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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:10:05 UTC
Update Date2020-02-26 21:24:56 UTC
HMDB IDHMDB0004062
Secondary Accession Numbers
  • HMDB04062
Metabolite Identification
Common NameGentisate aldehyde
DescriptionGentisate aldehyde belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Gentisate aldehyde is a substrate of the enzyme aldehyde oxidase 1 in Valine, leucine and isoleucine degradation, Tyrosine metabolism, Tryptophan metabolism, Vitamin B6 metabolism and Nicotinate and nicotinamide metabolism. Gentisate aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Gentisate aldehyde exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752296
Synonyms
ValueSource
GentisaldehydeChEBI
2,5-DihydroxybenzaldehydeKegg
Gentisic acid aldehydeGenerator
2,5-Dihydroxybenzaldehyde polymerHMDB
Gentisate aldehydeChEBI
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name2,5-dihydroxybenzaldehyde
Traditional Name2,5-dihydroxybenzaldehyde
CAS Registry Number1194-98-5
SMILES
OC1=CC(C=O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-4-5-3-6(9)1-2-7(5)10/h1-4,9-10H
InChI KeyCLFRCXCBWIQVRN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
  • Hydroquinone
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.54JIN,LJ ET AL. (1998)
Predicted Properties
PropertyValueSource
Water Solubility14.9 g/LALOGPS
logP1.02ALOGPS
logP1.73ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)8.76ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability12.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-00kp-5960000000-bec903f315e1845244d7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kp-5960000000-bec903f315e1845244d7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000f-3950000000-8e919d9041c538560134Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-1900000000-0b145e1b76109b0e3eb4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-7590000000-455567d8dfbc7e3dba5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-af21f8eeeeadcc46cbfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-04c4fa8144677146316eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-d411348adc0ce1a20115Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-62156de1635566675d5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-b2aa10703171a591e141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pvr-9500000000-27265e763c9f32220d26Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB023295
KNApSAcK IDNot Available
Chemspider ID64111
KEGG Compound IDC05585
BioCyc IDCPD-16722
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70949
PDB IDNot Available
ChEBI ID28508
Food Biomarker OntologyNot Available
VMH IDHC01522
References
Synthesis ReferenceZeng, Hanwei; Zhang, Ting; Liu, Lin; Lai, Weiming. Synthesis of hydroxybenzaldehydes by Reimer-Tiemann reaction with phase transfer catalyst. Huanan Ligong Daxue Xuebao, Ziran Kexueban (1997), 25(12), 70-74.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Gentisic acid + Hydrogen peroxide → Gentisate aldehyde + Oxygen + Waterdetails