NP-MRD: Showing NP-Card for s-methyl-l-ergothioneine (NP0229649)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 09:48:41 UTC

Updated at

2022-09-06 09:48:41 UTC

NP-MRD ID

NP0229649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

s-methyl-l-ergothioneine

Description

S-methyl-L-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. S-methyl-L-ergothioneine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. s-methyl-l-ergothioneine was first documented in 2004 (PMID: 15340692). Based on a literature review a small amount of articles have been published on S-methyl-L-ergothioneine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    5.1851    0.6339    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.5426   -0.7125 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -0.5977   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474   -1.3738   -2.1987 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.1024   -2.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -0.1580   -1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    0.4096   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435   -0.4385   -0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1873   -0.4823    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900   -1.1248    1.3192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    0.1773    2.3627 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.3117    0.0105    0.1697 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8835   -0.6494    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214   -0.3263   -1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.4388    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    0.1474   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2107    0.8659    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6087    1.5852    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101    0.2211    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -1.5635   -2.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8129    0.4262   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    1.4707   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -1.4798   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517    0.0571    2.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -1.0047    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -1.5587    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183   -1.1814   -1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.5218   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0521   -0.6264   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453    1.6607    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.8109    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    1.9476   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    0.8255    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  6 16  1  0
 16  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  6
 13 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  CHG  2  11  -1  12   1
M  END


  Mrv1652309062211482D          

 16 16  0  0  1  0            999 V2000
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6626    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6469   -1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401   -2.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126   -0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  6 16  1  0  0  0  0
  3 16  1  0  0  0  0
M  CHG  2  11  -1  12   1
M  END
> <DATABASE_ID>
NP0229649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=NC=C(C[C@@H](C([O-])=O)[N+](C)(C)C)N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N3O2S/c1-13(2,3)8(9(14)15)5-7-6-11-10(12-7)16-4/h6,8H,5H2,1-4H3,(H-,11,12,14,15)/t8-/m0/s1

> <INCHI_KEY>
GVQNHIYBRMFCMS-QMMMGPOBSA-N

> <FORMULA>
C10H17N3O2S

> <MOLECULAR_WEIGHT>
243.33

> <EXACT_MASS>
243.104147973

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.250147475499745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-[2-(methylsulfanyl)-1H-imidazol-5-yl]-2-(trimethylazaniumyl)propanoate

> <JCHEM_LOGP>
-3.4635818584103593

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.099795119457106

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9739557051989687

> <JCHEM_PKA_STRONGEST_BASIC>
5.170572756566728

> <JCHEM_POLAR_SURFACE_AREA>
68.81

> <JCHEM_REFRACTIVITY>
87.11119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-[2-(methylsulfanyl)-3H-imidazol-4-yl]-2-(trimethylammonio)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       1.060   3.620   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.268  -5.595   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.426  -4.027   0.000  0.00  0.00           O-1
HETATM   12  N   UNK     0       1.543  -3.104   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0       3.074  -3.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.382  -4.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.704  -1.572   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    6    3                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(+)-L-Methylergothioneine	ChEBI
(+)-L-S-Methylergothioneine	ChEBI
(+)-S-Methyl-L-ergothioneine	ChEBI
(+)-S-Methylergothioneine	ChEBI
(2S)-3-[2-(Methylsulfanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propionate	ChEBI
7S-(+)-Methylergothioneine	ChEBI
L-(+)-S-Methylergothioneine	ChEBI
L-S-Methylergothioneine	ChEBI
S-Methylergothioneine	ChEBI
(2S)-3-[2-(Methylsulfanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propionic acid	Generator
(2S)-3-[2-(Methylsulphanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propionate	Generator
(2S)-3-[2-(Methylsulphanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propionic acid	Generator

Chemical Formula

C₁₀H₁₇N₃O₂S

Average Mass

243.3300 Da

Monoisotopic Mass

243.10415 Da

IUPAC Name

(2S)-3-[2-(methylsulfanyl)-1H-imidazol-5-yl]-2-(trimethylazaniumyl)propanoate

Traditional Name

(2S)-3-[2-(methylsulfanyl)-3H-imidazol-4-yl]-2-(trimethylammonio)propanoate

CAS Registry Number

Not Available

SMILES

CSC1=NC=C(C[C@@H](C([O-])=O)[N+](C)(C)C)N1

InChI Identifier

InChI=1S/C10H17N3O2S/c1-13(2,3)8(9(14)15)5-7-6-11-10(12-7)16-4/h6,8H,5H2,1-4H3,(H-,11,12,14,15)/t8-/m0/s1

InChI Key

GVQNHIYBRMFCMS-QMMMGPOBSA-N

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
Aryl thioether
Imidazolyl carboxylic acid derivative
Alkylarylthioether
Aralkylamine
Imidazole
Heteroaromatic compound
Azole
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Azacycle
Thioether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Sulfenyl compound
Carboxylic acid
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:76620 )
amino-acid betaine (CHEBI:76620 )
methyl sulfide (CHEBI:76620 )

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	-3.5	ChemAxon
pKa (Strongest Acidic)	1.97	ChemAxon
pKa (Strongest Basic)	5.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.11 m³·mol⁻¹	ChemAxon
Polarizability	25.25 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

8281369

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10105842

PDB ID

Not Available

ChEBI ID

76620

Good Scents ID

Not Available

References

General References

Gross H, Reitner J, Konig GM: Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica. Naturwissenschaften. 2004 Sep;91(9):441-6. doi: 10.1007/s00114-004-0552-6. Epub 2004 Sep 1. [PubMed:15340692 ]
LOTUS database [Link]

Showing NP-Card for s-methyl-l-ergothioneine (NP0229649)

MOL for NP0229649 (s-methyl-l-ergothioneine)

3D MOL for NP0229649 (s-methyl-l-ergothioneine)

3D SDF for NP0229649 (s-methyl-l-ergothioneine)

3D-SDF for NP0229649 (s-methyl-l-ergothioneine)

PDB for NP0229649 (s-methyl-l-ergothioneine)

3D PDB for NP0229649 (s-methyl-l-ergothioneine)

SMILES for NP0229649 (s-methyl-l-ergothioneine)

INCHI for NP0229649 (s-methyl-l-ergothioneine)

Structure for NP0229649 (s-methyl-l-ergothioneine)

3D Structure for NP0229649 (s-methyl-l-ergothioneine)