Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:59:15 UTC
Update Date2021-10-13 08:33:24 UTC
HMDB IDHMDB0041319
Secondary Accession Numbers
  • HMDB41319
Metabolite Identification
Common NameCinnamyl anthranilate
DescriptionCinnamyl anthranilate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Cinnamyl anthranilate is a balsam, fruity, and grape tasting compound. Based on a literature review very few articles have been published on Cinnamyl anthranilate.
Structure
Data?1563863650
Synonyms
ValueSource
Cinnamyl anthranilic acidGenerator
2-Aminobenzoic acid 3-phenyl-2-propenyl esterHMDB
2-Propen-1-ol, 3-phenyl-, 1-(2-aminobenzoate)HMDB
2-Propen-1-ol, 3-phenyl-, 2-aminobenzoateHMDB
3-Phenyl-2-propen-1-ol 2-aminobenzoateHMDB
3-Phenyl-2-propen-1-yl 2-aminobenzoateHMDB
3-Phenyl-2-propen-1-yl anthranilateHMDB
3-Phenyl-2-propenyl anthranilateHMDB
3-Phenyl-2-propenylanthranilateHMDB
Anthranilic acid, cinnamyl esterHMDB
Benzoic acid, 2-amino-, 3-phenyl-2-propenyl esterHMDB
Cinnamyl 2-aminobenzoateHMDB
Cinnamyl alcohol, anthranilateHMDB
Cinnamyl anthranylateHMDB
Cinnamyl O-aminobenzoateHMDB
Cinnamylester kyseliny anthraniloveHMDB
FEMA 2295HMDB
(2Z)-3-Phenylprop-2-en-1-yl 2-aminobenzoic acidGenerator
3-Phenyl-2-propenyl-2-aminobenzoateMeSH
Cinnamyl anthranilateMeSH
Chemical FormulaC16H15NO2
Average Molecular Weight253.2958
Monoisotopic Molecular Weight253.110278729
IUPAC Name(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate
Traditional Name(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate
CAS Registry Number87-29-6
SMILES
NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6-
InChI KeyGABQNAFEZZDSCM-TWGQIWQCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Styrene
  • Vinylogous amide
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point64 °CNot Available
Boiling Point322.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.03 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.474 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP10(3.54) g/LALOGPS
logP10(4.13) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)19.39ChemAxon
pKa (Strongest Basic)2.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.71 m³·mol⁻¹ChemAxon
Polarizability28.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.21231661259
DarkChem[M-H]-157.22731661259
DeepCCS[M+H]+157.55630932474
DeepCCS[M-H]-155.19830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cinnamyl anthranilateNC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C13585.3Standard polar33892256
Cinnamyl anthranilateNC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C12280.2Standard non polar33892256
Cinnamyl anthranilateNC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C12337.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinnamyl anthranilate,1TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C12486.6Semi standard non polar33892256
Cinnamyl anthranilate,1TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C12464.1Standard non polar33892256
Cinnamyl anthranilate,2TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C2410.5Semi standard non polar33892256
Cinnamyl anthranilate,2TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C2402.8Standard non polar33892256
Cinnamyl anthranilate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C12702.4Semi standard non polar33892256
Cinnamyl anthranilate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C12681.9Standard non polar33892256
Cinnamyl anthranilate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2852.2Semi standard non polar33892256
Cinnamyl anthranilate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2866.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamyl anthranilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-6900000000-c67918c6b47914e2e6d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamyl anthranilate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamyl 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 - Cinnamyl anthranilate 10V, Positive-QTOFsplash10-0uy0-0690000000-85d2f32c193a1ae02a012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Positive-QTOFsplash10-014i-0910000000-3b4c9b53b568b901061c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Positive-QTOFsplash10-0v4i-9700000000-85c51499b0bd22ea95da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Negative-QTOFsplash10-0udi-2590000000-679d958bba4686930ee82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Negative-QTOFsplash10-000f-7910000000-cce12f47044d495547462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Negative-QTOFsplash10-0006-9500000000-0dd8d9c87d13e6219d3a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Positive-QTOFsplash10-00xr-0910000000-840743942c1c7339d58c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Positive-QTOFsplash10-00xu-2900000000-cefd8fe63dfd9522d9df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Positive-QTOFsplash10-00r6-7900000000-bf1164f59e89ddffff9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Negative-QTOFsplash10-0f7c-4390000000-4a5270f5d52a19bcd1072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Negative-QTOFsplash10-0006-9310000000-183323bd99f2d5d6838c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Negative-QTOFsplash10-0006-9000000000-f142da8ca3951731a32c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021238
KNApSAcK IDNot Available
Chemspider ID30777557
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54603882
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .