ChemFOnt: Showing chemical card for Erythrono-1,4-lactone (CFc000000250)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:36 UTC

Chemfont ID

CFc000000250

Molecule Identification

Common Name

Erythrono-1,4-lactone

Definition

Erythrono-1,4-lactone has been identified as a lactone of tetronic acid in the urine from normal adults and neonates. The formation of this compound may be a consequence of lactonization of erythronic acid during the extraction/isolation process. Lactonization is a potential problem when measuring acids that contain a hydroxyl group at the number 4 carbon, as lactones are formed under acidic conditions. Evidence indicates that most 4-hydroxy acids do not normally exist to any appreciable extent as lactones in urine. (PMID 1192581 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-Erythronolactone	ChEBI
Erythronic acid gamma-lactone	ChEBI
Erythronate g-lactone	Generator
Erythronate gamma-lactone	Generator
Erythronate γ-lactone	Generator
Erythronic acid g-lactone	Generator
Erythronic acid γ-lactone	Generator
(3R,4R)-Dihydro-3,4-dihydroxy-threono-1,4-lactone 2(3H)-furanone	HMDB
(3R,4R)-Rel-dihydro-3,4-dihydroxy-2(3H)-furanone	HMDB
3,4-Dihydroxydihydro-2(3H)-furanone	HMDB
D-Erythronic acid gamma-lactone	HMDB
delta-Erythronic acid gamma-lactone	HMDB
Dihydro-3,4-dihydroxy-cis-2(3H)-furanone	HMDB

Chemical Formula

C₄H₆O₄

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

IUPAC Name

(3R,4R)-3,4-dihydroxyoxolan-2-one

Traditional Name

erythrono-1,4-lactone

CAS Registry Number

17675-99-9

SMILES

O[C@@H]1COC(=O)[C@@H]1O

InChI Identifier

InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1

InChI Key

SGMJBNSHAZVGMC-PWNYCUMCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000349)

Source

Endogenous

Endogenous (HMDB: HMDB0000349)

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

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1240 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	1.02	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	22.85 m³·mol⁻¹	ChemAxon
Polarizability	9.84 Å³	ChemAxon
Number of Rings	1	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

HMDB0000349

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021972

KNApSAcK ID

C00052984

Chemspider ID

4483398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5338

PubChem Compound

5325915

PDB ID

Not Available

ChEBI ID

87625

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Isaac, I.; Aizel, G.; Stasik, I.; Wadouachi, A.; Beaupere, D. A new efficient access to glycono 1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system. Synlett (1998), (5), 475-476.

Showing chemical card for Erythrono-1,4-lactone (CFc000000250)

MOL for CFc000000250 (Erythrono-1,4-lactone)

3D MOL for CFc000000250 (Erythrono-1,4-lactone)

3D SDF for CFc000000250 (Erythrono-1,4-lactone)

3D-SDF for CFc000000250 (Erythrono-1,4-lactone)

PDB for CFc000000250 (Erythrono-1,4-lactone)

3D PDB for CFc000000250 (Erythrono-1,4-lactone)

SMILES for CFc000000250 (Erythrono-1,4-lactone)

INCHI for CFc000000250 (Erythrono-1,4-lactone)

Structure for CFc000000250 (Erythrono-1,4-lactone)

3D Structure for CFc000000250 (Erythrono-1,4-lactone)