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Details

Stereochemistry ACHIRAL
Molecular Formula C13H12O3
Molecular Weight 216.2326
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-METHOXY-2-NAPHTHYLACETIC ACID

SMILES

COC1=CC2=CC=C(CC(O)=O)C=C2C=C1

InChI

InChIKey=PHJFLPMVEFKEPL-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C13H12O3
Molecular Weight 216.2326
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

6-Methoxy-2-Naphthylacetic acid (6-MNA), an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half-life and has the tendency to penetrate well into synovial fluid. 6-MNA is a competitive inhibitor of Cox (cyclooxygenases).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P23219|||Q5T7T7
Gene ID: 5742.0
Gene Symbol: PTGS1
Target Organism: Homo sapiens (Human)
64.0 µM [IC50]
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
93.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Evidence for the involvement of cyclooxygenase activity in the development of cocaine sensitization.
2002 Jan-Feb
Low direct cytotoxicity of nabumetone on gastric mucosal cells.
2005 Sep
Evaluation of hydroxyimine as cytochrome P450-selective prodrug structure.
2006 Feb 9
High-throughput LC-MS/MS assay for 6-methoxy-2-naphthylacetic acid, an active metabolite of nabumetone in human plasma and its application to bioequivalence study.
2008 Nov
Patents

Sample Use Guides

In the indometacin-induced gastric mucosal injury, rats were treated with indometacin and then nabumetone or 6MNA (6-Methoxy-2-Naphthylacetic acid) was orally administered. Nabumetone prevented gastric damage accompanied by the reduction of neutrophil infiltration into gastric mucosa, but such an effect was not observed with 6MNA
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: 6MNA (6-Methoxy-2-Naphthylacetic acid) had variable effects on cyclooxygenase activity, depending on the concentration and was less potent and less effective than indomethacin. Sulphasalazine inhibited 15-PGDH in a concentration-dependent manner whereas 6MNA inhibited it only at high concentrations. Basal 5-lipoxy-genase (5-L) activity was attenuated by phenidone and unaltered by 6MNA but increased by nabumetone at the highest concentration. In the presence of arachidonic acid, to raise 5-LO activity, nabumetone, 6MNA, BW755C and phenidone apparently inhibited this activity. However, it was possible that both nabumetone and 6MNA inhibited a prostanoid-mediated stimulatory effect on 5-LO rather than effecting enzyme inhibition per se.
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:00 UTC 2023
Edited
by admin
on Sat Dec 16 08:35:00 UTC 2023
Record UNII
9H7K3YOD7Q
Record Status Validated (UNII)
Record Version
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Name Type Language
6-METHOXY-2-NAPHTHYLACETIC ACID
Systematic Name English
NAPROXEN SODIUM IMPURITY I [EP IMPURITY]
Common Name English
6MNA
Code English
NAPROXEN IMPURITY I [EP IMPURITY]
Common Name English
2-(6-METHOXY-2-NAPHTHYL)ACETIC ACID
Systematic Name English
6-METHOXY-2-NAPHTHALENEACETIC ACID
Systematic Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-
Systematic Name English
6-MNA
Common Name English
Code System Code Type Description
FDA UNII
9H7K3YOD7Q
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
CHEBI
35628
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
245-967-1
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID70178705
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
PUBCHEM
32176
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
CAS
23981-47-7
Created by admin on Sat Dec 16 08:35:01 UTC 2023 , Edited by admin on Sat Dec 16 08:35:01 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
UNSPECIFIED
EP
PARENT -> IMPURITY
UNSPECIFIED
EP