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D-Pantothenoyl-L-cysteine (M2MDB000696)

Record Information
Version2.0
Creation Date2012-05-31 14:09:43 -0600
Update Date2015-06-03 15:54:55 -0600
Secondary Accession Numbers
  • ECMDB06834
Identification
Name:D-Pantothenoyl-L-cysteine
DescriptionD-Pantothenoyl-L-cysteine is involved in the pantothenate and CoA biosynthesis pathway. D-Pantothenoyl-L-cysteine can be converted into (R)-4'-Phosphopantothenoyl-L-cysteine or Pantetheine by type pantothenate kinase [EC:2.7.1.33] or [4.1.1.30], respectively.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N-((R)-Pantothenoyl)-L-cysteine
  • N-Pantothenoylcystein
Chemical Formula:C12H22N2O6S
Weight:Average: 322.378
Monoisotopic: 322.119857136
InChI Key:QSYCTARXWYLMOF-CBAPKCEASA-N
InChI:InChI=1S/C12H22N2O6S/c1-12(2,6-15)9(17)10(18)13-4-3-8(16)14-7(5-21)11(19)20/h7,9,15,17,21H,3-6H2,1-2H3,(H,13,18)(H,14,16)(H,19,20)/t7-,9-/m0/s1
CAS number:Not Available
IUPAC Name:(2R)-2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}-3-sulfanylpropanoic acid
Traditional IUPAC Name:(2R)-2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}-3-sulfanylpropanoic acid
SMILES:CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alkylthiol
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP-0.7ALOGPS
logP-1.8ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area135.96 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.53 m³·mol⁻¹ChemAxon
Polarizability32.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + D-Pantothenoyl-L-cysteine <> ADP + 4-Phosphopantothenoylcysteine
Adenosine triphosphate + D-Pantothenoyl-L-cysteine > Adenosine diphosphate + 4-Phosphopantothenoylcysteine + 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, Positivesplash10-0uk9-6931000000-1ff79a87bb5d68b86a7aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6934240000-a68d9ecdade43ddbdff8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1937000000-554b650bf87d2950daa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kou-4911000000-0af94c33dbb350edcea6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-a36735225b47636cd7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3598000000-29c450146ff75faa2aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-6971000000-b4be5af001097dfff94cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-8ecde22009211664336fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0109000000-441198db040b055e9e10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0596-1912000000-b32a056115d8990b657fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-36870cbd66ac4adfa84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0409000000-b7fbc6f7034121ae2073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-4944000000-fd8a4fcca6cc1be29805View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01wf-9500000000-157bcba6f56ab54bc08eView in MoNA
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
1D NMR13C 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18416
HMDB IDHMDB06834
Pubchem Compound ID440217
Kegg IDC04079
ChemSpider ID389202
Wikipedia IDNot Available
BioCyc IDNot Available

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.
Protein Details
2. Oligopeptide transport system permease protein oppB
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
Protein Details
3. Oligopeptide transport system permease protein oppC
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

Protein Details
1. Oligopeptide transport system permease protein oppB
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
Protein Details
2. Oligopeptide transport system permease protein oppC
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