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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 11:37:22 UTC
Update Date2021-09-14 15:19:52 UTC
HMDB IDHMDB0004122
Secondary Accession Numbers
  • HMDB04122
Metabolite Identification
Common NameSelenocystine
DescriptionSelenocystine, also known as 3,3'-diselenodialanine, 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 carboxyl group (alpha carbon). More specifically, selenocystine is a diselenide consisting of two selenoamino acids that are attached together at their selenium atoms. This particular selenoamino acid is selenocysteine, the selenium analogue to cysteine (selenium being the element directly beneath sulphur in the periodic table); likewise, selenocystine is the selenium analogue to cystine. Since each constituent amino acid has a stereocentre, there are three different stereoisomers of selenocystine: D-selenocystine, L-selenocystine, and meso-selenocystine, the first two of which are optically active. Like other amino acids, L-selenocystine is the most common form within organisms; however, the D- and meso- forms have also been found (PMID: 30920149 ). Selenocystine is a solid that is moderately soluble in water. Due to the reactivity of selenocysteine, it is rarely encountered; rather, cells store selenium in the less reactive oxidized form of selenocystine or in a methylated form, such as selenomethionine (DOI: 10.1007/978-3-319-92405-2_3). When cells are grown in the absence of selenium, translation of selenoproteins terminates at the UGA codon, resulting in a truncated, non-functional enzyme. Unlike other amino acids present in biological proteins, selenocysteine is not coded for directly in the genetic code. Rather, the tRNA-bound seryl residue is converted to a selenocysteine residue by the pyridoxal phosphate-containing enzyme selenocysteine synthase (PMID: 17194211 ). Kurt Franke et al. indicated that there was evidence that selenium was in a form similar to that of cysteine, predating Thressa Stadtman’s discovery of the 21st amino acid by four decades (PMID: 26949981 ; J. Biol. Chem. 111:643). Selenocysteine may be denoted by the short forms Sec, U, or SeCys (Cys is used for cysteine), whereas selenocystine may be denoted by SeCys2. However, the literature sometimes uses SeCys for selenocystine and may cause confusion. Selenocystine has been found in animals, plants, and bacteria. It is being researched as treatment for cancer and for its antioxidant properties (PMID: 24763048 , 24030774 ). Selenium, in its various forms such as selenocystine, is essential for many species, including humans, yet it is also toxic to all organisms; hence, it has come to be referred to as the “essential poison” (PMID: 26949981 ; 6679541).
Structure
Data?1582752299
Synonyms
ValueSource
3,3'-DiselenobisalanineChEBI
3,3'-DiselenodialanineChEBI
Selenocystine, (D)-isomerMeSH
Selenocystine, (DL)-isomerMeSH
Selenocystine, (L)-isomerMeSH
D,L-SelenocystineHMDB
DL-SelenocystineHMDB
Selenium cystineHMDB
seleno-DL-CystineHMDB
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
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
  • 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

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity65.51 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.7430932474
DeepCCS[M-H]-140.9530932474
DeepCCS[M-2H]-178.26330932474
DeepCCS[M+Na]+153.80230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SelenocystineNC(C[Se][Se]CC(N)C(O)=O)C(O)=O2772.8Standard polar33892256
SelenocystineNC(C[Se][Se]CC(N)C(O)=O)C(O)=O2054.9Standard non polar33892256
SelenocystineNC(C[Se][Se]CC(N)C(O)=O)C(O)=O3082.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Selenocystine,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(N)C(=O)O2353.1Semi standard non polar33892256
Selenocystine,1TMS,isomer #2C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O)C(=O)O2443.2Semi standard non polar33892256
Selenocystine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(N)C(=O)O[Si](C)(C)C2363.0Semi standard non polar33892256
Selenocystine,2TMS,isomer #2C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O)C(=O)O[Si](C)(C)C2403.7Semi standard non polar33892256
Selenocystine,2TMS,isomer #3C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C)C(=O)O2419.3Semi standard non polar33892256
Selenocystine,2TMS,isomer #4C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O)C(=O)O2484.0Semi standard non polar33892256
Selenocystine,2TMS,isomer #5C[Si](C)(C)N(C(C[Se][Se]CC(N)C(=O)O)C(=O)O)[Si](C)(C)C2545.6Semi standard non polar33892256
Selenocystine,3TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2430.9Semi standard non polar33892256
Selenocystine,3TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2201.1Standard non polar33892256
Selenocystine,3TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2943.5Standard polar33892256
Selenocystine,3TMS,isomer #2C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2466.9Semi standard non polar33892256
Selenocystine,3TMS,isomer #2C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2195.6Standard non polar33892256
Selenocystine,3TMS,isomer #2C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2711.3Standard polar33892256
Selenocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2498.1Semi standard non polar33892256
Selenocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2222.7Standard non polar33892256
Selenocystine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3215.8Standard polar33892256
Selenocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2501.3Semi standard non polar33892256
Selenocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2270.7Standard non polar33892256
Selenocystine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3048.0Standard polar33892256
Selenocystine,3TMS,isomer #5C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2538.7Semi standard non polar33892256
Selenocystine,3TMS,isomer #5C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2256.3Standard non polar33892256
Selenocystine,3TMS,isomer #5C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2863.4Standard polar33892256
Selenocystine,4TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2473.4Semi standard non polar33892256
Selenocystine,4TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2250.9Standard non polar33892256
Selenocystine,4TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2334.1Standard polar33892256
Selenocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2510.0Semi standard non polar33892256
Selenocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2320.5Standard non polar33892256
Selenocystine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2829.9Standard polar33892256
Selenocystine,4TMS,isomer #3C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2531.4Semi standard non polar33892256
Selenocystine,4TMS,isomer #3C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2337.3Standard non polar33892256
Selenocystine,4TMS,isomer #3C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2513.7Standard polar33892256
Selenocystine,4TMS,isomer #4C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2524.4Semi standard non polar33892256
Selenocystine,4TMS,isomer #4C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2312.4Standard non polar33892256
Selenocystine,4TMS,isomer #4C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2556.6Standard polar33892256
Selenocystine,4TMS,isomer #5C[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2660.2Semi standard non polar33892256
Selenocystine,4TMS,isomer #5C[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2411.1Standard non polar33892256
Selenocystine,4TMS,isomer #5C[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2672.1Standard polar33892256
Selenocystine,5TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2506.4Semi standard non polar33892256
Selenocystine,5TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2356.0Standard non polar33892256
Selenocystine,5TMS,isomer #1C[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2260.5Standard polar33892256
Selenocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2658.2Semi standard non polar33892256
Selenocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2444.9Standard non polar33892256
Selenocystine,5TMS,isomer #2C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2414.5Standard polar33892256
Selenocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2647.9Semi standard non polar33892256
Selenocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2465.0Standard non polar33892256
Selenocystine,6TMS,isomer #1C[Si](C)(C)OC(=O)C(C[Se][Se]CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2231.0Standard polar33892256
Selenocystine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(N)C(=O)O2633.4Semi standard non polar33892256
Selenocystine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O)C(=O)O2688.5Semi standard non polar33892256
Selenocystine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(N)C(=O)O[Si](C)(C)C(C)(C)C2868.9Semi standard non polar33892256
Selenocystine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2911.0Semi standard non polar33892256
Selenocystine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2907.9Semi standard non polar33892256
Selenocystine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O2934.1Semi standard non polar33892256
Selenocystine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(C[Se][Se]CC(N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2984.7Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3131.4Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2765.0Standard non polar33892256
Selenocystine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3046.2Standard polar33892256
Selenocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O3154.4Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2735.2Standard non polar33892256
Selenocystine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2877.7Standard polar33892256
Selenocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3213.7Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2805.7Standard non polar33892256
Selenocystine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C[Se][Se]CC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3196.8Standard polar33892256
Selenocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3202.5Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2792.8Standard non polar33892256
Selenocystine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3095.4Standard polar33892256
Selenocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3229.4Semi standard non polar33892256
Selenocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2773.4Standard non polar33892256
Selenocystine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2976.1Standard polar33892256
Selenocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3369.2Semi standard non polar33892256
Selenocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2931.3Standard non polar33892256
Selenocystine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2770.8Standard polar33892256
Selenocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3439.1Semi standard non polar33892256
Selenocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3007.5Standard non polar33892256
Selenocystine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3025.2Standard polar33892256
Selenocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3461.2Semi standard non polar33892256
Selenocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2978.6Standard non polar33892256
Selenocystine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2843.6Standard polar33892256
Selenocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3470.2Semi standard non polar33892256
Selenocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2986.3Standard non polar33892256
Selenocystine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(C[Se][Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2871.8Standard polar33892256
Selenocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C3537.9Semi standard non polar33892256
Selenocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C3019.4Standard non polar33892256
Selenocystine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(C[Se][Se]CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2929.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Selenocystine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9130000000-c55a94399e4d94e19f4d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Selenocystine GC-MS (2 TMS) - 70eV, Positivesplash10-03di-6409000000-e41fde20a747a67699fb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Selenocystine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Selenocystine Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0002-0292000000-ce8a89b63e02634e7c692012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Selenocystine Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-03di-0910000000-1b451be7c581354d282d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Selenocystine Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-03di-1900000000-f1af7a069304108245172012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 10V, Positive-QTOFsplash10-000i-0059000000-121bdccbc5b0ebaabd1d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 20V, Positive-QTOFsplash10-00kr-2958000000-f752c3d47aa240db793b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 40V, Positive-QTOFsplash10-00kf-5190000000-98e30703affe569274e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 10V, Negative-QTOFsplash10-014i-0902000000-8ede9166d065b4b888062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 20V, Negative-QTOFsplash10-000j-9053000000-1cfd8e44516e1b7778742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 40V, Negative-QTOFsplash10-00xr-9410000000-01f3d836b426756376e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 10V, Positive-QTOFsplash10-000i-0009000000-f71f4753cd69636a74b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 20V, Positive-QTOFsplash10-0002-0291000000-3cce5bdaf0964b8122242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 40V, Positive-QTOFsplash10-0udi-0090000000-44a1ef8aa476bf5a16252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 10V, Negative-QTOFsplash10-015a-0957000000-6e5de7c48f1874bceccf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 20V, Negative-QTOFsplash10-00kb-4790000000-39ce9fc122656bf2cfc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Selenocystine 40V, Negative-QTOFsplash10-02mj-1950000000-d4bdd739e29dcfae21312021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB023316
KNApSAcK IDNot Available
Chemspider ID14376
KEGG Compound IDC05704
BioCyc IDCPD0-1562
BiGG IDNot Available
Wikipedia LinkSelenocysteine
METLIN ID7020
PubChem Compound15104
PDB IDNot Available
ChEBI ID28553
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  2. Montone CM, Antonelli M, Capriotti AL, Cavaliere C, La Barbera G, Piovesana S, Lagana A: Investigation of free and conjugated seleno-amino acids in wheat bran by hydrophilic interaction liquid chromatography with tandem mass spectrometry. J Sep Sci. 2019 May;42(10):1938-1947. doi: 10.1002/jssc.201900047. Epub 2019 Apr 15. [PubMed:30920149 ]
  3. Xu XM, Carlson BA, Mix H, Zhang Y, Saira K, Glass RS, Berry MJ, Gladyshev VN, Hatfield DL: Biosynthesis of selenocysteine on its tRNA in eukaryotes. PLoS Biol. 2007 Jan;5(1):e4. doi: 10.1371/journal.pbio.0050004. [PubMed:17194211 ]
  4. Reich HJ, Hondal RJ: Why Nature Chose Selenium. ACS Chem Biol. 2016 Apr 15;11(4):821-41. doi: 10.1021/acschembio.6b00031. Epub 2016 Mar 21. [PubMed:26949981 ]
  5. Fan C, Zheng W, Fu X, Li X, Wong YS, Chen T: Enhancement of auranofin-induced lung cancer cell apoptosis by selenocystine, a natural inhibitor of TrxR1 in vitro and in vivo. Cell Death Dis. 2014 Apr 24;5:e1191. doi: 10.1038/cddis.2014.132. [PubMed:24763048 ]