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Record Information
Version3.6
Creation Date2008-08-12 17:03:41 UTC
Update Date2016-02-11 01:07:59 UTC
HMDB IDHMDB06834
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Pantothenoyl-L-cysteine
DescriptionD-Pantothenoyl-L-cysteine is involved in the pantothenate and CoA biosynthesis pathway. D-Pantothenoyl-L-cysteine can be converted into (R)-4'-Phosphopantothenoyl-L-cysteine or Pantetheine by type I pantothenate kinase [EC:2.7.1.33] or [4.1.1.30], respectively.
Structure
Thumb
Synonyms
ValueSource
D-Pantothenoyl-L-cysteineChEBI
N-((R)-Pantothenoyl)-L-cysteineChEBI
N-PantothenoylcysteinHMDB
Chemical FormulaC12H22N2O6S
Average Molecular Weight322.378
Monoisotopic Molecular Weight322.119857136
IUPAC Name(2R)-2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}-3-sulfanylpropanoic acid
Traditional Name(2R)-2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}-3-sulfanylpropanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O
InChI Identifier
InChI=1S/C12H22N2O6S/c1-12(2,6-15)9(17)10(18)13-4-3-8(16)14-7(5-21)11(19)20/h7,9,15,17,21H,3-6H2,1-2H3,(H,13,18)(H,14,16)(H,19,20)/t7-,9-/m0/s1
InChI KeyInChIKey=QSYCTARXWYLMOF-CBAPKCEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Beta amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Fatty acyl
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.5 mg/mLALOGPS
logP-0.7ALOGPS
logP-1.8ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area135.96 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.53 m3·mol-1ChemAxon
Polarizability32.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1937000000-554b650bf87d2950daa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kou-4911000000-0af94c33dbb350edcea6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-a36735225b47636cd7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3598000000-29c450146ff75faa2aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-6971000000-b4be5af001097dfff94cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-8ecde22009211664336fView in MoNA
Biological Properties
Cellular LocationsNot Available
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 IDFDB024110
KNApSAcK IDNot Available
Chemspider ID389202
KEGG Compound IDC04079
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06834
Metagene LinkHMDB06834
METLIN IDNot Available
PubChem Compound440217
PDB IDNot Available
ChEBI ID18416
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 + D-Pantothenoyl-L-cysteine → ADP + 4-Phosphopantothenoylcysteinedetails
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 + D-Pantothenoyl-L-cysteine → ADP + 4-Phosphopantothenoylcysteinedetails
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 + D-Pantothenoyl-L-cysteine → ADP + 4-Phosphopantothenoylcysteinedetails
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 + D-Pantothenoyl-L-cysteine → ADP + 4-Phosphopantothenoylcysteinedetails