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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:19 UTC
Update Date2022-03-07 02:53:26 UTC
HMDB IDHMDB0032708
Secondary Accession Numbers
  • HMDB32708
Metabolite Identification
Common Name1-Naphthaleneacetic acid
DescriptionPlant growth regulator. 1-Naphthaleneacetic acid is used for control of preharvest fruit drop, flower induction and fruit thinning in various crops such as apples, potatoes, olives and citrus fruits.1-Naphthaleneacetic acid (NAA) is a plant hormone in the auxin family. It is a rooting agent and used for the vegetative propagation of plants from stem and leaf cutting. It is also used for plant tissue culture. NAA does not occur naturally. Under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides. (Wikipedia
Structure
Data?1563862295
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 Weight186.2066
Monoisotopic Molecular Weight186.068079564
IUPAC Name2-(naphthalen-1-yl)acetic acid
Traditional Nameplucker
CAS Registry Number86-87-3
SMILES
OC(=O)CC1=C2C=CC=CC2=CC=C1
InChI Identifier
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)
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 - 135.5 °CNot Available
Boiling Point373.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.42 mg/mL at 20 °CNot Available
LogP2.24Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.94131661259
DarkChem[M-H]-137.88531661259
DeepCCS[M+H]+139.24830932474
DeepCCS[M-H]-136.85230932474
DeepCCS[M-2H]-171.81930932474
DeepCCS[M+Na]+146.29830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Naphthaleneacetic acidOC(=O)CC1=C2C=CC=CC2=CC=C13287.0Standard polar33892256
1-Naphthaleneacetic acidOC(=O)CC1=C2C=CC=CC2=CC=C11759.0Standard non polar33892256
1-Naphthaleneacetic acidOC(=O)CC1=C2C=CC=CC2=CC=C11774.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Naphthaleneacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=CC2=CC=CC=C121812.8Semi standard non polar33892256
1-Naphthaleneacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC2=CC=CC=C122060.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Naphthaleneacetic acid EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Naphthaleneacetic acid EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Naphthaleneacetic acid EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae352018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Naphthaleneacetic acid EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthaleneacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-b2d7fccbd30cb458042c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthaleneacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-61aa1017aa8bebaf379a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthaleneacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthaleneacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 10V, Positive-QTOFsplash10-00kr-0900000000-7120093ba4bbf767a44c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 20V, Positive-QTOFsplash10-014r-0900000000-6cb2846bdf5a8ff0ae2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 40V, Positive-QTOFsplash10-00kf-1900000000-e7c306f143bdff24d1392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 10V, Negative-QTOFsplash10-000l-0900000000-d15319af97ab9db3a9fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 20V, Negative-QTOFsplash10-000l-0900000000-789eede2b113302ceded2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 40V, Negative-QTOFsplash10-00kf-0900000000-d12c6543cee99c510a522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 10V, Positive-QTOFsplash10-000l-0900000000-d2dea070830ade89485a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 20V, Positive-QTOFsplash10-0006-0900000000-65cd63299af3690ebab92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 40V, Positive-QTOFsplash10-0006-0900000000-3a8679ed148be31b9a942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 10V, Negative-QTOFsplash10-000l-0900000000-72713f05dba606ad63042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 20V, Negative-QTOFsplash10-0006-0900000000-ff59d913e74c5b78f6aa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthaleneacetic acid 40V, Negative-QTOFsplash10-0006-0900000000-2fa0469c8d57cb1961532021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01750
Phenol Explorer Compound IDNot Available
FooDB IDFDB010669
KNApSAcK IDC00020743
Chemspider ID6601
KEGG Compound IDC13014
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Naphthaleneacetic_acid
METLIN IDNot Available
PubChem Compound6862
PDB IDNLA
ChEBI ID32918
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1155701
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .