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Pantetheine (M2MDB000501)

Record Information
Version2.0
Creation Date2012-05-31 13:59:06 -0600
Update Date2015-06-03 15:54:23 -0600
Secondary Accession Numbers
  • ECMDB03426
Identification
Name:Pantetheine
DescriptionPantetheine is the mercaptoethyl conjugated amide analogue of pantothenic acid (Vitamin B5). The dimer of this compound, pantethine is more commonly known, and is considered to be a more potent form of vitamin B5 than pantothenic acid. Pantetheine is an intermediate in the production of coenzyme A, an intermediate in the pathway of coenzyme A formation.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (R)-Pantetheine
  • D-Pantetheine
  • Lactobacillus bulgaricus factor
  • LBF
  • Pantotheine
Chemical Formula:C11H22N2O4S
Weight:Average: 278.368
Monoisotopic: 278.130027892
InChI Key:ZNXZGRMVNNHPCA-UHFFFAOYSA-N
InChI:InChI=1S/C11H22N2O4S/c1-11(2,7-14)9(16)10(17)13-4-3-8(15)12-5-6-18/h9,14,16,18H,3-7H2,1-2H3,(H,12,15)(H,13,17)
CAS number:496-65-1
IUPAC Name:2,4-dihydroxy-3,3-dimethyl-N-{2-[(2-sulfanylethyl)carbamoyl]ethyl}butanamide
Traditional IUPAC Name:pantetheine
SMILES:CC(C)(CO)C(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
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP-0.1ALOGPS
logP-1.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area98.66 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity70.7 m³·mol⁻¹ChemAxon
Polarizability29.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Pantetheine <> ADP + Pantetheine 4'-phosphate
Pantetheine + Water + Pantetheine > Pantothenic acid + Cysteamine + Pantothenic acid
Pantetheine + Adenosine triphosphate + Pantetheine > Pantetheine 4'-phosphate + Adenosine diphosphate + pantotheine 4'-phosphate + ADP
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Pantothenate and CoA biosynthesis ec00770
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0irr-9850000000-e4fcca3c68a52e72a3daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9522200000-170f850fbccf97bf4dfbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-5690000000-a5cb9d4433d26f7a2ac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-9410000000-895050a718b98df8818eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hbc-9200000000-c3a563dd190af4f15252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2390000000-5ca6485cda20e56cabafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ka-6950000000-b90e9c6f3732fa15365aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-9300000000-12baf4bf4d07fb8992b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-74102e0d21631b5f176cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2900000000-8b6fdd5f7342396d976fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-8910000000-5a7f4294d5361d3252dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-e6596ba35ea7b2d6a1bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-6930000000-cd8c5ecad3eccc49fbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-9b89efff76cf7f21adb4View 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:Mandel, Alexander L.; La Clair, James J.; Burkart, Michael D. Modular Synthesis of Pantetheine and Phosphopantetheine. Organic Letters (2004), 6(26), 4801-4803.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16753
HMDB IDHMDB03426
Pubchem Compound ID479
Kegg IDC00831
ChemSpider ID466
WikipediaPantetheine
BioCyc IDCPD-511
EcoCyc IDCPD-511

Enzymes

Protein Details
1. Pantothenate kinase
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.