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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:00:08 UTC
HMDB IDHMDB0001016
Secondary Accession Numbers
  • HMDB01016
Metabolite Identification
Common NameD-4'-Phosphopantothenate
DescriptionD-4'-Phosphopantothenate is a product of the enzyme pantothenate kinase [EC 2.7.1.33] and is involved in the pantothenate and CoA biosynthesis pathway (KEGG). D-4'-Phosphopantothenate is an intermediate in coenzyme A (CoA) biosynthesis pathway. Coenzyme A is a cofactor of ubiquitous occurrence in plants, bacteria, and animals. It is needed in a large number of enzymatic reactions central to intermediary metabolism, including the oxidation of fatty acids, carbohydrates, and amino acids.
Structure
Thumb
Synonyms
ValueSource
(R)-4'-PhosphopantothenateHMDB
4'-P-PantothenateHMDB
4'-PhosphopantothenateHMDB
D-4'-Phosphopantothenic acidHMDB
Phosphopantothenic acidMeSH
Phosphopantothenic acid, calcium salt (2:1)MeSH
Phosphopantothenic acid, calcium salt, (R)-isomerMeSH
Chemical FormulaC9H18NO8P
Average Molecular Weight299.2149
Monoisotopic Molecular Weight299.077003069
IUPAC Name3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid
Traditional Name3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(O)=O
InChI Identifier
InChI=1S/C9H18NO8P/c1-9(2,5-18-19(15,16)17)7(13)8(14)10-4-3-6(11)12/h7,13H,3-5H2,1-2H3,(H,10,14)(H,11,12)(H2,15,16,17)
InChI KeyXHFVGHPGDLDEQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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 Solubility5.09 g/LALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.39 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity62.38 m³·mol⁻¹ChemAxon
Polarizability26.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-5392000000-359b42878651b9d9c2e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul0-7960000000-5e1d3f9b32192536e41dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-f9de3989fd11e22afcbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9370000000-f7d945402a704f305bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-14a239b738777adfeee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a3802c65fdf7fe039457View in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Pantothenate and CoA BiosynthesisPw000032Pw000032 greyscalePw000032 simpleMap00770
Displaying 1 entry
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 IDFDB022373
KNApSAcK IDNot Available
Chemspider ID128
KEGG Compound IDC03492
BioCyc ID4-P-PANTOTHENATE
BiGG ID41952
Wikipedia LinkNot Available
METLIN ID3427
PubChem Compound131
PDB IDNot Available
ChEBI ID15905
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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 + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
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 + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
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 + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
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 + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
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
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + N-((R)-4'-phosphopantothenoyl)-L-cysteinedetails
Adenosine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Adenosine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteinedetails
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteinedetails