P. aeruginosa Metabolome Database: (R)-Pantoate (PAMDB000865)

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

PAMDB000865

Identification

Name:

(R)-Pantoate

Description:

(r)-pantoate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)Pantoic acid is an alpha hydroxy acid which is a component of some biologically active compounds. The amide of pantoic acid with alanine is pantothenic acid (vitamin B5) and the amide with β-alanine is the pharmaceutical drug hopantenic acid. It is also a central component of coenzyme A. (WikiPedia)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2R)-2,4-dihydroxy-3,3-dimethylbutanoate
(2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid
(R)-Pantoic acid
2,4-DIHYDROXY-3,3-DIMETHYL-BUTYRATE
2,4-DIHYDROXY-3,3-dimethyl-butyric acid
L-Pantoate
L-Pantoic acid
PAF
Pantoate
Pantoic acid

Chemical Formula:

C₆H₁₁O₄

Average Molecular Weight:

147.151

Monoisotopic Molecular Weight:

147.066282414

InChI Key:

OTOIIPJYVQJATP-UHFFFAOYSA-M

InChI:

InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/p-1

CAS number:

470-29-1

IUPAC Name:

(2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid

Traditional IUPAC Name:

(R)-pantoic 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 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
Methyl-branched fatty acid
Short-chain hydroxy acid
Branched fatty acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
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

pantoic acid (CHEBI:18697 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	308.0 mg/mL	ALOGPS
logP	-0.59	ALOGPS
logP	-0.49	ChemAxon
logS	0.32	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.01 m³·mol^-1	ChemAxon
Polarizability	14.36 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
beta-Alanine + Adenosine triphosphate + (R)-Pantoate <> Adenosine monophosphate + Hydrogen ion + Pantothenic acid + Pyrophosphate
Adenosine triphosphate + (R)-Pantoate + beta-Alanine <> Adenosine monophosphate + Pyrophosphate + Pantothenic acid
(R)-Pantoate + NADP > 2-Dehydropantoate + NADPH
2-dehydropantoate + NADPH + Hydrogen ion + 2-Dehydropantoate + NADPH > NADP + (R)-pantoate + (R)-Pantoate
beta-Alanine + Adenosine triphosphate + (R)-pantoate + (R)-Pantoate > Adenosine monophosphate + Pyrophosphate + Hydrogen ion + Pantothenic acid + Pantothenic acid

Pathways:

Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770
beta-Alanine metabolism pae00410

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-1900000000-7d32d9fe2f4c45ee7840	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-9500000000-27fa4de1f52b9b39c2c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9100000000-4b387706b53ffaba5f68	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-2900000000-ea603b384234b8b971d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9600000000-c12f5dc91e63440b6213	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-921e587537e7f7b8173d	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	14737
HMDB ID	Not Available
Pubchem Compound ID	5289105
Kegg ID	C00522
ChemSpider ID	825
Wikipedia ID	Not Available
BioCyc ID	L-PANTOATE
EcoCyc ID	L-PANTOATE
Ligand Expo	PAF

(R)-Pantoate (PAMDB000865)

Structure for (R)-Pantoate (PAMDB000865)