P. aeruginosa Metabolome Database: 2-Dehydropantoate (PAMDB000576)

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

PAMDB000576

Identification

Name:

2-Dehydropantoate

Description:

2-dehydropantoate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)2-dehydropantoate is invovled in Pantothenate and CoA biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Dehydropantoic acid
2-Keto-pantoate
2-Keto-pantoic acid
2DHPA
Ketopantoate
Ketopantoic acid

Chemical Formula:

C₆H₉O₄

Average Molecular Weight:

145.1333

Monoisotopic Molecular Weight:

145.050083776

InChI Key:

PKVVTUWHANFMQC-UHFFFAOYSA-M

InChI:

InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)/p-1

CAS number:

Not Available

IUPAC Name:

4-hydroxy-3,3-dimethyl-2-oxobutanoic acid

Traditional IUPAC Name:

ketopantoic acid

SMILES:

CC(C)(CO)C(=O)C([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound 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

Methyl-branched fatty acid
Short-chain keto acid
Branched fatty acid
Fatty acyl
Beta-hydroxy ketone
Beta-ketoaldehyde
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo monocarboxylic acid (CHEBI:17094 )
hydroxy monocarboxylic acid (CHEBI:17094 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	109.0 mg/mL	ALOGPS
logP	-0.35	ALOGPS
logP	0.58	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	-2.8	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	33.47 m³·mol^-1	ChemAxon
Polarizability	13.83 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:

2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate
alpha-Ketoisovaleric acid + Water + 5,10-Methylene-THF + a-Ketoisovaleric acid <> 2-Dehydropantoate + Tetrahydrofolic acid
Water + alpha-Ketoisovaleric acid + 5,10-Methylene-THF <> 2-Dehydropantoate + Tetrahydrofolic acid
5,10-Methylene-THF + a-Ketoisovaleric acid + Water > Tetrahydrofolic acid + 2-Dehydropantoate
(R)-Pantoate + NADP > 2-Dehydropantoate + NADPH
2-dehydropantoate + NADPH + Hydrogen ion + 2-Dehydropantoate + NADPH > NADP + (R)-pantoate + (R)-Pantoate
a-Ketoisovaleric acid + 5,10-Methylene-THF + Water + 5,10-Methylene-THF > Tetrahydrofolic acid + 2-dehydropantoate + Tetrahydrofolic acid + 2-Dehydropantoate

Pathways:

Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770

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	splash10-0fba-1900000000-65021b449e2495c02885	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-9600000000-094d64c5b115d0ef1bb6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9100000000-e52d8a1685278ec9f7b6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-1900000000-f912860fc8aba37cf980	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gi1-7900000000-cd2194ab1aec775efa09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-9100000000-e74573027b9636f2c922	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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17094
HMDB ID	Not Available
Pubchem Compound ID	38
Kegg ID	C00966
ChemSpider ID	37
Wikipedia ID	Not Available
BioCyc ID	2-DEHYDROPANTOATE
EcoCyc ID	2-DEHYDROPANTOATE
Ligand Expo	KPL

2-Dehydropantoate (PAMDB000576)

Structure for 2-Dehydropantoate (PAMDB000576)