Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2019-11-26 03:09:12 UTC
Primary IDFDB013880
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHydroxypropanedioic acid
DescriptionHydroxypropanedioic acid, also known as 2-tartronic acid or 2-hydroxymalonate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Hydroxypropanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxypropanedioic acid has been detected, but not quantified in, potato. This could make hydroxypropanedioic acid a potential biomarker for the consumption of these foods.
CAS Number80-69-3
Structure
Thumb
Synonyms
SynonymSource
2-HydroxymalonateChEBI
2-Hydroxymalonic acidChEBI
2-Hydroxypropanedioic acidChEBI
2-Tartronic acidChEBI
Tartronic acidChEBI
Hydroxymalonic acidKegg
2-HydroxypropanedioateGenerator
2-TartronateGenerator
TartronateGenerator
HydroxymalonateGenerator
HydroxypropanedioateGenerator
Hydroxy-malonic acidHMDB
Propanedioic acid, hydroxy- (9ci)HMDB
Tartronic acid, 8ciHMDB
Malonic acid, hydroxy-biospider
Propanedioic acid, hydroxy- (9CI)biospider
Tartronic acid, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility182 g/LALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)2.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.33 m³·mol⁻¹ChemAxon
Polarizability8.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H4O5
IUPAC name2-hydroxypropanedioic acid
InChI IdentifierInChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)
InChI KeyROBFUDYVXSDBQM-UHFFFAOYSA-N
Isomeric SMILESOC(C(O)=O)C(O)=O
Average Molecular Weight120.0609
Monoisotopic Molecular Weight120.005873238
Classification
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 30.01%; H 3.36%; O 66.63%DFC
Melting PointMp 156-158° (rapid heating)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa2 4.74 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0ue9-0930000000-72836d646b8c3440486dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-008c-1983000000-a595fea5038ab6a983d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-0930000000-72836d646b8c3440486dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-008c-1983000000-a595fea5038ab6a983d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7k-0910000000-3c772d60bdd00371bb5dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fml-9300000000-ce47a47fbac5b3203273JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-9161000000-97e3c100b5034fcc3bdcJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-8900000000-16ebb5f175ac6ca39ab2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-3b2f9b0a130dd49117a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-3af4b557f3ccb85e572eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0e67c1f979c08e6c1324JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-c80ff83bde053c84f6d6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-eacff3e7b8c5b7a4bb46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umi-5900000000-43842f30c6f53f622e3cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-5cba6b9d751d47649575JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-7900000000-0b7d28cdb82196bf0fcfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gk9-9700000000-c950dc2924a2c4743ce6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adi-9000000000-6aa558d0b6aa291cb54fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-057i-9000000000-8869f8e57dc896c8634bJSpectraViewer | MoNA
ChemSpider ID44
ChEMBL IDNot Available
KEGG Compound IDC02287
Pubchem Compound ID45
Pubchem Substance IDNot Available
ChEBI ID16513
Phenol-Explorer IDNot Available
DrugBank IDDB03680
HMDB IDHMDB35227
CRC / DFC (Dictionary of Food Compounds) IDJJM09-U:JJM09-U
EAFUS IDNot Available
Dr. Duke IDHYDROXYMALONIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHydroxypropanedioic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).