Record Information
Version3.6
Creation Date2006-08-12 20:34:59 UTC
Update Date2013-02-09 00:12:33 UTC
HMDB IDHMDB03426
Secondary Accession NumbersNone
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
  1. (R)-Pantetheine
  2. D-Pantetheine
  3. Lactobacillus bulgaricus factor
  4. LBF
  5. Pantotheine
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 IUPAC 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
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassCarboxylic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • Secondary Alcohols
  • a small molecule(Cyc)
Substituents
  • Alkylthiol
  • Primary Alcohol
  • Thiol (Sulfanyl Compound)
Direct ParentSecondary Carboxylic Acid Amides
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pantothenate and CoA biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 area98.66ChemAxon
rotatable bond count8ChemAxon
refractivity70.7ChemAxon
polarizability29.33ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB023172
KNApSAcK IDNot Available
Chemspider ID466
KEGG Compound IDC00831
BioCyc IDPANTETHEINE-P
BiGG ID36144
Wikipedia LinkPantetheine
NuGOwiki LinkHMDB03426
Metagene LinkHMDB03426
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

Gene Name:
PANK4
Uniprot ID:
Q9NVE7
Reactions
Adenosine triphosphate + Pantetheine unknown ADP + Pantetheine 4'-phosphatedetails
Gene Name:
PANK2
Uniprot ID:
Q9BZ23
Reactions
Adenosine triphosphate + Pantetheine unknown ADP + Pantetheine 4'-phosphatedetails
Gene Name:
PANK1
Uniprot ID:
Q8TE04
Reactions
Adenosine triphosphate + Pantetheine unknown ADP + Pantetheine 4'-phosphatedetails
Gene Name:
PANK3
Uniprot ID:
Q9H999
Reactions
Adenosine triphosphate + Pantetheine unknown ADP + Pantetheine 4'-phosphatedetails
Gene Name:
VNN1
Uniprot ID:
O95497
Reactions
Pantetheine + Water unknown Pantothenic acid + Cysteaminedetails
Gene Name:
VNN2
Uniprot ID:
O95498
Reactions
Pantetheine + Water unknown Pantothenic acid + Cysteaminedetails
Gene Name:
VNN3
Uniprot ID:
Q9NY84
Reactions
Pantetheine + Water unknown Pantothenic acid + Cysteaminedetails