[2-(2,6-Dichloro-4-hydroxy-phenylamino)-phenyl]-acetic acid

ID: ALA1030

Chembl Id: CHEMBL1030

Cas Number: 64118-84-9

PubChem CID: 116545

Product Number: H135247

Max Phase: Preclinical

Molecular Formula: C14H11Cl2NO3

Molecular Weight: 312.15

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4'-Hydroxy-Diclofenac | 4'-Hydroxydiclofenac|4'-Hydroxy Diclofenac|64118-84-9|4-hydroxy diclofenac|(o-(2,6-Dichloro-4-hydroxyanilino)phenyl)acetic acid|CHEBI:59613|4'-OH DCF|{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid|2-[2-(2,6-dichloro-4-hydroxyanilino)phenyl]acetic acid|Benzeneacetic acid, 2-((2,6-dichloro-4-hydroxyphenyl)amino)-|NJF5O599EF|4'-HYDROXY-DICLOFENAC|2-(2-((2,6-Dichloro-4-hydroxyphenyl)amino)phenyl)acetic acid|2-[(2,6-Dichloro-4-hydroxyphenyl)amino]benzeneacetic AcidShow More⌵

Canonical SMILES:  O=C(O)Cc1ccccc1Nc1c(Cl)cc(O)cc1Cl

Standard InChI:  InChI=1S/C14H11Cl2NO3/c15-10-6-9(18)7-11(16)14(10)17-12-4-2-1-3-8(12)5-13(19)20/h1-4,6-7,17-18H,5H2,(H,19,20)

Standard InChI Key:  KGVXVPRLBMWZLG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1030

   4'-HYDROXY-DICLOFENAC

Molecule Features

Natural Product: Yes

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: 312.15

Molecular Weight (Monoisotopic): 311.0116

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 69.56

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 0.65

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.74

Np Likeness Score: -0.50

References

1. Moser P, Sallmann A, Wiesenberg I..  (1990)  Synthesis and quantitative structure-activity relationships of diclofenac analogues.,  33  (9): [PMID:2118185] [10.1021/jm00171a008]

2. Arvind K, Solomon KA, Rajan SS.  (2013)  QSAR studies on diclofenac analogues as potent cyclooxygenase inhibitors using CoMFA and CoMSIA,  [10.1007/s00044-013-0771-5]

3. Drug metabolism data, 

4. Tian Y, Shehata MA, Gauger SJ, Ng CKL, Solbak S, Thiesen L, Bruus-Jensen J, Krall J, Bundgaard C, Gibson KM, Wellendorph P, Frølund B..  (2022)  Discovery and Optimization of 5-Hydroxy-Diclofenac toward a New Class of Ligands with Nanomolar Affinity for the CaMKIIα Hub Domain.,  65  (9.0): [PMID:35500061] [10.1021/acs.jmedchem.1c02177]

Source

Source(2):

• Scientific Literature
• Curated Drug Metabolism Pathways