4-((1R,3S)-3-amino-2,2,3-trimethylcyclopentylamino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide

ID: ALA4096145

PubChem CID: 117769575

Max Phase: Preclinical

Molecular Formula: C22H27N5O

Molecular Weight: 377.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@H](Nc2c(C(N)=O)cnn3cc(-c4ccccc4)cc23)CC[C@]1(C)N

Standard InChI:  InChI=1S/C22H27N5O/c1-21(2)18(9-10-22(21,3)24)26-19-16(20(23)28)12-25-27-13-15(11-17(19)27)14-7-5-4-6-8-14/h4-8,11-13,18,26H,9-10,24H2,1-3H3,(H2,23,28)/t18-,22+/m1/s1

Standard InChI Key:  DIFGSGNUHRNWPK-GCJKJVERSA-N

Molfile:  

     RDKit          2D

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    8.5434  -12.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5423  -11.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520  -14.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509  -15.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7589  -16.1773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7571  -14.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4657  -14.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4705  -15.7638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2506  -16.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7279  -15.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2428  -14.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7547  -13.7227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4612  -13.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442  -14.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3440  -13.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366  -14.9491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2091  -13.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7541  -13.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3433  -12.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3358  -11.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457  -11.9112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5451  -15.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9553  -16.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7717  -16.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1769  -15.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7598  -14.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9447  -14.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  7  4  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  2  0
  7 13  1  0
 14 13  1  1
  4 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  2 14  1  0
 20 21  1  0
 20 22  1  1
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096145

   4-{[(1r,3s)-3-Amino-2,2,3-Trimethylcyclopentyl]amino}-6-Phenylpyrrolo[1,2-B]pyridazine-3-Carboxamide

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: 377.49

Molecular Weight (Monoisotopic): 377.2216

AlogP: 3.42

#Rotatable Bonds: 4

Polar Surface Area: 98.44

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: 10.05

CX LogP: 3.16

CX LogD: 0.66

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.47

References

1. Hynes J, Wu H, Kempson J, Duan JJ, Lu Z, Jiang B, Stachura S, Tokarski JS, Sack JS, Khan JA, Lippy JS, Zhang RF, Pitt S, Shen G, Gillooly K, McIntyre K, Carter PH, Barrish JC, Nadler SG, Salter-Cid LM, Fura A, Schieven GL, Pitts WJ, Wrobleski ST..  (2017)  Discovery of potent and efficacious pyrrolopyridazines as dual JAK1/3 inhibitors.,  27  (14): [PMID:28539220] [10.1016/j.bmcl.2017.05.043]

Source

Source(1):

• Scientific Literature