Dehydrobis(methylthio)gliotoxin

Details

• Internal ID: ee5d8a30-e117-471f-a495-749eeb426099
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolecarboxylic acids and derivatives
• IUPAC Name: (3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-10H-pyrazino[1,2-a]indole-1,4-dione
• SMILES (Canonical): CN1C(=O)C2(CC3=C(N2C(=O)C1(CO)SC)C(=CC=C3)O)SC
• SMILES (Isomeric): CN1C(=O)[C@@]2(CC3=C(N2C(=O)[C@@]1(CO)SC)C(=CC=C3)O)SC
• InChI: InChI=1S/C15H18N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,18-19H,7-8H2,1-3H3/t14-,15-/m1/s1
• InChI Key: BUSZSWVUELPPBM-HUUCEWRRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈N₂O₄S₂
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.07079941 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-10H-pyrazino(1,2-a)indole-1,4-dione
• (3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-10H-pyrazino[1,2-a]indole-1,4-dione
• RefChem:131466
• CHEMBL1088849
• BDBM50364110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5306	53.06%
Caco-2	+	0.6394	63.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6170	61.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.9347	93.47%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8899	88.99%
BSEP inhibitior	-	0.6786	67.86%
P-glycoprotein inhibitior	-	0.9264	92.64%
P-glycoprotein substrate	-	0.6848	68.48%
CYP3A4 substrate	+	0.5893	58.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7651	76.51%
CYP3A4 inhibition	-	0.7728	77.28%
CYP2C9 inhibition	-	0.5748	57.48%
CYP2C19 inhibition	-	0.6645	66.45%
CYP2D6 inhibition	-	0.8659	86.59%
CYP1A2 inhibition	-	0.7647	76.47%
CYP2C8 inhibition	-	0.8798	87.98%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6125	61.25%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9191	91.91%
Skin irritation	-	0.7871	78.71%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5769	57.69%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5208	52.08%
skin sensitisation	-	0.8613	86.13%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4559	45.59%
Acute Oral Toxicity (c)	III	0.5949	59.49%
Estrogen receptor binding	-	0.5193	51.93%
Androgen receptor binding	+	0.6773	67.73%
Thyroid receptor binding	+	0.5899	58.99%
Glucocorticoid receptor binding	+	0.6576	65.76%
Aromatase binding	+	0.6605	66.05%
PPAR gamma	+	0.7167	71.67%
Honey bee toxicity	-	0.9155	91.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8344	83.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.69%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.42%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.08%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.11%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.35%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.96%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.28%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 13989139
• LOTUS: LTS0268719
• wikiData: Q104946303