Showing metabocard for DL-Homocystine (BMDB0000575)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:03 UTC
Update Date2020-04-22 15:04:15 UTC
BMDB IDBMDB0000575
Secondary Accession Numbers
  • BMDB00575
Metabolite Identification
Common NameDL-Homocystine
DescriptionDL-Homocystine, also known as 4,4'-dithiobis, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-Homocystine, with regard to humans, has been found to be associated with the diseases such as methylmalonic acidemia and homocystinuria; DL-homocystine has also been linked to several inborn metabolic disorders including methylenetetrahydrofolate reductase deficiency, homocystinuria, and methylmalonic acidemia. Based on a literature review a significant number of articles have been published on DL-Homocystine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,4'-Dithiobis(2-aminobutyric acid)ChEBI
HomocystineKegg
4,4'-Dithiobis(2-aminobutyrate)Generator
4,4'-DithiobisHMDB
Chemical FormulaC8H16N2O4S2
Average Molecular Weight268.354
Monoisotopic Molecular Weight268.05514839
IUPAC Name2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid
Traditional Namehomocystine
CAS Registry Number870-93-9
SMILES
NC(CCSSCCC(N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)
InChI KeyZTVZLYBCZNMWCF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Organic disulfide
  • Amino acid
  • Dialkyldisulfide
  • Sulfenyl compound
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point263 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4.2ALOGPS
logP-5.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.38 m³·mol⁻¹ChemAxon
Polarizability26.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000575
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022123
KNApSAcK IDNot Available
Chemspider ID9616
KEGG Compound IDC01817
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5557
PubChem Compound10010
PDB IDNot Available
ChEBI ID17485
References
Synthesis ReferenceLang, K.; Keller, C. Effect of the cyclophorase system on sulfur-containing amino acids. Biochemische Zeitschrift (1955), 327 202-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available