1-Naphthaleneacetic acid (CED0006489)

Record Information
Version1.0
Creation Date2016-05-22 03:28:45 UTC
Update Date2026-08-18 15:46:41 UTC
Accession NumberCHEM016358
Identification
Common Name1-Naphthaleneacetic acid
ClassSmall Molecule
Description
1-Naphthaleneacetic acid (C12H10O2) is a chemical compound with an average molecular weight of 186.21 g/mol. 1-Naphthaleneacetic acid belongs to the naphthalenes, a class of benzenoids within the organic compounds. Biologically, it functions as a synthetic auxin (PMC8982072). Industrially, it is utilized as a softener and conditioner (PMC8982072). The compound has one recorded protein target, S-phase kinase-associated protein 1 (SKP1). This substance is found in or released from 36 recorded sources. These include electrical and electronic equipment, such as amplifiers, antennas, communication cables or conductors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials, among 15 other items. Within household cleaning and consumer products, it is associated with perfumes within detergents and soaps, ash trays, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and 4 additional sources. It is also found in building and construction materials, specifically tents or canopies, roofs, and fencing. In the context of food, food processing, and cookware, it is linked to food preservation and the preparation of wine, sparkling wine, or malt. Additionally, it is found in drinking water and water supply. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(Naphthalen-1-yl)acetic acidChEBI
1-Naphthylacetic acidChEBI
alpha-NAAChEBI
alpha-Naphthaleneacetic acidChEBI
NAAChEBI
NAPHTHALEN-1-yl-acetIC ACIDChEBI
Naphthalene-1-acetic acidChEBI
alpha-Naphthylacetic acidKegg
(Naphthalen-1-yl)acetateGenerator
1-NaphthylacetateGenerator
a-NAAGenerator
Α-naaGenerator
a-NaphthaleneacetateGenerator
a-Naphthaleneacetic acidGenerator
alpha-NaphthaleneacetateGenerator
Α-naphthaleneacetateGenerator
Α-naphthaleneacetic acidGenerator
NAPHTHALEN-1-yl-acetateGenerator
Naphthalene-1-acetateGenerator
a-NaphthylacetateGenerator
a-Naphthylacetic acidGenerator
alpha-NaphthylacetateGenerator
Α-naphthylacetateGenerator
Α-naphthylacetic acidGenerator
1-NaphthaleneacetateGenerator
(1-Naphthyl)acetic acid, bsi, isoHMDB
1-NAAHMDB
2-(alpha-Naphthyl)ethanoic acidHMDB
Fruitone NHMDB
PhyomoneHMDB
PlanofixHMDB
Tre-holdHMDB
1-Naphthaleneacetic acid, ammonium saltHMDB
1-Naphthaleneacetic acid, potassium saltHMDB
1-Naphthaleneacetic acid, sodium saltHMDB
Galle-donauHMDB
2-(1-Naphthyl)acetic acidHMDB
2-(Naphthalen-1-yl)acetic acidHMDB
Potassium 1-naphthaleneacetateHMDB
Sodium 1-naphthaleneacetateHMDB
1-Naphthaleneacetic acidChEBI
Chemical FormulaC12H10O2
Average Molecular Mass186.207 g/mol
Monoisotopic Mass186.068 g/mol
CAS Registry Number86-87-3
IUPAC Name2-(naphthalen-1-yl)acetic acid
Traditional Nameplucker
SMILESOC(=O)CC1=C2C=CC=CC2=CC=C1
InChI IdentifierInChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
InChI KeyPRPINYUDVPFIRX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.82 m³·mol⁻¹ChemAxon
Polarizability19.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0006-0900000000-217de62c6bdb645dae35Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-1900000000-782f3a027c45e64394b3Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-0900000000-217de62c6bdb645dae35Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-1900000000-782f3a027c45e64394b3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-0900000000-b2d7fccbd30cb458042cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-4900000000-61aa1017aa8bebaf379aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0900000000-7120093ba4bbf767a44cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0900000000-6cb2846bdf5a8ff0ae2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-1900000000-e7c306f143bdff24d139Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0900000000-d15319af97ab9db3a9feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0900000000-789eede2b113302cededNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-0900000000-d12c6543cee99c510a52Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0900000000-d2dea070830ade89485aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-65cd63299af3690ebab9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-3a8679ed148be31b9a94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0900000000-72713f05dba606ad6304Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-ff59d913e74c5b78f6aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-2fa0469c8d57cb196153Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1218.0Log mg/kg[690:2200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
pilocytic astrocytomadecreased_in_csf_inNot AvailablePMC4035491
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
496FencingBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
644Hook Or Eye FastenersTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureChaperone protein dnaKC3TRK2Escherichia coliPredicted (SEA)0.311397
Click to view 3D structureTrans-cinnamate 4-monooxygenaseQ04468Helianthus tuberosusPredicted (SEA)0.467095
Interleukin-8 structureClick to view 3D structureInterleukin-8P10145HumansPredicted (SEA)3.03612
Click to view 3D structureProstaglandin G/H synthase 2Q05769Mus musculusPredicted (SEA)7.16213
Click to view 3D structureCalcium/calmodulin-dependent protein kinase type II subunit alphaP11275Rattus norvegicusPredicted (SEA)0.467095
Chloride intracellular channel protein 1 structureClick to view 3D structureChloride intracellular channel protein 1O00299HumansPredicted (SEA)1.16774
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)22.8098
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)24.289
Click to view 3D structurePeptidoglycan-N-acetylglucosamine deacetylase BC_1974Q81EJ6Bacillus cereus (strain ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 /NCIMB 9373 / NRRL B-3711)Predicted (SEA)2.56902
Interferon alpha/beta receptor 1 structureClick to view 3D structureInterferon alpha/beta receptor 1P17181HumansPredicted (SEA)0.622794
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)17.5939
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)46.476
Click to view 3D structureTranscription factor SOX-18P43680Mus musculusPredicted (SEA)1.79053
Click to view 3D structureTranscription factor SOX-18P35713HumansPredicted (SEA)1.79053
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)168.076
Tryptase beta-2 structureClick to view 3D structureTryptase beta-2P20231HumansPredicted (SEA)4.5931
Click to view 3D structureChaperone protein PapDP15319Escherichia coliPredicted (SEA)0.0778492
Listeriolysin regulatory protein structureClick to view 3D structureListeriolysin regulatory proteinP22262Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)Predicted (SEA)0.155698
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)123.702
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)250.83
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)22.6541
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)149.704
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)30.5947
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)329.069
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)84.4664
Concentrations
Not Available
External Links
DrugBank IDDB01750
HMDB IDHMDB0032708
FooDB IDFDB010669
Phenol Explorer IDNot Available
KNApSAcK IDC00020743
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNLA
Wikipedia Link1-Naphthaleneacetic_acid
Chemspider ID6601
ChEBI ID32918
PubChem Compound ID6862
Kegg Compound IDC13014
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24272685
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24690897
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.