2-Amino-4-((1RS,2SR,3RS)-2,3-dihydroxycyclopentylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

ID: ALA4096327

PubChem CID: 137655941

Max Phase: Preclinical

Molecular Formula: C12H14N6O2

Molecular Weight: 274.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c2nc(N)nc(N[C@@H]3CC[C@@H](O)[C@H]3O)c12

Standard InChI:  InChI=1S/C12H14N6O2/c13-3-5-4-15-10-8(5)11(18-12(14)17-10)16-6-1-2-7(19)9(6)20/h4,6-7,9,19-20H,1-2H2,(H4,14,15,16,17,18)/t6-,7-,9+/m1/s1

Standard InChI Key:  XINWVEOLLNEWDD-BHNWBGBOSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    4.0887  -12.5674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875  -13.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956  -13.7959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938  -12.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024  -12.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5072  -13.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2872  -13.6308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7646  -12.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795  -12.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795  -13.7949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5263  -11.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743  -10.7513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913  -11.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824  -10.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922  -10.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1923   -9.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858  -10.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345  -11.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1650  -12.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734  -10.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
 11 12  3  0
  9 11  1  0
  4 13  1  0
 14 13  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 18 19  1  6
 17 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4096327

   ---

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: 274.28

Molecular Weight (Monoisotopic): 274.1178

AlogP: -0.29

#Rotatable Bonds: 2

Polar Surface Area: 143.87

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.04

CX Basic pKa: 6.82

CX LogP: -0.51

CX LogD: -0.62

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.51

Np Likeness Score: 0.09

References

1. Anthony NG, Baiget J, Berretta G, Boyd M, Breen D, Edwards J, Gamble C, Gray AI, Harvey AL, Hatziieremia S, Ho KH, Huggan JK, Lang S, Llona-Minguez S, Luo JL, McIntosh K, Paul A, Plevin RJ, Robertson MN, Scott R, Suckling CJ, Sutcliffe OB, Young LC, Mackay SP..  (2017)  Inhibitory Kappa B Kinase α (IKKα) Inhibitors That Recapitulate Their Selectivity in Cells against Isoform-Related Biomarkers.,  60  (16): [PMID:28737909] [10.1021/acs.jmedchem.7b00484]

Source

Source(1):

• Scientific Literature