Record Information
Version2.0
Creation Date2012-05-31 09:57:21 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00099
Identification
Name:L-Cystathionine
Description:Cystathionine is an intermediate in the synthesis of cysteine. It is generated from homocysteine and serine by cystathionine beta synthase. It is cleaved into cysteine and ketobutyrate by cystathionine gamma-lyase. (Wikipedia)
Structure
Thumb
Synonyms:
  • (R)-S-(2-amino-2-carboxyethyl)-L-Homocysteine
  • Cystathionine
  • L-(+)-Cystathionine
  • S-[(2R)-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
Chemical Formula:C7H14N2O4S
Weight:Average: 222.262
Monoisotopic: 222.067427636
InChI Key:ILRYLPWNYFXEMH-WHFBIAKZSA-N
InChI:InChI=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
CAS number:56-88-2
IUPAC Name:(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
Traditional IUPAC Name:L-cystathionine
SMILES:N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
State:Solid
Charge:0
Melting point:312 °C
Experimental Properties:
PropertyValueSource
Water Solubility:22 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility17.3 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.57 m3·mol-1ChemAxon
Polarizability22.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Nitrogen metabolismPW000755 Pw000755Pw000755 greyscalePw000755 simple
Sulfur metabolismPW000922 Pw000922Pw000922 greyscalePw000922 simple
methionine biosynthesisPW000814 Pw000814Pw000814 greyscalePw000814 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00fr-8950000000-640b4294e37e5a01048dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0f7c-7910000000-91f9f2b2dd44a3cdb276View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00or-1940000000-c0d688e4ea87ff3e03faView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00or-0980000000-7d816de782a902900d0eView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00fr-8950000000-640b4294e37e5a01048dView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0f7c-7910000000-91f9f2b2dd44a3cdb276View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00or-1940000000-c0d688e4ea87ff3e03faView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00or-0980000000-7d816de782a902900d0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-1980000000-99cb7d1da067e5436b09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e72725View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9200000000-fb776970b6ef36e72725View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00fr-0690000000-0b572de3fcbc7e2f13ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000t-0900000000-5788192b32aadd177e33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000b-4900000000-b86ac7de446a762365bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000j-9800000000-75ff1bc6e325692a9da9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kr-9100000000-6517562dc0f31a85afc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-0900000000-d1628d0a880f1b6e6d90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-9000000000-9a2e1e54b77216e2df72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0090000000-36678c2f0bf1b01cc9d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-05fr-0190000000-e575f57f0d76ef6afa49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00e9-0940000000-962ae510f06296b98878View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00e9-0940000000-27da1912eac54f485bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00fr-0690000000-82fe2198c98660008c04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-0900000000-58cceb69cceeff79606cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-4900000000-5877787c54120dc165c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000j-9800000000-fd29b0fcf62b73831829View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9100000000-6517562dc0f31a85afc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. Pubmed: 500809
  • Herrmann W, Schorr H, Bodis M, Knapp JP, Muller A, Stein G, Geisel J: Role of homocysteine, cystathionine and methylmalonic acid measurement for diagnosis of vitamin deficiency in high-aged subjects. Eur J Clin Invest. 2000 Dec;30(12):1083-9. Pubmed: 11122323
  • James SJ, Cutler P, Melnyk S, Jernigan S, Janak L, Gaylor DW, Neubrander JA: Metabolic biomarkers of increased oxidative stress and impaired methylation capacity in children with autism. Am J Clin Nutr. 2004 Dec;80(6):1611-7. Pubmed: 15585776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kraus JP, Janosik M, Kozich V, Mandell R, Shih V, Sperandeo MP, Sebastio G, de Franchis R, Andria G, Kluijtmans LA, Blom H, Boers GH, Gordon RB, Kamoun P, Tsai MY, Kruger WD, Koch HG, Ohura T, Gaustadnes M: Cystathionine beta-synthase mutations in homocystinuria. Hum Mutat. 1999;13(5):362-75. Pubmed: 10338090
  • Lefauconnier JM, Portemer C, Chatagner F: Free amino acids and related substances in human glial tumours and in fetal brain: comparison with normal adult brain. Brain Res. 1976 Nov 19;117(1):105-13. Pubmed: 186155
  • Ricci G, Santoro L, Achilli M, Matarese RM, Nardini M, Cavallini D: Similarity of the oxidation products of L-cystathionine by L-amino acid oxidase to those excreted by cystathioninuric patients. J Biol Chem. 1983 Sep 10;258(17):10511-7. Pubmed: 6885789
  • Shimizu H, Kakimoto Y, Sano I: A method of determination of cystathionine and its distribution in human brain. J Neurochem. 1966 Feb;13(2):65-73. Pubmed: 5936154
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Stabler SP, Lindenbaum J, Savage DG, Allen RH: Elevation of serum cystathionine levels in patients with cobalamin and folate deficiency. Blood. 1993 Jun 15;81(12):3404-13. Pubmed: 8507876
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Wisniewski K, Sturman JA, Devine E, Brown WT, Rudelli R, Wisniewski HM: Cystathionine disappearance with neuronal loss: a possible neuronal marker. Neuropediatrics. 1985 Aug;16(3):126-30. Pubmed: 4047345
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17482
HMDB IDHMDB00099
Pubchem Compound ID439258
Kegg IDC02291
ChemSpider ID388392
WikipediaCystathionine
BioCyc IDL-CYSTATHIONINE
EcoCyc IDL-CYSTATHIONINE

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
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:
metC
Uniprot ID:
P06721
Molecular weight:
43212
Reactions
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.
General function:
Involved in transferase activity
Specific function:
Acts as a beta-cystathionase and as a repressor of the maltose regulon
Gene Name:
malY
Uniprot ID:
P23256
Molecular weight:
43641
Reactions
L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppB
Uniprot ID:
P0AEF8
Molecular weight:
37497
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppC
Uniprot ID:
P0AEG1
Molecular weight:
32308
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppB
Uniprot ID:
P0AEF8
Molecular weight:
37497
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppC
Uniprot ID:
P0AEG1
Molecular weight:
32308
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022
General function:
Involved in transporter activity
Specific function:
Involved in a peptide intake transport system that plays a role in the resistance to antimicrobial peptides
Gene Name:
sapB
Uniprot ID:
P0AGH3
Molecular weight:
36038
General function:
Involved in transporter activity
Specific function:
Involved in a peptide intake transport system that plays a role in the resistance to antimicrobial peptides
Gene Name:
sapC
Uniprot ID:
P0AGH5
Molecular weight:
31548
General function:
Involved in peptide transporter activity
Specific function:
Proton-dependent permease that transports di- and tripeptides. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
Gene Name:
dtpB
Uniprot ID:
P36837
Molecular weight:
53575
General function:
Involved in peptide transporter activity
Specific function:
Probable proton-dependent permease that transports di- and tripeptides. Shows significantly higher specificity towards dipeptides
Gene Name:
yjdL
Uniprot ID:
P39276
Molecular weight:
53054
General function:
Involved in peptide transporter activity
Specific function:
Probable proton-dependent permease that transports dipeptides
Gene Name:
dtpD
Uniprot ID:
P75742
Molecular weight:
54158
General function:
Involved in peptide transporter activity
Specific function:
Proton-dependent permease that transports di- and tripeptides as well as structurally related peptidomimetics such as aminocephalosporins into the cell. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
Gene Name:
dtpA
Uniprot ID:
P77304
Molecular weight:
53991