Methyl 3-(5-amino-2-chloro-4-fluoro-3-methylbenzamido)-4-(4-methylpiperazin-1-yl)benzoate

ID: ALA3907289

PubChem CID: 132580838

Max Phase: Preclinical

Molecular Formula: C21H24ClFN4O3

Molecular Weight: 434.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(N2CCN(C)CC2)c(NC(=O)c2cc(N)c(F)c(C)c2Cl)c1

Standard InChI:  InChI=1S/C21H24ClFN4O3/c1-12-18(22)14(11-15(24)19(12)23)20(28)25-16-10-13(21(29)30-3)4-5-17(16)27-8-6-26(2)7-9-27/h4-5,10-11H,6-9,24H2,1-3H3,(H,25,28)

Standard InChI Key:  PLRPRYDOPJNKDZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   11.9675   -9.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9664  -10.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6744  -11.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3841  -10.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3813   -9.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6727   -9.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6742  -11.9510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0925  -11.1319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7995  -10.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5079  -11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7982   -9.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5045  -11.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2120  -12.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9201  -11.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9162  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2081  -10.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6702   -8.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3767   -8.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9613   -8.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9674  -12.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9653  -13.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6711  -13.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3807  -13.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3845  -12.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6678  -14.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0856   -8.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2026   -9.9006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6290  -12.3495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.6218  -10.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2129  -13.1699    0.0000 N   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
  3  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 10  1  0
  6 17  1  0
 17 18  1  0
 17 19  2  0
  7 20  1  0
  7 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 18 26  1  0
 16 27  1  0
 14 28  1  0
 15 29  1  0
 13 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3907289

   ---

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: 434.90

Molecular Weight (Monoisotopic): 434.1521

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 87.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.44

CX LogP: 3.46

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.37

References

1. Li DD, Wang ZH, Chen WL, Xie YY, You QD, Guo XK..  (2016)  Structure-based design of ester compounds to inhibit MLL complex catalytic activity by targeting mixed lineage leukemia 1 (MLL1)-WDR5 interaction.,  24  (22): [PMID:27720555] [10.1016/j.bmc.2016.09.073]

Source

Source(1):

• Scientific Literature