Showing Compound Threonic acid (FDB022331)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:16 UTC

Update date

2020-09-17 15:42:30 UTC

Primary ID

FDB022331

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Threonic acid

Description

Threonic 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 Number

3909-12-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Threonate	Generator
(R,s)-2,3,4-trihydroxy-butanoate	HMDB
(R,s)-2,3,4-trihydroxy-butanoic acid	HMDB
Threo-2,3,4-trihydroxybutyrate	HMDB
Threo-2,3,4-trihydroxybutyric acid	HMDB
Magnesium threonate	HMDB
Calcium threonate	HMDB
Threonic acid, (R-(r,s))-isomer	HMDB
2,3,4-Trihydroxy-(threo)-butanoic acid	HMDB
Calcium L-threonate	HMDB
Threonic acid, (r,r)-isomer	HMDB
ClariMem	HMDB
L-TAMS compound	HMDB
L-Threonic acid magnesium salt	HMDB
MMFS-01	HMDB
D-Threonate	HMDB
Threonic acid	MeSH
(R,S)-2,3,4-trihydroxy-Butanoate	hmdb
(R,S)-2,3,4-trihydroxy-Butanoic acid	hmdb
threo-2,3,4-Trihydroxybutyrate	hmdb
threo-2,3,4-Trihydroxybutyric acid	hmdb
threonate	hmdb

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

Chemical Formula

C4H8O5

IUPAC name

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

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 Key

JPIJQSOTBSSVTP-GBXIJSLDSA-N

Isomeric SMILES

OC[C@@H](O)[C@H](O)C(O)=O

Average Molecular Weight

136.1033

Monoisotopic Molecular Weight

136.037173366

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.

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:49059 )

Ontology

Disposition

Source:

Endogenous

Biological:

Microbe

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Threonic acid, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-5d71818cd6db7ec8d1ae	Spectrum
GC-MS	Threonic acid, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-5d71818cd6db7ec8d1ae	Spectrum
Predicted GC-MS	Threonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-08i0-9000000000-a6368075271779e24860	Spectrum
Predicted GC-MS	Threonic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i9-9135200000-540f14ba652277646ad0	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00kp-9400000000-65ee9acbf3bfc5e1217d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00l2-9100000000-530757fa85c48c04e4f7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014j-9100000000-0598e87e111f68c2e5ad	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-9200000000-091ade190af0ce52426c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-001i-0900000000-cb8ba6605d1dc85ddd48	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-1900000000-67a95eaf677d506929d7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9400000000-1a36117238ace5c088fe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0r2d-9100000000-62efa9ebb51e5c537e84	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-009l-9300000000-dd4e44912147d53588d4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9000000000-8f75a955a50587cab80c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-5add1fb2e5ea1ab055d4	2017-09-01	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum