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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:18:55 UTC

HMDB ID

HMDB0000498

Secondary Accession Numbers

HMDB00498

Metabolite Identification

Common Name

4-Deoxyerythronic acid

Description

4-Deoxyerythronic acid, also known as 2,3-dihydroxybutanoic acid, 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. 4-Deoxyerythronic acid exists in all living organisms, ranging from bacteria to humans. 4-Deoxyerythronic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-deoxyerythronic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Deoxyerythronic acid.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Deoxyerythronate	Generator
(+/-)-erythro-2,3-dihydroxybutyric acid	HMDB
(R,r)-2,3-dihydroxy-butanoate	HMDB
(R,r)-2,3-dihydroxy-butanoic acid	HMDB
(R,r)-2,3-dihydroxybutanoate	HMDB
(R,r)-2,3-dihydroxybutanoic acid	HMDB
(R,s)-2,3-dihydroxybutanoate	HMDB
(R,s)-2,3-dihydroxybutanoic acid	HMDB
2,3-Dihydroxybutanoic acid	HMDB
2,3-Erythro-dihydroxybutyrate	HMDB
2,3-Erythro-dihydroxybutyric acid	HMDB
4-Deoxy-erythronate	HMDB
4-Deoxy-erythronic acid	HMDB
4-Deoxytetronic acid	HMDB
Erythro-2,3-dihydroxybutyric acid	HMDB
(2R,3R)-2,3-Dihydroxybutanoate	HMDB

Chemical Formula

C₄H₈O₄

Average Molecular Weight

120.1039

Monoisotopic Molecular Weight

120.042258744

IUPAC Name

(2R,3R)-2,3-dihydroxybutanoic acid

Traditional Name

4-deoxyerythronic acid

CAS Registry Number

759-06-8

SMILES

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

InChI Identifier

InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3-/m1/s1

InChI Key

LOUGYXZSURQALL-PWNYCUMCSA-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
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Excreta

Urine

Cellular substructure

Macromolecular complex

Blood

Cytoplasm

Ingestion

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 Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	454 g/L	ALOGPS
logP	10^(-1.2) g/L	ALOGPS
logP	10^(-1.1) g/L	ChemAxon
logS	10^(0.58) g/L	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.1	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	2	ChemAxon
Refractivity	24.8 m³·mol⁻¹	ChemAxon
Polarizability	10.74 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

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.283	31661259
DarkChem	[M-H]-	121.611	31661259
AllCCS	[M+H]+	130.687	32859911
AllCCS	[M-H]-	122.092	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Deoxyerythronic acid,1TMS,#1	C[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1173.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TMS,#2	C[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1195.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TMS,#3	C[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1112.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#1	C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1283.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#2	C[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1246.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TMS,#3	C[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1249.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,3TMS,#1	C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1361.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#1	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	1435.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#2	C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1453.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,1TBDMS,#3	C[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1342.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#1	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1743.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#2	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1690.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,2TBDMS,#3	C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1693.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
4-Deoxyerythronic acid,3TBDMS,#1	C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1996.5	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9000000000-4f8b3914e68986e2fc76	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-7594000000-41795a8299b4ed9a75dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyerythronic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 4-Deoxyerythronic acid 10V, Positive-QTOF	splash10-0uk9-4900000000-e93ff8f7aad0f2c8fdea	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Positive-QTOF	splash10-0udr-9600000000-db7b2d4f0f4a450600e4	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Positive-QTOF	splash10-0a4r-9000000000-c6f2a60b94ceef71fa3a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Negative-QTOF	splash10-016r-9700000000-1e769b015c5e815e5fd1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Negative-QTOF	splash10-05di-9200000000-320d571457b8c5b1a0ac	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Negative-QTOF	splash10-0ab9-9000000000-222ebdab55908e04bc53	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Negative-QTOF	splash10-00or-9800000000-2fbe96770b983d31a58d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Negative-QTOF	splash10-004l-9000000000-a0881fec62969be92bad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Negative-QTOF	splash10-0a4l-9000000000-16140d690957c073bf98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 10V, Positive-QTOF	splash10-0002-9200000000-794a2a36a438372a84c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 20V, Positive-QTOF	splash10-0a4j-9000000000-1db4f99bbccdd36ec8b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyerythronic acid 40V, Positive-QTOF	splash10-0002-9000000000-488ae4d8cef018c0dfe1	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	5.0 +/- 3.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

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

FDB022077

KNApSAcK ID

Not Available

Chemspider ID

17215960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5484

PubChem Compound

13120901

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Owen, L. N. Oxygenation of crotonaldehyde. Journal of the Chemical Society (1943), 563-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kassel DB, Martin M, Schall W, Sweeley CC: Urinary metabolites of L-threonine in type 1 diabetes determined by combined gas chromatography/chemical ionization mass spectrometry. Biomed Environ Mass Spectrom. 1986 Oct;13(10):535-40. [PubMed:2947647 ]
Bultitude FW, Newham SJ: Identification of some abnormal metabolites in plasma from uremic subjects. Clin Chem. 1975 Aug;21(9):1329-34. [PubMed:1149237 ]

Showing metabocard for 4-Deoxyerythronic acid (HMDB0000498)

MOL for HMDB0000498 (4-Deoxyerythronic acid)

3D MOL for HMDB0000498 (4-Deoxyerythronic acid)

3D SDF for HMDB0000498 (4-Deoxyerythronic acid)

3D-SDF for HMDB0000498 (4-Deoxyerythronic acid)

PDB for HMDB0000498 (4-Deoxyerythronic acid)

3D PDB for HMDB0000498 (4-Deoxyerythronic acid)

SMILES for HMDB0000498 (4-Deoxyerythronic acid)

INCHI for HMDB0000498 (4-Deoxyerythronic acid)

Structure for HMDB0000498 (4-Deoxyerythronic acid)

3D Structure for HMDB0000498 (4-Deoxyerythronic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra