N-(3,5-dimethylphenyl)-4-(4-(4-fluorophenyl)-1-(piperidin-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

ID: ALA4521096

PubChem CID: 137701509

Max Phase: Preclinical

Molecular Formula: C26H27FN6

Molecular Weight: 442.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(Nc2nccc(-c3c(-c4ccc(F)cc4)ncn3C3CCNCC3)n2)c1

Standard InChI:  InChI=1S/C26H27FN6/c1-17-13-18(2)15-21(14-17)31-26-29-12-9-23(32-26)25-24(19-3-5-20(27)6-4-19)30-16-33(25)22-7-10-28-11-8-22/h3-6,9,12-16,22,28H,7-8,10-11H2,1-2H3,(H,29,31,32)

Standard InChI Key:  DGOVBHLIYNOJOQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    4.6954  -21.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942  -22.3678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023  -22.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1119  -22.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091  -21.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005  -21.1394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876  -21.1398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9874  -20.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974  -19.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6975  -19.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9892  -18.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2826  -19.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4071  -23.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458  -24.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9982  -24.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8154  -24.8515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0680  -24.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8399  -23.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4471  -24.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2237  -24.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3943  -23.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7823  -22.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0080  -23.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1713  -23.0656    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720  -23.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8040  -23.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0309  -22.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4204  -23.3138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884  -24.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3669  -24.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700  -18.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054  -18.6913    0.0000 C   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
  1  7  1  0
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  8  9  2  0
  9 10  1  0
 10 11  2  0
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 12 13  2  0
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 17 18  1  0
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  3 14  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 19  1  0
 22 25  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 15 26  1  0
 12 32  1  0
 10 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521096

   ---

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: 442.54

Molecular Weight (Monoisotopic): 442.2281

AlogP: 5.43

#Rotatable Bonds: 5

Polar Surface Area: 67.66

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.37

CX Basic pKa: 10.13

CX LogP: 5.07

CX LogD: 2.46

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -1.19

References

1. Divakaran A, Talluri SK, Ayoub AM, Mishra NK, Cui H, Widen JC, Berndt N, Zhu JY, Carlson AS, Topczewski JJ, Schonbrunn EK, Harki DA, Pomerantz WCK..  (2018)  Molecular Basis for the N-Terminal Bromodomain-and-Extra-Terminal-Family Selectivity of a Dual Kinase-Bromodomain Inhibitor.,  61  (20): [PMID:30253095] [10.1021/acs.jmedchem.8b01248]

2. Cui H, Divakaran A, Hoell ZJ, Ellingson MO, Scholtz CR, Zahid H, Johnson JA, Griffith EC, Gee CT, Lee AL, Khanal S, Shi K, Aihara H, Shah VH, Lee RE, Harki DA, Pomerantz WCK..  (2022)  A Structure-based Design Approach for Generating High Affinity BRD4 D1-Selective Chemical Probes.,  65  (3.0): [PMID:35007061] [10.1021/acs.jmedchem.1c01779]

3. Divakaran A, Scholtz CR, Zahid H, Lin W, Griffith EC, Lee RE, Chen T, Harki DA, Pomerantz WCK..  (2022)  Development of an N-Terminal BRD4 Bromodomain-Targeted Degrader.,  13  (10.0): [PMID:36262390] [10.1021/acsmedchemlett.2c00300]

Source

Source(1):

• Scientific Literature