NP-MRD: Showing NP-Card for thioneine (NP0271956)

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Record Information

Version

2.0

Created at

2022-09-08 18:25:04 UTC

Updated at

2022-09-08 18:25:05 UTC

NP-MRD ID

NP0271956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

thioneine

Description

Thioredoxin, also known as ergothioneine, 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. Thioredoxin is a very strong basic compound (based on its pKa). Thioredoxin may be a unique E. Coli metabolite. In humans, thioredoxin is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. An alpha-amino-acid cation obtained by protonation of the imidazole ring of ergothioneine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.7969    0.0299    1.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.5892    0.2084 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6452    0.8480    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6262    1.9364    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -0.1537   -0.9403 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1066   -1.2788   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124   -0.8300   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -1.7549    0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -1.0892    0.5319 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909    0.2325    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    1.5293    1.0628 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.3497    0.1015 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124   -0.6687   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   -0.5308   -1.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413   -1.3986   -2.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.7366    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -0.9724    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567   -0.0326    2.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887    1.4417   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.0163    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    1.5441    1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188    2.7208    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051    2.1395    0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966    1.9875   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.5426   -1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -2.1314   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410   -1.6864   -1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862   -2.8170   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4090   -1.4720    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515    2.4852    1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560   -2.2800   -2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 15  1  0
 13 14  2  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 15 31  1  0
M  CHG  1   2   1
M  END

 
  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>
NP0271956

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

Synonyms

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

Chemical Formula

C₉H₁₆N₃O₂S

Average Mass

230.3100 Da

Monoisotopic Mass

230.09577 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for thioneine (NP0271956)

MOL for NP0271956 (thioneine)

3D MOL for NP0271956 (thioneine)

3D SDF for NP0271956 (thioneine)

3D-SDF for NP0271956 (thioneine)

PDB for NP0271956 (thioneine)

3D PDB for NP0271956 (thioneine)

SMILES for NP0271956 (thioneine)

INCHI for NP0271956 (thioneine)

Structure for NP0271956 (thioneine)

3D Structure for NP0271956 (thioneine)