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

ID: ALA4099238

PubChem CID: 137661636

Max Phase: Preclinical

Molecular Formula: C18H18ClNO3

Molecular Weight: 331.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC#Cc1ccccc1Cl)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C18H18ClNO3/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:  CJXRUYLKNHUDNN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   21.4891  -15.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4879  -15.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1960  -16.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9056  -15.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9028  -15.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1942  -14.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6067  -14.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3129  -14.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0191  -13.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7283  -14.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4345  -13.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1437  -14.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4314  -13.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8499  -13.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5559  -14.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2599  -13.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2611  -13.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5520  -12.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8417  -13.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5551  -15.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8470  -15.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2624  -15.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6140  -16.3239    0.0000 Cl  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:

   

   ALA4099238

   ---

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: 331.80

Molecular Weight (Monoisotopic): 331.0975

AlogP: 3.50

#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: 3.07

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: -0.01

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: -0.44

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