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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:48:29 UTC
Update Date2022-03-07 02:53:16 UTC
HMDB IDHMDB0032208
Secondary Accession Numbers
  • HMDB32208
Metabolite Identification
Common NameCitronellyl anthranilate
DescriptionCitronellyl anthranilate belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a small amount of articles have been published on Citronellyl anthranilate.
Structure
Data?1563862231
Synonyms
ValueSource
Citronellyl anthranilic acidGenerator
2-AminobenzoateHMDB
3,7-Dimethyloct-6-enyl 2-aminobenzoateHMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-(2-aminobenzoate)HMDB
6-Octen-1-ol, 3,7-dimethyl-, 2-aminobenzoateHMDB
O-Aminobenzoic acidHMDB
3,7-Dimethyloct-6-en-1-yl 2-aminobenzoic acidGenerator
Chemical FormulaC17H25NO2
Average Molecular Weight275.3859
Monoisotopic Molecular Weight275.188529049
IUPAC Name3,7-dimethyloct-6-en-1-yl 2-aminobenzoate
Traditional Name3,7-dimethyloct-6-en-1-yl 2-aminobenzoate
CAS Registry Number68555-57-7
SMILES
CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C
InChI Identifier
InChI=1S/C17H25NO2/c1-13(2)7-6-8-14(3)11-12-20-17(19)15-9-4-5-10-16(15)18/h4-5,7,9-10,14H,6,8,11-12,18H2,1-3H3
InChI KeyLSJVFMHIFWWGDY-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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point365.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.053 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.108 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP5ALOGPS
logP5.07ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)2.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.01 m³·mol⁻¹ChemAxon
Polarizability32.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.17931661259
DarkChem[M-H]-165.63831661259
DeepCCS[M+H]+169.87230932474
DeepCCS[M-H]-167.51430932474
DeepCCS[M-2H]-200.430932474
DeepCCS[M+Na]+175.96530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citronellyl anthranilateCC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C3178.4Standard polar33892256
Citronellyl anthranilateCC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C2049.6Standard non polar33892256
Citronellyl anthranilateCC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C2208.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citronellyl anthranilate,1TMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C2311.7Semi standard non polar33892256
Citronellyl anthranilate,1TMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C2266.6Standard non polar33892256
Citronellyl anthranilate,2TMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C2250.9Semi standard non polar33892256
Citronellyl anthranilate,2TMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C2254.9Standard non polar33892256
Citronellyl anthranilate,1TBDMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C2493.3Semi standard non polar33892256
Citronellyl anthranilate,1TBDMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C2468.8Standard non polar33892256
Citronellyl anthranilate,2TBDMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2661.7Semi standard non polar33892256
Citronellyl anthranilate,2TBDMS,isomer #1CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2640.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl anthranilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-e33b66f36c4c3a5ad1b92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl anthranilate 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 - Citronellyl anthranilate 10V, Positive-QTOFsplash10-056r-0490000000-441d0ef74bf986ae4edf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Positive-QTOFsplash10-05g0-5920000000-89c5a4927181868e43372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Positive-QTOFsplash10-0q29-9300000000-2d4d820c7133e8bdf6562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Negative-QTOFsplash10-00di-2490000000-b894d45998fbd7509f8e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Negative-QTOFsplash10-000f-7920000000-8d8c356b5d5cb87786df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Negative-QTOFsplash10-0006-9400000000-998936f8493c00df96f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Negative-QTOFsplash10-00di-0090000000-eea24882311fb034a1612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Negative-QTOFsplash10-0006-9310000000-8081f343081f304b9ef32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Negative-QTOFsplash10-0006-9000000000-cda295e2422a06c522fb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Positive-QTOFsplash10-00fr-2940000000-0c7a751677e5245efaf02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Positive-QTOFsplash10-00e9-8910000000-dea508961b7816e7b46a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Positive-QTOFsplash10-00ec-9500000000-ad776ace980b2f1eded22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB009193
KNApSAcK IDNot Available
Chemspider ID98418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound109467
PDB IDNot Available
ChEBI ID172321
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004401
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.