1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

ID: ALA269550

Chembl Id: CHEMBL269550

Max Phase: Preclinical

Molecular Formula: C14H15NO4

Molecular Weight: 261.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(O)C(=O)N(Cc2ccccc2)C1

Standard InChI:  InChI=1S/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,16H,2,8-9H2,1H3

Standard InChI Key:  IGYRPDIWSYGHMY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA269550

   ---

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: 261.28

Molecular Weight (Monoisotopic): 261.1001

AlogP: 1.40

#Rotatable Bonds: 4

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.65

CX Basic pKa: ┄

CX LogP: 1.17

CX LogD: 1.17

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.83

Np Likeness Score: -0.60

References

1. Mylari BL, Beyer TA, Siegel TW..  (1991)  A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate, and its congeners.,  34  (3): [PMID:1900532] [10.1021/jm00107a020]

2. Ishii A, Kotani T, Nagaki Y, Shibayama Y, Toyomaki Y, Okukado N, Ienaga K, Okamoto K..  (1996)  Highly selective aldose reductase inhibitors. 1. 3-(Arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic acids.,  39  (9): [PMID:8627616] [10.1021/jm9508393]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6