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

ID: ALA4091542

PubChem CID: 137653428

Max Phase: Preclinical

Molecular Formula: C18H18FNO3

Molecular Weight: 315.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18FNO3/c19-14-11-9-13(10-12-14)5-1-4-8-17(21)20-16-7-3-2-6-15(16)18(22)23/h9-12H,2-4,6-8H2,(H,20,21)(H,22,23)

Standard InChI Key:  AQWGYJFRPFICJL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    1.6949  -24.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937  -25.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018  -26.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1114  -25.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086  -24.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000  -24.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125  -24.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187  -24.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249  -23.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9341  -24.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6403  -23.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495  -24.0327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6372  -22.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0557  -23.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7617  -24.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4657  -23.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4669  -22.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7578  -22.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0475  -22.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609  -24.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0528  -25.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4682  -25.2586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9857  -26.0982    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
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091542

   ---

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: 3.14

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: -0.47

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.52

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