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Showing Compound Pantetheine 4'-phosphate (FDB022609)

Record Information
Version1.0
Creation date2011-09-21 00:16:49 UTC
Update date2015-07-21 06:57:16 UTC
Primary IDFDB022609
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePantetheine 4'-phosphate
Description4'-phosphopantetheine 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). In most mammals, coenzyme A can be hydrolyzed to pantetheine and pantothenate in the intestinal lumen via the following series of reactions: coenzyme A leads to phosphopantetheine leads to pantetheine leads to pantothenate. The conversion of 4'-phosphopantetheine (4'-PP) to dephospho-CoA, is catalyzed by 4'-phosphopantetheine adenylyl-transferase. In mammalian systems, this step may occur in the mitochondria or in the cytosol. (PMID: 1746161) 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. [HMDB]
CAS Number2226-71-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4'-PhosphopantetheineChEBI
Pantotheine-4'-phosphateChEBI
PhosphopantetheineChEBI
PSH-4'-pChEBI
Pantotheine-4'-phosphoric acidGenerator
Pantetheine 4'-phosphoric acidGenerator
4'-PhosphopantotheineHMDB
D-Pantetheine 4'-phosphateHMDB
Phospho-pantotheineHMDB
Pantetheine-4'-phosphateMeSH
4'-OpantetheineChEBI
4'-OpantotheineHMDB
4'-phosphopantotheinehmdb
D-Pantetheine 4'-ateHMDB
O-PantotheineHMDB
OpantetheineChEBI
Pantetheine 4'-ateChEBI
Pantetheine 4'-ic acidGenerator
Pantetheine 4'-phosphatehmdb
Pantetheine 4'-phosphic acidhmdb
Pantotheine-4'-ateChEBI
Pantotheine-4'-ic acidGenerator
pantotheine-4'-phosphatehmdb
phospho-pantotheinehmdb
Psh-4'-PChEBI
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H23N2O7PS
IUPAC name[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid
InChI IdentifierInChI=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)
InChI KeyJDMUPRLRUUMCTL-UHFFFAOYSA-N
Isomeric SMILESCC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS
Average Molecular Weight358.348
Monoisotopic Molecular Weight358.096358302
Classification
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
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPantetheine 4'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-7921000000-38919c105245ede94f57Spectrum
Predicted GC-MSPantetheine 4'-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9633000000-e3c273cefb49d43405b0Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ir-7695000000-0ee6ed099c01445060c32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-9540000000-9e756a71b573d020fa6e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03nc-9300000000-d292b023d1133331f5462015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9225000000-72a847152c51b3a3daa22015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-f29815698df8b18a410a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-653db2061d8b7bf264f22015-09-15View Spectrum
NMRNot Available
ChemSpider ID962
ChEMBL IDNot Available
KEGG Compound IDC01134
Pubchem Compound ID987
Pubchem Substance IDNot Available
ChEBI ID16858
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01416
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36886
KNApSAcK IDNot Available
HET ID1H1T
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Fatty acid synthaseFASNP49327
Pantothenate kinase 4PANK4Q9NVE7
Pantothenate kinase 1PANK1Q8TE04
Pantothenate kinase 3PANK3Q9H999
Bifunctional coenzyme A synthaseCOASYQ13057
Mitochondrial 10-formyltetrahydrofolate dehydrogenaseALDH1L2Q3SY69
Acyl carrier protein, mitochondrialNDUFAB1O14561
Pathways
NameSMPDB LinkKEGG Link
Pantothenate and CoA BiosynthesisSMP00027 map00770
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference