ChemFOnt: Showing chemical card for Threonic acid (CFc000000753)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:14 UTC

Chemfont ID

CFc000000753

Molecule Identification

Common Name

Threonic acid

Definition

Threonic 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 in 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-Threonate	Kegg
(2R,3S)-2,3,4-Trihydroxybutanoic acid	Kegg
L-Threonic acid	Generator
(2R,3S)-2,3,4-Trihydroxybutanoate	Generator
Threonate	Generator
Threonic acid, (R-(r,s))-isomer	HMDB
2,3,4-Trihydroxy-(threo)-butanoic acid	HMDB
Threonic acid, (r,r)-isomer	HMDB
2,3,4-Trihydroxybutanoic acid	HMDB
2,3,4-Trihydroxybutyric acid	HMDB
Threonic acid	MeSH, HMDB

Chemical Formula

C₄H₈O₅

Average Molecular Weight

136.1033

Monoisotopic Molecular Weight

136.037173366

IUPAC Name

(2R,3S)-2,3,4-trihydroxybutanoic acid

Traditional Name

threonate

CAS Registry Number

7306-96-9

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 Key

JPIJQSOTBSSVTP-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar 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 Framework

Aliphatic acyclic compounds

External Descriptors

threonic acid (CHEBI:15908 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25105552)
Saliva (PMID: 22308371)

Organ

Placenta (HMDB: HMDB0000943)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 20669995)
Sweat (PMID: 26755145)

Cellular substructure

Cytoplasm (HMDB: HMDB0000943)

Source

Exogenous

Exogenous (HMDB: HMDB0000943)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000943)

Microbe

Microbe (HMDB: HMDB0000943)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000287)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	488 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.1	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.35 m³·mol⁻¹	ChemAxon
Polarizability	11.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000943

DrugBank ID

DB11192

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Threonic_acid

METLIN ID

Not Available

PubChem Compound

5460407

PDB ID

Not Available

ChEBI ID

15908

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Song 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.

Showing chemical card for Threonic acid (CFc000000753)

MOL for CFc000000753 (Threonic acid)

3D MOL for CFc000000753 (Threonic acid)

3D SDF for CFc000000753 (Threonic acid)

3D-SDF for CFc000000753 (Threonic acid)

PDB for CFc000000753 (Threonic acid)

3D PDB for CFc000000753 (Threonic acid)

SMILES for CFc000000753 (Threonic acid)

INCHI for CFc000000753 (Threonic acid)

Structure for CFc000000753 (Threonic acid)

3D Structure for CFc000000753 (Threonic acid)