2-(3-(2'-Fluoro-[1,1'-biphenyl]-4-yl)propanamido)cyclohex-1-ene-1-carboxylic acid

ID: ALA4100231

PubChem CID: 137662135

Max Phase: Preclinical

Molecular Formula: C22H22FNO3

Molecular Weight: 367.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccc(-c2ccccc2F)cc1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C22H22FNO3/c23-19-7-3-1-5-17(19)16-12-9-15(10-13-16)11-14-21(25)24-20-8-4-2-6-18(20)22(26)27/h1,3,5,7,9-10,12-13H,2,4,6,8,11,14H2,(H,24,25)(H,26,27)

Standard InChI Key:  OXFZQKJMXVWWHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   17.8951  -29.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6053  -28.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3187  -28.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0249  -28.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7382  -28.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0218  -27.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4485  -28.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1587  -28.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8668  -28.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8680  -27.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1548  -27.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4404  -27.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1579  -29.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4457  -30.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8693  -30.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1838  -28.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4739  -29.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4766  -29.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1949  -30.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9018  -29.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7696  -30.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0554  -29.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3502  -30.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3539  -31.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0687  -31.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7750  -31.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4901  -31.4620    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  1  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100231

   ---

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: 367.42

Molecular Weight (Monoisotopic): 367.1584

AlogP: 4.45

#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: 3.35

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 0.75

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.54

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