Record Information
Version2.0
Creation Date2012-05-31 14:08:08 -0600
Update Date2015-06-03 15:54:51 -0600
Secondary Accession Numbers
  • ECMDB06343
Identification
Name:Selenocystathionine
DescriptionSelenocystathionine is formed from selenohomocysteine by the enzyme cystathionine beta-synthase (EC 4.2.1.22), as a by-product of cystathionine synthesis. It is an intermediate in selenoamine acid metabolism.
Structure
Thumb
Synonyms:
  • 2-Amino-4-((2-amino-2-carboxyethyl)seleno)-Butanoate
  • 2-Amino-4-((2-amino-2-carboxyethyl)seleno)-Butanoic acid
  • 2-Amino-4-((2-amino-2-carboxyethyl)seleno)butanoate
  • 2-Amino-4-((2-amino-2-carboxyethyl)seleno)butanoic acid
  • Selenate
  • Selenic acid
  • Selenocystathionine
Chemical Formula:C7H14N2O4Se
Weight:Average: 269.16
Monoisotopic: 270.011878774
InChI Key:ZNWYDQPOUQRDLY-UHFFFAOYSA-N
InChI:InChI=1S/C7H14N2O4Se/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:2196-58-9
IUPAC Name:2-amino-4-[(2-amino-2-carboxyethyl)selanyl]butanoic acid
Traditional IUPAC Name:selenocystathionine
SMILES:NC(CC[Se]CC(N)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Selenoether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organoselenium 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:58 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility86.8 g/LALOGPS
logP-4ALOGPS
logP-7.4ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.2ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity56.89 m³·mol⁻¹ChemAxon
Polarizability21.05 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:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9420000000-a9e99a8fd86be0c5402aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006w-9610000000-67eb14a8bbb4d03ea463View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-2290000000-f2bec65ba3fa54257a2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1490000000-c8e7ba1b974d80ad06fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-4900000000-44733d945ca0a2123bddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0910000000-949e30f57858894ebee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uy0-5980000000-44fdd01e4d44e8a390bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-a128c15c6924127ebb1bView in MoNA
References
References:
  • Esaki N, Nakamura T, Tanaka H, Suzuki T, Morino Y, Soda K: Enzymatic synthesis of selenocysteine in rat liver. Biochemistry. 1981 Jul 21;20(15):4492-6. Pubmed: 6456763
  • Freeman JL, Zhang LH, Marcus MA, Fakra S, McGrath SP, Pilon-Smits EA: Spatial imaging, speciation, and quantification of selenium in the hyperaccumulator plants Astragalus bisulcatus and Stanleya pinnata. Plant Physiol. 2006 Sep;142(1):124-34. Epub 2006 Aug 18. Pubmed: 16920881
  • 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
  • Neuhierl, B., Thanbichler, M., Lottspeich, F., Bock, A. (1999). "A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation." J Biol Chem 274:5407-5414. Pubmed: 10026151
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18170
HMDB IDHMDB06343
Pubchem Compound ID98223
Kegg IDC05699
ChemSpider ID88693
Wikipedia IDNot Available
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 electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfG
Uniprot ID:
P0AAJ1
Molecular weight:
22752
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex cysAWTP involved in sulfate/thiosulfate import. Responsible for energy coupling to the transport system
Gene Name:
cysA
Uniprot ID:
P16676
Molecular weight:
41059
Reactions
ATP + H(2)O + sulfate(Out) = ADP + phosphate + sulfate(In).
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 dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfE
Uniprot ID:
P77374
Molecular weight:
89779
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfF
Uniprot ID:
P77783
Molecular weight:
89986
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
cysW
Uniprot ID:
P0AEB0
Molecular weight:
32537
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
cysU
Uniprot ID:
P16701
Molecular weight:
30292
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. This protein specifically binds thiosulfate and is involved in its transmembrane transport
Gene Name:
cysP
Uniprot ID:
P16700
Molecular weight:
37614
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. The C subunit anchors the other two subunits to the membrane and stabilize the catalytic subunits
Gene Name:
ynfH
Uniprot ID:
P76173
Molecular weight:
30523

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex cysAWTP involved in sulfate/thiosulfate import. Responsible for energy coupling to the transport system
Gene Name:
cysA
Uniprot ID:
P16676
Molecular weight:
41059
Reactions
ATP + H(2)O + sulfate(Out) = ADP + phosphate + sulfate(In).
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
cysW
Uniprot ID:
P0AEB0
Molecular weight:
32537
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
cysU
Uniprot ID:
P16701
Molecular weight:
30292
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. This protein specifically binds thiosulfate and is involved in its transmembrane transport
Gene Name:
cysP
Uniprot ID:
P16700
Molecular weight:
37614
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368