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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:36:45 UTC
Update Date2019-07-23 06:06:24 UTC
HMDB IDHMDB0030433
Secondary Accession Numbers
  • HMDB30433
Metabolite Identification
Common NameLinalyl anthranilate
DescriptionLinalyl anthranilate, also known as linalyl 2-aminobenzoate or fema 2637, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Linalyl anthranilate is a moderately basic compound (based on its pKa).
Structure
Data?1563861984
Synonyms
ValueSource
Linalyl anthranilic acidGenerator
1, 6-Octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoateHMDB
1,5-Dimethyl-1-vinyl-4-hexen-1-yl O-aminobenzoateHMDB
1,5-Dimethyl-1-vinyl-4-hexenyl anthranilateHMDB
1,5-Dimethyl-1-vinylhex-4-en-1-yl 2-aminobenzoateHMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoateHMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-(2-aminobenzoate)HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, O-aminobenzoateHMDB
3, 7-Dimethyl-1,6-octadien-3-yl, anthranilateHMDB
3,7-Dimethyl-1,6-octadien-3-ol 2-aminobenzoateHMDB
3,7-Dimethyl-1,6-octadien-3-yl 2-aminobenzoateHMDB
3,7-Dimethyl-1,6-octadien-3-yl O-aminobenzoateHMDB
3,7-Dimethyl-1,6-octadien-3-yl, anthranilateHMDB
4-Hexen-1-ol, 1,5-dimethyl-1-vinyl-, O-aminobenzoateHMDB
Anthranilic acid, 1, 5-dimethyl-1-vinyl-4-hexenyl esterHMDB
Anthranilic acid, 1,5-dimethyl-1-vinyl-4-hexenyl esterHMDB
Anthranilic acid, linalyl esterHMDB
FEMA 2637HMDB
Linalyl 2-aminobenzoateHMDB
Linalyl O-aminobenzoateHMDB
3,7-Dimethylocta-1,6-dien-3-yl 2-aminobenzoic acidGenerator
Chemical FormulaC17H23NO2
Average Molecular Weight273.37
Monoisotopic Molecular Weight273.172878985
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate
Traditional Name3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate
CAS Registry Number7149-26-0
SMILES
CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C
InChI Identifier
InChI=1S/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3
InChI KeyWHIJSULEEDNKPD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Aromatic monoterpenoid
  • Benzoate ester
  • Monocyclic monoterpenoid
  • Benzoic acid or derivatives
  • Aniline or substituted anilines
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP4.15ALOGPS
logP4.96ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)2.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.73 m³·mol⁻¹ChemAxon
Polarizability31.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7900000000-8b372620695c2c09d114Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1490000000-2ff0836fc2419ebb6d2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-8930000000-e50baae1ab9a7bd24d2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-9200000000-78eff87cd6542ffe8881Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2390000000-b3cb52c5e7311404b800Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9780000000-114d30b05b01cf86ce94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-cc4fea34d9c8b24925bdSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002297
KNApSAcK IDNot Available
Chemspider ID22005
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23535
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.