Showing Compound Card for Threonic acid (CDB006177)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:39 UTC
Updated at2020-11-18 16:34:40 UTC
CannabisDB IDCDB006177
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC4H8O5
Average Molecular Weight136.1
Monoisotopic Molecular Weight136.0372
IUPAC Name(2S,3R)-2,3,4-trihydroxybutanoic acid
Traditional Namethreonic acid
CAS Registry Number3909-12-4
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+/m1/s1
InChI KeyJPIJQSOTBSSVTP-GBXIJSLDSA-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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Dickkopf-related protein 1DKK110q21.1O94907 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Dickkopf-related protein 1DKK110q21.1O94907 details
Concentrations Data
Not Available
HMDB IDHMDB0000943
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022331
KNApSAcK IDNot Available
Chemspider ID133224
KEGG Compound IDC01620
BioCyc IDNot Available
BiGG ID38497
Wikipedia LinkThreonic acid
METLIN ID5891
PubChem Compound151152
PDB IDNot Available
ChEBI ID49059
References
General References
  1. 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. doi: 10.1076/ceyr.19.2.131.5334. [PubMed:10420182 ]
  2. 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 ]
  3. 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 ]