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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-08 17:53:42 UTC
HMDB IDHMDB0001016
Secondary Accession Numbers
  • HMDB0062700
  • HMDB01016
  • HMDB62700
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
Data?1588960422
Synonyms
ValueSource
(R)-4'-PhosphopantothenateChEBI
(R)-N-(2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-beta-alanineChEBI
N-[(2R)-2-Hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alanineChEBI
Phosphopantothenic acidChEBI
(R)-4'-Phosphopantothenic acidGenerator
(R)-N-(2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-b-alanineGenerator
(R)-N-(2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-β-alanineGenerator
N-[(2R)-2-Hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-b-alanineGenerator
N-[(2R)-2-Hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-β-alanineGenerator
PhosphopantothenateGenerator
D-4'-Phosphopantothenic acidGenerator
4'-PhosphopantothenateHMDB
Phosphopantothenic acid, calcium salt (2:1)HMDB
Phosphopantothenic acid, calcium salt, (R)-isomerHMDB
4'-Phospho-D-pantothenic acidHMDB
4'-Phosphopantothenic acidHMDB
4’-phospho-D-pantothenic acidHMDB
4’-phosphopantothenic acidHMDB
D-Pantothenic acid 4'-phosphateHMDB
D-Pantothenic acid 4’-phosphateHMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanineHMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanineHMDB
(R)-4'-PhosphonatopantothenateHMDB
(R)-4’-phosphonatopantothenateHMDB
(R)-4’-phosphopantothenateHMDB
4’-phosphopantothenateHMDB
D-4’-phosphopantothenateHMDB
D-4’-phosphopantothenic acidHMDB
D-4'-PhosphopantothenateChEBI
Chemical FormulaC9H18NO8P
Average Molecular Weight299.2149
Monoisotopic Molecular Weight299.077003069
IUPAC Name3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoic acid
Traditional Namephosphopantothenic acid
CAS Registry Number5875-50-3
SMILES
CC(C)(COP(O)(O)=O)[C@@H](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)/t7-/m0/s1
InChI KeyXHFVGHPGDLDEQO-ZETCQYMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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
Polarizability26.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9720000000-41704091b1bf13376017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9141000000-5b0b47ec4bcdae4b9de9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9320000000-cfdd61fa71ff49880f5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-9000000000-c93d1a5c4707410e2d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9270000000-b61365a2ce574c07d431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-ead403fde97da638fdc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-57aba113e2388577d6a9Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
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 IDNot Available
KNApSAcK IDC00019685
Chemspider ID37997
KEGG Compound IDC03492
BioCyc ID4-P-PANTOTHENATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound41635
PDB IDNot Available
ChEBI ID15905
Food Biomarker OntologyNot Available
VMH ID4PPAN
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