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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-09-13 07:30:40 UTC
Update Date2019-11-12 17:34:17 UTC
HMDB IDHMDB0126386
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(2,4-Dihydroxyphenyl)propanoic acid
Description3-(2,4-Dihydroxyphenyl)propanoic acid belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(2,4-Dihydroxyphenyl)propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). BioTransformer predicts that 3-(2,4-dihydroxyphenyl)propanoic acid is a product of 3-(2,4-dihydroxyphenyl)prop-2-enoic acid metabolism via a reduction-of-alpha-beta-unsaturated-compounds-pattern1 reaction occurring in human gut microbiota and catalyzed by the abkar1 enzyme (PMID: 30612223 ).
Structure
Data?1573580057
Synonyms
ValueSource
3-(2,4-Dihydroxyphenyl)propanoateGenerator
3-(24-Dihydroxyphenyl)propionic acidHMDB
3-(24-Dihydroxyphenyl)propionateHMDB
3-(2,4-Dihydroxyphenyl)propionic acidHMDB
DPPA acidHMDB
2,4-Dihydroxy-beta-phenylpropanoic acidHMDB
2,4-Dihydroxy-beta-phenylpropionic acidHMDB
2,4-Dihydroxy-β-phenylpropanoic acidHMDB
2,4-Dihydroxy-β-phenylpropionic acidHMDB
2,4-Dihydroxybenzenepropanoic acidHMDB
2,4-Dihydroxybenzenepropionic acidHMDB
2,4-Dihydroxyhydrocinnamic acidHMDB
2,4-Dihydroxyphenylpropanoic acidHMDB
2,4-Dihydroxyphenylpropionic acidHMDB
3-(2,4-Dihydroxyphenyl)propanoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3-(2,4-dihydroxyphenyl)propanoic acid
Traditional Name3-(2,4-dihydroxyphenyl)propanoic acid
CAS Registry Number5631-68-5
SMILES
OC(=O)CCC1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChI KeyHMCMTJPPXSGYJY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP0.99ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.93 m³·mol⁻¹ChemAxon
Polarizability17.76 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]+141.77931661259
DarkChem[M-H]-137.24831661259
DeepCCS[M+H]+137.68230932474
DeepCCS[M-H]-134.86230932474
DeepCCS[M-2H]-171.00130932474
DeepCCS[M+Na]+146.50630932474
AllCCS[M+H]+139.532859911
AllCCS[M+H-H2O]+135.332859911
AllCCS[M+NH4]+143.432859911
AllCCS[M+Na]+144.532859911
AllCCS[M-H]-137.732859911
AllCCS[M+Na-2H]-138.432859911
AllCCS[M+HCOO]-139.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(2,4-Dihydroxyphenyl)propanoic acidOC(=O)CCC1=C(O)C=C(O)C=C13463.6Standard polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acidOC(=O)CCC1=C(O)C=C(O)C=C11825.2Standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acidOC(=O)CCC1=C(O)C=C(O)C=C11924.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(2,4-Dihydroxyphenyl)propanoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C1O1985.5Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1CCC(=O)O1983.0Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(CCC(=O)O)C(O)=C11950.3Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C=C1O1956.8Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C1O[Si](C)(C)C2005.5Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(CCC(=O)O)C(O[Si](C)(C)C)=C11965.2Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C1976.3Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C1O2227.2Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1CCC(=O)O2226.0Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)O)C(O)=C12190.3Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O2462.2Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C2472.7Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=C12449.4Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)propanoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2654.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid GC-MS (3 TMS)splash10-014i-3791000000-bef2175a80b2c7076f792014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00ur-8069000000-3f85e33d83b8ccd8ab5e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0900000000-431a4bd63e14f02f80742017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic 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 - 3-(2,4-Dihydroxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-001i-0900000000-8c630648126e2cabb8dc2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-01qi-1900000000-909bd4c292780a758acf2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0a4l-9800000000-4ac99926dfa5413177002019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-01q0-0900000000-c77fb045d888651b55422021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-000i-0900000000-d25e56ed7c44594f75b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0006-9700000000-549f163dd4ceebb24cd32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-014i-0900000000-14f5f18e4ad4de601d262019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-00ri-1900000000-8fd392076be87b05b9012019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-0axr-9600000000-5dc1c991fb0fead7af252019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-00di-1900000000-ff543573c45979d54faf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-052r-2900000000-8f8402a4d8a4994c3dec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-00r2-9600000000-a69f9e6ab8af2a8e7bd22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB085261
KNApSAcK IDNot Available
Chemspider ID87007
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound96384
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. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

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
3-(2,4-Dihydroxyphenyl)propanoic acid → 6-[4-(2-carboxyethyl)-3-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(2,4-Dihydroxyphenyl)propanoic acid → 6-[2-(2-carboxyethyl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(2,4-Dihydroxyphenyl)propanoic acid → 6-{[3-(2,4-dihydroxyphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails