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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:52 UTC
HMDB IDHMDB01117
Secondary Accession NumbersNone
Metabolite Identification
Common 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 ).
Structure
Thumb
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'-PhosphopantothenoylcysteineHMDB
4-P-N-PantothenoylcysteineHMDB
N-((R)-4-Phosphopantothenoyl)-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 KeyInChIKey=XQYALQVLCNHCFT-CBAPKCEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These 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
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Beta amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity87.41 m3·mol-1ChemAxon
Polarizability36.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pantothenate and CoA BiosynthesisSMP00027map00770
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022432
KNApSAcK IDNot Available
Chemspider ID389278
KEGG Compound IDC04352
BioCyc IDR-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE
BiGG ID43650
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01117
Metagene LinkHMDB01117
METLIN IDNot Available
PubChem Compound440304
PDB IDNot Available
ChEBI ID15769
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. [14501115 ]
  2. Begley TP, Ealick SE: Enzymatic reactions involving novel mechanisms of carbanion stabilization. Curr Opin Chem Biol. 2004 Oct;8(5):508-15. [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. [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