5-amino-N-(4'-amino-4-(4-methylpiperazin-1-yl)-[1,1'-biphenyl]-3-yl)-2-chloro-4-fluoro-3-methylbenzamide

ID: ALA3885241

PubChem CID: 134131003

Max Phase: Preclinical

Molecular Formula: C25H27ClFN5O

Molecular Weight: 467.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(F)c(N)cc(C(=O)Nc2cc(-c3ccc(N)cc3)ccc2N2CCN(C)CC2)c1Cl

Standard InChI:  InChI=1S/C25H27ClFN5O/c1-15-23(26)19(14-20(29)24(15)27)25(33)30-21-13-17(16-3-6-18(28)7-4-16)5-8-22(21)32-11-9-31(2)10-12-32/h3-8,13-14H,9-12,28-29H2,1-2H3,(H,30,33)

Standard InChI Key:  HVMNEZGNJGWWQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   17.1034   -6.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8210   -6.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5222   -6.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2357   -6.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2438   -7.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5385   -8.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8291   -7.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9572   -8.0078    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.9410   -6.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5141   -5.5690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.0953   -5.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4022   -6.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6888   -6.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9834   -6.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2700   -6.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2619   -5.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9672   -5.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6807   -5.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9915   -7.6543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2859   -8.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2920   -8.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0036   -9.2887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7107   -8.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7062   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0086  -10.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9573   -4.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6615   -3.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6519   -3.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9387   -2.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2337   -3.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2468   -3.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5456   -8.8392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9276   -1.9311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  5  8  1  0
  4  9  1  0
  3 10  1  0
  1 11  2  0
  1 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 14 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 17 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
  6 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885241

   ---

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: 467.98

Molecular Weight (Monoisotopic): 467.1888

AlogP: 4.62

#Rotatable Bonds: 4

Polar Surface Area: 87.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.62

CX LogP: 4.27

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.49

Np Likeness Score: -1.19

References

1. Li DD, Chen WL, Wang ZH, Xie YY, Xu XL, Jiang ZY, Zhang XJ, You QD, Guo XK..  (2016)  High-affinity small molecular blockers of mixed lineage leukemia 1 (MLL1)-WDR5 interaction inhibit MLL1 complex H3K4 methyltransferase activity.,  124  [PMID:27598236] [10.1016/j.ejmech.2016.08.036]

2. Chen WL,Li DD,Chen X,Wang YZ,Xu JJ,Jiang ZY,You QD,Guo XK.  (2020)  Proton pump inhibitors selectively suppress MLL rearranged leukemia cells via disrupting MLL1-WDR5 protein-protein interaction.,  188  [PMID:31923859] [10.1016/j.ejmech.2019.112027]

Source

Source(1):

• Scientific Literature