NP-MRD: Showing NP-Card for (2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate (NP0327694)

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Record Information

Version

2.0

Created at

2022-09-12 10:30:14 UTC

Updated at

2022-09-12 10:30:14 UTC

NP-MRD ID

NP0327694

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate

Description

Ergothioneine, also known as sympectothion, 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. (2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate is found in Hyacinthoides non-scripta. (2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate was first documented in 1952 (PMID: 13034359). Ergothioneine is a very strong basic compound (based on its pKa) (PMID: 15795384) (PMID: 15030958).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.7248    0.0330   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    0.2130    0.0163 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.7560    1.6087    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615   -0.5245    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404   -0.2564   -0.3789 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5851    0.5456    0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930    0.1992    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005   -0.6673    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0222   -0.7184    0.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9659    0.1151   -0.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2418    0.3694   -1.9518 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511    0.6798   -1.0057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -1.7143   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666   -2.3658    0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.5343   -1.2257 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2905    0.3099   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -0.9869   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    0.7270   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210    1.8862    0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    2.2693   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2241    1.8049    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880   -0.6321    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682    0.1129    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213   -1.4580    0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3442   -0.0023   -1.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4650    1.6069   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729    0.5375    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5555   -1.2338    1.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8436   -1.2876    0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    1.3633   -1.7045 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  2  0
 10 12  1  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
 12 30  1  0
M  CHG  2   2   1  15  -1
M  END


  Mrv1652310301918472D          

 15 15  0  0  0  0            999 V2000
10001.067210000.2586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.352110000.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.510310000.5149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10001.0672 9999.4319    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.7845 9999.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3500 9999.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0672 9998.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.784510000.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.499610000.2586    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10001.784510001.4967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.963510000.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.296110000.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5510 9999.4828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3760 9999.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.630910000.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  1  0  0  0
  1  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 14 15  2  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 12  3  2  0  0  0  0
M  CHG  2   4   1   9  -1
M  END
> <DATABASE_ID>
NP0327694

> <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)/t7-/m0/s1

> <INCHI_KEY>
SSISHJJTAXXQAX-ZETCQYMHSA-N

> <FORMULA>
C9H15N3O2S

> <MOLECULAR_WEIGHT>
229.299

> <EXACT_MASS>
229.088497429

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.498800549659087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-4.047872099397327

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
7.852522464253925

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.884701843879959

> <JCHEM_PKA_STRONGEST_BASIC>
5.311255391075792

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
68.6873

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ergothioneine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-19         0                                  
HETATM    1  C   UNK     0    8668.6598667.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3248667.917   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0    8662.0198667.628   0.000  0.00  0.00           S+0
HETATM    4  N   UNK     0    8668.6598665.606   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0    8669.9988664.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.3208664.833   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.6598663.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8669.9988667.917   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.3338667.149   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0    8669.9988669.461   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8664.7328668.071   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8663.4868667.166   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8663.9628665.701   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8665.5028665.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9788667.166   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1   15                                                       
CONECT    3   12                                                            
CONECT    4    1    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   15                                                       
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   15   13                                                       
CONECT   15   14   11    2                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate	ChEBI
(AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	ChEBI
(S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide	ChEBI
2-Mercaptohistidine trimethylbetaine	ChEBI
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate	ChEBI
Ergothioneine thiol	ChEBI
Ergothionine	ChEBI
Erythrothioneine	ChEBI
L-Ergothioneine	ChEBI
L-Thioneine	ChEBI
Sympectothion	ChEBI
Thiolhistidine-betaine	ChEBI
Thiolhistidinebetaine	ChEBI
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acid	Generator
(AlphaS)-a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	Generator
(AlphaS)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	Generator
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid	Generator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate	Generator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid	Generator
2 Thiol L histidine betaine	HMDB
2-Thiol-L-histidine-betaine	HMDB
Thioneine	HMDB

Chemical Formula

C₉H₁₅N₃O₂S

Average Mass

229.2990 Da

Monoisotopic Mass

229.08850 Da

IUPAC Name

{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide

Traditional Name

ergothioneine

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)/t7-/m0/s1

InChI Key

SSISHJJTAXXQAX-ZETCQYMHSA-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

Species Name	Source	Reference
Hyacinthoides non-scripta	LOTUS Database	35616633

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
Imidazolyl carboxylic acid derivative
Aralkylamine
Imidazole-2-thione
Azole
Imidazole
Quaternary ammonium salt
Heteroaromatic compound
Tetraalkylammonium salt
Thiourea
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Amine
Organosulfur compound
Organic oxide
Organic salt
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

amino-acid betaine (CHEBI:4828 )
L-histidine derivative (CHEBI:4828 )

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	-1.7	ALOGPS
logP	-4	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	5.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.69 m³·mol⁻¹	ChemAxon
Polarizability	23.5 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

HMDB0003045

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB004217

KNApSAcK ID

Not Available

Chemspider ID

4508619

KEGG Compound ID

C05570

BioCyc ID

CPD-15276

BiGG ID

Not Available

Wikipedia Link

Ergothioneine

METLIN ID

PubChem Compound

5351619

PDB ID

Not Available

ChEBI ID

4828

Good Scents ID

Not Available

References

General References

OHARA M, TOMITA K, WATANABE R, KONO K, WATANABE K: Estimation of ergothioneine in urine, blood and organs by determination of the alkaline perhydrol-labile sulfur. Jpn J Med Sci Biol. 1952 Oct;5(5):259-63. doi: 10.7883/yoken1952.5.259. [PubMed:13034359 ]
Grundemann D, Harlfinger S, Golz S, Geerts A, Lazar A, Berkels R, Jung N, Rubbert A, Schomig E: Discovery of the ergothioneine transporter. Proc Natl Acad Sci U S A. 2005 Apr 5;102(14):5256-61. doi: 10.1073/pnas.0408624102. Epub 2005 Mar 28. [PubMed:15795384 ]
Deiana M, Rosa A, Casu V, Piga R, Assunta Dessi M, Aruoma OI: L-ergothioneine modulates oxidative damage in the kidney and liver of rats in vivo: studies upon the profile of polyunsaturated fatty acids. Clin Nutr. 2004 Apr;23(2):183-93. doi: 10.1016/S0261-5614(03)00108-0. [PubMed:15030958 ]
LOTUS database [Link]

Showing NP-Card for (2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate (NP0327694)

MOL for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

3D MOL for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

3D SDF for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

3D-SDF for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

PDB for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

3D PDB for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

SMILES for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

INCHI for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

Structure for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)

3D Structure for NP0327694 ((2s)-3-(2-sulfanyl-3h-imidazol-4-yl)-2-(trimethylammonio)propanoate)