7-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-N-hydroxyoctanamide

ID: ALA4095596

PubChem CID: 137654793

Max Phase: Preclinical

Molecular Formula: C17H22N6O2

Molecular Weight: 342.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CCCCCC(=O)NO)n1cc(-c2ncnc3[nH]ccc23)cn1

Standard InChI:  InChI=1S/C17H22N6O2/c1-12(5-3-2-4-6-15(24)22-25)23-10-13(9-21-23)16-14-7-8-18-17(14)20-11-19-16/h7-12,25H,2-6H2,1H3,(H,22,24)(H,18,19,20)

Standard InChI Key:  RTLKDFQWSQARBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.3921   -6.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6817   -6.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9724   -6.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2620   -6.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5507   -6.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8402   -6.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1310   -6.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1286   -5.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3897   -5.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1013   -6.8315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1038   -7.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4206   -6.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6724   -6.5107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279   -7.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -7.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3381   -7.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403  -10.0815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3560   -9.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6888   -9.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2038   -8.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896   -8.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9648  -10.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5034   -9.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6753  -10.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  9  2  0
  1 10  1  0
 10 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 12 16  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 24 25  2  0
 23 25  1  0
 19 23  1  0
 20 24  1  0
 15 21  1  0
  7 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095596

   ---

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: 342.40

Molecular Weight (Monoisotopic): 342.1804

AlogP: 2.84

#Rotatable Bonds: 8

Polar Surface Area: 108.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: 3.91

CX LogP: 1.92

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.33

Np Likeness Score: -0.65

References

1. Yao L, Mustafa N, Tan EC, Poulsen A, Singh P, Duong-Thi MD, Lee JXT, Ramanujulu PM, Chng WJ, Yen JJY, Ohlson S, Dymock BW..  (2017)  Design and Synthesis of Ligand Efficient Dual Inhibitors of Janus Kinase (JAK) and Histone Deacetylase (HDAC) Based on Ruxolitinib and Vorinostat.,  60  (20): [PMID:28953386] [10.1021/acs.jmedchem.7b00678]

2. Chu-Farseeva YY, Mustafa N, Poulsen A, Tan EC, Yen JJY, Chng WJ, Dymock BW..  (2018)  Design and synthesis of potent dual inhibitors of JAK2 and HDAC based on fusing the pharmacophores of XL019 and vorinostat.,  158  [PMID:30243158] [10.1016/j.ejmech.2018.09.024]

Source

Source(1):

• Scientific Literature