Pantetheine 4'-phosphate (YMDB00308)

Identification
YMDB IDYMDB00308
NamePantetheine 4'-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPantetheine 4'-phosphate, also known as 4'-phosphopantetheine or PSH-4'-p, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Pantetheine 4'-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Pantetheine 4'-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4'-Phosphopantetheine
  • 4'-phosphopantotheine
  • D-Pantetheine 4'-phosphate
  • Pantetheine 4'-phosphate
  • Pantetheine 4'-phosphic acid
  • pantotheine-4'-phosphate
  • phospho-pantotheine
  • Phosphopantetheine
  • PSH-4'-p
  • Pantotheine-4'-phosphoric acid
  • Pantetheine 4'-phosphoric acid
  • Pantetheine-4'-phosphate
CAS number2226-71-3
WeightAverage: 358.348
Monoisotopic: 358.096358302
InChI KeyJDMUPRLRUUMCTL-UHFFFAOYSA-N
InChIInChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19)
IUPAC Name[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid
Traditional IUPAC Namepantetheine 4'-phosphate
Chemical FormulaC11H23N2O7PS
SMILES[H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])S[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 monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Secondary alcohol
  • Alkylthiol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen 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 Solubility0.38 g/LALOGPS
logP-0.71ALOGPS
logP-1.7ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area145.19 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.58 m³·mol⁻¹ChemAxon
Polarizability34.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • 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 ReactionsNot Available
KEGG Reactions
water + Coenzyme A → Adenosine 3',5'-diphosphate + Pantetheine 4'-phosphate + hydron
Adenosine triphosphate + Pantetheine 4'-phosphate + hydron → Pyrophosphate + Dephospho-CoA
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, Positivesplash10-000t-7921000000-38919c105245ede94f57JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9633000000-e3c273cefb49d43405b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ir-7695000000-0ee6ed099c01445060c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-9540000000-9e756a71b573d020fa6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03nc-9300000000-d292b023d1133331f546JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9225000000-72a847152c51b3a3daa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-f29815698df8b18a410aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-653db2061d8b7bf264f2JSpectraViewer
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
  • 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:Masuda, Toru; Fujii, Shoichiro; Takanohashi, Kunio. Pantetheine 4'-phosphate. Jpn. Tokkyo Koho (1971), 3 pp.
External Links:
ResourceLink
CHEBI ID16858
HMDB IDHMDB01416
Pubchem Compound ID987
Kegg IDC01134
ChemSpider ID962
FOODB IDFDB022609
WikipediaPhosphopantetheine
BioCyc IDPANTETHEINE-P

Enzymes

Protein Details
1. Mitochondrial holo-[acyl-carrier-protein] synthase
General function:
Involved in magnesium ion binding
Specific function:
Transfers the 4'-phosphopantetheine moiety from coenzyme A to a Ser of mitochondrial acyl-carrier-protein
Gene Name:
PPT2
Uniprot ID:
Q12036
Molecular weight:
19973.0
Reactions
CoA-(4'-phosphopantetheine) + apo-[acyl-carrier-protein] → adenosine 3',5'-bisphosphate + holo-[acyl-carrier-protein].
Protein Details
2. Uncharacterized protein YGR277C
General function:
Involved in nucleotidyltransferase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P53332
Molecular weight:
34306.30078
Reactions
ATP + pantetheine 4'-phosphate → diphosphate + 3'-dephospho-CoA.