrast
Synonyms Click here for help
HCA2969
Database Links Click here for help
CAS Registry No. 401904-75-4 (source: WHO INN record)
GtoPdb PubChem SID 387065593
PubChem CID 10120218
Search Google for chemical match using the InChIKey YQKBOUPIOWUMTE-NRFANRHFSA-N
Search Google for chemicals with the same backbone YQKBOUPIOWUMTE
Search PubMed clinical trials carotegrast
Search PubMed titles carotegrast
Search PubMed titles/abstracts carotegrast
UniChem Compound Search for chemical match using the InChIKey YQKBOUPIOWUMTE-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey YQKBOUPIOWUMTE-NRFANRHFSA-N