Record Information
Version2.0
Creation Date2015-06-04 15:12:54 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23749
Identification
Name:Thioredoxin
Description:Proteins that act as antioxidants by facilitating the reduction of other proteins by cysteine thiol-disulfide exchange
Structure
Thumb
Synonyms:
  • 2 Thiol L histidine betaine
  • 2-Thiol-L-histidine-betaine
  • Thioneine
Chemical Formula:C9H16N3O2S
Weight:Average: 230.31
Monoisotopic: 230.095774361
InChI Key:SSISHJJTAXXQAX-ZETCQYMHSA-O
InChI:InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/p+1/t7-/m0/s1
CAS number:52500-60-4
IUPAC Name:[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium
Traditional IUPAC Name:[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium
SMILES:C[N+](C)(C)[C@@H](CC1=CNC(S)=N1)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • Aralkylamine
  • Imidazole-2-thione
  • Tetraalkylammonium salt
  • Heteroaromatic compound
  • Quaternary ammonium salt
  • Imidazole
  • Azole
  • Thiourea
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic cation
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0392 mg/mLALOGPS
logP-0.09ALOGPS
logP-4.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)5.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.98 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.96 m3·mol-1ChemAxon
Polarizability23.88 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Glutathione metabolismPW000833 Pw000833Pw000833 greyscalePw000833 simple
Pyrimidine metabolismPW000942 Pw000942Pw000942 greyscalePw000942 simple
Sulfur metabolismPW000922 Pw000922Pw000922 greyscalePw000922 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID3037043
Kegg IDC00342
ChemSpider ID2300896
Wikipedia IDErgothioneine
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidation-reduction process
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R1 contains the binding sites for both substrates and allosteric effectors and carries out the actual reduction of the ribonucleotide. It also provides redox- active cysteines
Gene Name:
nrdA
Uniprot ID:
P00452
Molecular weight:
85774
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin.
General function:
Involved in oxidation-reduction process
Specific function:
Thioredoxin + NADP(+) = thioredoxin disulfide + NADPH
Gene Name:
trxB
Uniprot ID:
P0A9P4
Molecular weight:
34623
Reactions
Thioredoxin + NADP(+) = thioredoxin disulfide + NADPH.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
cysK
Uniprot ID:
P0ABK5
Molecular weight:
34489
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product
Gene Name:
cysM
Uniprot ID:
P16703
Molecular weight:
32664
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
General function:
Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:
Reduction of activated sulfate into sulfite
Gene Name:
cysH
Uniprot ID:
P17854
Molecular weight:
27976
Reactions
Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide = 3'-phosphoadenylyl sulfate + thioredoxin.
General function:
Involved in catalytic activity
Specific function:
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
Gene Name:
nrdD
Uniprot ID:
P28903
Molecular weight:
80022
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin.
General function:
Involved in oxidoreductase activity
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R2F contains the tyrosyl radical required for catalysis
Gene Name:
nrdF
Uniprot ID:
P37146
Molecular weight:
36443
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin.
General function:
Involved in oxidation-reduction process
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R1E contains the binding sites for both substrates and allosteric effectors and carries out the actual reduction of the ribonucleotide
Gene Name:
nrdE
Uniprot ID:
P39452
Molecular weight:
80478
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin.
General function:
Involved in oxidoreductase activity
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. R2 contains the tyrosyl radical required for catalysis
Gene Name:
nrdB
Uniprot ID:
P69924
Molecular weight:
43517
Reactions
2'-deoxyribonucleoside diphosphate + thioredoxin disulfide + H(2)O = ribonucleoside diphosphate + thioredoxin.