Record Information
Version2.0
Creation Date2012-05-31 13:52:13 -0600
Update Date2015-06-03 15:54:06 -0600
Secondary Accession Numbers
  • ECMDB01416
Identification
Name:Pantetheine 4'-phosphate
DescriptionPantetheine 4'-phosphate is a metabolite in the pantothenate and coenzyme A biosynthesis pathway. It can be generated from pantatheine (via pantothenate kinase 1) or R-4'-phospho-pantothenoyl-L-cysteine (via phosphopantothenoylcysteine decarboxylase) or dephospho-CoA (via 4'-phosphopantetheine adenylyl-transferase and ectonucleotide pyrophosphatase). The conversion of pantetheine 4'-phosphate (4'-PP) to dephospho-CoA, is catalyzed by 4'-phosphopantetheine adenylyl-transferase. It has been identified as an essential cofactor in in the biosynthesis of fatty acids, polyketides, depsipeptides, peptides, and compounds derived from both carboxylic and amino acid precursors. In particular it is a key prosthetic group of acyl carrier protein (ACP) and peptidyl carrier proteins (PCP) and aryl carrier proteins (ArCP) derived from Coenzyme A. Phosphopantetheine fulfils two demands. Firstly, the intermediates remain covalently linked to the synthases (or synthetases) in an energy-rich thiol ester linkage. Secondly, the flexibility and length of phosphopantetheine chain (approximately 2 nm) allows the covalently tethered intermediates to have access to spatially distinct enzyme active sites.
Structure
Thumb
Synonyms:
  • 4'-Phosphopantetheine
  • 4'-Phosphopantotheine
  • D-Pantetheine 4'-phosphate
  • D-Pantetheine 4'-phosphoric acid
  • P4'P
  • Pantetheine 4'-phosphate
  • Pantetheine 4'-phosphoric acid
  • Pantotheine-4'-phosphate
  • Pantotheine-4'-phosphoric acid
  • Phospho-pantotheine
  • Phosphopantetheine
  • Phosphopantotheine
Chemical Formula:C11H23N2O7PS
Weight:Average: 358.348
Monoisotopic: 358.096358302
InChI Key:JDMUPRLRUUMCTL-VIFPVBQESA-N
InChI:InChI=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)/t9-/m0/s1
CAS number:2226-71-3
IUPAC Name:[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid
Traditional IUPAC Name:4'-phosphopantetheine
SMILES:CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)NCCS
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
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Alkylthiol
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP-0.71ALOGPS
logP-1.7ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area145.19 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.58 m³·mol⁻¹ChemAxon
Polarizability34.34 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ir-7695000000-0ee6ed099c01445060c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-9540000000-9e756a71b573d020fa6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03nc-9300000000-d292b023d1133331f546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9225000000-72a847152c51b3a3daa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-f29815698df8b18a410aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-653db2061d8b7bf264f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0198000000-31a4eeaf91d985eb015eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-7894000000-00ac7fb9fa39b755520eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-5970000000-1b9585d88704c0e60525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-a4738c795089df64016bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-6019000000-7dc9a9f2905a74e22cf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9210000000-ea17c20bd5395348f9dbView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Masuda, Toru; Fujii, Shoichiro; Takanohashi, Kunio. Pantetheine 4'-phosphate. Jpn. Tokkyo Koho (1971), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16858
HMDB IDHMDB01416
Pubchem Compound ID987
Kegg IDC01134
ChemSpider ID962
Wikipedia IDPhosphopantetheine
BioCyc IDPANTETHEINE-P
EcoCyc IDPANTETHEINE-P
Ligand ExpoPNS

Enzymes

General function:
Involved in pantothenate kinase activity
Specific function:
ATP + (R)-pantothenate = ADP + (R)-4'- phosphopantothenate
Gene Name:
coaA
Uniprot ID:
P0A6I3
Molecular weight:
36359
Reactions
ATP + (R)-pantothenate = ADP + (R)-4'-phosphopantothenate.
General function:
Involved in catalytic activity
Specific function:
Reversibly transfers an adenylyl group from ATP to 4'- phosphopantetheine, yielding dephospho-CoA (dPCoA) and pyrophosphate
Gene Name:
coaD
Uniprot ID:
P0A6I6
Molecular weight:
17837
Reactions
ATP + pantetheine 4'-phosphate = diphosphate + 3'-dephospho-CoA.
General function:
Involved in phosphopantothenate--cysteine ligase activity
Specific function:
Catalyzes two steps in the biosynthesis of coenzyme A. In the first step cysteine is conjugated to 4'-phosphopantothenate to form 4-phosphopantothenoylcysteine, in the latter compound is decarboxylated to form 4'-phosphopantotheine
Gene Name:
coaBC
Uniprot ID:
P0ABQ0
Molecular weight:
43438
Reactions
N-((R)-4'-phosphopantothenoyl)-L-cysteine = pantotheine 4'-phosphate + CO(2).
CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-((R)-4'-phosphopantothenoyl)-L-cysteine.
General function:
Involved in [acyl-carrier-protein] phosphodiesterase activity
Specific function:
Converts holo-ACP to apo-ACP by hydrolytic cleavage of the phosphopantetheine prosthetic group from ACP
Gene Name:
acpH
Uniprot ID:
P21515
Molecular weight:
22961
Reactions
Holo-[acyl-carrier-protein] + H(2)O = 4'-phosphopantetheine + apo-[acyl-carrier-protein].
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022