MiMeDB: Showing metabocard for Thioredoxin (MMDBc0031902)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:54:11 UTC

Update Date

2022-08-31 18:25:53 UTC

Metabolite ID

MMDBc0031902

Metabolite Identification

Common Name

Thioredoxin

Description

Proteins that act as antioxidants by facilitating the reduction of other proteins by cysteine thiol-disulfide exchange

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006041517122D          
 
 15 15  0  0  1  0            999 V2000
    5.7339  -11.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4483  -12.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629  -11.9215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8773  -12.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5918  -11.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8773  -13.1590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629  -11.0966    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.8884  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4595  -10.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629  -10.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6477  -11.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406  -10.9295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281  -11.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9802  -12.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5948  -11.7318    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  1 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  1 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
MMDBc0031902

> <DATABASE_NAME>
MIME

> <SMILES>
C[N+](C)(C)[C@@H](CC1=CNC(S)=N1)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
SSISHJJTAXXQAX-ZETCQYMHSA-O

> <FORMULA>
C9H16N3O2S

> <MOLECULAR_WEIGHT>
230.31

> <EXACT_MASS>
230.095774361

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.88402941993481

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-4.266046853397856

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
7.851163887242994

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8737686544662813

> <JCHEM_PKA_STRONGEST_BASIC>
5.065570718584845

> <JCHEM_POLAR_SURFACE_AREA>
65.97999999999999

> <JCHEM_REFRACTIVITY>
70.9593

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      10.703 -22.253   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.037 -23.024   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.371 -22.253   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.704 -23.024   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.038 -22.253   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.704 -24.564   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      13.371 -20.714   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      14.725 -19.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.058 -19.956   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.371 -19.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.542 -20.722   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.036 -20.402   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.266 -21.735   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.296 -22.880   0.000  0.00  0.00           N+0
HETATM   15  S   UNK     0       6.710 -21.899   0.000  0.00  0.00           S+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    1                                                       
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
Ergothioneine	ChEBI
Ergothioneine cation	ChEBI
2 Thiol L histidine betaine	MeSH
2-Thiol-L-histidine-betaine	MeSH
Thioneine	MeSH

Molecular Formula

C₉H₁₆N₃O₂S

Average Mass

230.31

Monoisotopic Mass

230.095774361

IUPAC Name

[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium

Traditional Name

[(1S)-1-carboxy-2-(2-sulfanyl-1H-imidazol-4-yl)ethyl]trimethylazanium

CAS Registry Number

52500-60-4

SMILES

C[N+](C)(C)[C@@H](CC1=CNC(S)=N1)C(O)=O

InChI Identifier

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

InChI Key

SSISHJJTAXXQAX-ZETCQYMHSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Aralkylamine
Imidazole-2-thione
Azole
Imidazole
Quaternary ammonium salt
Heteroaromatic compound
Tetraalkylammonium salt
Thiourea
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-4.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	5.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.96 m³·mol⁻¹	ChemAxon
Polarizability	23.88 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0390000000-814fea6fcc4cab4d98ff	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0970000000-c3a8f181cc2c984ea0e1	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-5900000000-df4a636fbb845cfeda99	2019-02-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05570

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thioredoxin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

134344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for Thioredoxin (MMDBc0031902)

MOL for #<Metabolite:0x00007fed142ca688>

3D MOL for #<Metabolite:0x00007fed142ca688>

3D SDF for #<Metabolite:0x00007fed142ca688>

3D-SDF for #<Metabolite:0x00007fed142ca688>

PDB for #<Metabolite:0x00007fed142ca688>

3D PDB for #<Metabolite:0x00007fed142ca688>

SMILES for #<Metabolite:0x00007fed142ca688>

INCHI for #<Metabolite:0x00007fed142ca688>

Structure for #<Metabolite:0x00007fed142ca688>

3D Structure for #<Metabolite:0x00007fed142ca688>