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Details

Stereochemistry ACHIRAL
Molecular Formula C12H10O2
Molecular Weight 186.2066
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-Naphthaleneacetic Acid

SMILES

OC(=O)CC1=CC=CC2=C1C=CC=C2

InChI

InChIKey=PRPINYUDVPFIRX-UHFFFAOYSA-N
InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)

HIDE SMILES / InChI
Molecular Formula C12H10O2
Molecular Weight 186.2066
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: Paranjape, K., Gowariker, V., Krishnamurthy, V.N., Gowariker, S. (2014) "The Pesticide Encyclopedia", p.319 Retrieved from https://books.google.ru/books?id=cnDHBgAAQBAJ

Sodium 1-Naphthaleneacetate (SODIUM 1-NAPHTHALENEACETATE) is a plant growth regulator. It has being shown that root application of certain concentration of sodium naphthalene acetate (SNA) could promote the growth of tomato seedlings by increasing the tomato root activity, protective enzymes activity, Pn and regulating endogenous hormone concentration under suboptimum temperature and light condition.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
horse butyrylcholinesteras
4
Target ID: horse butyrylcholinesteras
Substrate
661
α-naphthyl acetate esterase
4
Target ID: α-naphthyl acetate esterase
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Galle-Donau

Approved Use

GALLE-DONAU - Dragees are used to treat Bile deposits and functional disorders of the gall bladder and bile ducts without organic causes.

Launch Date

1962
Primary
Approved
8583
Galle-Donau

Approved Use

GALLE-DONAU - Dragees are used to treat Bile deposits and functional disorders of the gall bladder and bile ducts without organic causes.

