N-((R)-(2-amino-5-chloro-4-pyrimidinyl)(7-(4-(1-hydroxy-1-methylethyl)-2-pyridinyl)-1-benzothiophen-2-yl)methyl)cyclopropanesulfonamide

ID: ALA3746034

PubChem CID: 76903476

Max Phase: Preclinical

Molecular Formula: C24H24ClN5O3S2

Molecular Weight: 530.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)c1ccnc(-c2cccc3cc([C@H](NS(=O)(=O)C4CC4)c4nc(N)ncc4Cl)sc23)c1

Standard InChI:  InChI=1S/C24H24ClN5O3S2/c1-24(2,31)14-8-9-27-18(11-14)16-5-3-4-13-10-19(34-22(13)16)21(30-35(32,33)15-6-7-15)20-17(25)12-28-23(26)29-20/h3-5,8-12,15,21,30-31H,6-7H2,1-2H3,(H2,26,28,29)/t21-/m0/s1

Standard InChI Key:  IPVRCFZXAYJSOI-NRFANRHFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3746034

   N-[(R)-(2-amino-5-chloropyrimidin-4-yl)-[7-[4-(2-hydroxypropan-2-yl)pyridin-2-yl]-1-benzothiophen-2-yl]methyl]cyclopropanesulfonamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 530.08

Molecular Weight (Monoisotopic): 529.1009

AlogP: 4.39

#Rotatable Bonds: 7

Polar Surface Area: 131.09

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.50

CX Basic pKa: 3.90

CX LogP: 3.48

CX LogD: 3.46

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: -0.72

References

1. Pennington LD, Bartberger MD, Croghan MD, Andrews KL, Ashton KS, Bourbeau MP, Chen J, Chmait S, Cupples R, Fotsch C, Helmering J, Hong FT, Hungate RW, Jordan SR, Kong K, Liu L, Michelsen K, Moyer C, Nishimura N, Norman MH, Reichelt A, Siegmund AC, Sivits G, Tadesse S, Tegley CM, Van G, Yang KC, Yao G, Zhang J, Lloyd DJ, Hale C, St Jean DJ..  (2015)  Discovery and Structure-Guided Optimization of Diarylmethanesulfonamide Disrupters of Glucokinase-Glucokinase Regulatory Protein (GK-GKRP) Binding: Strategic Use of a N → S (nN → σ*S-X) Interaction for Conformational Constraint.,  58  (24): [PMID:26551034] [10.1021/acs.jmedchem.5b01367]

Source

Source(1):

• Scientific Literature