CWHM12   Click here for help

GtoPdb Ligand ID: 10495

Synonyms: CWHM 12 | CWHM-12
Compound class: Synthetic organic
Comment: CWHM12 is a pan αv integrin antagonist [1]. It was used to determine that αv integrin activation regulates fibrosis in models of organ fibrosis. These findings suggest that targeting all αv integrins may have clinical utility in the treatment of a broad range of fibrotic diseases. The S enantiomer of CWHM12 is the bioactive form; the R enantiomer does not inhibit any of the five αv-containing integrins in vitro.
Structurally, CWHM12 is a small-molecule RGD peptidomimetic antagonist in which the arginine (R) mimetic is a cyclic guanidino-substituted phenyl group and the aspartic acid (D) mimetic is a phenyl-substituted β amino acid. These two residues are linked by a glycine (G).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 12
Topological polar surface area 172.38
Molecular weight 589.15
XLogP 3.33
No. Lipinski's rules broken 1
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Canonical SMILES OC1CNC(=NC1)Nc1cc(O)cc(c1)C(=O)NCC(=O)NC(c1cc(Br)cc(c1)C(C)(C)C)CC(=O)O
Isomeric SMILES OC1CNC(=NC1)Nc1cc(O)cc(c1)C(=O)NCC(=O)N[C@H](c1cc(Br)cc(c1)C(C)(C)C)CC(=O)O
InChI InChI=1S/C26H32BrN5O6/c1-26(2,3)16-4-14(5-17(27)8-16)21(10-23(36)37)32-22(35)13-28-24(38)15-6-18(9-19(33)7-15)31-25-29-11-20(34)12-30-25/h4-9,20-21,33-34H,10-13H2,1-3H3,(H,28,38)(H,32,35)(H,36,37)(H2,29,30,31)/t21-/m0/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S)-3-(3-bromo-5-tert-butylphenyl)-3-[[2-[[3-hydroxy-5-[(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino]benzoyl]amino]acetyl]amino]propanoic acid
Synonyms Click here for help
CWHM 12 | CWHM-12
Database Links Click here for help
CAS Registry No. 1564286-55-0 (source: PubChem)
ChEMBL Ligand CHEMBL3319237
GtoPdb PubChem SID 387065577
PubChem CID 72949858
Search Google for chemical match using the InChIKey YDHAGPCZRFQPOI-NRFANRHFSA-N
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UniChem Compound Search for chemical match using the InChIKey YDHAGPCZRFQPOI-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey YDHAGPCZRFQPOI-NRFANRHFSA-N