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Record Information
Version4.0
Creation Date2006-08-12 20:34:59 UTC
Update Date2017-10-23 19:04:03 UTC
HMDB IDHMDB0003426
Secondary Accession Numbers
  • HMDB03426
Metabolite Identification
Common NamePantetheine
DescriptionPantetheine is the mercaptoethyl conjugated amide analogue of pantothenic acid (Vitamin B5). The dimer of this compound, pantethine is more commonly known, and is considered to be a more potent form of vitamin B5 than pantothenic acid. Pantetheine is an intermediate in the production of Coenzyme A by the body. An intermediate in the pathway of coenzyme A formation in mammalian liver and some microorganisms.
Structure
Thumb
Synonyms
ValueSource
(R)-PantetheineHMDB
D-PantetheineHMDB
Lactobacillus bulgaricus factorHMDB
LBFHMDB
PantotheineHMDB
Chemical FormulaC11H22N2O4S
Average Molecular Weight278.368
Monoisotopic Molecular Weight278.130027892
IUPAC Name2,4-dihydroxy-3,3-dimethyl-N-{2-[(2-sulfanylethyl)carbamoyl]ethyl}butanamide
Traditional Namepantetheine
CAS Registry Number496-65-1
SMILES
CC(C)(CO)C(O)C(=O)NCCC(=O)NCCS
InChI Identifier
InChI=1S/C11H22N2O4S/c1-11(2,7-14)9(16)10(17)13-4-3-8(15)12-5-6-18/h9,14,16,18H,3-7H2,1-2H3,(H,12,15)(H,13,17)
InChI KeyZNXZGRMVNNHPCA-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
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility0.41 g/LALOGPS
logP-0.1ALOGPS
logP-1.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area98.66 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity70.7 m³·mol⁻¹ChemAxon
Polarizability29.33 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, Positivesplash10-0irr-9850000000-e4fcca3c68a52e72a3daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9522200000-170f850fbccf97bf4dfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-5690000000-a5cb9d4433d26f7a2ac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-9410000000-895050a718b98df8818eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hbc-9200000000-c3a563dd190af4f15252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2390000000-5ca6485cda20e56cabafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ka-6950000000-b90e9c6f3732fa15365aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-9300000000-12baf4bf4d07fb8992b4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Malonic AciduriaPw000207Pw000207 greyscalePw000207 simpleNot Available
Malonyl-coa decarboxylase deficiencyPw000478Pw000478 greyscalePw000478 simpleNot Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersPw000208Pw000208 greyscalePw000208 simpleNot Available
Pantothenate and CoA BiosynthesisPw000032Pw000032 greyscalePw000032 simpleMap00770
Propanoate MetabolismPw000149Pw000149 greyscalePw000149 simpleMap00640
Displaying all 5 entries
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 IDFDB023172
KNApSAcK IDNot Available
Chemspider ID466
KEGG Compound IDC00831
BioCyc IDCPD-511
BiGG ID36144
Wikipedia LinkPantetheine
METLIN ID6928
PubChem Compound479
PDB IDNot Available
ChEBI ID16753
References
Synthesis ReferenceMandel, Alexander L.; La Clair, James J.; Burkart, Michael D. Modular Synthesis of Pantetheine and Phosphopantetheine. Organic Letters (2004), 6(26), 4801-4803.
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 + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
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 + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
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 + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
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 + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine.
Gene Name:
VNN1
Uniprot ID:
O95497
Molecular weight:
57011.16
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails
General function:
Not Available
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine. Involved in the thymus homing of bone marrow cells. May regulate beta-2 integrin-mediated cell adhesion, migration and motility of neutrophil.
Gene Name:
VNN2
Uniprot ID:
O95498
Molecular weight:
33256.93
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails
General function:
Not Available
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine.
Gene Name:
VNN3
Uniprot ID:
Q9NY84
Molecular weight:
Not Available
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails