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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:30:47 UTC
Update Date2021-10-13 06:35:10 UTC
HMDB IDHMDB0033752
Secondary Accession Numbers
  • HMDB33752
Metabolite Identification
Common Name3-(2-Hydroxyphenyl)propanoic acid
Description3-(2-Hydroxyphenyl)propanoic acid, also known as melilotic acid or melilotate, 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-Hydroxyphenyl)propanoic acid exists in all living organisms, ranging from bacteria to humans. 3-(2-Hydroxyphenyl)propanoic acid has been detected, but not quantified in, several different foods, such as bilberries (Vaccinium myrtillus), chinese cinnamons (Cinnamomum aromaticum), herbs and spices, pulses, and red beetroots (Beta vulgaris var. rubra). This could make 3-(2-hydroxyphenyl)propanoic acid a potential biomarker for the consumption of these foods. 3-(2-Hydroxyphenyl)propanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 3-(2-Hydroxyphenyl)propanoic acid.
Structure
Data?1563862454
Synonyms
ValueSource
2-Hydroxybenzenepropanoic acidChEBI
3-(2-Hydroxyphenyl)propionic acidChEBI
3-(O-Hydroxyphenyl) propionic acidChEBI
Melilotic acidChEBI
O-Hydroxyphenylpropionic acidChEBI
2-HydroxyphenylpropanoateKegg
MelilotateKegg
3-(2-Hydroxyphenyl)propionateKegg
2-HydroxybenzenepropanoateGenerator
3-(O-Hydroxyphenyl) propionateGenerator
O-HydroxyphenylpropionateGenerator
2-Hydroxyphenylpropanoic acidGenerator
3-(2-Hydroxyphenyl)propanoateGenerator
2-Hydroxy-benzenepropanoic acidHMDB
2-Hydroxybenzenepropanoic acid, 9ciHMDB
3-(2-Hydroxyphenyl) propanoic acidHMDB
3-(2-Hydroxyphenyl) propionateHMDB
3-(O-Hydroxyphenyl)propionic acid, 8ciHMDB
beta -(O-Hydroxyphenyl)propionic acidHMDB
beta-(O-Hydroxyphenyl)propionic acidHMDB
Hydrocoumaric acidHMDB
O-Hydroxyhydrocinnamic acidHMDB
OHPAMeSH
Ortho-hydroxyphenylpropionic acidMeSH
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(2-hydroxyphenyl)propanoic acid
Traditional Namemelilotic acid
CAS Registry Number495-78-3
SMILES
OC(=O)CCC1=CC=CC=C1O
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)
InChI KeyCJBDUOMQLFKVQC-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point82 - 83 °CNot Available
Boiling Point335.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility17370 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.100 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available134.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002154
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.76 g/LALOGPS
logP10(1.12) g/LALOGPS
logP10(1.75) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.77 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]+137.14731661259
DarkChem[M-H]-132.56131661259
DeepCCS[M+H]+134.9530932474
DeepCCS[M-H]-132.52930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(2-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC=CC=C1O3089.9Standard polar33892256
3-(2-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC=CC=C1O1543.0Standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC=CC=C1O1627.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(2-Hydroxyphenyl)propanoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=CC=C1O1624.5Semi standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC=C1CCC(=O)O1672.3Semi standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=CC=C1O[Si](C)(C)C1676.1Semi standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=CC=C1O1868.7Semi standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC=C1CCC(=O)O1911.0Semi standard non polar33892256
3-(2-Hydroxyphenyl)propanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=CC=C1O[Si](C)(C)C(C)(C)C2160.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-MS (2 TMS)splash10-01r6-1920000000-ecd488078d5985eafbfb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-MS (Non-derivatized)splash10-01r6-1920000000-ecd488078d5985eafbfb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-b8cabfe5c488ee1ed6042017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3900000000-58936d8a48b093519ddf2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-6b8bf956c803144896702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-9be30b68ac3a0ad3df6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid LC-ESI-QQ , negative-QTOFsplash10-00di-0900000000-0dbababdf59aa8829b0c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid LC-ESI-QQ , negative-QTOFsplash10-05fr-0900000000-168a901fccbb4f1968d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-1900000000-d8ea269e67bd24e633aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-5900000000-337a9131168ae129bf9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid , negative-QTOFsplash10-00di-0900000000-43f2a467bcbee742fee22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0a4i-0900000000-9adde0cc4bea462de6612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-00di-0900000000-de3ff31763098e280e322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-05fr-0900000000-5777067548061cda18bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 35V, Negative-QTOFsplash10-00di-0900000000-d7b812ec743763dc8ed22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 35V, Negative-QTOFsplash10-05fr-0900000000-ee2762870ca42fef29432021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-014j-0900000000-5cf8803d756201d8053a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-05fs-2900000000-6784db2a14b98ff73d392016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-056r-9300000000-20e163ee7cf68d1903d52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-014i-0900000000-03d3c3e2a1e37e56c6642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-01b9-1900000000-1aab1942696c4a143efb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-0a4l-9400000000-e8222e98d8f7bc4e7bde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 10V, Positive-QTOFsplash10-00di-1900000000-b7a29c579ef060cdc6302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 20V, Positive-QTOFsplash10-0ab9-3900000000-b1e43f2b95b1157320912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 40V, Positive-QTOFsplash10-004i-9200000000-217c3ef57768e4d5c9a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 10V, Negative-QTOFsplash10-00di-0900000000-fdb6c955b5072a411a8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 20V, Negative-QTOFsplash10-0fk9-1900000000-940a0dff66b02484072d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxyphenyl)propanoic acid 40V, Negative-QTOFsplash10-00kf-9400000000-209c76387b87ff609feb2021-09-24Wishart 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 Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome
details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011887
KNApSAcK IDC00002756
Chemspider ID850
KEGG Compound IDC01198
BioCyc IDMELILOTATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound873
PDB IDNot Available
ChEBI ID16104
Food Biomarker OntologyNot Available
VMH IDMELT
MarkerDB IDNot Available
Good Scents IDrw1185661
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
3-(2-Hydroxyphenyl)propanoic acid → 6-[2-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(2-Hydroxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[3-(2-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails