4-(5-((2-Carboxycyclohex-1-en-1-yl)amino)-5-oxopent-1-yn-1-yl)benzoic acid

ID: ALA4081260

PubChem CID: 137648318

Max Phase: Preclinical

Molecular Formula: C19H19NO5

Molecular Weight: 341.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC#Cc1ccc(C(=O)O)cc1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C19H19NO5/c21-17(20-16-7-3-2-6-15(16)19(24)25)8-4-1-5-13-9-11-14(12-10-13)18(22)23/h9-12H,2-4,6-8H2,(H,20,21)(H,22,23)(H,24,25)

Standard InChI Key:  MONVNASQEVKMMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   35.9921  -19.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9910  -20.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6990  -20.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4087  -20.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4059  -19.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6973  -18.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1098  -18.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8160  -18.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5221  -18.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2314  -18.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9375  -18.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6468  -18.4981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.9345  -17.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3530  -18.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0589  -18.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7630  -18.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7641  -17.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0550  -16.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3448  -17.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0582  -19.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3501  -19.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.7655  -19.7239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2830  -20.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5756  -20.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2823  -21.3808    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
  7  8  3  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  2  0
 20 22  1  0
  2 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081260

   ---

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: 341.36

Molecular Weight (Monoisotopic): 341.1263

AlogP: 2.55

#Rotatable Bonds: 5

Polar Surface Area: 103.70

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.06

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: -3.97

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.18

References

1. Bobileva O, Ikaunieks M, Duburs G, Mandrika I, Petrovska R, Klovins J, Loza E..  (2017)  Synthesis and evaluation of (E)-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists.,  25  (16): [PMID:28668361] [10.1016/j.bmc.2017.06.028]

Source

Source(1):

• Scientific Literature