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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:36 UTC

Update Date

2023-02-21 17:20:02 UTC

HMDB ID

HMDB0031204

Secondary Accession Numbers

HMDB31204

Metabolite Identification

Common Name

4-Hydroxy-2-oxobutanoic acid

Description

4-Hydroxy-2-oxobutanoic acid, also known as g-hydroxy-a-ketobutyric acid, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Based on a literature review very few articles have been published on 4-Hydroxy-2-oxobutanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-2-oxobutanoate	Generator
4-Hydroxy-2-oxo-butanoic acid	HMDB
g-Hydroxy-a-ketobutyric acid	HMDB

Chemical Formula

C₄H₆O₄

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

IUPAC Name

4-hydroxy-2-oxobutanoic acid

Traditional Name

4-hydroxy-2-oxobutanoic acid

CAS Registry Number

22136-38-5

SMILES

OCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O4/c5-2-1-3(6)4(7)8/h5H,1-2H2,(H,7,8)

InChI Key

PUWWONYMIXRVQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Beta-hydroxy ketone
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031204)
Cytoplasm (HMDB: HMDB0031204)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031204)

Source

Endogenous

Endogenous (HMDB: HMDB0031204)

Plant

Plant (HMDB: HMDB0031204)

Exogenous

Food

Food (HMDB: HMDB0031204)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031204)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	203 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.51	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.39 m³·mol⁻¹	ChemAxon
Polarizability	10.14 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.533	31661259
DarkChem	[M-H]-	118.219	31661259
DeepCCS	[M+H]+	124.582	30932474
DeepCCS	[M-H]-	121.782	30932474
DeepCCS	[M-2H]-	158.106	30932474
DeepCCS	[M+Na]+	132.717	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	124.1	32859911
AllCCS	[M+NH4]+	132.3	32859911
AllCCS	[M+Na]+	133.4	32859911
AllCCS	[M-H]-	122.6	32859911
AllCCS	[M+Na-2H]-	125.7	32859911
AllCCS	[M+HCOO]-	129.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.43 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9036 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	206.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	775.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	62.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	258.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	591.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	582.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	790.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	655.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	322.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2-oxobutanoic acid	OCCC(=O)C(O)=O	2187.1	Standard polar	33892256
4-Hydroxy-2-oxobutanoic acid	OCCC(=O)C(O)=O	1410.3	Standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid	OCCC(=O)C(O)=O	1107.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2-oxobutanoic acid,1TMS,isomer #1	C[Si](C)(C)OCCC(=O)C(=O)O	1226.7	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CCO	1223.0	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CCO)C(=O)O	1309.9	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TMS,isomer #1	C[Si](C)(C)OCCC(=O)C(=O)O[Si](C)(C)C	1365.2	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TMS,isomer #2	C[Si](C)(C)OCC=C(O[Si](C)(C)C)C(=O)O	1431.3	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(=CCO)O[Si](C)(C)C	1351.2	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,3TMS,isomer #1	C[Si](C)(C)OCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1486.4	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,3TMS,isomer #1	C[Si](C)(C)OCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1421.0	Standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC(=O)C(=O)O	1507.8	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCO	1471.6	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CCO)C(=O)O	1542.4	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1795.5	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1885.7	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(=CCO)O[Si](C)(C)C(C)(C)C	1818.5	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2097.8	Semi standard non polar	33892256
4-Hydroxy-2-oxobutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1980.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2-oxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-d0698ba038fb5d80f822	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2-oxobutanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-006t-9710000000-69d2970585db07d452c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2-oxobutanoic 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-Hydroxy-2-oxobutanoic acid 10V, Positive-QTOF	splash10-0udi-5900000000-0f6e948f61492d54b2d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 20V, Positive-QTOF	splash10-0k9t-9300000000-28903bba658087b82336	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-acd931ff66cf173f13d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 10V, Negative-QTOF	splash10-014i-9600000000-134036db6972db438011	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 20V, Negative-QTOF	splash10-00ds-9100000000-8bdecbb3506f8407b332	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-70fc01d526a0dea4fff2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 10V, Negative-QTOF	splash10-00xu-9300000000-c27713d5d449f8261506	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 20V, Negative-QTOF	splash10-0abc-9000000000-69800db2e7337c8e0ca7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-d03872d32ed723681677	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 10V, Positive-QTOF	splash10-0zmm-9200000000-d0d888f695ef34dea50a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-ab2177a215acd5680e34	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2-oxobutanoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-b26bc7baa541a6fbbc02	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Extracellular

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

FDB003226

KNApSAcK ID

Not Available

Chemspider ID

10137246

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11963036

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxy-2-oxobutanoic acid (HMDB0031204)

MOL for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

3D MOL for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

3D SDF for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

3D-SDF for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

PDB for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

3D PDB for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

SMILES for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

INCHI for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

Structure for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

3D Structure for HMDB0031204 (4-Hydroxy-2-oxobutanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra