Record Information
Version1.0
Creation date2011-09-21 00:13:53 UTC
Update date2015-07-21 06:57:12 UTC
Primary IDFDB022432
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Phosphopantothenoylcysteine
Description4-Phosphopantothenoylcysteine (PPC) is an intermediate in the biosynthetic machinery (pathway) that converts pantothenate (vitamin B5) into coenzyme A (CoA). The enzyme Phosphopantothenoylcysteine decarboxylase catalyzes the decarboxylation of PPC to 4'-phosphopantetheine. Coenzyme A is the principal acyl carrier and is required for many synthetic and degradative reactions in intermediary metabolism, and is an essential cofactor in all living systems. (PMID: 15450493, 16371361, 14501115) [HMDB]
CAS Number7196-09-0
Structure
Thumb
Synonyms
SynonymSource
(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
(R)-4'-O-N-Pantothenoyl-L-cysteineHMDB
(R)-4'-Opantothenoyl-L-cysteineChEBI
(R)-4'-phospho-N-pantothenoyl-L-cysteinehmdb
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(onooxy)butyl]-b-alanyl]-L-cysteineHMDB
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(onooxy)butyl]-beta-alanyl]-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'-O-N-PantothenoylcysteineHMDB
4'-Opantothenoyl-L-cysteineHMDB
4'-OpantothenoylcysteineHMDB
4'-P-N-pantothenoylcysteinehmdb
4'-phospho-N-pantothenoylcysteinehmdb
4'-phosphopantothenoylcysteinehmdb
N-((R)-4-Opantothenoyl)-L-cysteineHMDB
N-((R)-4-phosphopantothenoyl)-L-cysteinehmdb
N-((R)-4'-Opantothenoyl)-L-cysteineChEBI
N-((R)-4'-phosphopantothenoyl)-L-cysteinehmdb
N-[(R)-4'-Opantothenoyl]-L-cysteineChEBI
Pantothenoylcysteine 4'-ateHMDB
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H23N2O9PS
IUPAC name(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
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
Isomeric SMILESCC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O
Average Molecular Weight402.358
Monoisotopic Molecular Weight402.086187546
Classification
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
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Phosphopantothenoylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-5932000000-e19576ea46e3ff55ea4aSpectrum
Predicted GC-MS4-Phosphopantothenoylcysteine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-9320110000-ce6b2ea6ec578a33da61Spectrum
Predicted GC-MS4-Phosphopantothenoylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zpu-1937300000-2b4945f44032ac443f6fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1933000000-9a014207b8622cc17a3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-28cae0532b597370b8c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9t-9233300000-4a81e1df035282c806d8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-3d01cdfc14c84e5ac1aeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9066cc0fc827f0850dd4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0019700000-b5f554e2b39106e9b142Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-4946100000-539d27a701be7ae98539Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kml-2942000000-db53628649a31094886fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010900000-45017c3ef01c5d32f9a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugj-9386600000-4f3317f2957ab1d4dabaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9400000000-fd5c1ffc893118d72018Spectrum
NMRNot Available
ChemSpider ID389278
ChEMBL IDNot Available
KEGG Compound IDC04352
Pubchem Compound ID440304
Pubchem Substance IDNot Available
ChEBI ID15769
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01117
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID43650
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Pantothenate kinase 4PANK4Q9NVE7
Pantothenate kinase 1PANK1Q8TE04
Pantothenate kinase 3PANK3Q9H999
Phosphopantothenate--cysteine ligasePPCSQ9HAB8
Pathways
NameSMPDB LinkKEGG Link
Pantothenate and CoA BiosynthesisSMP00027 map00770
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference