You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
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, cytidine monophosphate and 4'-phosphopantothenoylcysteine can be biosynthesized from D-4'-phosphopantothenate, cytidine triphosphate, and L-cysteine; which is mediated by the enzyme phosphopantothenate-cysteine ligase. In addition, 4'-phosphopantothenoylcysteine can be converted into 4'-phosphopantetheine through the action of the enzyme phosphopantothenoylcysteine decarboxylase. In yeast, 4'-phosphopantothenoylcysteine is involved in the metabolic pathway called the beta-alanine metabolism pathway.
Structure
Thumb
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
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
Polarizability36.24 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-CysteineCytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
4-Phosphopantothenoylcysteine + hydronCarbon dioxide + 4'-phosphopantetheine
D-4'-Phosphopantothenate + Cytidine triphosphate + L-CysteineCytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
4-Phosphopantothenoylcysteine + hydronCarbon dioxide + 4'-phosphopantetheine
KEGG Reactions
D-4'-Phosphopantothenate + L-Cysteine + Cytidine triphosphatePyrophosphate + 4-Phosphopantothenoylcysteine + Cytidine monophosphate + hydron
4-Phosphopantothenoylcysteine + hydronCarbon dioxide + Pantetheine 4'-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.