Pantetheine 4'-phosphate (PAMDB000379)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000379
Identification
Name: Pantetheine 4'-phosphate
Description:Pantetheine 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 358.348
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Beta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.375 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.58 m3·mol-1ChemAxon
Polarizability34.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Hydrogen ion + Pantetheine 4'-phosphate <> Dephospho-CoA + Pyrophosphate
4-Phosphopantothenoylcysteine + Hydrogen ion <> Carbon dioxide + Pantetheine 4'-phosphate + pantotheine 4'-phosphate
Acyl-carrier protein + Water + Acyl-carrier protein <> Pantetheine 4'-phosphate + Apo-[acyl-carrier-protein]
Adenosine triphosphate + Pantetheine <> ADP + Pantetheine 4'-phosphate
Adenosine triphosphate + Pantetheine 4'-phosphate <> Pyrophosphate + Dephospho-CoA
4-Phosphopantothenoylcysteine <> Pantetheine 4'-phosphate + Carbon dioxide
Hydrogen ion + 4-Phosphopantothenoylcysteine > Pantetheine 4'-phosphate + Carbon dioxide
Holo-[acyl-carrier-protein] + Water > Pantetheine 4'-phosphate + apo-[acyl-carrier-protein]
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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 IDNot Available
BioCyc IDPANTETHEINE-P
EcoCyc IDPANTETHEINE-P
Ligand ExpoPNS

Enzymes

Protein Details
• Phosphopantetheine adenylyltransferase
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
Locus Tag:
PA0363
Molecular weight:
17.8 kDa
Reactions
ATP + pantetheine 4'-phosphate = diphosphate + 3'-dephospho-CoA.
Protein Details
• Coenzyme A biosynthesis bifunctional protein coaBC
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
Locus Tag:
PA5320
Molecular weight:
43.1 kDa
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.

Transporters