(E)-2-(5-Phenylpent-2-enamido)cyclohex-1-ene-1-carboxylic acid

ID: ALA4083723

PubChem CID: 137645601

Max Phase: Preclinical

Molecular Formula: C18H21NO3

Molecular Weight: 299.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/CCc1ccccc1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C18H21NO3/c20-17(13-7-4-10-14-8-2-1-3-9-14)19-16-12-6-5-11-15(16)18(21)22/h1-3,7-9,13H,4-6,10-12H2,(H,19,20)(H,21,22)/b13-7+

Standard InChI Key:  NAPQUZBIWSOOFS-NTUHNPAUSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   26.0051   -8.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7153   -7.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4287   -8.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1390   -7.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8524   -8.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1359   -6.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5627   -7.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2728   -8.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9810   -7.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9821   -6.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2689   -6.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5545   -6.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2720   -9.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5598   -9.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9835   -9.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2958   -7.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5855   -8.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8754   -7.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1656   -8.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1682   -9.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8866   -9.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5934   -9.0560    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  1  0
  4  6  2  0
  5  7  1  0
  7  8  2  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083723

   ---

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: 299.37

Molecular Weight (Monoisotopic): 299.1521

AlogP: 3.20

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.50

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: -0.11

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 0.39

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