3-(4-fluorophenyl)-2-hydroxyacrylic acid

ID: ALA4129710

Cas Number: 207910-84-7

PubChem CID: 56968856

Max Phase: Preclinical

Molecular Formula: C9H7FO3

Molecular Weight: 182.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C(O)=C/c1ccc(F)cc1

Standard InChI:  InChI=1S/C9H7FO3/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,11H,(H,12,13)/b8-5-

Standard InChI Key:  SOBWLKLZARZQOX-YVMONPNESA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   23.6559   -8.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6547   -9.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3628   -9.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0724   -9.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0696   -8.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3610   -8.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9467   -9.7668    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.7758   -8.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4850   -8.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4881   -9.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1912   -8.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9004   -8.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1881   -7.3018    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
  2  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4129710

   3-(4-Fluorophenyl)-2-hydroxyacrylic acid

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: 182.15

Molecular Weight (Monoisotopic): 182.0379

AlogP: 1.81

#Rotatable Bonds: 2

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.85

CX Basic pKa: ┄

CX LogP: 1.76

CX LogD: -1.73

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.54

Np Likeness Score: -0.11

References

1. Zhang D, Markoulides MS, Stepanovs D, Rydzik AM, El-Hussein A, Bon C, Kamps JJAG, Umland KD, Collins PM, Cahill ST, Wang DY, von Delft F, Brem J, McDonough MA, Schofield CJ..  (2018)  Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases.,  26  (11): [PMID:29655609] [10.1016/j.bmc.2018.02.043]

2. Burkett DJ, Wyatt BN, Mews M, Bautista A, Engel R, Dockendorff C, Donaldson WA, St Maurice M..  (2019)  Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors.,  27  (18): [PMID:31351848] [10.1016/j.bmc.2019.07.027]

Source

Source(1):

• Scientific Literature