aplaviroc   

GtoPdb Ligand ID: 805

Synonyms: AK-602 | GW 873140 | GW873140A
Compound class: Synthetic organic
Comment: Aplaviroc was being investigated in clinical trial as a potential treatment for HIV infection. Concerns over liver toxicity [3] and low efficacy [1] lead to termination of the development project.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 119.41
Molecular weight 577.32
XLogP 5.53
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCN1C(=O)C(NC(=O)C21CCN(CC2)Cc1ccc(cc1)Oc1ccc(cc1)C(=O)O)C(C1CCCCC1)O
Isomeric SMILES CCCCN1C(=O)[C@H](NC(=O)C21CCN(CC2)Cc1ccc(cc1)Oc1ccc(cc1)C(=O)O)[C@@H](C1CCCCC1)O
InChI InChI=1S/C33H43N3O6/c1-2-3-19-36-30(38)28(29(37)24-7-5-4-6-8-24)34-32(41)33(36)17-20-35(21-18-33)22-23-9-13-26(14-10-23)42-27-15-11-25(12-16-27)31(39)40/h9-16,24,28-29,37H,2-8,17-22H2,1H3,(H,34,41)(H,39,40)/t28-,29-/m1/s1
InChI Key GWNOTCOIYUNTQP-FQLXRVMXSA-N
Classification
Compound class Synthetic organic
IUPAC Name
4-[4-[[(3R)-1-butyl-3-[(R)-cyclohexyl-hydroxymethyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid
International Nonproprietary Names
INN number INN
8708 aplaviroc
Synonyms
AK-602 | GW 873140 | GW873140A
Database Links
CAS Registry No. 461443-59-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1255794
GtoPdb PubChem SID 135649948
PubChem CID 3001322
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Wikipedia Aplaviroc