US8933098, 1::US8933099, 1

ID: ALA3686863

Cas Number: 1529760-74-4

PubChem CID: 72695136

Max Phase: Preclinical

Molecular Formula: C21H25N3O4

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2CCC(O)CC2)nc1C(=O)Nc1c(C)cc(C(=O)O)cc1C

Standard InChI:  InChI=1S/C21H25N3O4/c1-12-4-5-17(24-8-6-16(25)7-9-24)22-19(12)20(26)23-18-13(2)10-15(21(27)28)11-14(18)3/h4-5,10-11,16,25H,6-9H2,1-3H3,(H,23,26)(H,27,28)

Standard InChI Key:  WOJKYHBOHSQZDW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -5.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -5.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -9.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2639  -10.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422  -10.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2395    3.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
 17 18  1  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
  5 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3686863

   4-[[6-(4-Hydroxy-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoic acid

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: 383.45

Molecular Weight (Monoisotopic): 383.1845

AlogP: 2.92

#Rotatable Bonds: 4

Polar Surface Area: 102.76

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.16

CX Basic pKa: 2.23

CX LogP: 3.35

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.11

References

1.  (2015)  Dimethyl-benzoic acid compounds, 

2.  (2015)  Monocyclic pyridine derivative, 

3. Blanco MJ, Vetman T, Chandrasekhar S, Fisher MJ, Harvey A, Kuklish SL, Chambers M, Lin C, Mudra D, Oskins J, Wang XS, Yu XP, Warshawsky AM..  (2016)  Identification and biological activity of 6-alkyl-substituted 3-methyl-pyridine-2-carbonyl amino dimethyl-benzoic acid EP4 antagonists.,  26  (9): [PMID:27020304] [10.1016/j.bmcl.2016.03.041]

Source

Source(2):

• Scientific Literature
• BindingDB Database