(1R,2S,3R,5R)-3-(2-(2,6-dimethylpyridin-4-ylamino)-5-(quinolin-2-yl)pyrimidin-4-ylamino)-5-(hydroxymethyl)cyclopentane-1,2-diol

ID: ALA3601192

PubChem CID: 118453722

Max Phase: Preclinical

Molecular Formula: C26H28N6O3

Molecular Weight: 472.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2ncc(-c3ccc4ccccc4n3)c(N[C@@H]3C[C@H](CO)[C@@H](O)[C@H]3O)n2)cc(C)n1

Standard InChI:  InChI=1S/C26H28N6O3/c1-14-9-18(10-15(2)28-14)29-26-27-12-19(21-8-7-16-5-3-4-6-20(16)30-21)25(32-26)31-22-11-17(13-33)23(34)24(22)35/h3-10,12,17,22-24,33-35H,11,13H2,1-2H3,(H2,27,28,29,31,32)/t17-,22-,23-,24+/m1/s1

Standard InChI Key:  LKWUVRWXZPRGNM-BMZZKGLRSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA3601192

   (1R,2S,3R,5R)-3-[[2-[(2,6-dimethylpyridin-4-yl)amino]-5-quinolin-2-ylpyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol

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: 472.55

Molecular Weight (Monoisotopic): 472.2223

AlogP: 2.96

#Rotatable Bonds: 6

Polar Surface Area: 136.31

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.66

CX Basic pKa: 8.61

CX LogP: 1.65

CX LogD: 0.49

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: -0.24

References

1. Seganish WM, McElroy WT, Herr RJ, Brumfield S, Greenlee WJ, Harding J, Komanduri V, Matasi J, Prakash KC, Tulshian D, Yang J, Yet L, Devito K, Fossetta J, Garlisi CG, Lundell D, Niu X, Sondey C..  (2015)  Initial optimization and series evolution of diaminopyrimidine inhibitors of interleukin-1 receptor associated kinase 4.,  25  (16): [PMID:26115573] [10.1016/j.bmcl.2015.05.097]

Source

Source(1):

• Scientific Literature