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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:19 UTC
Update Date2019-07-23 06:11:35 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
alpha-NAAChEBI
alpha-Naphthaleneacetic acidChEBI
NAAChEBI
NAPHTHALEN-1-yl-acetIC ACIDChEBI
Naphthalene-1-acetic acidChEBI
alpha-Naphthylacetic acidKegg
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
1-Naphthylacetic acidHMDB
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
1-Naphthaleneacetic acidChEBI
1-NaphthylacetateGenerator
2-(1-Naphthyl)acetic acidMeSH
2-(Naphthalen-1-yl)acetic acidMeSH
Potassium 1-naphthaleneacetateMeSH
Sodium 1-naphthaleneacetateMeSH
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

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134.5 - 135.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.42 mg/mL at 20 °CNot Available
LogP2.24Not 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae35Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae35Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-b2d7fccbd30cb458042cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-61aa1017aa8bebaf379aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-7120093ba4bbf767a44cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-6cb2846bdf5a8ff0ae2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-1900000000-e7c306f143bdff24d139Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0900000000-d15319af97ab9db3a9feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0900000000-789eede2b113302cededSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-0900000000-d12c6543cee99c510a52Spectrum
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 IDNot Available
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 ID
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.. .