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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:05:20 UTC

Update Date

2023-02-21 17:28:19 UTC

HMDB ID

HMDB0040531

Secondary Accession Numbers

HMDB40531

Metabolite Identification

Common Name

2-Hydroxy-4-oxopentanoic acid

Description

2-Hydroxy-4-oxopentanoic acid is found in alcoholic beverages. 2-Hydroxy-4-oxopentanoic acid is formed in beer wort fermentation Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. 2-Hydroxy-4-oxopentanoic acid is one of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. 2-Hydroxy-4-oxopentanoic acid is an excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-4-oxopentanoate	Generator
2-Hydroxy-4-oxovaleric acid	HMDB
a-Hydroxy-b-acetylpropionic acid	HMDB
a-Hydroxylevulinic acid	HMDB
Acetolactic acid	HMDB

Chemical Formula

C₅H₈O₄

Average Molecular Weight

132.1146

Monoisotopic Molecular Weight

132.042258744

IUPAC Name

2-hydroxy-4-oxopentanoic acid

Traditional Name

2-hydroxy-4-oxopentanoic acid

CAS Registry Number

54031-97-9

SMILES

CC(=O)CC(O)C(O)=O

InChI Identifier

InChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h4,7H,2H2,1H3,(H,8,9)

InChI Key

QTSNVMMGKAPSRT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040531)
Cell membrane (HMDB: HMDB0040531)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040531)

Source

Exogenous

Food

Food (HMDB: HMDB0040531)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040531)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	181 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	6.30	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	181 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-0.78	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	-3.9	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	28.43 m³·mol⁻¹	ChemAxon
Polarizability	11.97 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]+	128.762	31661259
DarkChem	[M-H]-	123.246	31661259
DeepCCS	[M+H]+	126.108	30932474
DeepCCS	[M-H]-	123.325	30932474
DeepCCS	[M-2H]-	159.798	30932474
DeepCCS	[M+Na]+	134.646	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	124.6	32859911
AllCCS	[M+Na-2H]-	127.3	32859911
AllCCS	[M+HCOO]-	130.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-oxopentanoic acid	CC(=O)CC(O)C(O)=O	2461.8	Standard polar	33892256
2-Hydroxy-4-oxopentanoic acid	CC(=O)CC(O)C(O)=O	946.6	Standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid	CC(=O)CC(O)C(O)=O	1201.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #1	CC(=O)CC(O[Si](C)(C)C)C(=O)O	1246.7	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #2	CC(=O)CC(O)C(=O)O[Si](C)(C)C	1212.3	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #3	CC(=CC(O)C(=O)O)O[Si](C)(C)C	1328.6	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #4	C=C(CC(O)C(=O)O)O[Si](C)(C)C	1315.9	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #1	CC(=O)CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1341.2	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #2	CC(=CC(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	1462.0	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #3	C=C(CC(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	1402.6	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #4	CC(=CC(O)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1392.9	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #5	C=C(CC(O)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1360.1	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #1	CC(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1499.7	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #1	CC(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1435.3	Standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #2	C=C(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1444.5	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #2	C=C(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1453.9	Standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #1	CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O	1484.1	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #2	CC(=O)CC(O)C(=O)O[Si](C)(C)C(C)(C)C	1448.2	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #3	CC(=CC(O)C(=O)O)O[Si](C)(C)C(C)(C)C	1585.5	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #4	C=C(CC(O)C(=O)O)O[Si](C)(C)C(C)(C)C	1545.1	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #1	CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1768.0	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #2	CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C	1928.6	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #3	C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C	1823.2	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #4	CC(=CC(O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1838.7	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #5	C=C(CC(O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1806.2	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #1	CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2123.7	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #1	CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2071.0	Standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #2	C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2067.9	Semi standard non polar	33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #2	C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2059.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-e66d04210bcdaaec0f1f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0076-9340000000-7e77e0de3e7fb5124421	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic 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 - 2-Hydroxy-4-oxopentanoic acid 10V, Positive-QTOF	splash10-014i-7900000000-134b9829ef446615f81e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Positive-QTOF	splash10-014j-9300000000-8172fac34150117643bf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Positive-QTOF	splash10-014l-9000000000-1ba9dbbb6e61f679b4c4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Negative-QTOF	splash10-001i-6900000000-18c236e3427ea498fa32	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Negative-QTOF	splash10-01w0-9300000000-431e5906f2009cacfd36	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Negative-QTOF	splash10-0avu-9000000000-12a74b10e2c2bfca1fb9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Negative-QTOF	splash10-01q9-7900000000-c98cddec2196e78ceb4d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Negative-QTOF	splash10-0006-9000000000-7df4f2d0321e470c3da6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Negative-QTOF	splash10-052f-9000000000-3f203d80defce9fc9425	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Positive-QTOF	splash10-014r-9000000000-8ebf358e48c5c00cee6f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Positive-QTOF	splash10-0006-9000000000-d5b8515c60ed019f79b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-3a78789c386089a42b49	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB020299

KNApSAcK ID

Not Available

Chemspider ID

8278736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10103208

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

Holland LZ: Developmental biology: a chordate with a difference. Nature. 2007 May 10;447(7141):153-5. [PubMed:17495912 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Hydroxy-4-oxopentanoic acid (HMDB0040531)

MOL for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

3D MOL for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

3D SDF for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

3D-SDF for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

PDB for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

3D PDB for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

SMILES for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

INCHI for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

Structure for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

3D Structure for HMDB0040531 (2-Hydroxy-4-oxopentanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra