P. aeruginosa Metabolome Database: D-2-Hydroxyglutaric acid (PAMDB000155)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000155

Identification

Name:

D-2-Hydroxyglutaric acid

Description:

D-2-Hydroxyglutaric acid is a member of the chemical class known as Short-chain Hydroxy Acids and Derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(R)-2-hydroxy-Pentanedioate
(R)-2-hydroxy-Pentanedioic acid
(R)-2-Hydroxyglutarate
(R)-2-Hydroxyglutaric acid
(R)-a-Hydroxyglutarate
(R)-a-Hydroxyglutaric acid
(R)-alpha-Hydroxyglutarate
(R)-alpha-Hydroxyglutaric acid
(R)-α-Hydroxyglutarate
(R)-α-Hydroxyglutaric acid
2-Hydroxy-D-Glutarate
2-Hydroxy-D-Glutaric acid
D-2-Hydroxyglutarate
D-2-Hydroxyglutaric acid
D-a-Hydroxyglutarate
D-a-Hydroxyglutaric acid
D-alpha-Hydroxyglutarate
D-alpha-Hydroxyglutaric acid
D-α-Hydroxyglutarate
D-α-Hydroxyglutaric acid

Chemical Formula:

C₅H₈O₅

Average Molecular Weight:

148.114

Monoisotopic Molecular Weight:

148.037173366

InChI Key:

HWXBTNAVRSUOJR-UHFFFAOYSA-N

InChI:

InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)

CAS number:

13095-47-1

IUPAC Name:

2-hydroxypentanedioic acid

Traditional IUPAC Name:

2-hydroxyglutaric acid

SMILES:

OC(CCC(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Hydroxy fatty acid
Short-chain hydroxy acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

>300 °C

Experimental Properties:

Property	Value	Source
LogP:	-0.979	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	157.0 mg/mL	ALOGPS
logP	-1	ALOGPS
logP	-0.82	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	29.63 m³·mol^-1	ChemAxon
Polarizability	12.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

D-2-Hydroxyglutaric acid + NAD > Oxoglutaric acid + NADH
3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate

Pathways:

Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-4a286f23e047b386c273	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0lz0-9600000000-6b6214d1086f381022a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9100000000-02ce88ad8bf7c4b7f22a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-2900000000-6750865d94d1d2564b29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zi9-8900000000-8cdd78454ba0d2069b3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-1ef9312d29d127c85bf8	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	32796
HMDB ID	HMDB00606
Pubchem Compound ID	43
Kegg ID	C02630
ChemSpider ID	42
Wikipedia ID	Alpha-Hydroxyglutaric acid
BioCyc ID	Not Available

D-2-Hydroxyglutaric acid (PAMDB000155)

Structure for D-2-Hydroxyglutaric acid (PAMDB000155)