Launch Date

1962
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

inducer
1087
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

CYP1A2
2153
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
2633
 inconclusive [IC50 12.3018 uM]
CYP19A1
430
 no
CYP3A4
2633
 no
CYP1A2
2333
 yes [IC50 22.4458 uM]
CYP2D6
2546
 yes [IC50 6.3261 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Determination of organophosphorus pesticide residues in vegetables by an enzyme inhibition method using α-naphthyl acetate esterase extracted from wheat flour.
2012-04
Nitric oxide plays a central role in determining lateral root development in tomato.
2004-04
Direct organogenesis of Mandevilla illustris (Vell) Woodson and effects of its aqueous extract on the enzymatic and toxic activities of Crotalus durissus terrificus snake venom.
2004-03
Transformation of the monocotyledonous Alstroemeria by Agrobacterium tumefaciens.
2004-03
Somatic embryogenesis from leaf explants of Australian fan flower, Scaevola aemula R. Br.
2004-01
Interaction between two auxin-resistant mutants and their effects on lateral root formation in rice (Oryza sativa L.).
2003-12
Aux/IAA gene family is conserved in the gymnosperm, loblolly pine (Pinus taeda).
2003-12
Flavonoid-related regulation of auxin accumulation in Agrobacterium tumefaciens-induced plant tumors.
2003-12
Isoenzymes of peroxidase and esterase related to morphogenesis in Mammillaria gracillis Pfeiff. tissue culture.
2003-11
Arabidopsis AtGSTF2 is regulated by ethylene and auxin, and encodes a glutathione S-transferase that interacts with flavonoids.
2003-11
p-Chlorophenoxyisobutyric acid impairs auxin response in Arabidopsis root.
2003-11
Brassinosteroids promote root growth in Arabidopsis.
2003-11
Characterization of a wound-inducible cytochrome P450 gene ( CYP72A29) that is down-regulated during crown gall tumorigenesis in potato tuber.
2003-11
[Use of 1- and 2-thionaphthylacetates as cholinesterase substrates].
2003-10-28
Osgstu3 and osgtu4, encoding tau class glutathione S-transferases, are heavy metal- and hypoxic stress-induced and differentially salt stress-responsive in rice roots.
2003-10-23
Ospdr9, which encodes a PDR-type ABC transporter, is induced by heavy metals, hypoxic stress and redox perturbations in rice roots.
2003-10-23
Fast kinetic determination of 1-naphthylacetic acid in commercial formulations, soils, and fruit samples using stopped-flow phosphorimetry.
2003-10-22
Aggregation and reactivity of the dilithium and dicesium enediolates of 1-naphthylacetic acid.
2003-10-17
Micropropagation of Polygonum multiflorum THUNB and quantitative analysis of the anthraquinones emodin and physcion formed in in vitro propagated shoots and plants.
2003-10
Somatic embryogenesis in sisal ( Agave sisalana Perr. ex. Engelm).
2003-10
An effective method for axillary bud culture and RAPD analysis of cloned plants in tetraploid black locust.
2003-10
[Effect of abiotic elicitation and calcium ions on production of explant cultures of Rheum palmatum L].
2003-09
Efficient regeneration from cotyledon protoplasts in Arabidopsis thaliana.
2003-09
Auxin up-regulates MtSERK1 expression in both Medicago truncatula root-forming and embryogenic cultures.
2003-09
[Specific features of the development of Siberian stone pine megagametophytes and embryos in vitro].
2003-08-29
Thermotolerant guard cell protoplasts of tree tobacco do not require exogenous hormones to survive in culture and are blocked from reentering the cell cycle at the G1-to-S transition.
2003-08
Efficient in vitro direct shoot organogenesis and regeneration of fertile plants from embryo explants of Bambara groundnut ( Vigna subterranea L. Verdc.).
2003-08
Direct somatic embryogenesis and synthetic seed production from Paulownia elongata.
2003-08
[Effect of auxins on production of coumarin in a suspension culture of Angelica archangelica L].
2003-07
Production of alkaloids by in vitro culture of Erythrina americana Miller.
2003-07
The function of ascorbate oxidase in tobacco.
2003-07
Regeneration of Acer caudatifolium Hayata plantlets from juvenile explants.
2003-07
High-frequency shoot multiplication in Curcuma longa L using thidiazuron.
2003-07
Plant regeneration from callus of apomictic and sexual lines of Paspalum simplex and RFLP analysis of regenerated plants.
2003-07
Micropropagation of Thapsia garganica--a medicinal plant.
2003-06
Remarkably enhanced excimer formation of naphthylacetate in cation-charged gamma-cyclodextrin.
2003-05-15
[Effect of jasminic acid on production of anthracene derivatives in cultures of Rheum palmatum L].
2003-05
Intercalibration of chromatographic methods for auxino phytodrugs in Solanaceae.
2003-04-18
Production of ajmalicine and ajmaline in hairy root cultures of Rauvolfia micrantha Hook f., a rare and endemic medicinal plant.
2003-04
Development of Linum flavum hairy root cultures for production of coniferin.
2003-04
[Determination of captafol, cyhexatin, 1-naphthylacetic acid and quintozene in apple, Japanese pear and melon by simultaneous extraction].
2003-04
Transgene expression in broccoli (Brassica oleracea var. italica) clones propagated in vitro via leaf explants.
2003-04
Encapsulation of nodal cuttings and shoot tips for storage and exchange of cassava germplasm.
2003-04
Camptothecin biosynthetic genes in hairy roots of Ophiorrhiza pumila: cloning, characterization and differential expression in tissues and by stress compounds.
2003-04
Production of haploids of neem (Azadirachta indica A. Juss.) by anther culture.
2003-02
Intramolecular excimer formation in a naphthalene-appended dinuclear iron-oxo complex.
2003-01-27
Rapid in vitro multiplication and ex vitro rooting of Rotula aquatica Lour., a rare rhoeophytic woody medicinal plant.
2003-01
In vitro regeneration of roots of Phyla nodiflora and Leptadenia reticulata, and comparison of roots from cultured and natural plants for secondary metabolites.
2002-12
[Method for determining nitrogen-containing cationic surface-active agents using butyrylcholinesterase].
2002-08-03
Lipolytic and esterolytic activities in posterior lingual glands of rat: a histochemical study.
2002
Patents

Patents

04362712
5
05068244
5
06117901
7
06559141
7
08003669
5
JP1013006A
5
JP1085016A
4
JPH01106802A
4
JPH01247083A
4
JPH02242624A
10
JPH02276580A
5
JPH0257954A
4
JPH04104743A
4
JPH04228016A
4
JPH0491784A
10
JPH05194445A
4
JPH05244837A
4
JPH07170870A
4
JPS56161302A
6
JPS5815938A
4
JPS58201982A
10
JPS60112808A
4
JPS60259196A
10
US4152869
4

