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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:22 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033932
Secondary Accession Numbers
  • HMDB33932
Metabolite Identification
Common NameCinnatriacetin A
DescriptionCinnatriacetin A belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Cinnatriacetin A has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make cinnatriacetin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cinnatriacetin A.
Structure
Data?1563862483
Synonyms
ValueSource
FH 2HMDB
(5Z)-14-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}tetradec-5-en-8,10,12-triynoateGenerator
Cinnatriacetin aMeSH
Chemical FormulaC23H20O5
Average Molecular Weight376.4019
Monoisotopic Molecular Weight376.13107375
IUPAC Name(5Z)-14-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}tetradec-5-en-8,10,12-triynoic acid
Traditional Name(5Z)-14-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}tetradec-5-en-8,10,12-triynoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC\C=C/CC#CC#CC#CCOC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C23H20O5/c24-21-16-13-20(14-17-21)15-18-23(27)28-19-11-9-7-5-3-1-2-4-6-8-10-12-22(25)26/h4,6,13-18,24H,2,8,10,12,19H2,(H,25,26)/b6-4-,18-15+
InChI KeyUGVOYXYFLWZKOM-MJLPGFBBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0086 g/LALOGPS
logP4.33ALOGPS
logP5.21ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity110.41 m³·mol⁻¹ChemAxon
Polarizability42.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+180.19830932474
DeepCCS[M-H]-177.8430932474
DeepCCS[M-2H]-211.82630932474
DeepCCS[M+Na]+187.25730932474
AllCCS[M+H]+187.332859911
AllCCS[M+H-H2O]+184.732859911
AllCCS[M+NH4]+189.732859911
AllCCS[M+Na]+190.332859911
AllCCS[M-H]-188.632859911
AllCCS[M+Na-2H]-189.032859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cinnatriacetin AOC(=O)CCC\C=C/CC#CC#CC#CCOC(=O)\C=C\C1=CC=C(O)C=C15867.7Standard polar33892256
Cinnatriacetin AOC(=O)CCC\C=C/CC#CC#CC#CCOC(=O)\C=C\C1=CC=C(O)C=C13389.9Standard non polar33892256
Cinnatriacetin AOC(=O)CCC\C=C/CC#CC#CC#CCOC(=O)\C=C\C1=CC=C(O)C=C13795.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinnatriacetin A,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC/C=C\CC#CC#CC#CCOC(=O)/C=C/C1=CC=C(O)C=C13500.8Semi standard non polar33892256
Cinnatriacetin A,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OCC#CC#CC#CC/C=C\CCCC(=O)O)C=C13607.9Semi standard non polar33892256
Cinnatriacetin A,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC/C=C\CC#CC#CC#CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13591.5Semi standard non polar33892256
Cinnatriacetin A,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC#CC#CC#CCOC(=O)/C=C/C1=CC=C(O)C=C13744.7Semi standard non polar33892256
Cinnatriacetin A,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OCC#CC#CC#CC/C=C\CCCC(=O)O)C=C13858.8Semi standard non polar33892256
Cinnatriacetin A,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC#CC#CC#CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C14058.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinnatriacetin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-1922000000-730bd80c1de16d98aeda2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnatriacetin A GC-MS (2 TMS) - 70eV, Positivesplash10-066r-5593240000-5247f31d13b9d5b10e252017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnatriacetin A 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 - Cinnatriacetin A 10V, Positive-QTOFsplash10-056s-0639000000-26aa90d2b13475764fc12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 20V, Positive-QTOFsplash10-0292-0921000000-a55785cacd53f60a6e932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 40V, Positive-QTOFsplash10-0002-3900000000-3aec07a358b09a88c4982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 10V, Negative-QTOFsplash10-01ta-0927000000-c39cd805d90972f3a3932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 20V, Negative-QTOFsplash10-03dj-0911000000-607b171a136630f49cbe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 40V, Negative-QTOFsplash10-06r2-3910000000-fb78ba618ae75112144e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 10V, Negative-QTOFsplash10-02di-0908000000-d25d5c31f8a12be3f8e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 20V, Negative-QTOFsplash10-066r-4912000000-653b8bd29204c6b413042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 40V, Negative-QTOFsplash10-014i-2900000000-b09969b1dd3f38fb579f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 10V, Positive-QTOFsplash10-0002-0924000000-094cb6978386eb4dd4ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 20V, Positive-QTOFsplash10-00kb-0900000000-a936d9678ae23e17af8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnatriacetin A 40V, Positive-QTOFsplash10-014i-0900000000-266e3c528b906ec82dd02021-09-22Wishart 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 IDFDB012135
KNApSAcK IDC00015372
Chemspider ID8152407
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9976815
PDB IDNot Available
ChEBI ID175825
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .