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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 11:34:05 UTC
Update Date2019-07-23 05:46:04 UTC
HMDB IDHMDB0004119
Secondary Accession Numbers
  • HMDB04119
Metabolite Identification
Common NameSelenohomocysteine
DescriptionSelenohomocysteine is the precursor of selenocysteine, which is synthesized by catalysis of cystathionine beta-synthase (EC 4.2.1.22) and cystathionine gamma-lyase (EC 4.4.1.1), in mammalian systems (both enzymes require pyridoxal phosphate). Selenohomocysteine (lactone) has been found to be a competitive and irreversible inhibitor of lysyl oxidase; this may relate to the development of connective tissue defects seen in homocystinuria. L-Selenohomocysteine also can serve as a substituent donor in the beta-replacement reaction to yield selenocystathionine. (PMID: 10609891 , 9405445 , 6456763 , 3338973 ).
Structure
Data?1563860764
Synonyms
ValueSource
2-Amino-4-selanyl-butanoateHMDB
2-Amino-4-selanyl-butanoic acidHMDB
Se-selenocysteineHMDB
Chemical FormulaC4H9NO2Se
Average Molecular Weight182.08
Monoisotopic Molecular Weight182.979850365
IUPAC Name2-amino-4-selanylbutanoic acid
Traditional Name2-amino-4-selanylbutanoic acid
CAS Registry Number29412-93-9
SMILES
NC(CC[SeH])C(O)=O
InChI Identifier
InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)
InChI KeyRCWCGLALNCIQNM-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
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Selenol
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility210 g/LALOGPS
logP-3.1ALOGPS
logP-3.9ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)1.41ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.16 m³·mol⁻¹ChemAxon
Polarizability12.78 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, Positivesplash10-000l-9700000000-352f9ff331c2001e7287Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-5900000000-85f2ee5926effe8a0470Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-1900000000-8c5ef30ac2fe25f165feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0900000000-2b4556d8cf18b53be4d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5900000000-2d48596c12bbf13ea974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-17c55a96eff48db32ab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01x9-6900000000-1285534df513770bbd95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-fa4748f901bed9dc4482Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023315
KNApSAcK IDNot Available
Chemspider ID389632
KEGG Compound IDC05698
BioCyc IDNot Available
BiGG ID46312
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440763
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Soda K, Oikawa T, Esaki N: Vitamin B6 enzymes participating in selenium amino acid metabolism. Biofactors. 1999;10(2-3):257-62. [PubMed:10609891 ]
  2. Liu G, Nellaiappan K, Kagan HM: Irreversible inhibition of lysyl oxidase by homocysteine thiolactone and its selenium and oxygen analogues. Implications for homocystinuria. J Biol Chem. 1997 Dec 19;272(51):32370-7. [PubMed:9405445 ]
  3. 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 ]
  4. Esaki N, Seraneeprakarn V, Tanaka H, Soda K: Purification and characterization of Clostridium sticklandii D-selenocystine alpha, beta-lyase. J Bacteriol. 1988 Feb;170(2):751-6. [PubMed:3338973 ]

Enzymes

General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
Reactions
Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamate → Selenomethionine + Tetrahydropteroyltri-L-glutamatedetails
General function:
Involved in adenosylhomocysteinase activity
Specific function:
Not Available
Gene Name:
AHCYL2
Uniprot ID:
Q96HN2
Molecular weight:
66592.445
Reactions
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteinedetails
General function:
Involved in adenosylhomocysteinase activity
Specific function:
Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine.
Gene Name:
AHCY
Uniprot ID:
P23526
Molecular weight:
47715.715
Reactions
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteinedetails
General function:
Involved in adenosylhomocysteinase activity
Specific function:
Not Available
Gene Name:
AHCYL1
Uniprot ID:
O43865
Molecular weight:
53753.0
Reactions
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteinedetails
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