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Record Information
Version3.6
Creation Date2007-05-23 01:13:43 UTC
Update Date2016-02-11 01:07:29 UTC
HMDB IDHMDB06343
Secondary Accession NumbersNone
Metabolite Identification
Common NameSelenocystathionine
DescriptionSelenocystathionine is formed from Selenohomocysteine by the enzyme cystathionine beta-synthase (EC 4.2.1.22), as a by-product of cystathionine synthesis. Selenocystathionine is consumed in the diet, and is one of the main compounds present in plants that tend to hyperaccumulate selenium and use it as an elemental plant defense mechanism. (PMID: 10026151 , 6456763 , 16920881 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-4-[(2-amino-2-Carboxyethyl)selanyl]butyric acidChEBI
SelenocystathioninesChEBI
2-amino-4-((2-amino-2-Carboxyethyl)seleno)-butanoateHMDB
2-amino-4-((2-amino-2-Carboxyethyl)seleno)-butanoic acidHMDB
2-amino-4-((2-amino-2-Carboxyethyl)seleno)butanoateHMDB
2-amino-4-((2-amino-2-Carboxyethyl)seleno)butanoic acidHMDB
Chemical FormulaC7H14N2O4Se
Average Molecular Weight269.16
Monoisotopic Molecular Weight270.011878774
IUPAC Name2-amino-4-[(2-amino-2-carboxyethyl)selanyl]butanoic acid
Traditional Nameselenocystathionine
CAS Registry Number2196-58-9
SMILES
NC(CC[Se]CC(N)C(O)=O)C(O)=O
InChI Identifier
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)
InChI KeyInChIKey=ZNWYDQPOUQRDLY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Selenoether
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point58 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility86.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity56.89 m3·mol-1ChemAxon
Polarizability21.05 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023895
KNApSAcK IDNot Available
Chemspider ID88693
KEGG Compound IDC05699
BioCyc IDNot Available
BiGG ID46314
Wikipedia LinkSelenate
NuGOwiki LinkHMDB06343
Metagene LinkHMDB06343
METLIN IDNot Available
PubChem Compound98223
PDB IDNot Available
ChEBI ID26630
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neuhierl B, Thanbichler M, Lottspeich F, Bock A: A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation. J Biol Chem. 1999 Feb 26;274(9):5407-14. [10026151 ]
  2. 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. [6456763 ]
  3. 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. [16920881 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. Also involved in the biosynthesis of sulfated L-selectin ligands in endothelial cells.
Gene Name:
PAPSS1
Uniprot ID:
O43252
Molecular weight:
70832.725
Reactions
Adenosine triphosphate + Selenocystathionine → Pyrophosphate + Adenylylselenatedetails
General function:
Involved in ATP binding
Specific function:
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. May have a important role in skeletogenesis during postnatal growth (By similarity).
Gene Name:
PAPSS2
Uniprot ID:
O95340
Molecular weight:
69969.8
Reactions
Adenosine triphosphate + Selenocystathionine → Pyrophosphate + Adenylylselenatedetails
General function:
Involved in pyridoxal phosphate binding
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:
CTH
Uniprot ID:
P32929
Molecular weight:
41259.91
Reactions
Selenocystathionine + Water → Selenocysteine + Ammonia + 2-Ketobutyric aciddetails
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
Gene Name:
CBS
Uniprot ID:
P35520
Molecular weight:
60586.05
Reactions
L-Serine + Selenohomocysteine → Selenocystathionine + Waterdetails