ID: ALA1105

Max Phase: Unknown

Molecular Formula: C13H12O3

Molecular Weight: 216.24

Molecule Type: Small molecule

Representations

Synonyms (1): 6-methoxy-2-naphthylacetic acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc2cc(CC(=O)O)ccc2c1

Standard InChI:  InChI=1S/C13H12O3/c1-16-12-5-4-10-6-9(7-13(14)15)2-3-11(10)8-12/h2-6,8H,7H2,1H3,(H,14,15)

Standard InChI Key:  PHJFLPMVEFKEPL-UHFFFAOYSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 216.24

Molecular Weight (Monoisotopic): 216.0786

AlogP: 2.48

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.16

CX Basic pKa:

CX LogP: 2.44

CX LogD: -0.62

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.86

Np Likeness Score: -0.09

References

1. Hellberg MR, Namil A, Delgado P, David KC, Kessler TL, Graff G, Haggard KS, Nixon JC..  (1999)  Novel esters and amides of nonsteroidal antiinflammatory carboxylic acids as antioxidants and antiproliferative agents.,  42  (2): [PMID:9925732] [10.1021/jm980430o]

2. Hsu N, Cai D, Damodaran K, Gomez RF, Keck JG, Laborde E, Lum RT, Macke TJ, Martin G, Schow SR, Simon RJ, Villar HO, Wick MM, Beroza P..  (2004)  Novel cyclooxygenase-1 inhibitors discovered using affinity fingerprints.,  47  (20): [PMID:15369391] [10.1021/jm049950b]

3. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

4. Windsor MA, Hermanson DJ, Kingsley PJ, Xu S, Crews BC, Ho W, Keenan CM, Banerjee S, Sharkey KA, Marnett LJ..  (2012)  Substrate-Selective Inhibition of Cyclooxygenase-2: Development and Evaluation of Achiral Profen Probes.,  3  (9): [PMID:22984634] [10.1021/ml3001616]

5. Goudie AC, Gaster LM, Lake AW, Rose CJ, Freeman PC, Hughes BO, Miller D..  (1978)  4-(6-Methoxy-2-naphthyl)butan-2-one and related analogues, a novel structural class of antiinflammatory compounds.,  21  (12): [PMID:722734] [10.1021/jm00210a016]

6. Drug metabolism data, 

7. DrugMatrix,  [10.6019/CHEMBL3885881]

8. Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM..  (2016)  Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor.,  59  (16): [PMID:27486833] [10.1021/acs.jmedchem.6b00160]

9. Unpublished dataset, 

Source

Source(4):

• Scientific Literature
• DrugMatrix
• Curated Drug Metabolism Pathways
• Active Ingredient of a Prodrug