Sample Use Guides

In Vivo Use Guide
Curator's Comment: GALLE-DONAU
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Carboxylesterases from different strains of Myzus persicae were examined to try to understand their contribution to insecticide resistance. Homogenates of resistant aphids hydrolysed paraoxon 60 times faster than did those of susceptible aphids, yet the purified enzymes from both sources had identical catalytic-centre activities towards this substrate and also towards naphth-1-yl acetate, the latter being hydrolysed by both 2x10(6) times faster than paraoxon. K(m) for naphth-1-yl acetate was 0.131 mm, and for paraoxon 75 pm.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:08 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:08 GMT 2025
Record UNII
33T7G7757C
Record Status Validated (UNII)
Record Version
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Name Type Language
1-Naphthaleneacetic Acid
INCI   MI   WHO-DD  
INCI  
Official Name English
1-NAPHTHYLACETIC ACID
JAN  
Preferred Name English
2-(1-NAPHTHYL)ACETIC ACID
Systematic Name English
.ALPHA.-NAPHTHALENEACETIC ACID
Systematic Name English
1-NAPHTHYLACETIC ACID [JAN]
Common Name English
PHYOMONE
Brand Name English
GERMON
Brand Name English
RHIZOPON B
Brand Name English
FRUITOFIX
Brand Name English
NAA
Common Name English
ALPHA-NAPHTHYLACETIC ACID [HSDB]
Common Name English
RASIN
Brand Name English
.ALPHA.-NAA
Common Name English
RHODOFIX
Brand Name English
N 40
Code English
PLANOFIX
Brand Name English
TRE-HOLD
Brand Name English
NAFTAL
Brand Name English
N 10
Code English
2-(.ALPHA.-NAPHTHYL)ETHANOIC ACID
Systematic Name English
NAFUSAKU
Brand Name English
ALPHA-NAPHTHALENEACETIC ACID
Systematic Name English
BIOKOR
Brand Name English
NAPHTHALENEACETIC ACID
Systematic Name English
ETIFIX
Brand Name English
ALMAN
Brand Name English
1-NAA
Common Name English
VARDHAK
Brand Name English
FRUITONE N
Brand Name English
NAPHTHALEN-1-YLACETIC ACID
Systematic Name English
NAPHTHYLACETIC ACID [MART.]
Common Name English
.ALPHA.-NAPHTHYLACETIC ACID
Systematic Name English
NAPHAZOLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Common Name English
STIMOLANTE 66F
Brand Name English
PLANOFIXE
Brand Name English
CELMONE
Brand Name English
AGRONAA
Brand Name English
ANU
Common Name English
POMOXON
Brand Name English
1-naphthaleneacetic acid [WHO-DD]
Common Name English
NAPHTHYLACETIC ACID
MART.  
Systematic Name English
2-(NAPHTHALEN-1-YL)ACETIC ACID
Systematic Name English
RAIZON 05
Brand Name English
1-NAPHTHALENEACETIC ACID [MI]
Common Name English
NSC-15772
Code English
Classification Tree Code System Code
EPA PESTICIDE CODE 56002
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
FDA ORPHAN DRUG 731020
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
Code System Code Type Description
CHEBI
32918
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
WIKIPEDIA
1-NAPHTHALENEACETIC ACID
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
NSC
15772
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
FDA UNII
33T7G7757C
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-705-8
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
EVMPD
SUB12674MIG
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
SMS_ID
100000078271
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
PUBCHEM
6862
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID8020915
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
MESH
C034182
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
HSDB
2038
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
EVMPD
SUB33662
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
ALTERNATIVE
DRUG BANK
DB01750
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
CAS
86-87-3
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY
MERCK INDEX
m7726
Created by admin on Mon Mar 31 17:45:08 GMT 2025 , Edited by admin on Mon Mar 31 17:45:08 GMT 2025
PRIMARY Merck Index
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