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Record Information
Version3.6
Creation Date2006-08-13 11:34:05 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04119
Secondary Accession NumbersNone
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
Thumb
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 KeyInChIKey=RCWCGLALNCIQNM-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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Selenol
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
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 Solubility210.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.16 m3·mol-1ChemAxon
Polarizability12.78 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, Positivesplash10-001r-1900000000-8c5ef30ac2fe25f165feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0900000000-2b4556d8cf18b53be4d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5900000000-2d48596c12bbf13ea974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-17c55a96eff48db32ab4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01x9-6900000000-1285534df513770bbd95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-fa4748f901bed9dc4482View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
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 IDFDB023315
KNApSAcK IDNot Available
Chemspider ID389632
KEGG Compound IDC05698
BioCyc IDSELENOHOMOCYSTEINE
BiGG ID46312
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04119
Metagene LinkHMDB04119
METLIN IDNot Available
PubChem Compound440763
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Soda K, Oikawa T, Esaki N: Vitamin B6 enzymes participating in selenium amino acid metabolism. Biofactors. 1999;10(2-3):257-62. [10609891 ]
  3. 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. [9405445 ]
  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. [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