Record Information
Version2.0
Creation Date2012-10-10 12:22:28 -0600
Update Date2015-09-13 15:15:34 -0600
Secondary Accession Numbers
  • ECMDB23216
Identification
Name:pantotheine 4'-phosphate
DescriptionA phosphopantetheine that has formula C11H23N2O7PS
Structure
Thumb
Synonyms:
  • Pantetheine 4'-phosphate
  • Pantetheine 4'-phosphoric acid
  • Pantotheine 4'-phosphoric acid
  • Pantotheine-4'-phosphate
  • Pantotheine-4'-phosphoric acid
  • Phosphopantetheine
  • Phosphopantotheine
Chemical Formula:C11H23N2O7PS
Weight:Average: 358.348
Monoisotopic: 358.096358302
InChI Key:JDMUPRLRUUMCTL-UHFFFAOYSA-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)
CAS number:2226-71-3
IUPAC Name:[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid
Traditional IUPAC Name:pantetheine 4'-phosphate
SMILES:CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS
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
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)-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:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-7921000000-38919c105245ede94f57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9633000000-e3c273cefb49d43405b0View in MoNA
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:
  • Tahiliani AG, Beinlich CJ: Pantothenic acid in health and disease. Vitam Horm. 1991;46:165-228. Pubmed: 1746161
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

Enzymes

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 dephospho-CoA kinase activity
Specific function:
Catalyzes the phosphorylation of the 3'-hydroxyl group of dephosphocoenzyme A to form coenzyme A
Gene Name:
coaE
Uniprot ID:
P0A6I9
Molecular weight:
22622
Reactions
ATP + 3'-dephospho-CoA = ADP + 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.