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Record Information
Version	2.0
Creation Date	2012-05-31 13:45:29 -0600
Update Date	2015-06-03 15:53:45 -0600
Secondary Accession Numbers	ECMDB01117
Identification
Name:	4-Phosphopantothenoylcysteine
Description	4-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)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x98ab0494> Close
Synonyms:	(R)-4'-phospho-N-pantothenoyl-L-cysteine (R)-4'-phosphopantothenoyl-L-cysteine (R)-N-[N-[2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-b-alanyl]-L-Cysteine (R)-N-[N-[2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl]-L-Cysteine (R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanyl]-L-cysteine 4'-P-N-Pantothenoylcysteine 4'-Phospho-N-pantothenoylcysteine 4'-Phosphopantothenoyl-L-cysteine 4'-Phosphopantothenoylcysteine 4'PPC 4-P-N-Pantothenoylcysteine N-((R)-4'-Phosphopantothenoyl)-L-cysteine N-((R)-4-Phosphopantothenoyl)-L-cysteine N-[(R)-4'-Phosphopantothenoyl]-L-cysteine Pantothenoylcysteine 4'-phosphate Pantothenoylcysteine 4'-phosphoric acid PPC
Chemical Formula:	C12H23N2O9PS
Weight:	Average: 402.358 Monoisotopic: 402.086187546
InChI Key:	XQYALQVLCNHCFT-CBAPKCEASA-N
InChI:	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
CAS number:	7196-09-0
IUPAC Name:	(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
Traditional IUPAC Name:	(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid
SMILES:	CC(C)(COP(O)(O)=O)[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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Peptidomimetics
Sub Class	Hybrid peptides
Direct Parent	Hybrid peptides
Alternative Parents	N-acyl-L-alpha-amino acids Cysteine and derivatives Beta amino acids and derivatives Monoalkyl phosphates Monosaccharides N-acyl amines Secondary carboxylic acid amides Secondary alcohols Alkylthiols Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Organic oxides
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 Framework	Aliphatic acyclic compounds
External Descriptors	L-cysteine derivative (CHEBI:15769 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.34 g/L ALOGPS logP -0.88 ALOGPS logP -2 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 1.78 ChemAxon pKa (Strongest Basic) -3.8 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 182.49 Ų ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 87.41 m³·mol⁻¹ ChemAxon Polarizability 36.25 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine > 4-Phosphopantothenoylcysteine + Cytidine monophosphate + Hydrogen ion + Pyrophosphate 4-Phosphopantothenoylcysteine + Hydrogen ion <> Carbon dioxide + Pantetheine 4'-phosphate + pantotheine 4'-phosphate 4-Phosphopantothenoylcysteine <> Pantetheine 4'-phosphate + Carbon dioxide Adenosine triphosphate + D-4'-Phosphopantothenate + L-Cysteine <> Adenosine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteine Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine <> Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteine Adenosine triphosphate + D-Pantothenoyl-L-cysteine <> ADP + 4-Phosphopantothenoylcysteine Hydrogen ion + 4-Phosphopantothenoylcysteine > Pantetheine 4'-phosphate + Carbon dioxide 4-Phosphopantothenoylcysteine > pantotheine 4'-phosphate + Carbon dioxide Cytidine triphosphate + (R)-4'-phosphopantothenate + L-Cysteine > Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteine Adenosine triphosphate + D-Pantothenoyl-L-cysteine > Adenosine diphosphate + 4-Phosphopantothenoylcysteine + ADP Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine + D-4'-Phosphopantothenate > Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteine + Cytidine monophosphate 4-Phosphopantothenoylcysteine > Pantetheine 4'-phosphate + Carbon dioxide + pantotheine 4'-phosphate D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine + D-4'-Phosphopantothenate > Cytidine monophosphate + Pyrophosphate + Hydrogen ion + 4-Phosphopantothenoylcysteine + Cytidine monophosphate 4-Phosphopantothenoylcysteine + Hydrogen ion > Carbon dioxide + 4'-phosphopantetheine + 4'-phosphopantetheine D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine >4 4-Phosphopantothenoylcysteine + Cytidine monophosphate + Hydrogen ion + Pyrophosphate D-4'-Phosphopantothenate + Cytidine triphosphate + L-Cysteine >4 4-Phosphopantothenoylcysteine + Cytidine monophosphate + Hydrogen ion + Pyrophosphate
SMPDB Pathways:	Pantothenate and CoA biosynthesis PW000828
KEGG Pathways:	Metabolic pathways eco01100 Pantothenate and CoA biosynthesis ec00770
EcoCyc Pathways:	coenzyme A biosynthesis COA-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001j-5932000000-e19576ea46e3ff55ea4a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00dj-9320110000-ce6b2ea6ec578a33da61 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0zpu-1937300000-2b4945f44032ac443f6f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ab9-1933000000-9a014207b8622cc17a3f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00dl-6900000000-28cae0532b597370b8c8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f9t-9233300000-4a81e1df035282c806d8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9210000000-3d01cdfc14c84e5ac1ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-9066cc0fc827f0850dd4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0pb9-0019700000-b5f554e2b39106e9b142 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4j-4946100000-539d27a701be7ae98539 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0kml-2942000000-db53628649a31094886f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0010900000-45017c3ef01c5d32f9a8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0ugj-9386600000-4f3317f2957ab1d4daba View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0059-9400000000-fd5c1ffc893118d72018 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Begley, T. P., Ealick, S. E. (2004). "Enzymatic reactions involving novel mechanisms of carbanion stabilization." Curr Opin Chem Biol 8:508-515. Pubmed: 15450493 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 Kupke T, Schwarz W: 4'-phosphopantetheine biosynthesis in Archaea. J Biol Chem. 2006 Mar 3;281(9):5435-44. Epub 2005 Dec 21. Pubmed: 16371361 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. Pubmed: 14501115 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15769 HMDB ID HMDB01117 Pubchem Compound ID 440304 Kegg ID C04352 ChemSpider ID 389278 Wikipedia ID Not Available BioCyc ID R-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE EcoCyc ID R-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE

Enzymes