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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:03 UTC
Update Date2023-02-21 17:21:15 UTC
HMDB IDHMDB0031725
Secondary Accession Numbers
  • HMDB31725
Metabolite Identification
Common Name(E)-3-(2-Hydroxyphenyl)-2-propenal
Description(E)-3-(2-Hydroxyphenyl)-2-propenal belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal (E)-3-(2-Hydroxyphenyl)-2-propenal has been detected, but not quantified in, chinese cinnamons (Cinnamomum aromaticum). This could make (e)-3-(2-hydroxyphenyl)-2-propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-3-(2-Hydroxyphenyl)-2-propenal.
Structure
Data?1677000075
SynonymsNot Available
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name(2E)-3-(2-hydroxyphenyl)prop-2-enal
Traditional Name(2E)-3-(2-hydroxyphenyl)prop-2-enal
CAS Registry Number60125-23-7
SMILES
OC1=CC=CC=C1\C=C\C=O
InChI Identifier
InChI=1S/C9H8O2/c10-7-3-5-8-4-1-2-6-9(8)11/h1-7,11H/b5-3+
InChI KeyBSDNZCQPDVTDET-HWKANZROSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamaldehydes
Sub ClassNot Available
Direct ParentCinnamaldehydes
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha,beta-unsaturated aldehyde
  • Enal
  • Aldehyde
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131 - 132 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.14 g/LALOGPS
logP2.07ALOGPS
logP1.67ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.12 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+131.14630932474
DeepCCS[M-H]-128.57230932474
DeepCCS[M-2H]-164.8430932474
DeepCCS[M+Na]+139.88830932474
AllCCS[M+H]+131.032859911
AllCCS[M+H-H2O]+126.432859911
AllCCS[M+NH4]+135.332859911
AllCCS[M+Na]+136.532859911
AllCCS[M-H]-128.732859911
AllCCS[M+Na-2H]-129.932859911
AllCCS[M+HCOO]-131.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-3-(2-Hydroxyphenyl)-2-propenalOC1=CC=CC=C1\C=C\C=O2320.3Standard polar33892256
(E)-3-(2-Hydroxyphenyl)-2-propenalOC1=CC=CC=C1\C=C\C=O1410.5Standard non polar33892256
(E)-3-(2-Hydroxyphenyl)-2-propenalOC1=CC=CC=C1\C=C\C=O1484.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E)-3-(2-Hydroxyphenyl)-2-propenal,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1/C=C/C=O1654.1Semi standard non polar33892256
(E)-3-(2-Hydroxyphenyl)-2-propenal,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1/C=C/C=O1905.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-ac2eb21d29159860eb582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-6930000000-181d7583f47bf2b68a922017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 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 - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Positive-QTOFsplash10-0002-0900000000-aaea5a64a4ae76da27332016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Positive-QTOFsplash10-000t-4900000000-f5a22f9b719e2cf3c8092016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Positive-QTOFsplash10-0a6u-9300000000-c4624fa0468fab374cf22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Negative-QTOFsplash10-0002-0900000000-7f812f78efb7808aece32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Negative-QTOFsplash10-0002-1900000000-c88971a408cfdc0b27a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Negative-QTOFsplash10-0006-9400000000-36c8dbc04c63542f182d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Negative-QTOFsplash10-014i-0900000000-972f865a96261dcb891a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Negative-QTOFsplash10-014i-0900000000-06171ad407ac98e9b2a52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Negative-QTOFsplash10-014i-9300000000-2cbda1718cb4dbcce0122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Positive-QTOFsplash10-0592-0900000000-37cf9ecd0820f286aeed2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Positive-QTOFsplash10-0zfr-3900000000-8b807998f5cd06d1ab9f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Positive-QTOFsplash10-0udi-7900000000-6b921145859c90c4715d2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011996
KNApSAcK IDNot Available
Chemspider ID4476786
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318169
PDB IDNot Available
ChEBI IDNot Available
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
(E)-3-(2-Hydroxyphenyl)-2-propenal → 3,4,5-trihydroxy-6-{2-[(1E)-3-oxoprop-1-en-1-yl]phenoxy}oxane-2-carboxylic aciddetails