Record Information
Version1.0
Creation Date2016-09-30 23:04:34 UTC
Update Date2020-05-21 16:29:02 UTC
BMDB IDBMDB0003426
Secondary Accession Numbers
  • BMDB03426
Metabolite Identification
Common NamePantetheine
DescriptionPantetheine, also known as LBF, 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. Pantetheine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pantetheine exists in all living organisms, ranging from bacteria to humans. In cattle, pantetheine is involved in the metabolic pathway called the propanoate metabolism pathway.
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
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
  • 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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003426
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023172
KNApSAcK IDNot Available
Chemspider ID466
KEGG Compound IDC00831
BioCyc IDNot Available
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:
Lipid transport and metabolism
Specific function:
Catalyzes the synthesis of acetyl-CoA from short-chain fatty acids (By similarity). Propionate is the preferred substrate but can also utilize acetate and butyrate with a much lower affinity.
Gene Name:
ACSS3
Uniprot ID:
A7MB45
Molecular weight:
74805.0
Reactions
Propinol adenylate + Adenosine triphosphate + Pantetheine → Propionyl-CoA + Adenosine monophosphate + Pyrophosphatedetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
General function:
Involved in pantetheine hydrolase activity
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:
Q58CQ9
Molecular weight:
56947.0
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails
General function:
Lipid transport and metabolism
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis (PubMed:1907568). Accessory and non-catalytic subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), which functions in the transfer of electrons from NADH to the respiratory chain (PubMed:1907568, PubMed:10852722, PubMed:18721790).
Gene Name:
NDUFAB1
Uniprot ID:
P52505
Molecular weight:
17402.0
General function:
Involved in ATP binding
Specific function:
Plays a role in the physiological regulation of coenzyme A (CoA) levels.
Gene Name:
PANK3
Uniprot ID:
Q08DA5
Molecular weight:
41117.0
Reactions
Pantetheine + Adenosine triphosphate → Pantetheine 4'-phosphate + ADPdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
AceCS2
Uniprot ID:
Q9BEA3
Molecular weight:
74310.0
Reactions
Propionyl-CoA + Adenosine monophosphate + Pyrophosphate → Propinol adenylate + Adenosine triphosphate + Pantetheinedetails