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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-05-23 01:13:43 UTC
Update Date2019-07-23 05:47:18 UTC
HMDB IDHMDB0006343
Secondary Accession Numbers
  • HMDB06343
Metabolite Identification
Common NameSelenocystathionine
DescriptionSelenocystathionine, also known as secysta, 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). Selenocystathionine is a very strong basic compound (based on its pKa). Selenocystathionine exists in all living species, ranging from bacteria to humans. Within humans, selenocystathionine participates in a number of enzymatic reactions. In particular, selenocystathionine can be converted into selenocysteine and 2-ketobutyric acid through the action of the enzyme cystathionine gamma-lyase. In addition, selenocystathionine can be biosynthesized from L-serine and selenohomocysteine; which is catalyzed by the enzyme cystathionine beta-synthase. In humans, selenocystathionine is involved in selenoamino acid metabolism.
Structure
Data?1563860838
Synonyms
ValueSource
2-Amino-4-[(2-amino-2-carboxyethyl)selanyl]butyric acidChEBI
SelenocystathioninesChEBI
2-Amino-4-[(2-amino-2-carboxyethyl)selanyl]butyrateGenerator
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
SeCystaHMDB
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 KeyZNWYDQPOUQRDLY-UHFFFAOYSA-N
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9420000000-a9e99a8fd86be0c5402aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006w-9610000000-67eb14a8bbb4d03ea463Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-2290000000-f2bec65ba3fa54257a2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1490000000-c8e7ba1b974d80ad06fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-4900000000-44733d945ca0a2123bddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0910000000-949e30f57858894ebee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uy0-5980000000-44fdd01e4d44e8a390bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9600000000-a128c15c6924127ebb1bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023895
KNApSAcK IDNot Available
Chemspider ID88693
KEGG Compound IDC05699
BioCyc IDNot Available
BiGG ID46314
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98223
PDB IDNot Available
ChEBI ID26630
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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