2-(4-(4-(4-(5-fluoro-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)cyclohex-3-enyl)piperidin-1-yl)acetic acid

ID: ALA4874984

PubChem CID: 90419912

Max Phase: Preclinical

Molecular Formula: C27H30FN3O3

Molecular Weight: 463.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1-c1ccnc2[nH]c(C3=CCC(C4CCN(CC(=O)O)CC4)CC3)cc12

Standard InChI:  InChI=1S/C27H30FN3O3/c1-34-25-7-6-20(28)14-22(25)21-8-11-29-27-23(21)15-24(30-27)19-4-2-17(3-5-19)18-9-12-31(13-10-18)16-26(32)33/h4,6-8,11,14-15,17-18H,2-3,5,9-10,12-13,16H2,1H3,(H,29,30)(H,32,33)

Standard InChI Key:  QMCUOTZYJAWGFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    2.6153   -9.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141  -10.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290  -11.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454  -10.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0426   -9.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272   -9.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555   -9.4648    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8993  -11.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852  -10.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3288  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144  -12.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139  -13.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3288  -13.5962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0428  -12.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502  -13.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308  -13.4210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3060  -12.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1310  -12.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489  -13.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3703  -13.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7803  -12.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3626  -12.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5349  -12.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6053  -12.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0154  -13.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8368  -13.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2494  -12.7323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8345  -12.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068  -12.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0744  -12.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4880  -13.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3130  -13.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0765  -14.1601    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
 22 25  1  0
 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  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874984

   US9796708, Example 1339

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: 463.55

Molecular Weight (Monoisotopic): 463.2271

AlogP: 5.36

#Rotatable Bonds: 6

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: 1.91

CX Basic pKa: 9.82

CX LogP: 1.63

CX LogD: 1.63

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.51

Np Likeness Score: -0.21

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