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

ID: ALA4063682

PubChem CID: 137635325

Max Phase: Preclinical

Molecular Formula: C18H19NO4

Molecular Weight: 313.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H19NO4/c20-14-11-9-13(10-12-14)5-1-4-8-17(21)19-16-7-3-2-6-15(16)18(22)23/h9-12,20H,2-4,6-8H2,(H,19,21)(H,22,23)

Standard InChI Key:  NMJKTRUTPRUSCO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   11.9964  -15.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9953  -16.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7033  -16.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4130  -16.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4102  -15.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7015  -15.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1141  -15.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8203  -14.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5264  -14.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2357  -14.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9418  -14.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6511  -14.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9388  -13.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3572  -14.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0632  -14.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7673  -14.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7684  -13.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0593  -12.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3491  -13.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0625  -15.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3544  -15.8224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7698  -15.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2873  -16.6634    0.0000 O   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:

   

   ALA4063682

   ---

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: 313.35

Molecular Weight (Monoisotopic): 313.1314

AlogP: 2.55

#Rotatable Bonds: 4

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: 3.15

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: -0.91

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.75

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