ChemFOnt: Showing chemical card for 2-Hydroxy-4-oxopentanoic acid (CFc000021407)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:12 UTC

Chemfont ID

CFc000021407

Molecule Identification

Common Name

2-Hydroxy-4-oxopentanoic acid

Definition

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 SDF PDB SMILES InChI

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

Functional 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

Exogenous (HMDB: HMDB0040531)

Food

Food (HMDB: HMDB0040531)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040531)

Physical Properties

Predicted 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

External Links

HMDB ID

HMDB0040531

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

References

Synthesis Reference

Not Available

Showing chemical card for 2-Hydroxy-4-oxopentanoic acid (CFc000021407)

MOL for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

3D MOL for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

3D SDF for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

3D-SDF for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

PDB for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

3D PDB for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

SMILES for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

INCHI for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

Structure for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)

3D Structure for CFc000021407 (2-Hydroxy-4-oxopentanoic acid)