Compounds > naphthaleneacetamide
Page last updated: 2024-11-05

naphthaleneacetamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Naphthaleneacetamide (NAA) is a synthetic auxin, a plant hormone that plays a crucial role in regulating growth and development. NAA is typically synthesized by the reaction of naphthalene with chloroacetyl chloride, followed by amination. NAA exhibits a wide range of effects on plants, including promoting root development, stimulating cell division and elongation, and influencing fruit ripening. It is commonly used in agriculture as a rooting hormone, a herbicide, and a plant growth regulator. NAA's effectiveness as a rooting hormone makes it valuable for plant propagation through cuttings and grafting. Its herbicidal properties are exploited in controlling weeds in various crops. Additionally, NAA's ability to stimulate fruit set and development is beneficial in increasing crop yields. Research on NAA continues to investigate its mechanisms of action, optimize its application, and explore its potential in promoting plant growth and enhancing crop production.'

naphthaleneacetamide: RN given refers to compound with unknown acetamide position [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-naphthaleneacetamide : A member of the class of naphthalenes that is naphthalene which is substituted by a 2-amino-2-oxoethyl group at position 1. It is a synthetic auxin that is widely used in agriculture to promote the growth of numerous fruits, for root cuttings and as a fruit thinning agent. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6861
CHEMBL ID3186653
CHEBI ID81810
SCHEMBL ID66670
MeSH IDM0084363

Synonyms (77)

Synonym
AC-5791
AKOS003421730
wln: l66j b1vz
86-86-2
.alpha.-naphthaleneacetic acid amide
.alpha.-naphthaleneacetamide
frufix
.alpha.-naphthylacetamide
naam
nsc-34862
rosetone
1-naphthylamine, n-acetyl-
amid-thin
1-naphthylacetamide
dirigol n
1-naphthaleneacetamide
amid-thin w
naphthalene acetamide
2-(1-naphthyl)acetamide
nsc34862
2-naphthalen-1-ylacetamide
1-naphthalene acetamide
1-naphthyl-acetamide
2-(1-naphthyl)acetamide [bsi:iso]
alpha-naphthaleneacetamide ,
ai3-52514
epa pesticide chemical code 056001
brn 1945547
alpha-naphthylacetamide
alpha-naa amide
naphthaleneacetamide
amid kyseliny 1-naftyloctove [czech]
einecs 201-704-2
caswell no. 588
nsc 34862
alpha-naphthaleneacetic acid amide
NCGC00164051-01
FT-0656243
xfnjvkmnnvcyek-uhfffaoysa-
inchi=1/c12h11no/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7h,8h2,(h2,13,14)
N0624
NCGC00164051-02
1-naphthyl acetamide
C18533
NCGC00257603-01
dtxcid30914
cas-86-86-2
tox21_200049
dtxsid3020914 ,
2-(naphthalen-1-yl)acetamide
31093-43-3
11kax3rj28 ,
4-09-00-02426 (beilstein handbook reference)
unii-11kax3rj28
amid kyseliny 1-naftyloctove
FS-3193
AM20050060
.alpha.-naa amide
naphthyl)acetamide, 2-(1-
SCHEMBL66670
CHEBI:81810 ,
dirigol-n
W-104054
CHEMBL3186653
mfcd00004047
1-naphthylacetamide, pestanal(r), analytical standard
(naphthalen-1-yl)acetamide (1-naphthylacetamide)
1-naphthaleneacetamide; (naphthalen-1-yl)acetamide; 1-naphthylacetamide
a-naphthaleneacetamide
2-(1-naphthyl)acetamide, iso
2(1-naphthyl)acetamide
CS-W023166
Q4545795
2-(1-naphthyl)ethanamide
D70476
1-naphthyl acetamide 100 microg/ml in acetonitrile
SY021125
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
synthetic auxinA synthetic compound exhibiting auxin activity.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
primary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency68.51990.001022.650876.6163AID1224838; AID1224893
estrogen nuclear receptor alphaHomo sapiens (human)Potency4.59700.000229.305416,493.5996AID743069; AID743075
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's1 (14.29)18.2507
2000's1 (14.29)29.6817
2010's4 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.95

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.95 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index30.68 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.95)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
5-hydroxytryptophan
5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.		2.0610hydroxytryptophanhuman metabolite;
neurotransmitter
salicylic acid
Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).		1.9910monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
indoleacetamide
indoleacetamide: article does not mention position of acetamide group; amide of indole-3-acetic acid (IAA), the natural auxin found in plants. indole-3-acetamide : A member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA).		2.0210indoles;
monocarboxylic acid amide;
N-acylammonia		bacterial metabolite;
fungal metabolite;
plant metabolite
indoleacetic acid
indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.		2.0210indole-3-acetic acids;
monocarboxylic acid		auxin;
human metabolite;
mouse metabolite;
plant hormone;
plant metabolite
hydroxyindoleacetic acid
(5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.		2.0610indole-3-acetic acidsdrug metabolite;
human metabolite;
mouse metabolite
ethyl methanesulfonate
Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.		1.9910methanesulfonate esteralkylating agent;
antineoplastic agent;
carcinogenic agent;
genotoxin;
mutagen;
teratogenic agent
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		2.0610erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
1-naphthaleneacetic acid
1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.		2.0810naphthylacetic acidsynthetic auxin
2-naphthoxyacetic acid
2-naphthoxyacetic acid: used as plant hormone to promote the growth of roots on clippings, to prevent fruit from falling prematurely; structure		2.0810naphthyloxyacetic acid
2-naphthylacetic acid
2-naphthylacetic acid: RN given refers to parent cpd. 2-naphthylacetic acid : A naphthylacetic acid carrying a carboxy group at position 2.		2.0810naphthylacetic acid
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		2.0610copper group element atom;
elemental gold
benzo-1,2,3-thiadiazole
[no description available]		1.9910
2,6-dichloroisonicotinic acid
2,6-dichloroisonicotinic acid: an ascorbate peroxidase antagonist; RN given refers to parent cpd. 2,6-dichloroisonicotinic acid : A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.		1.9910monocarboxylic acid;
organochlorine compound;
pyridines		EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor
aluminum
Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.		2.110boron group element atom;
elemental aluminium;
metal atom
ammonium sulfate
Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.		2.0210ammonium salt;
inorganic sulfate salt		fertilizer
sepharose
agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.		2.0210
salicylates
Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.		1.9910monohydroxybenzoateplant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0810
Argentaffinoma
[description not available]		02.0610
Carcinoid Tumor
A usually small, slow-growing neoplasm composed of islands of rounded, oxyphilic, or spindle-shaped cells of medium size, with moderately small vesicular nuclei, and covered by intact mucosa with a yellow cut surface. The tumor can occur anywhere in the gastrointestinal tract (and in the lungs and other sites); approximately 90% arise in the appendix. It is now established that these tumors are of neuroendocrine origin and derive from a primitive stem cell. (From Stedman, 25th ed & Holland et al., Cancer Medicine, 3d ed, p1182)		02.0610
Diathesis
[description not available]		01.9910