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Identification
YMDB IDYMDB00245
NameL-Cystathionine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Cystathionine belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. L-Cystathionine is a very strong basic compound (based on its pKa). L-Cystathionine exists in all living species, ranging from bacteria to humans. Within yeast, L-cystathionine participates in a number of enzymatic reactions. In particular, L-cystathionine can be biosynthesized from homocysteine, pyruvic acid, and ammonium; which is catalyzed by the enzyme cystathionine beta-lyase. In addition, L-cystathionine can be biosynthesized from homocysteine and L-serine; which is mediated by the enzyme cystathionine beta-synthase. In yeast, L-cystathionine is involved in the metabolic pathway called the cysteine metabolism pathway. L-Cystathionine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (R)-S-(2-amino-2-carboxyethyl)-L-Homocysteine
  • [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoate
  • [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoic acid
  • Cystathionine
  • L-(+)-Cystathionine
  • S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteine
  • S-(beta-Amino-beta-carboxyethyl)homocysteine
  • S-(b-Amino-b-carboxyethyl)homocysteine
  • S-(Β-amino-β-carboxyethyl)homocysteine
CAS number56-88-2
WeightAverage: 222.262
Monoisotopic: 222.067427636
InChI KeyILRYLPWNYFXEMH-WHFBIAKZSA-N
InChIInChI=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)/t4-,5-/m0/s1
IUPAC Name(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
Traditional IUPAC NameL-cystathionine
Chemical FormulaC7H14N2O4S
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])SC([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Dialkylthioether
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point312 °C
Experimental Properties
PropertyValueReference
Water Solubility22 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
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
Polarizability22.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Glycine, serine and threonine metabolismec00260 Map00260
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Homocysteine + Pyruvic acid + Ammoniumwater + L-Cystathionine
Homocysteine + L-Serinewater + L-Cystathionine
water + L-CystathionineAmmonium + L-Cysteine + 2-Ketobutyric acid
KEGG Reactions
L-Cystathionine + waterL-Homocysteine + Pyruvic acid + Ammonium
L-Homocysteine + L-SerineL-Cystathionine + water
L-Cystathionine + waterL-Cysteine + Ammonium + 2-Ketobutyric acid
L-Cysteine + O-Acetyl-L-homoserineAcetic acid + L-Cystathionine + hydron
O-Succinyl-L-homoserine + L-CysteineL-Cystathionine + hydron + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Jhee, K. H., McPhie, P., Miles, E. W. (2000). "Yeast cystathionine beta-synthase is a pyridoxal phosphate enzyme but, unlike the human enzyme, is not a heme protein." J Biol Chem 275:11541-11544.10766767
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Yamagata, Shuzo; Akamatsu, Tsuyoshi; Iwama, Tomonori. Immobilization of Saccharomyces cerevisiae cystathionine gamma-lyase and application of the product to cystathionine synthesis. Applied and Environmental Microbiology (2004), 70(6), 3766-3768.
External Links:
ResourceLink
CHEBI ID17482
HMDB IDHMDB00099
Pubchem Compound ID439258
Kegg IDC02291
ChemSpider ID388392
FOODB IDFDB001976
WikipediaCystathionine
BioCyc IDL-CYSTATHIONINE

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Gene Name:
CYS3
Uniprot ID:
P31373
Molecular weight:
42541.69922
Reactions
L-cystathionine + H(2)O → L-cysteine + NH(3) + 2-oxobutanoate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q12198
Molecular weight:
64222.80078
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
STR2
Uniprot ID:
P47164
Molecular weight:
72349.89844
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
Gene Name:
STR3
Uniprot ID:
P53101
Molecular weight:
51828.0
Reactions
L-cystathionine + H(2)O → L-homocysteine + NH(3) + pyruvate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
Gene Name:
IRC7
Uniprot ID:
P43623
Molecular weight:
36971.10156
Reactions
L-cystathionine + H(2)O → L-homocysteine + NH(3) + pyruvate.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
L-serine + L-homocysteine = L-cystathionine + H(2)O
Gene Name:
CYS4
Uniprot ID:
P32582
Molecular weight:
56021.30078
Reactions
L-serine + L-homocysteine → L-cystathionine + H(2)O.