trans-4-(3-(4-(4-fluorophenoxy)cyclohexyl)ureido)benzoic acid

ID: ALA3100011

Max Phase: Preclinical

Molecular Formula: C20H21FN2O4

Molecular Weight: 372.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C(=O)O)cc1)N[C@H]1CC[C@H](Oc2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C20H21FN2O4/c21-14-3-9-17(10-4-14)27-18-11-7-16(8-12-18)23-20(26)22-15-5-1-13(2-6-15)19(24)25/h1-6,9-10,16,18H,7-8,11-12H2,(H,24,25)(H2,22,23,26)/t16-,18-

Standard InChI Key:  GVMGPQHXRIFVME-SAABIXHNSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   26.1559  -16.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1548  -17.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8695  -17.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5860  -17.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5831  -16.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8677  -16.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3010  -17.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0148  -17.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7300  -17.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0135  -16.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4437  -17.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1593  -17.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8710  -17.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8740  -16.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1590  -16.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4412  -16.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5893  -16.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3028  -16.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2983  -17.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0110  -17.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7273  -17.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7265  -16.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0132  -16.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4414  -17.7249    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.4413  -16.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4411  -15.2412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7270  -16.4788    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
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11  9  1  6
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  1
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
  1 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100011

   ---

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: 372.40

Molecular Weight (Monoisotopic): 372.1485

AlogP: 4.04

#Rotatable Bonds: 5

Polar Surface Area: 87.66

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.14

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -1.07

References

1. Chen T, Takrouri K, Hee-Hwang S, Rana S, Yefidoff-Freedman R, Halperin J, Natarajan A, Morisseau C, Hammock B, Chorev M, Aktas BH..  (2013)  Explorations of substituted urea functionality for the discovery of new activators of the heme-regulated inhibitor kinase.,  56  (23): [PMID:24261904] [10.1021/jm400793v]

Source

Source(1):

• Scientific Literature