D-4'-Phosphopantothenate (YMDB00272)

Identification
YMDB IDYMDB00272
NameD-4'-Phosphopantothenate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-4'-Phosphopantothenate 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). D-4'-Phosphopantothenate exists in all living species, ranging from bacteria to humans. 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; which is mediated by the enzyme phosphopantothenate-cysteine ligase. In yeast, D-4'-phosphopantothenate is involved in the metabolic pathway called pantothenate and coa biosynthesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (R)-4'-phosphopantothenate
  • 4'-P-Pantothenate
  • 4'-phosphopantothenate
  • D-4'-Phosphopantothenate
  • D-4'-Phosphopantothenic acid
  • Phosphopantothenic acid
  • Phosphopantothenic acid, calcium salt (2:1)
  • Phosphopantothenic acid, calcium salt, (R)-isomer
CAS numberNot Available
WeightAverage: 299.2149
Monoisotopic: 299.077003069
InChI KeyXHFVGHPGDLDEQO-UHFFFAOYSA-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)
IUPAC Name3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid
Traditional IUPAC Name3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid
Chemical FormulaC9H18NO8P
SMILES[H]OC(=O)C([H])([H])C([H])([H])N([H])C(=O)C([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])O[H]
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.51 g/LALOGPS
logP-2.1ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
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
Polarizability26.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
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 Reactions
Pantothenic acid + Adenosine triphosphate D-4'-Phosphopantothenate + ADP + hydron
Pantothenic acid + Adenosine triphosphate → ADP + hydron + D-4'-Phosphopantothenate
D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
KEGG Reactions
Adenosine triphosphate + (R)-Pantothenic acid → D-4'-Phosphopantothenate + hydron + ADP
D-4'-Phosphopantothenate + L-Cysteine + Cytidine triphosphate → Pyrophosphate + 4-Phosphopantothenoylcysteine + Cytidine monophosphate + hydron
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 (2 TMS) - 70eV, Positivesplash10-0002-9421200000-fd48be28cb334abd9b30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-5392000000-359b42878651b9d9c2e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul0-7960000000-5e1d3f9b32192536e41dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-f9de3989fd11e22afcbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9370000000-f7d945402a704f305bbaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-14a239b738777adfeee4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a3802c65fdf7fe039457JSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15905
HMDB IDHMDB01016
Pubchem Compound ID41635
Kegg IDC03492
ChemSpider ID128
FOODB IDFDB022373
Wikipedia IDNot Available
BioCyc ID4-P-PANTOTHENATE

Enzymes

Protein Details
1. Uncharacterized protein YIL083C
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40506
Molecular weight:
41892.69922
Reactions
CTP + (R)-4'-phosphopantothenate + L-cysteine → CMP + PPi + N-((R)-4'-phosphopantothenoyl)-L-cysteine.
Protein Details
2. 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.