Record Information
Version1.0
Creation date2011-09-21 00:12:16 UTC
Update date2020-09-17 15:42:30 UTC
Primary IDFDB022331
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameThreonic acid
DescriptionThreonic acid also known as threonate, belongs to the class of organic compounds known as sugar acids. Sugar acids are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a weak acid (based on its pKa). Threonic acid is derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). Threonic acid is probably derived from glycated proteins or from the degradation of ascorbic acid. It is a normal component is aqueous humour and blood (PMID: 10420182). One recent 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 a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). Threonate has also been found to be a microbial metabolite (PMID: 20615997).
CAS Number3909-12-4
Structure
Thumb
Synonyms
SynonymSource
ThreonateGenerator
(R*,s*)-2,3,4-trihydroxy-butanoateHMDB
(R*,s*)-2,3,4-trihydroxy-butanoic acidHMDB
Threo-2,3,4-trihydroxybutyrateHMDB
Threo-2,3,4-trihydroxybutyric acidHMDB
Magnesium threonateHMDB
Calcium threonateHMDB
Threonic acid, (R-(r*,s*))-isomerHMDB
2,3,4-Trihydroxy-(threo)-butanoic acidHMDB
Calcium L-threonateHMDB
Threonic acid, (r*,r*)-isomerHMDB
ClariMemHMDB
L-TAMS compoundHMDB
L-Threonic acid magnesium saltHMDB
MMFS-01HMDB
D-ThreonateHMDB
Threonic acidMeSH
(R*,S*)-2,3,4-trihydroxy-Butanoatehmdb
(R*,S*)-2,3,4-trihydroxy-Butanoic acidhmdb
threo-2,3,4-Trihydroxybutyratehmdb
threo-2,3,4-Trihydroxybutyric acidhmdb
threonatehmdb
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
Chemical FormulaC4H8O5
IUPAC name(2S,3R)-2,3,4-trihydroxybutanoic acid
InChI IdentifierInChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1
InChI KeyJPIJQSOTBSSVTP-GBXIJSLDSA-N
Isomeric SMILESOC[C@@H](O)[C@H](O)C(O)=O
Average Molecular Weight136.1033
Monoisotopic Molecular Weight136.037173366
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSThreonic acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0930000000-5d71818cd6db7ec8d1aeSpectrum
GC-MSThreonic acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0930000000-5d71818cd6db7ec8d1aeSpectrum
Predicted GC-MSThreonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08i0-9000000000-a6368075271779e24860Spectrum
Predicted GC-MSThreonic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i9-9135200000-540f14ba652277646ad0Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kp-9400000000-65ee9acbf3bfc5e1217d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00l2-9100000000-530757fa85c48c04e4f72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014j-9100000000-0598e87e111f68c2e5ad2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9200000000-091ade190af0ce52426c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0900000000-cb8ba6605d1dc85ddd482020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1900000000-67a95eaf677d506929d72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9400000000-1a36117238ace5c088fe2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r2d-9100000000-62efa9ebb51e5c537e842017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-009l-9300000000-dd4e44912147d53588d42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9000000000-8f75a955a50587cab80c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-5add1fb2e5ea1ab055d42017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID133224
ChEMBL IDNot Available
KEGG Compound IDC01620
Pubchem Compound ID151152
Pubchem Substance IDNot Available
ChEBI ID15908
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00943
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID38497
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference