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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:38:47 UTC
Update Date2019-07-23 06:34:55 UTC
HMDB IDHMDB0041727
Secondary Accession Numbers
  • HMDB41727
Metabolite Identification
Common NameDihydrosinapic acid
DescriptionDihydrosinapic acid is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Dihydrosinapic acid is a metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1563863695
Synonyms
ValueSource
DihydrosinapateGenerator
HDMPA CPDMeSH
3-(4'-Hydroxyl-3',5'-dimethoxyphenyl)propionic acidMeSH
3-(4-Hydroxy-3,5-dimethoxyphenyl)propanoateGenerator
3-(4-Hydroxy-3,5-dimethoxyphenyl)propionic acidHMDB
4-Hydroxy-3,5-dimethoxybenzenepropanoic acidHMDB
4-Hydroxy-3,5-dimethoxyhydrocinnamic acidHMDB
Dihydrosinapic acidHMDB
Chemical FormulaC11H14O5
Average Molecular Weight226.2259
Monoisotopic Molecular Weight226.084123558
IUPAC Name3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid
Traditional Name3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid
CAS Registry Number14897-78-0
SMILES
COC1=CC(CCC(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H14O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h5-6,14H,3-4H2,1-2H3,(H,12,13)
InChI KeyBPPVOXVSMSXBEI-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
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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 Solubility0.86 g/LALOGPS
logP1.08ALOGPS
logP1.44ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.87 m³·mol⁻¹ChemAxon
Polarizability22.74 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, Positivesplash10-0159-1920000000-8a9733148f93eed742d6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g0-9053000000-a16fdee870db6a9332b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-a72d146fe1e30e487fc3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-0930000000-3f606694130a453bae1fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-5900000000-0647c5cb279aa50ba81bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-7fa30296843f5e09bee3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-1980000000-e8696eecf7eb3a60add7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-ffd7fc3aafdae2ce2d09JSpectraViewer | MoNA
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
FoodDB IDFDB029893
KNApSAcK IDNot Available
Chemspider ID76391
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound84681
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
  2. 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 ]