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Showing metabocard for N-Acetylcystathionine (HMDB0002381)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2020-02-26 21:24:07 UTC
HMDB IDHMDB0002381
Secondary Accession Numbers
  • HMDB02381
Metabolite Identification
Common NameN-Acetylcystathionine
DescriptionN-Acetylcystathionine, also known as nac-cysta, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylcystathionine is a very strong basic compound (based on its pKa). N-Acetylcystathionine, with regard to humans, has been linked to the inborn metabolic disorder cystathioninuria.
Structure
Data?1582752247
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-MonoacetylcystathionineHMDB
Nac-cystaHMDB
S-(2-(Acetylamino)-2-carboxyethyl)-L-homocysteineHMDB
S-(L-2-(Acetylamino)-2-carboxyethyl)-L-homocysteineHMDB
(2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)butanoateHMDB
(2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)butanoateHMDB
(2S)-2-Amino-4-({2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)butanoic acidHMDB
Chemical FormulaC9H16N2O5S
Average Molecular Weight264.299
Monoisotopic Molecular Weight264.077992322
IUPAC Name(2S)-2-amino-4-[(2-carboxy-2-acetamidoethyl)sulfanyl]butanoic acid
Traditional Name(2S)-2-amino-4-[(2-carboxy-2-acetamidoethyl)sulfanyl]butanoic acid
CAS Registry Number20619-80-1
SMILES
CC(=O)NC(CSCC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H16N2O5S/c1-5(12)11-7(9(15)16)4-17-3-2-6(10)8(13)14/h6-7H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t6-,7?/m0/s1
InChI KeyQWACVTVBTRSCRL-PKPIPKONSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cysteine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Acetamide
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Dialkylthioether
  • Thioether
  • Sulfenyl compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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 Solubility3.53 g/LALOGPS
logP-3ALOGPS
logP-3.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity61.01 m³·mol⁻¹ChemAxon
Polarizability26.06 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, Positivesplash10-006x-9220000000-72ff365709580fd404f5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9311000000-ad841d4cc92e0e5ed39bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0590000000-db0ea3d4b6872a696df6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05px-7930000000-14a2bb074489a863d8c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8i-8900000000-a064391c7ff453f93812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1790000000-5e1a61a1973e6b217935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3940000000-b45c7441294a69453464Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0540-9400000000-1c9a833247eb0f22dd70Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified<40 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified20.0 (8.8-31.0) umol/mmol creatinineChildren (1-13 years old)BothGamma-Cystathionase deficiency
    • MetaGene: Metabol...
 details
Associated Disorders and Diseases
Disease References
Cystathioninuria
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022987
KNApSAcK IDNot Available
Chemspider ID134252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6656
PubChem Compound152314
PDB IDNot Available
ChEBI ID88610
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
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. Ito O, Zhang J, Zhang M, Sagara Y, Masuoka N, Ubuka T, Kodama H: Priming effect of N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine in human neutrophils and tyrosyl phosphorylation of 45 kDa protein. Clin Chim Acta. 1997 Oct 31;266(2):93-104. [PubMed:9437538 ]