4-Phosphopantothenoylcysteine (CHEM035080)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:28:29 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035080
Identification
Common Name4-Phosphopantothenoylcysteine
ClassSmall Molecule
Description4'-Phosphopantothenoylcysteine, also known as 4'-phosphopantothenoylcysteine, 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. 4'-Phosphopantothenoylcysteine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4'-Phosphopantothenoylcysteine exists in all living species, ranging from bacteria to humans. 4'-Phosphopantothenoylcysteine participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and 4'-phosphopantothenoylcysteine can be biosynthesized from cytidine triphosphate, D-4'-phosphopantothenate, and L-cysteine; which is mediated by the enzyme phosphopantothenate--cysteine ligase. In addition, 4'-Phosphopantothenoylcysteine can be converted into pantetheine 4'-phosphate; which is mediated by the enzyme phosphopantothenoylcysteine decarboxylase. In cattle, 4'-phosphopantothenoylcysteine is involved in the metabolic pathway called pantothenate and CoA biosynthesis pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R)-4'-Phosphopantothenoyl-L-cysteineChEBI
N-((R)-4'-Phosphopantothenoyl)-L-cysteineChEBI
N-[(R)-4'-Phosphopantothenoyl]-L-cysteineChEBI
(R)-4'-Phospho-N-pantothenoyl-L-cysteineHMDB
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-b-alanyl]-L-cysteineHMDB
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl]-L-cysteineHMDB
4'-p-N-PantothenoylcysteineHMDB
4'-Phospho-N-pantothenoylcysteineHMDB
4'-Phosphopantothenoyl-L-cysteineHMDB
4-p-N-PantothenoylcysteineHMDB
N-((R)-4-Phosphopantothenoyl)-L-cysteineHMDB
Pantothenoylcysteine 4'-phosphateHMDB
Pantothenylcysteine 4'-phosphateHMDB
4'-PhosphopantothenoylcysteineHMDB
4’-Phosphopantothenoyl-L-cysteineHMDB
4’-PhosphopantothenoylcysteineHMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl-L-cysteineHMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanyl-L-cysteineHMDB
Pantothenoylcysteine 4’-phosphateHMDB
Chemical FormulaC12H23N2O9PS
Average Molecular Mass402.358 g/mol
Monoisotopic Mass402.086 g/mol
CAS Registry Number7196-09-0
IUPAC Name(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
Traditional Name(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
SMILESCC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O
InChI IdentifierInChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1
InChI KeyXQYALQVLCNHCFT-CBAPKCEASA-N
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
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP-0.88ALOGPS
logP-2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area182.49 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity87.41 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-5932000000-e19576ea46e3ff55ea4aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9320110000-ce6b2ea6ec578a33da61Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zpu-1937300000-2b4945f44032ac443f6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1933000000-9a014207b8622cc17a3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-28cae0532b597370b8c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9t-9233300000-4a81e1df035282c806d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-3d01cdfc14c84e5ac1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9066cc0fc827f0850dd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0019700000-b5f554e2b39106e9b142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-4946100000-539d27a701be7ae98539Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-2942000000-db53628649a31094886fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010900000-45017c3ef01c5d32f9a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugj-9386600000-4f3317f2957ab1d4dabaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9400000000-fd5c1ffc893118d72018Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001117
FooDB IDFDB022432
Phenol Explorer IDNot Available
KNApSAcK IDC00019633
BiGG ID43650
BioCyc IDR-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389278
ChEBI ID15769
PubChem Compound ID440304
Kegg Compound IDC04352
YMDB IDYMDB00400
ECMDB IDECMDB01117
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Begley TP, Ealick SE: Enzymatic reactions involving novel mechanisms of carbanion stabilization. Curr Opin Chem Biol. 2004 Oct;8(5):508-15.
2. Kupke T, Schwarz W: 4'-phosphopantetheine biosynthesis in Archaea. J Biol Chem. 2006 Mar 3;281(9):5435-44. Epub 2005 Dec 21.
3. Manoj N, Ealick SE: Unusual space-group pseudosymmetry in crystals of human phosphopantothenoylcysteine decarboxylase. Acta Crystallogr D Biol Crystallogr. 2003 Oct;59(Pt 10):1762-6. Epub 2003 Sep 19.