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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:49:40 UTC
Update Date2019-07-23 07:14:36 UTC
HMDB IDHMDB0060559
Secondary Accession Numbers
  • HMDB60559
Metabolite Identification
Common NameAcetaminophen cystein
DescriptionAcetaminophen cystein, also known as paracetamol cysteine or aa-cysteine, belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Acetaminophen cystein is a very strong basic compound (based on its pKa). Within humans, acetaminophen cystein participates in a number of enzymatic reactions. In particular, acetaminophen cystein can be biosynthesized from NAPQI and glutathione through its interaction with the enzymes glutathione S-transferase p and glutathione S-transferase theta-1. In addition, acetaminophen cystein can be converted into acetaminophen cystein through its interaction with the enzyme multidrug resistance-associated protein 1. In humans, acetaminophen cystein is involved in acetaminophen metabolism pathway.
Structure
Data?1563866076
Synonyms
ValueSource
Paracetamol cysteineHMDB
AA-cysteineHMDB
Acetaminophen cysteineMeSH
Chemical FormulaC11H14N2O3S
Average Molecular Weight254.305
Monoisotopic Molecular Weight254.072513014
IUPAC Name(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid
Traditional Name(2R)-2-amino-3-({4-[(1-hydroxyethylidene)amino]phenyl}sulfanyl)propanoic acid
CAS Registry NumberNot Available
SMILES
CC(O)=NC1=CC=C(SC[C@H](N)C(O)=O)C=C1
InChI Identifier
InChI=1S/C11H14N2O3S/c1-7(14)13-8-2-4-9(5-3-8)17-6-10(12)11(15)16/h2-5,10H,6,12H2,1H3,(H,13,14)(H,15,16)/t10-/m0/s1
InChI KeyZOZXXYPCOKGXOE-JTQLQIEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • L-alpha-amino acid
  • Alpha-amino acid
  • Acetanilide
  • N-acetylarylamine
  • Anilide
  • N-arylamide
  • Thiophenol ether
  • Aryl thioether
  • Alkylarylthioether
  • Benzenoid
  • Monocyclic benzene moiety
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.42 m³·mol⁻¹ChemAxon
Polarizability26.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-044l-8970000000-5c778be04752360df8eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01c9-9743000000-11992e3486bb1de35597Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1490000000-651187c3825b168ab24dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06di-1940000000-c69f3e5dd0de3df47b0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gic-3900000000-3bb28136fd14a5691177Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-1490000000-1b4f05b101e91fba5e7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1910000000-55f1adf01057650c3204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-9500000000-065b9ad7f744a497808cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83997
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available