GSK2838232   Click here for help

GtoPdb Ligand ID: 12680

Synonyms: example 51 [WO2013090664A1] | GSK-2838232 | GSK-8232 | GSK232
Compound class: Synthetic organic
Comment: GSK2838232 is an investigational HIV maturation inhibitor [2-3]. This class of compounds bind to the HIV-1 gag protein and disrupt its cleavage by the viral protease that is crucial for forming new mature and infectious virus particles [4,6]. This mechanism is proposed to maintain antiviral efficacy against drug-resistant strains of HIV-1.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 107.38
Molecular weight 809.56
XLogP 8.75
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(C)C1=C2[C@H]3CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2(CC1=O)[C@H](CN(CCN(C)C)CC6=CC=C(C=C6)Cl)O)OC(=O)CC(C)(C)C(=O)O
Isomeric SMILES CC(C)C1=C2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC[C@]2(CC1=O)[C@H](CN(CCN(C)C)CC6=CC=C(C=C6)Cl)O)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C
InChI InChI=1S/C48H73ClN2O6/c1-30(2)40-34(52)26-48(37(53)29-51(25-24-50(10)11)28-31-12-14-32(49)15-13-31)23-22-46(8)33(41(40)48)16-17-36-45(7)20-19-38(57-39(54)27-43(3,4)42(55)56)44(5,6)35(45)18-21-47(36,46)9/h12-15,30,33,35-38,53H,16-29H2,1-11H3,(H,55,56)/t33-,35+,36-,37+,38+,45+,46-,47-,48+/m1/s1
InChI Key MEOWKUXNVNJAMY-PZFKGGKESA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-[[(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-[(1R)-2-[(4-chlorophenyl)methyl-[2-(dimethylamino)ethyl]amino]-1-hydroxyethyl]-5a,5b,8,8,11a-pentamethyl-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3H-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
Synonyms Click here for help
example 51 [WO2013090664A1] | GSK-2838232 | GSK-8232 | GSK232
Database Links Click here for help
BindingDB Ligand 271401
CAS Registry No. 1443460-91-0 (source: PubChem)
ChEMBL Ligand CHEMBL4303141
GtoPdb PubChem SID 483123228
PubChem CID 71580991
Search Google for chemical match using the InChIKey MEOWKUXNVNJAMY-PZFKGGKESA-N
Search Google for chemicals with the same backbone MEOWKUXNVNJAMY
UniChem Compound Search for chemical match using the InChIKey MEOWKUXNVNJAMY-PZFKGGKESA-N
UniChem Connectivity Search for chemical match using the InChIKey MEOWKUXNVNJAMY-PZFKGGKESA-N