Ergothioneine

Details

• Internal ID: c603ba6e-6519-44b9-b06b-1c9c7b419264
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Histidine and derivatives
• IUPAC Name: (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• SMILES (Canonical): C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
• SMILES (Isomeric): C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]
• 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
• InChI Key: SSISHJJTAXXQAX-ZETCQYMHSA-N
• Popularity: 550 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₅N₃O₂S
• Molecular Weight: 229.30 g/mol
• Exact Mass: 229.08849790 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.56
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 497-30-3
• L-(+)-Ergothioneine
• L-Ergothioneine
• Sympectothion
• Ergothionine
• l-Thioneine
• Thiolhistidine-betaine
• Thioneine
• (S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate
• BDZ3DQM98W
• Thiasine
• (S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide
• UNII-BDZ3DQM98W
• erythrothioneine
• ergothioneine thiol
• ergothioneine thione
• NSC 7175
• thiolhistidinebetaine
• EINECS 207-843-5
• MFCD00167474
• Ergothioneine L-(+)
• ergothioneine thione form
• AI3-23492
• ERGOTHIONEINE [MI]
• ergothioneine (thione form)
• ERGOTHIONEINE [INCI]
• SCHEMBL188140
• CHEBI:4828
• SCHEMBL9985141
• CHEMBL5209630
• CHEBI:82707
• DTXSID901020082
• HMS2089D04
• 2-mercaptohistidine trimethylbetaine
• HY-N1914
• AKOS027325505
• CCG-207908
• (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• 1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)-
• 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (S)-
• CS-0018211
• D83035
• AB01275464-01
• A930109
• Ergothionine;L-(+)-Ergothioneine;Erythrothioneine
• Q614788
• (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate
• (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
• 3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate
• Nalpha,Nalpha,Nalpha-trimethyl-2-sulfanylidene-2,3-dihydro-L-histidine
• (2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• (2S)-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• (.ALPHA.S)-.ALPHA.-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT
• (alphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt
• 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)-
• 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (alphaS)-
• 1H-Imidazole-4-ethaniminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)-
• Ammonium, (1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethyl-, hydroxide, inner salt, L-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5594	55.94%
Caco-2	-	0.6862	68.62%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.7301	73.01%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9060	90.60%
P-glycoprotein inhibitior	-	0.9834	98.34%
P-glycoprotein substrate	-	0.8461	84.61%
CYP3A4 substrate	-	0.6019	60.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8485	84.85%
CYP3A4 inhibition	-	0.8582	85.82%
CYP2C9 inhibition	-	0.8793	87.93%
CYP2C19 inhibition	-	0.8700	87.00%
CYP2D6 inhibition	-	0.9163	91.63%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	-	0.9328	93.28%
CYP inhibitory promiscuity	-	0.8901	89.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5410	54.10%
Eye corrosion	-	0.9784	97.84%
Eye irritation	-	0.5451	54.51%
Skin irritation	-	0.7415	74.15%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7403	74.03%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.6717	67.17%
skin sensitisation	-	0.8319	83.19%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8218	82.18%
Acute Oral Toxicity (c)	III	0.5752	57.52%
Estrogen receptor binding	-	0.8621	86.21%
Androgen receptor binding	-	0.8094	80.94%
Thyroid receptor binding	-	0.7328	73.28%
Glucocorticoid receptor binding	-	0.8056	80.56%
Aromatase binding	-	0.6692	66.92%
PPAR gamma	-	0.6391	63.91%
Honey bee toxicity	-	0.9634	96.34%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.6621	66.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.61%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.68%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.78%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.01%	97.25%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.87%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.10%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.27%	99.17%
CHEMBL2535	P11166	Glucose transporter	80.68%	98.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.25%	93.03%

Plants that contains it

• Hyacinthoides non-scripta

Cross-Links

• PubChem: 5351619
• LOTUS: LTS0271548
• wikiData: Q614788