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

ID: ALA4083762

PubChem CID: 137647495

Max Phase: Preclinical

Molecular Formula: C22H23NO4

Molecular Weight: 365.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccc(-c2cccc(O)c2)cc1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C22H23NO4/c24-18-5-3-4-17(14-18)16-11-8-15(9-12-16)10-13-21(25)23-20-7-2-1-6-19(20)22(26)27/h3-5,8-9,11-12,14,24H,1-2,6-7,10,13H2,(H,23,25)(H,26,27)

Standard InChI Key:  OXNOGHLVIWCQGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   26.8264  -23.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5367  -23.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2500  -23.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9562  -23.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6696  -23.8469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9531  -22.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3799  -23.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0900  -23.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7982  -23.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7993  -22.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0861  -22.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3717  -22.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0892  -24.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3770  -25.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8006  -25.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1151  -23.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4053  -23.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4079  -24.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1263  -25.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8331  -24.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7009  -25.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9867  -24.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2815  -25.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2853  -25.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0000  -26.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7064  -25.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0071  -27.1516    0.0000 O   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
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083762

   ---

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: 365.43

Molecular Weight (Monoisotopic): 365.1627

AlogP: 4.02

#Rotatable Bonds: 6

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.37

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 0.31

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.06

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