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Showing metabocard for N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine (HMDB02194)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:40 -0600
Update Date 2013-02-08 17:11:32 -0700
HMDB ID HMDB02194
Secondary Accession Numbers None
Metabolite Identification
Common Name N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine
Description N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine is a cystathione metabolite found in the urine of patients with cystathionuria (PMID 8750604 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (R)-4-(2-acetamido-2-carboxyethylthio)-2-oxobutanoate
  2. (R)-4-(2-acetamido-2-carboxyethylthio)-2-oxobutanoic acid
  3. NAc-OCPC
Chemical Formula C9H13NO6S
Average Molecular Weight 263.268
Monoisotopic Molecular Weight 263.046357843
IUPAC Name 4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid
Traditional IUPAC Name 4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid
CAS Registry Number 622368-00-7
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 Key AHFWWWFNCBRMIV-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
Substituents
  • Alpha Keto Acid
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Ketone
  • Secondary Carboxylic Acid Amide
  • Thioether
Direct Parent N-acyl-alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.22 g/L ALOGPS
LogP -0.23 ALOGPS
LogP -0.42 ChemAxon
LogS -2.33 ALOGPS
pKa (strongest acidic) 2.73 ChemAxon
pKa (strongest basic) -1.5 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 120.77 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 58.5 ChemAxon
Polarizability 24.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022896
KNApSAcK ID Not Available
Chemspider ID 13628313 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02194 Link_out
Metagene Link HMDB02194 Link_out
METLIN ID 6537 Link_out
PubChem Compound 20849151 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Pankau, 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 Link_out
  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 Link_out