Showing metabocard for Pantetheine (BMDB0003426)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
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
MOLSDFPDBSMILESInChI
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
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-74102e0d21631b5f176cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2900000000-8b6fdd5f7342396d976fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-8910000000-5a7f4294d5361d3252dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-e6596ba35ea7b2d6a1bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-6930000000-cd8c5ecad3eccc49fbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-9b89efff76cf7f21adb4View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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

Enzyme Details
1. Acyl-CoA synthetase short-chain family member 3, mitochondrial
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
Enzyme Details
2. Fatty acid synthase
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
Enzyme Details
3. Pantetheinase
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
Enzyme Details
4. Acyl carrier protein, mitochondrial
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
Enzyme Details
5. Pantothenate kinase 3
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
Enzyme Details
6. Acetyl-coenzyme A synthetase
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