2-hydroxy-3-(4-hydroxyphenyl)-2-propenoic acid

ID: ALA4463181

Cas Number: 10589-28-3

PubChem CID: 636708

Max Phase: Preclinical

Molecular Formula: C9H8O4

Molecular Weight: 180.16

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-

Standard InChI Key:  GQYBCIHRWMPOOF-YVMONPNESA-N

Molfile:  

 
     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   19.3980  -22.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3980  -22.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1033  -23.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085  -22.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8085  -22.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1033  -21.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5174  -21.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2239  -22.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9328  -21.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6394  -22.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9352  -20.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2215  -22.9763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6909  -23.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  8 12  1  0
  2 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4463181

   2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 180.16

Molecular Weight (Monoisotopic): 180.0423

AlogP: 1.38

#Rotatable Bonds: 2

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.97

CX Basic pKa: ┄

CX LogP: 1.31

CX LogD: -2.17

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.47

Np Likeness Score: 0.91

References

1. 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