2-Amino-4-(3-(hydroxymethyl)phenyl)-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

ID: ALA4095624

PubChem CID: 137653144

Max Phase: Preclinical

Molecular Formula: C14H11N5O

Molecular Weight: 265.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c2nc(N)nc(-c3cccc(CO)c3)c12

Standard InChI:  InChI=1S/C14H11N5O/c15-5-10-6-17-13-11(10)12(18-14(16)19-13)9-3-1-2-8(4-9)7-20/h1-4,6,20H,7H2,(H3,16,17,18,19)

Standard InChI Key:  VWQRYITYQPASHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    3.7709  -12.0019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697  -12.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778  -13.2304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4760  -11.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846  -11.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894  -12.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694  -13.0654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468  -12.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9617  -11.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617  -13.2295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2086  -10.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4565  -10.1859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707  -10.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1788  -10.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768   -9.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4673   -9.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7585   -9.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640  -10.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0481   -9.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -8.3389    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
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  4 13  1  0
 17 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095624

   ---

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: 265.28

Molecular Weight (Monoisotopic): 265.0964

AlogP: 1.57

#Rotatable Bonds: 2

Polar Surface Area: 111.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.36

CX Basic pKa: 4.87

CX LogP: 1.49

CX LogD: 1.49

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: -0.49

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