3-(5-tert-Butylisoxazol-3-yl)-4-((3-chlorophenyl)diazenyl)-1H-pyrazol-5-amine

ID: ALA3593479

PubChem CID: 137091080

Max Phase: Preclinical

Molecular Formula: C16H17ClN6O

Molecular Weight: 344.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(-c2n[nH]c(N)c2/N=N/c2cccc(Cl)c2)no1

Standard InChI:  InChI=1S/C16H17ClN6O/c1-16(2,3)12-8-11(23-24-12)13-14(15(18)22-20-13)21-19-10-6-4-5-9(17)7-10/h4-8H,1-3H3,(H3,18,20,22)/b21-19+

Standard InChI Key:  QPRYHWMWMOIDQO-XUTLUUPISA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872   -1.9607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100   -6.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -6.0211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7951   -7.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -8.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -7.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -9.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5737  -10.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6339  -10.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  1  1  0
  4  8  1  0
  2  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 10  2  0
 14 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3593479

   ---

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: 344.81

Molecular Weight (Monoisotopic): 344.1152

AlogP: 5.01

#Rotatable Bonds: 3

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.90

CX Basic pKa: 1.70

CX LogP: 4.80

CX LogD: 4.79

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -1.49

References

1. Ye N, Zhu Y, Chen H, Liu Z, Mei FC, Wild C, Chen H, Cheng X, Zhou J..  (2015)  Structure-Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N'-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists.,  58  (15): [PMID:26151319] [10.1021/acs.jmedchem.5b00635]

Source

Source(1):

• Scientific Literature