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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2020-02-26 21:23:55 UTC
HMDB IDHMDB0002194
Secondary Accession Numbers
  • HMDB02194
Metabolite Identification
Common NameN-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine
DescriptionN-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine, also known as (R)-4-(2-acetamido-2-carboxyethylthio)-2-oxobutanoate or nac-OCPC, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752235
Synonyms
ValueSource
(R)-4-(2-Acetamido-2-carboxyethylthio)-2-oxobutanoateHMDB
(R)-4-(2-Acetamido-2-carboxyethylthio)-2-oxobutanoic acidHMDB
NAc-OCPCHMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-oxobutanoateHMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoateHMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoic acidHMDB
N-Acetyl-S-(3-oxo-3-carboxy-N-propyl)cysteineMeSH
Chemical FormulaC9H13NO6S
Average Molecular Weight263.268
Monoisotopic Molecular Weight263.046357843
IUPAC Name4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid
Traditional Name4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid
CAS Registry Number622368-00-7
SMILES
CC(=O)N[C@@H](CSCCC(=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H13NO6S/c1-5(11)10-6(8(13)14)4-17-3-2-7(12)9(15)16/h6H,2-4H2,1H3,(H,10,11)(H,13,14)(H,15,16)/t6-/m0/s1
InChI KeyAHFWWWFNCBRMIV-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Short-chain keto acid
  • Thia fatty acid
  • Alpha-keto acid
  • Dicarboxylic acid or derivatives
  • Keto acid
  • Fatty acyl
  • Acetamide
  • Alpha-hydroxy ketone
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ketone
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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 Solubility1.22 g/LALOGPS
logP-0.23ALOGPS
logP-0.42ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)2.73ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.77 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity58.5 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0006-9320000000-21335ec3997d84a833ffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00r5-9744000000-9c809a5689e68bd0dceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il1-1590000000-6940905073c10894c7d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l1-4920000000-e0e63094e181793e90b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-9500000000-5ccba883f4b5ca55b9aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1690000000-42488e6d5ae9973a6d71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03el-4920000000-a3213f11944fbb140598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9500000000-c1314663a0d84af4d149Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022896
KNApSAcK IDNot Available
Chemspider ID13628313
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6537
PubChem Compound20849151
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferencePankau, Wolf Matthias; Moenninghoff, Sven; von Kiedrowski, Guenter. Thermostable and monoconjugable gold clusters with a dodecadentate thioether ligand gripper. Angewandte Chemie, International Edition (2006), 45(12), 1889-1891.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Watanabe H, Fujita Y, Sugahara K, Kodama H, Ohmori S: Identification of NAc-HCPC and NAc-beta-CEC, and qualitative analyses of sulphur amino acids in the urine of a patient with cystathioninuria using liquid chromatography/atmospheric pressure ionization mass spectrometry. Biol Mass Spectrom. 1991 Oct;20(10):602-8. [PubMed:1793738 ]
  2. Zhang J, Masuoka N, Ubuka T, Sugahara K, Kodama H: Identification of N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine in the urine of a patient with cystathioninuria using LC/APCI-MS. J Inherit Metab Dis. 1995;18(6):675-81. [PubMed:8750604 ]