(1s,4s)-4-(4-(4-(5-fluoro-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)cyclohexanecarboxylic acid

ID: ALA4861217

Max Phase: Preclinical

Molecular Formula: C26H28FN3O3

Molecular Weight: 449.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1-c1ccnc2[nH]c(C3=CCN([C@H]4CC[C@@H](C(=O)O)CC4)CC3)cc12

Standard InChI:  InChI=1S/C26H28FN3O3/c1-33-24-7-4-18(27)14-21(24)20-8-11-28-25-22(20)15-23(29-25)16-9-12-30(13-10-16)19-5-2-17(3-6-19)26(31)32/h4,7-9,11,14-15,17,19H,2-3,5-6,10,12-13H2,1H3,(H,28,29)(H,31,32)/t17-,19+

Standard InChI Key:  JQQQJMZBOAYKKR-IZAXUBKRSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   14.0366  -17.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0355  -18.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7503  -18.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4668  -18.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4639  -17.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7485  -16.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1769  -16.8235    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.3206  -18.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6065  -18.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7501  -19.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0358  -19.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0352  -20.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7502  -20.9550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4642  -19.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4714  -20.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2521  -20.7798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7274  -20.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2403  -19.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5523  -20.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9680  -20.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7894  -20.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1994  -20.0968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7817  -19.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9540  -19.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0244  -20.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4367  -20.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2581  -20.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6709  -20.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2558  -19.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4282  -19.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4959  -20.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9093  -20.8038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9074  -19.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 15  1  0
 14 10  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 17 19  1  0
 19 20  1  0
 19 24  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 25 22  1  1
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  1  1
 31 32  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4861217

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 449.53

Molecular Weight (Monoisotopic): 449.2115

AlogP: 5.11

#Rotatable Bonds: 5

Polar Surface Area: 78.45

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.34

CX Basic pKa: 9.51

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.57

Np Likeness Score: -0.28

References

1. Tong Y, Florjancic AS, Clark RF, Lai C, Mastracchio A, Zhu GD, Smith ML, Kovar PJ, Shaw B, Albert DH, Qiu W, Longenecker KL, Liu X, Olson AM, Osterling DJ, Tahir SK, Phillips DC, Leverson JD, Souers AJ, Penning TD..  (2021)  Balancing Properties with Carboxylates: A Lead Optimization Campaign for Selective and Orally Active CDK9 Inhibitors.,  12  (7.0): [PMID:34267880] [10.1021/acsmedchemlett.1c00161]

Source

Source(1):

• Scientific Literature