(R)-4'-phosphopantothenic acid (YMDB00749)

Identification
YMDB IDYMDB00749
Name(R)-4'-phosphopantothenic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-4'-Phosphopantothenate, also known as phosphopantothenic acid, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. D-4'-Phosphopantothenate is an extremely weak basic (essentially neutral) compound (based on its pKa). Within yeast, D-4'-phosphopantothenate participates in a number of enzymatic reactions. In particular, D-4'-phosphopantothenate can be biosynthesized from pantothenic acid; which is mediated by the enzyme pantothenate kinase. In addition, D-4'-phosphopantothenate, cytidine triphosphate, and L-cysteine can be converted into cytidine monophosphate and 4'-phosphopantothenoylcysteine through the action of the enzyme phosphopantothenate-cysteine ligase. In yeast, D-4'-phosphopantothenate is involved in the metabolic pathway called the beta-alanine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (r)-4-phosphopantothenate
  • (R)-4'-phosphopantothenate
  • (R)-N-(2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-beta-alanine
  • 4'-P-Pantothenate
  • 4'-phosphopantothenate
  • D-4'-Phosphopantothenate
  • D-4'-Phosphopantothenic acid
  • N-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alanine
  • phosphopantothenic acid
  • (R)-4'-Phosphopantothenic acid
  • (R)-N-(2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-b-alanine
  • (R)-N-(2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-β-alanine
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-b-alanine
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-β-alanine
  • Phosphopantothenate
  • Phosphopantothenic acid, calcium salt (2:1)
  • Phosphopantothenic acid, calcium salt, (R)-isomer
  • 4'-Phospho-D-pantothenic acid
  • 4'-Phosphopantothenic acid
  • 4’-phospho-D-pantothenic acid
  • 4’-phosphopantothenic acid
  • D-Pantothenic acid 4'-phosphate
  • D-Pantothenic acid 4’-phosphate
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanine
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanine
  • (R)-4'-Phosphonatopantothenate
  • (R)-4’-phosphonatopantothenate
  • (R)-4’-phosphopantothenate
  • 4’-phosphopantothenate
  • D-4’-phosphopantothenate
  • D-4’-phosphopantothenic acid
CAS numberNot Available
WeightAverage: 299.2149
Monoisotopic: 299.077003069
InChI KeyXHFVGHPGDLDEQO-ZETCQYMHSA-N
InChIInChI=1S/C9H18NO8P/c1-9(2,5-18-19(15,16)17)7(13)8(14)10-4-3-6(11)12/h7,13H,3-5H2,1-2H3,(H,10,14)(H,11,12)(H2,15,16,17)/t7-/m0/s1
IUPAC Name3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoic acid
Traditional IUPAC Namephosphopantothenic acid
Chemical FormulaC9H18NO8P
SMILESCC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.09 g/LALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.39 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity62.38 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
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 ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9720000000-41704091b1bf13376017JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9141000000-5b0b47ec4bcdae4b9de9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9320000000-cfdd61fa71ff49880f5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-9000000000-c93d1a5c4707410e2d61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9270000000-b61365a2ce574c07d431JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-ead403fde97da638fdc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-57aba113e2388577d6a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2296000000-391c82c7a505e9c802caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-9241000000-b0f7eb9f3a7d6f4ec655JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udu-8920000000-0c09af15c101c82e1d13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0090000000-832ae76b1a16ae3ea75cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-4090000000-f6c91ebb49be49cd09ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-1f482bd5f3b51408f3afJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15905
HMDB IDHMDB01016
Pubchem Compound ID41635
Kegg IDC03492
ChemSpider ID37997
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc ID4-P-PANTOTHENATE

Enzymes

Protein Details
1. Pantothenate kinase
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.