2-Amino-4-((1R,4R)-4-hydroxycyclohexylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide

ID: ALA4092101

PubChem CID: 137655801

Max Phase: Preclinical

Molecular Formula: C13H18N6O2

Molecular Weight: 290.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c[nH]c2nc(N)nc(N[C@H]3CC[C@H](O)CC3)c12

Standard InChI:  InChI=1S/C13H18N6O2/c14-10(21)8-5-16-11-9(8)12(19-13(15)18-11)17-6-1-3-7(20)4-2-6/h5-7,20H,1-4H2,(H2,14,21)(H4,15,16,17,18,19)/t6-,7-

Standard InChI Key:  MGGSRUMGOBISBK-LJGSYFOKSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.6237  -11.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225  -12.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387  -12.4796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3368  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0535  -11.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0584  -12.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8473  -12.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3301  -11.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8395  -10.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3315  -10.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107  -12.4784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177   -9.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6146   -8.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049   -8.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950   -8.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9135  -10.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0902  -10.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8976  -10.0090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5336   -9.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -8.3734    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
  4 10  1  0
  2 11  1  0
 12 10  1  1
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  1  0
 18 19  1  0
 18 20  2  0
 15 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4092101

   ---

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: 290.33

Molecular Weight (Monoisotopic): 290.1491

AlogP: 0.35

#Rotatable Bonds: 3

Polar Surface Area: 142.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.62

CX Basic pKa: 7.70

CX LogP: -0.30

CX LogD: -0.93

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: -0.48

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