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Identification
YMDB IDYMDB00203
Name(R)-Pantothenic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionR-Pantothenate (vitamin B5) is the amide between (R)-pantoate and beta-alanine. It is a precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A (CoA) and acyl carrier protein in bacteria and eukaryotes. Only plants and microorganisms (including some eukaryotic microbes, such as S. cerevisiae) can synthesize pantothenate de novo - animals require a dietary supplement. [Biocyc PANTOTHENATE and COA-PWY]
Structure
Thumb
Synonyms
  • (+)-Pantothenate
  • (+)-Pantothenic acid
  • (D)-(+)-Pantothenate
  • (D)-(+)-Pantothenic acid
  • (R)-N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine, ion(1-)
  • (R)-pantothenate
  • Chick antidermatitis factor
  • D-Pantothenate
  • D-Pantothenic acid
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine
  • delta-Pantothenate
  • delta-Pantothenic acid
  • Kyselina pantothenova
  • Kyselina pantothenova [Czech]
  • N-(2,4-dihydroxy-3,3-dimethylbutanoyl)-beta-alaninate
  • N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine
  • Pantothenate
  • pantothenic acid
  • Pantothenic Acid [BAN]
  • Vitamin B3
  • Vitamin B5
  • (R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine
  • D-(+)-Pantothenic acid
  • N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-beta-alanine
  • PANTOTHENOIC ACID
  • Pantothen pharmaselect
  • (R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-b-alanine
  • (R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-β-alanine
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-β-alanine
  • D-(+)-Pantothenate
  • N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-b-alanine
  • N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-β-alanine
  • PANTOTHENOate
  • (R)-Pantothenic acid
  • b5, Vitamin
  • Pantothenate, zinc
  • b 5, Vitamin
  • Calcium pantothenate
  • Pantothenate, calcium
  • Vitamin b 5
  • Dexol
  • Zinc pantothenate
CAS number79-83-4
WeightAverage: 219.235
Monoisotopic: 219.110672659
InChI KeyGHOKWGTUZJEAQD-ZETCQYMHSA-N
InChIInChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1
IUPAC Name3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid
Traditional IUPAC Name(+)-pantothenic acid
Chemical FormulaC9H17NO5
SMILESCC(C)(CO)[C@@H](O)C(=O)NCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility60.5 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.51 m³·mol⁻¹ChemAxon
Polarizability21.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Organoleptic PropertiesNot Available
SMPDB Pathways
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
beta-Alanine metabolismec00410 Map00410
SMPDB ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + (R)-Pantothenic acidD-4'-Phosphopantothenate + hydron + ADP
Adenosine triphosphate + (R)-Pantoic acid + Beta-AlanineAdenosine monophosphate + Pyrophosphate + (R)-Pantothenic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
2 ± 1 µM hops, malted barleyanaerobicBaker's yeastAlcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
1 ± 0 µM grape juiceanaerobicBaker's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1950000000-e17ccf50735fd5171fc4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6t-3921000000-6a2222a87b5ffd328ceeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-9785638e8fe83ade2497JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfr-0920000000-5f3d78d9671cf3e9e436JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-1ad24073d09589d69733JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-8910000000-e9fba0c36e325b52e91fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fs-9665200000-38141a3794d53c37aba5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4077cb3290a3d501c967JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9520000000-21cefac627d830ed5bbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9400000000-d7cac2e845877b5d4c45JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-a56de6ea4cc94ead9287JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-958b1047fc59d5fa55abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9100000000-5cf3012f98b80b72b87cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-5220625c440a0e4d0e1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-da413d79b085b05c74faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000j-9410000000-e4934ca5cda48554f8bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0090000000-d74155da6ca6fff432c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9560000000-663aa7cea0b521907df1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-9200000000-475c18425c9352988ee1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01bc-9000000000-afcfa162e86332d3cfa2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-421f28522574e5fa8eaeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-9470000000-cfd10935dbbb59770f3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-460a4bec2421708c0e18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-2190000000-6eec23d0d7031fc1e28bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-9460000000-a6391c9eace085a7cd68JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006x-9450000000-f677ff82e7d7f3f58ba1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-9230000000-5d3b471f56b2c2e5535bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-12b30ec690e561fbee15JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-167b8eb76324b5c3850aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3790000000-e2e626db270df267d7dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fki-7910000000-01cff3f952409e9e9550JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-a56f834482e2844f6924JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • White, W. H., Gunyuzlu, P. L., Toyn, J. H. (2001). "Saccharomyces cerevisiae is capable of de Novo pantothenic acid biosynthesis involving a novel pathway of beta-alanine production from spermine." J Biol Chem 276:10794-10800.11154694
  • Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Kataoka, Michihiko; Shimizu, Sakayu; Doi, Yukiko; Yamada, Hideaki. Stereospecific reduction of ethyl 2'-ketopantothenate to ethyl D-(+)-pantothenate with microbial cells as a catalyst. Applied and Environmental Microbiology (1990), 56(11), 3595-7.
External Links:
ResourceLink
CHEBI ID46905
HMDB IDHMDB00210
Pubchem Compound ID6613
Kegg IDC00864
ChemSpider ID6361
FOODB IDFDB011817
WikipediaPantothenic acid
BioCyc IDPANTOTHENATE

Enzymes

General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration
Gene Name:
Not Available
Uniprot ID:
Q04430
Molecular weight:
40902.89844
Reactions
ATP + (R)-pantothenate → ADP + (R)-4'-phosphopantothenate.
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.

Transporters

General function:
Involved in transmembrane transport
Specific function:
Transports pantothenate into the cell. Also involved in the catabolite repression-mediated regulation of ergosterol biosynthesis and in fenpropimorph resistance
Gene Name:
FEN2
Uniprot ID:
P25621
Molecular weight:
58256.0