You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:46 UTC
HMDB IDHMDB0000943
Secondary Accession Numbers
  • HMDB0062620
  • HMDB00943
  • HMDB62620
Metabolite Identification
Common NameThreonic acid
DescriptionThreonic acid, also known as threonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID: 21034532 ). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component is aqueous humour and blood (PMID: 10420182 ). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID: 20615997 ).
Structure
Data?1582752166
Synonyms
ValueSource
L-ThreonateKegg
(2R,3S)-2,3,4-Trihydroxybutanoic acidKegg
(2R,3S)-2,3,4-TrihydroxybutanoateGenerator
Threonic acid, (R-(r*,s*))-isomerHMDB
Threonic acidHMDB
2,3,4-Trihydroxy-(threo)-butanoic acidHMDB
ThreonateHMDB
Threonic acid, (r*,r*)-isomerHMDB
L-Threonic acidGenerator
2,3,4-Trihydroxybutanoic acidHMDB
2,3,4-Trihydroxybutyric acidHMDB
Chemical FormulaC4H8O5
Average Molecular Weight136.1033
Monoisotopic Molecular Weight136.037173366
IUPAC Name(2R,3S)-2,3,4-trihydroxybutanoic acid
Traditional Namethreonate
CAS Registry Number7306-96-9
SMILES
OC[C@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1
InChI KeyJPIJQSOTBSSVTP-STHAYSLISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Sugar acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility53 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility488 g/LALOGPS
logP-2.1ALOGPS
logP-2.1ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.35 m³·mol⁻¹ChemAxon
Polarizability11.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gc3-1980000000-1134cc7dbfebc81101f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-9000000000-8d139618fe1977b7f75cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-05i9-9135200000-540f14ba652277646ad0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kp-9400000000-65ee9acbf3bfc5e1217dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00l2-9100000000-530757fa85c48c04e4f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014j-9100000000-0598e87e111f68c2e5adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-3900000000-2b3d3fb29e0133c070faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-9c5553554eff5afd7d2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r6v-9100000000-b760f5ab8de654f72611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-009l-9300000000-cea0b9791733d92b7dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abl-9100000000-5893bc2f3c3758ba4459Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-b86ae9d1fd6d44595e98Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified14.8 (8.6-36.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified63.0 +/- 21.0 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified88.928 +/- 40.543 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified10.0 +/- 7.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified20.8 (10.2 - 39.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified14.2 (4.2-36.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified13.4 (5.1-46.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.5 (2.1-13.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified3.1(1.7-13.7) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
gastric cancer
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
superficial gastric cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SweatDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specifiedscreen-positive CF details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified114.997 +/- 87.963 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. 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 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Stomach cancer
  1. Yu L, Aa J, Xu J, Sun M, Qian S, Cheng L, Yang S, Shi R: Metabolomic phenotype of gastric cancer and precancerous stages based on gas chromatography time-of-flight mass spectrometry. J Gastroenterol Hepatol. 2011 Aug;26(8):1290-7. doi: 10.1111/j.1440-1746.2011.06724.x. [PubMed:21443661 ]
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB11192
Phenol Explorer Compound IDNot Available
FooDB IDFDB030975
KNApSAcK IDC00034314
Chemspider ID4573940
KEGG Compound IDC01620
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThreonic_acid
METLIN IDNot Available
PubChem Compound5460407
PDB IDNot Available
ChEBI ID15908
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSong J Z; Huang D P; Tian S J; Sun Z P Determination of L-threonate in calcium L-threonate preparations by capillary electrophoresis with indirect UV detection. Electrophoresis (1999), 20(9), 1850-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Chalmers RA, Lawson AM, Hauschildt S, Watts RW: The urinary excretion of glycollic acid and threonic acid by xylitol-infused patients and their relationship to the possible role of 'active glycoladehyde' in the transketolase reaction in vivo. Biochem Soc Trans. 1975;3(4):518-21. [PubMed:1183712 ]
  3. Harding JJ, Hassett PC, Rixon KC, Bron AJ, Harvey DJ: Sugars including erythronic and threonic acids in human aqueous humour. Curr Eye Res. 1999 Aug;19(2):131-6. [PubMed:10420182 ]
  4. Leveque N, Mac-Mary S, Muret P, Makki S, Aubin F, Kantelip JP, Heusele C, S S, Humbert P: Evaluation of a sunscreen photoprotective effect by ascorbic acid assessment in human dermis using microdialysis and gas chromatography mass spectrometry. Exp Dermatol. 2005 Mar;14(3):176-81. [PubMed:15740589 ]
  5. Watts RW, Hauschildt S, Chalmers RA, Lawson AM: Metabolic investigations during xylitol infusion. Int Z Vitam Ernahrungsforsch Beih. 1976;15:216-25. [PubMed:821885 ]
  6. van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]
  7. Kwack MH, Ahn JS, Kim MK, Kim JC, Sung YK: Preventable effect of L-threonate, an ascorbate metabolite, on androgen-driven balding via repression of dihydrotestosterone-induced dickkopf-1 expression in human hair dermal papilla cells. BMB Rep. 2010 Oct;43(10):688-92. doi: 10.5483/BMBRep.2010.43.10.688. [PubMed:21034532 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]