Record Information
Version1.0
Creation date2010-04-08 22:14:56 UTC
Update date2019-11-26 03:18:44 UTC
Primary IDFDB020299
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-4-oxopentanoic acid
DescriptionFormed 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. 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. 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). 2-Hydroxy-4-oxopentanoic acid is found in alcoholic beverages.
CAS Number54031-97-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP-0.9ALOGPS
logP-0.78ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.43 m³·mol⁻¹ChemAxon
Polarizability11.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O4
IUPAC name2-hydroxy-4-oxopentanoic acid
InChI IdentifierInChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h4,7H,2H2,1H3,(H,8,9)
InChI KeyQTSNVMMGKAPSRT-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CC(O)C(O)=O
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Hydroxy-4-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-e66d04210bcdaaec0f1fSpectrum
Predicted GC-MS2-Hydroxy-4-oxopentanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0076-9340000000-7e77e0de3e7fb5124421Spectrum
Predicted GC-MS2-Hydroxy-4-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-7900000000-134b9829ef446615f81e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9300000000-8172fac34150117643bf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-1ba9dbbb6e61f679b4c42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-6900000000-18c236e3427ea498fa322015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w0-9300000000-431e5906f2009cacfd362015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avu-9000000000-12a74b10e2c2bfca1fb92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-7900000000-c98cddec2196e78ceb4d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-7df4f2d0321e470c3da62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-3f203d80defce9fc94252021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-9000000000-8ebf358e48c5c00cee6f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-d5b8515c60ed019f79b82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3a78789c386089a42b492021-09-24View Spectrum
NMRNot Available
ChemSpider ID8278736
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10103208
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40531
CRC / DFC (Dictionary of Food Compounds) IDMNT28-R:MNT28-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference