Cystathionine (ECMDB21649) (M2MDB002043)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (179)
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
MOLSDFPDBSMILESInChI
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:
Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acid
Cystathionine + Succinic acid <> O-Succinyl-L-homoserine + L-Cysteine
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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

Protein Details
1. Cystathionine gamma-synthase
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.
Protein Details
2. Cystathionine beta-lyase metC
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.
Protein Details
3. Protein malY
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.