Record Information
Version2.0
Creation Date2012-08-15 08:51:31 -0600
Update Date2015-09-13 12:56:17 -0600
Secondary Accession Numbers
  • ECMDB21649
Identification
Name:Cystathionine
DescriptionAllocystathionine is a product of enzyme cystathionine synthetase [EC 2.5.1.48] which converts homocysteine to allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase [4.4.1.8] in the same pathway. (KEGG); Cystathionine is an intermediate in the synthesis of cysteine.
Structure
Thumb
Synonyms:
  • 2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoate
  • 2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid
  • 2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoate
  • 2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acid
  • A-Amino-g-(2-amino-2-carboxyethylmercapto)-Butyrate
  • A-Amino-g-(2-amino-2-carboxyethylmercapto)-Butyric acid
  • alpha-amino-gamma-(2-amino-2-carboxyethylmercapto)-Butyrate
  • Alpha-amino-gamma-(2-amino-2-carboxyethylmercapto)-Butyric acid
  • Cystathionine
  • DL-Allocystathionine
  • DL-Cystathionine
  • DL-S-(2-amino-2-carboxyethyl)-Homocysteine
  • S-(2-Amino-2-carboxyethyl)homocysteine
  • α-amino-γ-(2-amino-2-carboxyethylmercapto)-Butyrate
  • α-amino-γ-(2-amino-2-carboxyethylmercapto)-Butyric acid
Chemical Formula:C7H14N2O4S
Weight:Average: 222.262
Monoisotopic: 222.067427636
InChI Key:ILRYLPWNYFXEMH-UHFFFAOYSA-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)
CAS number:535-34-2
IUPAC Name:(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
Traditional IUPAC Name:L-cystathionine
SMILES:NC(CCSCC(N)C(O)=O)C(O)=O
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
State:Solid
Charge:0
Melting point:281°C
Experimental Properties:
PropertyValueSource
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
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
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-EI-TOF (Non-derivatized)splash10-00fr-8950000000-640b4294e37e5a01048dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f7c-7910000000-91f9f2b2dd44a3cdb276View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00or-1940000000-c0d688e4ea87ff3e03faView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00or-0980000000-7d816de782a902900d0eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9410000000-9487e9168e86a2297931View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dm-9665000000-608a6335880ad1c2519dView 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, Positivesplash10-05di-1930000000-887e3ad7da04e4f1aac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01uc-6900000000-563444ac8ab717997268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-9700000000-35397d8e2ab2c6582c52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0970000000-d0f0a96ca41d1f751c26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3910000000-22200c974305822456d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9300000000-0dfaab5efe3438889c3cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17755
HMDB IDHMDB00455
Pubchem Compound ID834
Kegg IDC00542
ChemSpider ID811
WikipediaCystathionine
BioCyc IDNot Available

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.