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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:30 UTC
Update Date2022-03-07 02:53:13 UTC
HMDB IDHMDB0032057
Secondary Accession Numbers
  • HMDB32057
Metabolite Identification
Common Name(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid
Description(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid, also known as 3-(2,3-dihydroxyphenyl)acrylate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid has been detected, but not quantified in, roman camomiles (Chamaemelum nobile). This could make (e)-3-(2,3-dihydroxyphenyl)-2-propenoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid.
Structure
Data?1563862213
Synonyms
ValueSource
3-(2,3-Dihydroxyphenyl)-2-propenoic acidChEBI
3-(2,3-Dihydroxyphenyl)acrylic acidChEBI
3-(2,3-Dihydroxyphenyl)-2-propenoateGenerator
3-(2,3-Dihydroxyphenyl)acrylateGenerator
(e)-3-(2,3-Dihydroxyphenyl)-2-propenoateGenerator
ADPribose 2'-phosphateHMDB
APXHMDB
2,3-DihydroxycinnamateGenerator
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name3-(2,3-dihydroxyphenyl)prop-2-enoic acid
Traditional Name2,3-dihydroxycinnamic acid
CAS Registry Number38481-04-8
SMILES
OC(=O)C=CC1=C(O)C(O)=CC=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)
InChI KeySIUKXCMDYPYCLH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.66 g/LALOGPS
logP1.66ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings1ChemAxon
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]+142.38531661259
DarkChem[M-H]-135.39231661259
DeepCCS[M+H]+137.68330932474
DeepCCS[M-H]-135.28730932474
DeepCCS[M-2H]-170.35630932474
DeepCCS[M+Na]+144.83130932474
AllCCS[M+H]+138.332859911
AllCCS[M+H-H2O]+134.032859911
AllCCS[M+NH4]+142.332859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-134.232859911
AllCCS[M+Na-2H]-134.932859911
AllCCS[M+HCOO]-135.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acidOC(=O)C=CC1=C(O)C(O)=CC=C13413.9Standard polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acidOC(=O)C=CC1=C(O)C(O)=CC=C11794.6Standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acidOC(=O)C=CC1=C(O)C(O)=CC=C11836.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CC=CC(O)=C1O2110.4Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TMS,isomer #2C[Si](C)(C)OC1=C(O)C=CC=C1C=CC(=O)O1985.6Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=CC(C=CC(=O)O)=C1O1995.6Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CC=CC(O[Si](C)(C)C)=C1O2029.4Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C=CC1=CC=CC(O)=C1O[Si](C)(C)C2009.4Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=CC(C=CC(=O)O)=C1O[Si](C)(C)C1996.3Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C=CC1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C2042.1Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC(O)=C1O2355.3Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC=C1C=CC(=O)O2277.8Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC(C=CC(=O)O)=C1O2286.4Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O2547.0Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C2533.6Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC(C=CC(=O)O)=C1O[Si](C)(C)C(C)(C)C2562.7Semi standard non polar33892256
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2768.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0900000000-5750614cca6786ac5b1f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5149000000-c43f9e3eea6dc7cf478f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 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-(2,3-Dihydroxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-03di-0900000000-44b9a48999fe377a92992015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 20V, Positive-QTOFsplash10-03dr-1900000000-20778098331cd15e948e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 40V, Positive-QTOFsplash10-056r-9700000000-6ae51d6153dca13a0a942015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 10V, Negative-QTOFsplash10-004i-0900000000-f9ba26903c27c6fb0a5d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 20V, Negative-QTOFsplash10-01ti-0900000000-69b5bceb0e88f63a7bd72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 40V, Negative-QTOFsplash10-0a4i-3900000000-e47dd58a9a230a9fb78b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 10V, Negative-QTOFsplash10-002r-0900000000-a54c94dd8b9d66011f762021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 20V, Negative-QTOFsplash10-000i-0900000000-ff2fcba215fea0578e7c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 40V, Negative-QTOFsplash10-001i-3900000000-f8420acef19e9f5414db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-01q9-0900000000-a484b6b259791cb239c42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 20V, Positive-QTOFsplash10-00kr-0900000000-8b407247a3c3a5ca7e462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid 40V, Positive-QTOFsplash10-0fb9-9500000000-fe57620236acad0cd5a02021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart 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 IDFDB002699
KNApSAcK IDNot Available
Chemspider ID21865585
KEGG Compound IDC12623
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282146
PDB IDNot Available
ChEBI ID48681
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 magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 3-(2-hydroxy-3-methoxyphenyl)prop-2-enoic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic aciddetails
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-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-[3-(2-carboxyeth-1-en-1-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-[2-(2-carboxyeth-1-en-1-yl)-6-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-{[3-(2,3-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-{3-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-{2-[(1E)-2-carboxyeth-1-en-1-yl]-6-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 6-{[(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in NAD+ nucleosidase activity
Specific function:
Synthesizes cyclic ADP-ribose, a second messenger that elicits calcium release from intracellular stores. May be involved in pre-B-cell growth.
Gene Name:
BST1
Uniprot ID:
Q10588
Molecular weight:
35723.545
Reactions
NADP + Water → Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic aciddetails
General function:
Involved in NAD+ nucleosidase activity
Specific function:
Synthesizes cyclic ADP-ribose, a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:
CD38
Uniprot ID:
P28907
Molecular weight:
34328.145
Reactions
NADP + Water → Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → 3-[2-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic aciddetails
(E)-3-(2,3-Dihydroxyphenyl)-2-propenoic acid → (2E)-3-[2-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic aciddetails