Showing metabocard for 4-Phosphopantothenoylcysteine (BMDB0001117)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:17 UTC
Update Date2020-05-21 16:28:34 UTC
BMDB IDBMDB0001117
Secondary Accession Numbers
  • BMDB01117
Metabolite Identification
Common Name4-Phosphopantothenoylcysteine
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.
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 Weight402.358
Monoisotopic Molecular Weight402.086187546
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
CAS Registry Number7196-09-0
SMILES
CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-5932000000-e19576ea46e3ff55ea4aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9320110000-ce6b2ea6ec578a33da61View 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, Positivesplash10-0zpu-1937300000-2b4945f44032ac443f6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1933000000-9a014207b8622cc17a3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-28cae0532b597370b8c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9t-9233300000-4a81e1df035282c806d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-3d01cdfc14c84e5ac1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9066cc0fc827f0850dd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0019700000-b5f554e2b39106e9b142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-4946100000-539d27a701be7ae98539View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-2942000000-db53628649a31094886fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010900000-45017c3ef01c5d32f9a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugj-9386600000-4f3317f2957ab1d4dabaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9400000000-fd5c1ffc893118d72018View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001117
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022432
KNApSAcK IDC00019633
Chemspider ID389278
KEGG Compound IDC04352
BioCyc IDR-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE
BiGG ID43650
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440304
PDB IDNot Available
ChEBI ID15769
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Pantothenate kinase 3
General function:
Involved in ATP binding
Specific function:
Plays a role in the physiological regulation of coenzyme A (CoA) levels.
Gene Name:
PANK3
Uniprot ID:
Q08DA5
Molecular weight:
41117.0
Reactions
Adenosine triphosphate + D-Pantothenoyl-L-cysteine → ADP + 4-Phosphopantothenoylcysteinedetails
Enzyme Details
2. Phosphopantothenoylcysteine decarboxylase
General function:
Not Available
Specific function:
Not Available
Gene Name:
PPCDC
Uniprot ID:
Q58DB8
Molecular weight:
25180.0
Reactions
4-Phosphopantothenoylcysteine → Pantetheine 4'-phosphate + Carbon dioxidedetails