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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:27 UTC
HMDB IDHMDB0001117
Secondary Accession Numbers
  • HMDB0062257
  • HMDB01117
  • HMDB62257
Metabolite Identification
Common Name4'-Phosphopantothenoylcysteine
Description4'-Phosphopantothenoylcysteine, also known as pantothenoylcysteine 4'-phosphate, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 4'-phosphopantothenoylcysteine participates in a number of enzymatic reactions. In particular, cytidine monophosphate and 4'-phosphopantothenoylcysteine can be biosynthesized from cytidine triphosphate, D-4'-phosphopantothenate, and L-cysteine through the action of the enzyme phosphopantothenate--cysteine ligase. 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 into 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
Thumb
Synonyms
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH ID4PPCYS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Begley TP, Ealick SE: Enzymatic reactions involving novel mechanisms of carbanion stabilization. Curr Opin Chem Biol. 2004 Oct;8(5):508-15. [PubMed:15450493 ]
  3. 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 ]

Enzymes

General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK4
Uniprot ID:
Q9NVE7
Molecular weight:
85990.12
Reactions
Adenosine triphosphate + D-Pantothenoyl-L-cysteine → ADP + 4'-Phosphopantothenoylcysteinedetails
General function:
Involved in pantothenate kinase activity
Specific function:
May be the master regulator of the CoA biosynthesis (By similarity).
Gene Name:
PANK2
Uniprot ID:
Q9BZ23
Molecular weight:
30753.12
Reactions
Adenosine triphosphate + D-Pantothenoyl-L-cysteine → ADP + 4'-Phosphopantothenoylcysteinedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK1
Uniprot ID:
Q8TE04
Molecular weight:
35578.965
Reactions
Adenosine triphosphate + D-Pantothenoyl-L-cysteine → ADP + 4'-Phosphopantothenoylcysteinedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK3
Uniprot ID:
Q9H999
Molecular weight:
41093.695
Reactions
Adenosine triphosphate + D-Pantothenoyl-L-cysteine → ADP + 4'-Phosphopantothenoylcysteinedetails
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the first step in the biosynthesis of coenzyme A from vitamin B5, where cysteine is conjugated to 4'-phosphopantothenate to form 4-phosphopantothenoylcysteine.
Gene Name:
PPCS
Uniprot ID:
Q9HAB8
Molecular weight:
15645.035
Reactions
Adenosine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Adenosine monophosphate + Pyrophosphate + 4'-Phosphopantothenoylcysteinedetails
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + 4'-Phosphopantothenoylcysteinedetails
General function:
Involved in catalytic activity
Specific function:
Necessary for the biosynthesis of coenzyme A. Catalyzes the decarboxylation of 4-phosphopantothenoylcysteine to form 4'-phosphopantotheine.
Gene Name:
PPCDC
Uniprot ID:
Q96CD2
Molecular weight:
22394.965
Reactions
4'-Phosphopantothenoylcysteine → Pantetheine 4'-phosphate + Carbon dioxidedetails