(Z)-2-hydroxy-4-oxo-4-phenylbut-2-enoic acid

ID: ALA467389

Chembl Id: CHEMBL467389

Cas Number: 113416-61-8

PubChem CID: 5496307

Max Phase: Preclinical

Molecular Formula: C10H8O4

Molecular Weight: 192.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C(O)=C/C(=O)c1ccccc1

Standard InChI:  InChI=1S/C10H8O4/c11-8(6-9(12)10(13)14)7-4-2-1-3-5-7/h1-6,12H,(H,13,14)/b9-6-

Standard InChI Key:  MNQJVITWJHOBFE-TWGQIWQCSA-N

Alternative Forms

1. Parent:

   

   ALA467389

   (2Z)-2-hydroxy-4-oxo-4-phenylbut-2-enoic 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: 192.17

Molecular Weight (Monoisotopic): 192.0423

AlogP: 1.40

#Rotatable Bonds: 3

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.47

CX Basic pKa:

CX LogP: 1.19

CX LogD: -2.32

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.43

Np Likeness Score: 0.24

References

1. Zeng LF, Jiang XH, Sanchez T, Zhang HS, Dayam R, Neamati N, Long YQ..  (2008)  Novel dimeric aryldiketo containing inhibitors of HIV-1 integrase: effects of the phenyl substituent and the linker orientation.,  16  (16): [PMID:18644730] [10.1016/j.bmc.2008.07.008]

2. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

3. Baughman BM, Jake Slavish P, DuBois RM, Boyd VA, White SW, Webb TR..  (2012)  Identification of influenza endonuclease inhibitors using a novel fluorescence polarization assay.,  7  (3): [PMID:22211528] [10.1021/cb200439z]

4. Tomassini J, Selnick H, Davies ME, Armstrong ME, Baldwin J, Bourgeois M, Hastings J, Hazuda D, Lewis J, McClements W..  (1994)  Inhibition of cap (m7GpppXm)-dependent endonuclease of influenza virus by 4-substituted 2,4-dioxobutanoic acid compounds.,  38  (12): [PMID:7695269] [10.1128/aac.38.12.2827]

5. Sechi M, Innocenti A, Pala N, Rogolino D, Carcelli M, Scozzafava A, Supuran CT..  (2012)  Inhibition of α-class cytosolic human carbonic anhydrases I, II, IX and XII, and β-class fungal enzymes by carboxylic acids and their derivatives: new isoform-I selective nanomolar inhibitors.,  22  (18): [PMID:22901388] [10.1016/j.bmcl.2012.07.094]

6. Yan Z, Zhang L, Fu H, Wang Z, Lin J..  (2014)  Design of the influenza virus inhibitors targeting the PA endonuclease using 3D-QSAR modeling, side-chain hopping, and docking.,  24  (2): [PMID:24365156] [10.1016/j.bmcl.2013.12.026]

7. Ju H, Zhang J, Huang B, Kang D, Huang B, Liu X, Zhan P..  (2017)  Inhibitors of Influenza Virus Polymerase Acidic (PA) Endonuclease: Contemporary Developments and Perspectives.,  60  (9): [PMID:28118010] [10.1021/acs.jmedchem.6b01227]

8. Cvijetić IN, Verbić TŽ, Ernesto de Resende P, Stapleton P, Gibbons S, Juranić IO, Drakulić BJ, Zloh M..  (2018)  Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains.,  143  [PMID:29133041] [10.1016/j.ejmech.2017.10.045]

9. Subbaiah MAM, Meanwell NA..  (2021)  Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design.,  64  (19.0): [PMID:34591488] [10.1021/acs.jmedchem.1c01215]

Source

Source(1):

• Scientific Literature