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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:44 UTC

HMDB ID

HMDB0000349

Secondary Accession Numbers

HMDB0002475
HMDB00349
HMDB02475

Metabolite Identification

Common Name

Erythrono-1,4-lactone

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000349)

Source

Endogenous

Endogenous (HMDB: HMDB0000349)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	124.089	31661259
DarkChem	[M-H]-	120.051	31661259
AllCCS	[M+H]+	126.524	32859911
AllCCS	[M-H]-	118.247	32859911
DeepCCS	[M+H]+	128.24	30932474
DeepCCS	[M-H]-	126.326	30932474
DeepCCS	[M-2H]-	161.827	30932474
DeepCCS	[M+Na]+	135.961	30932474
AllCCS	[M+H]+	126.5	32859911
AllCCS	[M+H-H2O]+	121.7	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	118.2	32859911
AllCCS	[M+Na-2H]-	120.8	32859911
AllCCS	[M+HCOO]-	123.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erythrono-1,4-lactone	O[C@@H]1COC(=O)[C@@H]1O	2308.9	Standard polar	33892256
Erythrono-1,4-lactone	O[C@@H]1COC(=O)[C@@H]1O	1156.7	Standard non polar	33892256
Erythrono-1,4-lactone	O[C@@H]1COC(=O)[C@@H]1O	1289.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erythrono-1,4-lactone,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O	1296.7	Semi standard non polar	33892256
Erythrono-1,4-lactone,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C(=O)OC[C@H]1O	1276.0	Semi standard non polar	33892256
Erythrono-1,4-lactone,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O[Si](C)(C)C	1410.0	Semi standard non polar	33892256
Erythrono-1,4-lactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O	1506.1	Semi standard non polar	33892256
Erythrono-1,4-lactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@H]1O	1519.2	Semi standard non polar	33892256
Erythrono-1,4-lactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C	1834.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (2 TMS)	splash10-0udi-1920000000-8bf103e6bad44eb52cac	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized)	splash10-0udi-1920000000-8bf103e6bad44eb52cac	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-63c53760143cd2044873	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (2 TMS) - 70eV, Positive	splash10-0fki-9430000000-f0cfa4e00daeb540aee7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Positive-QTOF	splash10-0gb9-1900000000-d7d529471e146551a470	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Positive-QTOF	splash10-0uxr-1900000000-7e70d7eac9b72e1cbd36	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Positive-QTOF	splash10-0a4l-9100000000-7a95b8e64f0d366b4101	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Negative-QTOF	splash10-014i-2900000000-c877a9861f0a9e0fa947	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Negative-QTOF	splash10-014j-8900000000-874d13e11592fe389a74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Negative-QTOF	splash10-006x-9000000000-295d5454144b0a74cb00	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Negative-QTOF	splash10-00di-9100000000-ccaaa47150cc978a00b9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Negative-QTOF	splash10-0a4l-9000000000-07ca8b081361da8d614e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Negative-QTOF	splash10-0006-9000000000-846eebab9a9caa26cce6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Positive-QTOF	splash10-0udi-6900000000-fde995765993269b5d05	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Positive-QTOF	splash10-0007-9100000000-11a72527d4f24a67775b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Positive-QTOF	splash10-0007-9000000000-f1bef05a855750753132	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581 ]

Showing metabocard for Erythrono-1,4-lactone (HMDB0000349)

MOL for HMDB0000349 (Erythrono-1,4-lactone)

3D MOL for HMDB0000349 (Erythrono-1,4-lactone)

3D SDF for HMDB0000349 (Erythrono-1,4-lactone)

3D-SDF for HMDB0000349 (Erythrono-1,4-lactone)

PDB for HMDB0000349 (Erythrono-1,4-lactone)

3D PDB for HMDB0000349 (Erythrono-1,4-lactone)

SMILES for HMDB0000349 (Erythrono-1,4-lactone)

INCHI for HMDB0000349 (Erythrono-1,4-lactone)

Structure for HMDB0000349 (Erythrono-1,4-lactone)

3D Structure for HMDB0000349 (Erythrono-1,4-lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra