2-(5-(2-Fluorophenyl)pent-4-ynamido)cyclohex-1-ene-1-carboxylic acid

ID: ALA4072283

PubChem CID: 137639493

Max Phase: Preclinical

Molecular Formula: C18H18FNO3

Molecular Weight: 315.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC#Cc1ccccc1F)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C18H18FNO3/c19-15-10-4-1-7-13(15)8-2-6-12-17(21)20-16-11-5-3-9-14(16)18(22)23/h1,4,7,10H,3,5-6,9,11-12H2,(H,20,21)(H,22,23)

Standard InChI Key:  MGVBXQPPYUJBKH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   33.6644  -14.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6632  -15.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3713  -16.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0809  -15.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0781  -14.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3695  -14.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7820  -14.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4882  -14.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1944  -13.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9036  -14.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6098  -13.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3190  -14.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6067  -12.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0252  -13.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7312  -14.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4352  -13.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4364  -12.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7273  -12.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0171  -12.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7304  -14.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0223  -15.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4377  -15.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7893  -16.1960    0.0000 F   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
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072283

   ---

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: 315.34

Molecular Weight (Monoisotopic): 315.1271

AlogP: 2.99

#Rotatable Bonds: 4

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: 3.03

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.55

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