(R)-Pantoic acid (YMDB00376)

Identification

YMDB ID

YMDB00376

Name

(R)-Pantoic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Pantoic acid, also known as pantoate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review very few articles have been published on Pantoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(R)-Pantoate
Pantoate
Pantoic acid
(R)-Pantoic acid

CAS number

470-29-1

Weight

Average: 148.1571
Monoisotopic: 148.073558872

InChI Key

OTOIIPJYVQJATP-BYPYZUCNSA-N

InChI

InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1

IUPAC Name

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

Traditional IUPAC Name

(R)-pantoic acid

Chemical Formula

C₆H₁₂O₄

SMILES

CC(C)(CO)[C@@H](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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Pantothenate and CoA biosynthesis	PW002463
beta-Alanine metabolism	PW002381

KEGG Pathways

Pantothenate and CoA biosynthesis	ec00770
beta-Alanine metabolism	ec00410

SMPDB Reactions

Not Available

KEGG Reactions

2-Dehydropantoic acid + NADPH + hydron → NADP + (R)-Pantoic acid

Adenosine triphosphate + (R)-Pantoic acid + Beta-Alanine → Adenosine monophosphate + Pyrophosphate + (R)-Pantothenic acid + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-9300000000-1533cf69a587ccbc946b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-7d32d9fe2f4c45ee7840	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-9500000000-27fa4de1f52b9b39c2c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9100000000-4b387706b53ffaba5f68	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-2900000000-ea603b384234b8b971d2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9600000000-c12f5dc91e63440b6213	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-921e587537e7f7b8173d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-d6c062a26d684557b37c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ba-9500000000-a1678e241f40c3991ed8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i3-9000000000-ff04a60d16aa9928a044	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-4900000000-8f94035a9aca264573f0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-074i-9100000000-d5f8b375fb7c5c114d19	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-eff6aae246d496dfde6f	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18697
HMDB ID	HMDB0240389
Pubchem Compound ID	439251
Kegg ID	C00522
ChemSpider ID	388387
FOODB ID	Not Available
Wikipedia ID	Pantoic acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. Ketol-acid reductoisomerase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: (R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:: ILV5
Uniprot ID:: P06168
Molecular weight:: 44368.10156

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 oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:: PAN5
Uniprot ID:: P38787
Molecular weight:: 42820.89844

Reactions

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

Protein Details

3. Pantoate--beta-alanine ligase

General function:: Involved in pantoate-beta-alanine ligase activity
Specific function:: Required for pantothenic acid biosynthesis
Gene Name:: PAN6
Uniprot ID:: P40459
Molecular weight:: 35031.89844

Reactions

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

Structure for #<Compound:0xb11d48e8>

Enzymes

Reactions

Reactions

Reactions