IMPPAT Phytochemical information: 
Ergothioneine

Ergothioneine
Summary

SMILES: [O-]C(=O)[C@@H]([N+](C)(C)C)Cc1c[nH]c(=S)[nH]1
InChI: 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
InChIKey: SSISHJJTAXXQAX-ZETCQYMHSA-N
DeepSMILES: [O-]C=O)[C@@H][N+]C)C)C))Ccc[nH]c=S)[nH]5
Scaffold Graph/Node/Bond level: S=c1[nH]cc[nH]1
Scaffold Graph/Node level: SC1NCCN1
Scaffold Graph level: CC1CCCC1
Functional groups: CC(=O)[O-]; C[N+](C)(C)C; c[nH]c; c=S
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
Synonymous chemical names:
ergothioneine, Ergothioneine, orgothionenine
External chemical identifiers:
CID:CID_5351619; ChEBI:CHEBI:82707; FDASRS:BDZ3DQM98W; SureChEMBL:SCHEMBL188140; MolPort-046-767-503
Chemical structure download


Ergothioneine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 229.31
Log P RDKit -0.56
Topological polar surface area (Å2) RDKit 71.71
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Ergothioneine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.536798


Ergothioneine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No