Bisdethiobis(Methylthio)Gliotoxin

Details

• Internal ID: 1f2fc844-b9ce-4a76-949e-dcf41873c5a3
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-6,10-dihydro-5aH-pyrazino[1,2-a]indole-1,4-dione
• InChI: InChI=1S/C15H20N2O4S2/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/h4-6,10-11,18-19H,7-8H2,1-3H3/t10-,11-,14+,15+/m0/s1
• InChI Key: OVBAGMZLGLXSBN-UOVKNHIHSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀N₂O₄S₂
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.08644947 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.03
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• bis(methylthio)gliotoxin
• 74149-38-5
• FR-49175
• FR 49175
• (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-6,10-dihydro-5aH-pyrazino[1,2-a]indole-1,4-dione
• CHEMBL1088981
• dimethylgliotoxin
• AC1L4YI4
• BmGT
• S,S-Dimethyl gliotoxin
• bis(methylsulfanyl)gliotoxin
• Bis(methylthio)gliotoxin, 99%
• GTPL3150
• SCHEMBL18652994
• DTXSID70995590
• 3R,10Ar-Dithiomethyl Gliotoxin A
• HY-N9710
• BDBM50315535
• MFCD00133146
• AKOS040761419
• Bis(methylthio)gliotoxin (FR-49175)
• NCGC00380667-01
• CS-0203642
• Q27077740
• Bis(methylthio)gliotoxin (FR-49175) is known as a PAF receptor ligand.
• (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-1H,2H,3H,4H,5aH,6H,10H,10aH-piperazino[1,2-a]indole-1,4-dione
• (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylthio)-2,3,5a,6,10,10a-hexahydropyrazino[1,2-a]indole-1,4-dione
• 6-Hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-2,3,5a,6,10,10a-hexahydropyrazino[1,2-a]indole-1,4-dione
• Pyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6,10,10a-hexahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylthio)-, (3R-(3alpha,5abeta,6beta,10aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7114	71.14%
Caco-2	+	0.5512	55.12%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5799	57.99%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7899	78.99%
BSEP inhibitior	-	0.6230	62.30%
P-glycoprotein inhibitior	-	0.9127	91.27%
P-glycoprotein substrate	-	0.5964	59.64%
CYP3A4 substrate	+	0.6030	60.30%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8102	81.02%
CYP3A4 inhibition	-	0.8899	88.99%
CYP2C9 inhibition	-	0.7205	72.05%
CYP2C19 inhibition	-	0.7479	74.79%
CYP2D6 inhibition	-	0.8773	87.73%
CYP1A2 inhibition	-	0.7328	73.28%
CYP2C8 inhibition	-	0.8270	82.70%
CYP inhibitory promiscuity	-	0.6801	68.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5110	51.10%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9895	98.95%
Skin irritation	-	0.7471	74.71%
Skin corrosion	-	0.9182	91.82%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4175	41.75%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5863	58.63%
Acute Oral Toxicity (c)	III	0.5186	51.86%
Estrogen receptor binding	-	0.6358	63.58%
Androgen receptor binding	+	0.6481	64.81%
Thyroid receptor binding	+	0.6208	62.08%
Glucocorticoid receptor binding	+	0.5554	55.54%
Aromatase binding	-	0.5935	59.35%
PPAR gamma	-	0.5769	57.69%
Honey bee toxicity	-	0.8699	86.99%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7608	76.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.67%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.06%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.96%	95.56%
CHEMBL4208	P20618	Proteasome component C5	88.41%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.35%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.05%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.59%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.42%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.14%	91.11%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.01%	98.46%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 194564
• LOTUS: LTS0148976
• wikiData: Q27077740