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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2015-01-30 22:04:27 UTC
Update Date2019-07-23 07:17:49 UTC
HMDB IDHMDB0062121
Secondary Accession Numbers
  • HMDB62121
Metabolite Identification
Common NameDihydroferulic acid
DescriptionDihydroferulic acid, also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid or dihydroconiferylate, is classified as a member of the phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Dihydroferulic acid is considered to be slightly soluble (in water) and acidic. Dihydroferulic acid is a phenolic acid metabolite and was found to be significantly elevated in serum after whole grain consumption which makes this compound a potential serum biomarker of whole grain intake (PMID: 25646321 ).
Structure
Data?1563866269
Synonyms
ValueSource
3-(4-Hydroxy-3-methoxyphenyl)propionic acidChEBI
Dihydroconiferylic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionateGenerator
DihydroconiferylateGenerator
HydroferulateGenerator
(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acidHMDB
3-(3’-Methoxy-4’-hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acidHMDB
3-Methoxy-4-hydroxyphenylpropionic acidHMDB
3-Methoxyphloretic acidHMDB
4-Hydroxy-3-methoxybenzenepropanoic acidHMDB
DHFAHMDB
Dihydroferulic acidHMDB
Hydroferulic acidHMDB
Shorbic acidHMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acidHMDB
β-(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
β-3-Methoxy-4-hydroxyphenylpropionic acidHMDB
Chemical FormulaC10H12O4
Average Molecular Weight196.1999
Monoisotopic Molecular Weight196.073558872
IUPAC Name3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Namehomovanillinic acid
CAS Registry Number1135-23-5
SMILES
COC1=C(O)C=CC(CCC(O)=O)=C1
InChI Identifier
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
InChI KeyBOLQJTPHPSDZHR-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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.3 g/LALOGPS
logP1.03ALOGPS
logP1.59ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.41 m³·mol⁻¹ChemAxon
Polarizability19.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0900000000-326c8295f745d6de85d0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9053000000-50b6ef8efef449290129JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-0e26134b0d0191f7ee92JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug1-0900000000-7168875369e00ead2dcdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbr-5900000000-7d74ece7efd4fcc57d7aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-eb9b945ab0bf9d6f5dc3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-aa8130dbec23e196888aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7900000000-b403cda9802707e7ecbfJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000600 +/- 0.000200 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
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. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029987
KNApSAcK IDC00040946
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14340
PDB IDNot Available
ChEBI ID86612
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rechner AR, Spencer JP, Kuhnle G, Hahn U, Rice-Evans CA: Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med. 2001 Jun 1;30(11):1213-22. [PubMed:11368919 ]
  2. Redeuil K, Smarrito-Menozzi C, Guy P, Rezzi S, Dionisi F, Williamson G, Nagy K, Renouf M: Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. J Chromatogr A. 2011 Jul 22;1218(29):4678-88. doi: 10.1016/j.chroma.2011.05.050. Epub 2011 May 26. [PubMed:21676405 ]
  3. Ludwig IA, Paz de Pena M, Concepcion C, Alan C: Catabolism of coffee chlorogenic acids by human colonic microbiota. Biofactors. 2013 Nov-Dec;39(6):623-32. doi: 10.1002/biof.1124. Epub 2013 Aug 1. [PubMed:23904092 ]
  4. Lang R, Dieminger N, Beusch A, Lee YM, Dunkel A, Suess B, Skurk T, Wahl A, Hauner H, Hofmann T: Bioappearance and pharmacokinetics of bioactives upon coffee consumption. Anal Bioanal Chem. 2013 Oct;405(26):8487-503. doi: 10.1007/s00216-013-7288-0. Epub 2013 Aug 28. [PubMed:23982107 ]
  5. Stalmach A, Williamson G, Crozier A: Impact of dose on the bioavailability of coffee chlorogenic acids in humans. Food Funct. 2014 Aug;5(8):1727-37. doi: 10.1039/c4fo00316k. [PubMed:24947504 ]
  6. Wang P, Chen H, Zhu Y, McBride J, Fu J, Sang S: Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. J Nutr. 2015 Feb;145(2):239-45. doi: 10.3945/jn.114.206508. Epub 2014 Dec 17. [PubMed:25644343 ]
  7. Mills CE, Tzounis X, Oruna-Concha MJ, Mottram DS, Gibson GR, Spencer JP: In vitro colonic metabolism of coffee and chlorogenic acid results in selective changes in human faecal microbiota growth. Br J Nutr. 2015 Apr 28;113(8):1220-7. doi: 10.1017/S0007114514003948. Epub 2015 Mar 26. [PubMed:25809126 ]
  8. Tan S, Calani L, Bresciani L, Dall'asta M, Faccini A, Augustin MA, Gras SL, Del Rio D: The degradation of curcuminoids in a human faecal fermentation model. Int J Food Sci Nutr. 2015;66(7):790-6. doi: 10.3109/09637486.2015.1095865. [PubMed:26471074 ]
  9. Sanchez-Bridge B, Renouf M, Sauser J, Beaumont M, Actis-Goretta L: The roasting process does not influence the extent of conjugation of coffee chlorogenic and phenolic acids. Biofactors. 2016 May;42(3):259-67. doi: 10.1002/biof.1268. Epub 2016 Feb 22. [PubMed:26899568 ]
  10. Vitaglione P, Mennella I, Ferracane R, Rivellese AA, Giacco R, Ercolini D, Gibbons SM, La Storia A, Gilbert JA, Jonnalagadda S, Thielecke F, Gallo MA, Scalfi L, Fogliano V: Whole-grain wheat consumption reduces inflammation in a randomized controlled trial on overweight and obese subjects with unhealthy dietary and lifestyle behaviors: role of polyphenols bound to cereal dietary fiber. Am J Clin Nutr. 2015 Feb;101(2):251-61. doi: 10.3945/ajcn.114.088120. Epub 2014 Dec 3. [PubMed:25646321 ]
  11. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

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
Dihydroferulic acid → 6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Dihydroferulic acid → 3,4,5-trihydroxy-6-{[3-(4-hydroxy-3-methoxyphenyl)propanoyl]oxy}oxane-2-carboxylic 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
Dihydroferulic acid → Dihydroferulic acid 4-O-sulfatedetails