Record Information
Version1.0
Creation date2010-04-08 22:05:11 UTC
Update date2019-11-26 02:56:49 UTC
Primary IDFDB001976
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Cystathionine
DescriptionIsolated from Phallus impudicus (common stinkhorn) Cystathionine is a dipeptide formed by serine and homocysteine. Cystathioninuria is a prominent manifestation of vitamin-B6 deficiency. The transsulfuration of methionine yields homocysteine, which combines with serine to form cystathionine, the proximate precursor of cysteine through the enzymatic activity of cystathionase. In conditions in which cystathionine gamma-synthase or cystathionase is deficient, for example, there is cystathioninuria. Although cystathionine has not been detected in normal human serum or plasma by most conventional methods, gas chromatographic/mass spectrometric methodology detected a mean concentration of cystathionine in normal human serum of 140 nM, with a range of 65 to 301 nM.567 Cystathionine concentrations in CSF have been 10, 1, and 0.5 uM, and "not detected." Only traces (i.e., <1 uM) of cystathionine are present in normal CSF.587. gamma-Cystathionase deficiency provided the first instance in which, in a human, the major biochemical abnormality due to a defined enzyme defect was clearly shown to be alleviated by administration of large doses of pyridoxine. The response in gamma-cystathionase-deficient patients is not attributable to correction of a preexisting deficiency of this vitamin. (OMMBID, Chap. 88); Cystathionine is an intermediate in the synthesis of cysteine. L-Cystathionine is found in many foods, some of which are spirulina, greenthread tea, gooseberry, and quinoa.
CAS Number56-88-2
Structure
Thumb
Synonyms
SynonymSource
CystathioneChEBI
DL-CystathionineChEBI
(R)-S-(2-amino-2-carboxyethyl)-L-Homocysteinebiospider
[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoateHMDB
[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoic acidHMDB
Cystathioninebiospider
Cystathionine (6CI,7CI)biospider
Cystathionine, l-biospider
Cystathionine, L- (8CI)biospider
L-(+)-cystathioninebiospider
L-Cystathioninedb_source
L-Homocysteine, S-((2R)-2-amino-2-carboxyethyl)-biospider
L-Homocysteine, S-(2-amino-2-carboxyethyl)-, (R)-biospider
L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]-biospider
L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]- (9CI)biospider
S-(b-amino-b-Carboxyethyl)homocysteineGenerator
S-(beta-amino-beta-carboxyethyl)homocysteinebiospider
S-(β-amino-β-carboxyethyl)homocysteineGenerator
S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteinebiospider
Predicted Properties
PropertyValueSource
Water Solubility17.3 g/LALOGPS
logP-4ALOGPS
logP-5.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.57 m³·mol⁻¹ChemAxon
Polarizability22.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H14N2O4S
IUPAC name2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid
InChI IdentifierInChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)
InChI KeyILRYLPWNYFXEMH-UHFFFAOYSA-N
Isomeric SMILESNC(CCSCC(N)C(O)=O)C(O)=O
Average Molecular Weight222.262
Monoisotopic Molecular Weight222.067427636
Classification
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 37.83%; H 6.35%; N 12.60%; O 28.79%; S 14.43%DFC
Melting PointMp 282-283° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical Rotation[a]20D +24.5 (c, 1 in 1N HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1940000000-1388f9f7ee0c2695b9d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sc-6900000000-8a91a47639d4cb5361acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-9800000000-1a8f7f3af9a25864d89dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0980000000-f204ce08c3c67593f6d5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00si-2920000000-9ccbb781c5a13eb5743eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9400000000-5f87c712790077294561Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-4940000000-7532e86a5529a25a2c9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9200000000-81b9675b58af641c6806Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-d6e5d148f3f2fa935284Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1920000000-4294fc275740c65fbb36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6900000000-d8835185df7f1240386bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-27cb7fe765a4fc3d8968Spectrum
NMRNot Available
ChemSpider ID388392
ChEMBL IDNot Available
KEGG Compound IDC02291
Pubchem Compound ID439258
Pubchem Substance IDNot Available
ChEBI ID17482
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00099
CRC / DFC (Dictionary of Food Compounds) IDBDB74-H:CBV26-N
EAFUS IDNot Available
Dr. Duke IDCYSTATHIONINE
BIGG ID39523
KNApSAcK IDC00007498
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCystathionine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cystathionine gamma-lyaseCTHP32929
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Methionine MetabolismSMP00033 map00270
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).