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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:10:47 UTC
Update Date2019-01-11 19:49:46 UTC
HMDB IDHMDB0035227
Secondary Accession Numbers
  • HMDB35227
Metabolite Identification
Common NameHydroxypropanedioic acid
DescriptionHydroxypropanedioic acid is found in potato. Tartronic acid or 2-hydroxymalonic acid is a dicarboxylic acid with the structural formula of HOOCCH(OH)COOH. (Wikipedia).
Structure
Data?1547236185
Synonyms
ValueSource
2-HydroxymalonateChEBI
2-Hydroxymalonic acidChEBI
2-Hydroxypropanedioic acidChEBI
2-Tartronic acidChEBI
Tartronic acidChEBI
HydroxypropanedioateGenerator
2-HydroxypropanedioateGenerator
2-TartronateGenerator
TartronateGenerator
Hydroxy-malonic acidHMDB
HydroxymalonateHMDB
Hydroxymalonic acidHMDB
Propanedioic acid, hydroxy- (9ci)HMDB
Tartronic acid, 8ciHMDB
Chemical FormulaC3H4O5
Average Molecular Weight120.0609
Monoisotopic Molecular Weight120.005873238
IUPAC Name2-hydroxypropanedioic acid
Traditional Nametartronic acid
CAS Registry Number80-69-3
SMILES
OC(C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)
InChI KeyROBFUDYVXSDBQM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0ue9-0930000000-72836d646b8c3440486dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-008c-1983000000-a595fea5038ab6a983d2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-0930000000-72836d646b8c3440486dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-008c-1983000000-a595fea5038ab6a983d2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7k-0910000000-3c772d60bdd00371bb5dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fml-9300000000-ce47a47fbac5b3203273View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-9161000000-97e3c100b5034fcc3bdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-8900000000-16ebb5f175ac6ca39ab2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-3b2f9b0a130dd49117a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-3af4b557f3ccb85e572eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-0e67c1f979c08e6c1324View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-c80ff83bde053c84f6d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-eacff3e7b8c5b7a4bb46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0umi-5900000000-43842f30c6f53f622e3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-5cba6b9d751d47649575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-7900000000-0b7d28cdb82196bf0fcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gk9-9700000000-c950dc2924a2c4743ce6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adi-9000000000-6aa558d0b6aa291cb54fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-057i-9000000000-8869f8e57dc896c8634bView in 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 IDFDB013880
KNApSAcK IDNot Available
Chemspider ID44
KEGG Compound IDC02287
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxymalonic_acid
METLIN IDNot Available
PubChem Compound45
PDB IDNot Available
ChEBI ID16513
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guerranti R, Pagani R, Neri S, Errico SV, Leoncini R, Marinello E: Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives. Biochim Biophys Acta. 2001 Nov 7;1568(1):45-52. [PubMed:11731084 ]
  2. Jacob J, Grimmer G: [Occurrence of alkyl-hydroxymalonic acids in uropygial gland secretions of birds (author's transl)]. Hoppe Seylers Z Physiol Chem. 1973 Dec;354(12):1648-50. [PubMed:4803853 ]
  3. VEITCH FP, BRIERLEY GP: The quantitative determination of tartronic acid (hydroxymalonic acid) in urine and tissues. Biochim Biophys Acta. 1962 Apr 23;58:567-73. [PubMed:14039995 ]
  4. Knope KE, Kimura H, Yasaka Y, Nakahara M, Andrews MB, Cahill CL: Investigation of in situ oxalate formation from 2,3-pyrazinedicarboxylate under hydrothermal conditions using nuclear magnetic resonance spectroscopy. Inorg Chem. 2012 Mar 19;51(6):3883-90. doi: 10.1021/ic3000944. Epub 2012 Feb 24. [PubMed:22360688 ]
  5. Shen JM, Chen ZL, Xu ZZ, Li XY, Xu BB, Qi F: Kinetics and mechanism of degradation of p-chloronitrobenzene in water by ozonation. J Hazard Mater. 2008 Apr 15;152(3):1325-31. Epub 2007 Aug 8. [PubMed:17889996 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Hydroxypropanedioic acid → 2-(sulfooxy)propanedioic aciddetails
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
Hydroxypropanedioic acid → 2-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]propanedioic aciddetails
Hydroxypropanedioic acid → 6-[(2-carboxy-2-hydroxyacetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME3
Uniprot ID:
Q16798
Molecular weight:
67067.875
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Molecular weight:
53585.73
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]