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

ID: ALA4060899

PubChem CID: 137635425

Max Phase: Preclinical

Molecular Formula: C18H18FNO4

Molecular Weight: 331.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC#Cc1ccc(O)cc1F)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C18H18FNO4/c19-15-11-13(21)10-9-12(15)5-1-4-8-17(22)20-16-7-3-2-6-14(16)18(23)24/h9-11,21H,2-4,6-8H2,(H,20,22)(H,23,24)

Standard InChI Key:  JJMDNSVHZBHZGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.0209  -19.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198  -20.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278  -21.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375  -20.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347  -19.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260  -19.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386  -19.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8448  -18.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5509  -18.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602  -18.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9663  -18.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6756  -18.9727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9632  -17.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817  -18.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0877  -18.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7918  -18.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7929  -17.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838  -17.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3736  -17.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0869  -19.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3788  -20.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7943  -20.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117  -21.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458  -21.0372    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
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4060899

   ---

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: 331.34

Molecular Weight (Monoisotopic): 331.1220

AlogP: 2.69

#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: 3.05

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: -0.80

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.25

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