NP-MRD: Showing NP-Card for Ergothioneine (NP0046403)

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Record Information

Version

1.0

Created at

2022-03-17 19:57:28 UTC

Updated at

2022-03-17 19:57:28 UTC

NP-MRD ID

NP0046403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergothioneine

Description

Ergothioneine is found in Aspergillus fumigatus, Flammulina velutipes and Neurospora crassa.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920102D          

 15 15  0  0  0  0            999 V2000
    1.2822    4.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4572    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   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
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    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
    0.9803   -0.1553    0.0000 N   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
    1.2822    3.1768    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.7112    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
M  CHG  1  12   1
M  END
> <DATABASE_ID>
NP0046403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)C(CC1=CN=C(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

> <INCHI_KEY>
SSISHJJTAXXQAX-UHFFFAOYSA-O

> <FORMULA>
C9H16N3O2S

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.096322461

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.84252614608674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-4.047872099397327

> <ALOGPS_LOGS>
-3.83

> <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>
71.525

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[1-carboxy-2-(2-sulfanyl-3H-imidazol-4-yl)ethyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       2.393   7.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.853   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.933   5.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.727   3.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       2.393   5.930   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       5.061   4.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.727   2.080   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0      -0.615  -1.536   0.000  0.00  0.00           S+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4    6    7                                                       
CONECT    5    6   10                                                       
CONECT    6    4    5   11                                                  
CONECT    7    4    8   12                                                  
CONECT    8    7   13   14                                                  
CONECT    9   10   11   15                                                  
CONECT   10    5    9                                                       
CONECT   11    6    9                                                       
CONECT   12    1    2    3    7                                             
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₆N₃O₂S

Average Mass

230.3070 Da

Monoisotopic Mass

230.09632 Da

IUPAC Name

[1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium

Traditional Name

[1-carboxy-2-(2-sulfanyl-3H-imidazol-4-yl)ethyl]trimethylazanium

CAS Registry Number

497-30-3

SMILES

C[N+](C)(C)C(CC1=CN=C(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

InChI Key

SSISHJJTAXXQAX-UHFFFAOYSA-O

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus fumigatus	Fungi	KNApSAcK
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Flammulina velutipes	Fungi	KNApSAcK
Neurospora crassa	Fungi	KNApSAcK

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
Aralkylamine
Imidazole-2-thione
Azole
Imidazole
Quaternary ammonium salt
Heteroaromatic compound
Tetraalkylammonium salt
Thiourea
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic salt
Organic nitrogen compound
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	-0.27	ALOGPS
logP	-4	ChemAxon
logS	-3.8	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	3	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	23.84 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

FDB004217

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergothioneine

METLIN ID

Not Available

PubChem Compound

10344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ergothioneine (NP0046403)

MOL for NP0046403 (Ergothioneine)

3D MOL for NP0046403 (Ergothioneine)

3D SDF for NP0046403 (Ergothioneine)

3D-SDF for NP0046403 (Ergothioneine)

PDB for NP0046403 (Ergothioneine)

3D PDB for NP0046403 (Ergothioneine)

SMILES for NP0046403 (Ergothioneine)

INCHI for NP0046403 (Ergothioneine)

Structure for NP0046403 (Ergothioneine)

3D Structure for NP0046403 (Ergothioneine)