ChemFOnt: Showing chemical card for (S)-3,4-Dihydroxybutyric acid (CFc000000239)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:35 UTC

Chemfont ID

CFc000000239

Molecule Identification

Common Name

(S)-3,4-Dihydroxybutyric acid

Definition

3,4-Dihydroxybutyric acid (also known as 3,4-Dihydroxybutanoic acid or 3,4-DB, or 2-deoxytetronic acid, or 2-DTA) is a normal human urinary metabolite that is excreted in increased concentration in patients with succinic semialdehyde dehydrogenase (SSADH) deficiency (PMID 12127325 ), which is a genetic disorder. SSADH deficiency is caused by an enzyme deficiency in GABA degradation. The most constant features with this disease are developmental delay, hypotonia and intellectual disability. Nearly half of SSADH patients exhibit ataxia, behavioral problems, seizures, and hyporeflexia. Normal adults excrete 0.37 +/- 0.15 (SD) mmoles of 3,4-dihydroxybutyrate per 24 hr. 3,4-dihydroxybutyrate is also detectable in blood. The renal clearance of 3,4-dihydroxybutyrate is roughly equal that of creatinine. 3,4-dihydroxybutyric acid has also been found in foods and is believed to be formed via the degradation (cooking) of di- and poly-saccharides (PMID: 1167165 ). 3,4-Dihydroxybutyric acid is believed to play a role in satiety or the feeling of fullness and suppresses food intake (PMID: 3191387 ; PMID: 6720928 ). 3,4-dihydroxybutyric acid is also elevated in the serum of individuals with dementia and may even serve as a predictive biomarker for dementia (PMID: 25177334 ). 3,4-Dihydroxybutyric acid is also a metabolite produced in Escherichia (PMID: 28342964 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-3,4-Dihydroxybutyrate	Generator
(S)-3,4-Dihydroxy-butyric acid	HMDB
(S)-3,4-Dihydroxybutanoate	HMDB
(S)-3,4-Dihydroxybutanoic acid	HMDB
2-Deoxytetronate	HMDB
2-Deoxytetronic acid	HMDB
3,4-Dihydroxybutanoate	HMDB
3,4-Dihydroxybutanoic acid	HMDB
3,4-Dihydroxybutanoic acid, (S)-isomer	HMDB
3,4-Dihydroxybutanoic acid, monosodium salt	HMDB

Chemical Formula

C₄H₈O₄

Average Molecular Weight

120.1039

Monoisotopic Molecular Weight

120.042258744

IUPAC Name

3,4-dihydroxybutanoic acid

Traditional Name

3,4-dihydroxybutanoic acid

CAS Registry Number

51267-44-8

SMILES

OCC(O)CC(O)=O

InChI Identifier

InChI=1S/C4H8O4/c5-2-3(6)1-4(7)8/h3,5-6H,1-2H2,(H,7,8)

InChI Key

DZAIOXUZHHTJKN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Short-chain hydroxy acid
Fatty acid
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

omega-hydroxy fatty acid (CHEBI:86371 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Cerebrospinal Fluid (CSF) (PMID: 8412012)
Cerebrospinal fluid (HMDB: HMDB0000337)

Excreta

Biofluid or Excreta

Urine (PMID: 1167165)
Feces (PMID: 20669995)

Source

Endogenous

Endogenous (HMDB: HMDB0000337)

Microbe

Escherichia coli (HMDB: HMDB0000337)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Aldehyde dehydrogenase deficiency (MarkerDB: MDB00000147)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	832 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.4	ChemAxon
logS	0.84	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	25.01 m³·mol⁻¹	ChemAxon
Polarizability	10.91 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

HMDB0000337

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021961

KNApSAcK ID

C00052139

Chemspider ID

133026

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

150929

PDB ID

Not Available

ChEBI ID

86371

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Cho, Yik-haeng; Chun, Jongpil; Park, Youngmi; Roh, Kyoungrok; Yu, Hosung; Hwang, Daeil. Process for preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives. PCT Int. Appl. (2000), 29 pp.

Showing chemical card for (S)-3,4-Dihydroxybutyric acid (CFc000000239)

MOL for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

3D MOL for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

3D SDF for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

3D-SDF for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

PDB for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

3D PDB for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

SMILES for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

INCHI for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

Structure for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)

3D Structure for CFc000000239 ((S)-3,4-Dihydroxybutyric acid)