ECMDB: (R)-Pantoate (ECMDB20016) (M2MDB000865)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (795)

Record Information

Version

2.0

Creation Date

2012-05-31 14:23:02 -0600

Update Date

2015-09-17 15:42:03 -0600

Secondary Accession Numbers

ECMDB20016

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

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

Weight:

Average: 147.151
Monoisotopic: 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

Description

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

Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
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 g/L	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
(R)-Pantoate + NADP <> 2-Dehydropantoate + NADPH + Hydrogen ion
Adenosine triphosphate + (R)-Pantoate + beta-Alanine <> Adenosine monophosphate + Pyrophosphate + Pantothenic acid
(R)-Pantoate + NADP < Hydrogen ion + 2-Dehydropantoate + NADPH
beta-Alanine + (R)-Pantoate + Adenosine triphosphate > Hydrogen ion + Pantothenic acid + Pyrophosphate + Adenosine monophosphate
Adenosine triphosphate + (R)-Pantoate + beta-Alanine > Adenosine monophosphate + Pyrophosphate + (R)-pantothenate
(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
2 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
2 2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate
beta-Alanine + Adenosine triphosphate + (R)-Pantoate <> Adenosine monophosphate + Hydrogen ion + Pantothenic acid + Pyrophosphate

SMPDB Pathways:

Pantothenate and CoA biosynthesis	PW000828
beta-Alanine metabolism	PW000896

KEGG Pathways:

Metabolic pathways eco01100
Pantothenate and CoA biosynthesis ec00770
beta-Alanine metabolism ec00410

EcoCyc Pathways:

phosphopantothenate biosynthesis I PANTO-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-9300000000-1533cf69a587ccbc946b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-d6c062a26d684557b37c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ba-9500000000-a1678e241f40c3991ed8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i3-9000000000-ff04a60d16aa9928a044	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-4900000000-8f94035a9aca264573f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-074i-9100000000-d5f8b375fb7c5c114d19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-eff6aae246d496dfde6f	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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	HMDB0240389
Pubchem Compound ID	5289105
Kegg ID	C00522
ChemSpider ID	825
Wikipedia ID	Pantoic acid
BioCyc ID	L-PANTOATE
EcoCyc ID	L-PANTOATE
Ligand Expo	PAF

Enzymes

Protein Details

1. Ketol-acid reductoisomerase

General function:: Involved in oxidation-reduction process
Specific function:: (R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:: ilvC
Uniprot ID:: P05793
Molecular weight:: 54069

Reactions

(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) = (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.

Protein Details

2. 2-dehydropantoate 2-reductase

General function:: Involved in oxidation-reduction process
Specific function:: Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:: panE
Uniprot ID:: P0A9J4
Molecular weight:: 33871

Reactions

(R)-pantoate + NADP(+) = 2-dehydropantoate + NADPH.

Protein Details

3. Pantothenate synthetase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the condensation of pantoate with beta-alanine in an ATP-dependent reaction via a pantoyl-adenylate intermediate
Gene Name:: panC
Uniprot ID:: P31663
Molecular weight:: 31597

Reactions

ATP + (R)-pantoate + beta-alanine = AMP + diphosphate + (R)-pantothenate.

(R)-Pantoate (ECMDB20016) (M2MDB000865)

Structure for #<Compound:0xab3a2464>

Enzymes

Reactions

Reactions

Reactions