carotegrast   

GtoPdb Ligand ID: 10511

Synonyms: HCA2969
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].
2D Structure
Click here for structure editor
Physico-chemical Properties
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
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
Compound class Synthetic organic
Prodrug carotegrast methyl
IUPAC Name
(2S)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[6-(dimethylamino)-1-methyl-2,4-dioxoquinazolin-3-yl]phenyl]propanoic acid
International Nonproprietary Names
INN number INN
9224 carotegrast
Synonyms
HCA2969
Database Links
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
Search UniChem for chemical match using the InChIKey YQKBOUPIOWUMTE-NRFANRHFSA-N
Search UniChem for chemicals with the same backbone YQKBOUPIOWUMTE