4-Phosphopantothenoylcysteine (YMDB00400)

Identification
YMDB IDYMDB00400
Name4-Phosphopantothenoylcysteine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4'-Phosphopantothenoylcysteine, also known as pantothenoylcysteine 4'-phosphate, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. 4'-Phosphopantothenoylcysteine is an extremely weak basic (essentially neutral) compound (based on its pKa). 4'-Phosphopantothenoylcysteine exists in all living species, ranging from bacteria to humans. Within yeast, 4'-phosphopantothenoylcysteine participates in a number of enzymatic reactions. In particular, 4'-phosphopantothenoylcysteine can be converted into 4'-phosphopantetheine; which is catalyzed by the enzyme fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase. In addition, cytidine monophosphate and 4'-phosphopantothenoylcysteine can be biosynthesized from D-4'-phosphopantothenate, cytidine triphosphate, and L-cysteine; which is catalyzed by the enzyme phosphopantothenate-cysteine ligase. In yeast, 4'-phosphopantothenoylcysteine is involved in the metabolic pathway called pantothenate and coa biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (R)-4'-phospho-N-pantothenoyl-L-cysteine
  • (R)-N-[N-[2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-b-alanyl]-L-Cysteine
  • (R)-N-[N-[2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl]-L-Cysteine
  • 4-P-N-pantothenoylcysteine
  • 4'-P-N-pantothenoylcysteine
  • 4'-phospho-N-pantothenoylcysteine
  • 4'-Phosphopantothenoyl-L-cysteine
  • 4'-phosphopantothenoylcysteine
  • N-((R)-4-phosphopantothenoyl)-L-cysteine
  • N-((R)-4'-phosphopantothenoyl)-L-cysteine
  • Pantothenoylcysteine 4'-phosphate
  • (R)-4'-Phosphopantothenoyl-L-cysteine
  • N-[(R)-4'-Phosphopantothenoyl]-L-cysteine
  • Pantothenylcysteine 4'-phosphate
  • 4’-Phosphopantothenoyl-L-cysteine
  • 4’-Phosphopantothenoylcysteine
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl-L-cysteine
  • N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanyl-L-cysteine
  • Pantothenoylcysteine 4’-phosphate
CAS number7196-09-0
WeightAverage: 402.358
Monoisotopic: 402.086187546
InChI KeyXQYALQVLCNHCFT-CBAPKCEASA-N
InChIInChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1
IUPAC Name(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
Traditional IUPAC Name(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
Chemical FormulaC12H23N2O9PS
SMILES[H]OC(=O)[C@@]([H])(N([H])C(=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])C([H])([H])S[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • 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 Solubility0.34 g/LALOGPS
logP-0.88ALOGPS
logP-2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area182.49 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity87.41 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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
D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
4-Phosphopantothenoylcysteine + hydron → Carbon dioxide + 4'-phosphopantetheine
D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
4-Phosphopantothenoylcysteine + hydron → Carbon dioxide + 4'-phosphopantetheine
KEGG Reactions
D-4'-Phosphopantothenate + L-Cysteine + Cytidine triphosphate → Pyrophosphate + 4-Phosphopantothenoylcysteine + Cytidine monophosphate + hydron
4-Phosphopantothenoylcysteine + hydron → Carbon dioxide + Pantetheine 4'-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-5932000000-e19576ea46e3ff55ea4aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9320110000-ce6b2ea6ec578a33da61JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zpu-1937300000-2b4945f44032ac443f6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1933000000-9a014207b8622cc17a3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-28cae0532b597370b8c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9t-9233300000-4a81e1df035282c806d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-3d01cdfc14c84e5ac1aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9066cc0fc827f0850dd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0019700000-b5f554e2b39106e9b142JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-4946100000-539d27a701be7ae98539JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-2942000000-db53628649a31094886fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010900000-45017c3ef01c5d32f9a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugj-9386600000-4f3317f2957ab1d4dabaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9400000000-fd5c1ffc893118d72018JSpectraViewer
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:
  • 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:
ResourceLink
CHEBI ID15769
HMDB IDHMDB01117
Pubchem Compound ID440304
Kegg IDC04352
ChemSpider ID389278
FOODB IDFDB022432
Wikipedia IDNot Available
BioCyc IDR-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE

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.