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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 11:37:22 UTC
Update Date2017-12-20 20:16:06 UTC
HMDB IDHMDB0004122
Secondary Accession Numbers
  • HMDB04122
Metabolite Identification
Common NameSelenocystine
DescriptionSelenocystine, also known as selenocystine, (dl)-isomer or 3,3'-diselenobisalanine, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Selenocystine is soluble (in water) and an extremely strong acidic compound (based on its pKa). Selenocystine can be found primarily in blood. Within the cell, selenocystine is primarily located in the cytoplasm (predicted from logP). In humans, selenocystine is involved in the selenoamino acid metabolism. Selenocystine is present in several enzymes (for example glutathione peroxidases, tetraiodothyronine 5' deiodinases, thioredoxin reductases, formate dehydrogenases, glycine reductases, selenophosphate synthetase 2, methionine-R-sulfoxide reductase B1 (SEPX1), and some hydrogenases) (Wikipedia). Selenocystine is a substrate for glutathione peroxidase 1..
Structure
Thumb
Synonyms
ValueSource
3,3'-DiselenobisalanineChEBI
3,3'-DiselenodialanineChEBI
D,L-SelenocystineHMDB
DL-SelenocystineHMDB
Selenium cystineHMDB
seleno-DL-CystineHMDB
Selenocystine, (L)-isomerMeSH
Selenocystine, (DL)-isomerMeSH
Selenocystine, (D)-isomerMeSH
Chemical FormulaC6H12N2O4Se2
Average Molecular Weight334.09
Monoisotopic Molecular Weight335.912750538
IUPAC Name2-amino-3-[(2-amino-2-carboxyethyl)diselanyl]propanoic acid
Traditional Nameselenocystine
CAS Registry Number1464-43-3
SMILES
NC(C[Se][Se]CC(N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)
InChI KeyJULROCUWKLNBSN-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
  • Dicarboxylic acid or derivatives
  • Diselenide group
  • Amino acid
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility50.7 g/LALOGPS
logP-3.9ALOGPS
logP-7.9ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)0.64ChemAxon
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity65.51 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9130000000-c55a94399e4d94e19f4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-6409000000-e41fde20a747a67699fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0002-0292000000-ce8a89b63e02634e7c69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-0910000000-1b451be7c581354d282dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03di-1900000000-f1af7a06930410824517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0059000000-121bdccbc5b0ebaabd1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2958000000-f752c3d47aa240db793bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5190000000-98e30703affe569274e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0902000000-8ede9166d065b4b88806View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-9053000000-1cfd8e44516e1b777874View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-9410000000-01f3d836b426756376e4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Selenoamino Acid MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleMap00450
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.074 (0.074-0.090) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023316
KNApSAcK IDNot Available
Chemspider ID14376
KEGG Compound IDC05704
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7020
PubChem Compound15104
PDB IDNot Available
ChEBI ID28553
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61. [PubMed:12425725 ]