compound 6 [PMID: 29769246]   Click here for help

GtoPdb Ligand ID: 13195

Synonyms: Cmpd-6 [PMID: 34580163]
Compound class: Synthetic organic
Comment: This ligand acts as a positive allosteric modulator (PAM) of β2-adrenoceptor activity [1-2].
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 152.48
Molecular weight 611.82
XLogP 3.5
No. Lipinski's rules broken 2
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)N(C)S(=O)(=O)C1=CC=C(C(=C1)C(=O)N[C@H](CC2=CC=C(C=C2)C(C)(C)C)CC(=O)N)SC3=CC=C(C=C3)OC
Isomeric SMILES NC(C[C@@H](CC1=CC=C(C=C1)C(C)(C)C)NC(C2=C(C=CC(=C2)S(N(C)C(C)C)(=O)=O)SC3=CC=C(C=C3)OC)=O)=O
InChI InChI=1S/C32H41N3O5S2/c1-21(2)35(6)42(38,39)27-16-17-29(41-26-14-12-25(40-7)13-15-26)28(20-27)31(37)34-24(19-30(33)36)18-22-8-10-23(11-9-22)32(3,4)5/h8-17,20-21,24H,18-19H2,1-7H3,(H2,33,36)(H,34,37)/t24-/m1/s1
InChI Key XBWGFMNXTKZHDW-XMMPIXPASA-N
References
1. Ahn S, Pani B, Kahsai AW, Olsen EK, Husemoen G, Vestergaard M, Jin L, Zhao S, Wingler LM, Rambarat PK et al.. (2018)
Small-Molecule Positive Allosteric Modulators of the β2-Adrenoceptor Isolated from DNA-Encoded Libraries.
Mol Pharmacol, 94 (2): 850-861. [PMID:29769246]
2. Pani B, Ahn S, Rambarat PK, Vege S, Kahsai AW, Liu A, Valan BN, Staus DP, Costa T, Lefkowitz RJ. (2021)
Unique Positive Cooperativity Between the β-Arrestin-Biased β-Blocker Carvedilol and a Small Molecule Positive Allosteric Modulator of the β2-Adrenergic Receptor.
Mol Pharmacol, 100 (5): 513-525. [PMID:34580163]