Dehydroxymethylbis(dethio)bis(methylthio)gliotoxin
| Internal ID | 11bb8291-de9b-4ec2-b447-f38f9c32d3e0 |
| 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-2-methyl-3,10a-bis(methylsulfanyl)-3,5a,6,10-tetrahydropyrazino[1,2-a]indole-1,4-dione |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C14H18N2O3S2/c1-15-12(20-2)11(18)16-10-8(5-4-6-9(10)17)7-14(16,21-3)13(15)19/h4-6,9-10,12,17H,7H2,1-3H3/t9-,10-,12+,14+/m0/s1 |
| InChI Key | AHKQNTDHDXRTKQ-BQSGVUBFSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C14H18N2O3S2 |
| Molecular Weight | 326.40 g/mol |
| Exact Mass | 326.07588479 g/mol |
| Topological Polar Surface Area (TPSA) | 111.00 Ų |
| XlogP | 0.40 |
| Atomic LogP (AlogP) | 0.66 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 2 |
| (3R,5aS,6S,10aR)-6-hydroxy-2-methyl-3,10a-bis(methylsulfanyl)-3,5a,6,10-tetrahydropyrazino(1,2-a)indole-1,4-dione |
| (3R,5aS,6S,10aR)-6-hydroxy-2-methyl-3,10a-bis(methylsulfanyl)-3,5a,6,10-tetrahydropyrazino[1,2-a]indole-1,4-dione |
| (3R,6aR,7S,10bR)-7-hydroxy-2-methyl-3,10b-bis(methylsulfanyl)-3,6,6a,7-tetrahydropyrazino(2,1-a)isoindole-1,4-dione |
| (3R,6aR,7S,10bR)-7-hydroxy-2-methyl-3,10b-bis(methylsulfanyl)-3,6,6a,7-tetrahydropyrazino[2,1-a]isoindole-1,4-dione |
| RefChem:131574 |
| CHEBI:215233 |
| (3R,5aS,6S,10aR)-6-hydroxy-2-methyl-3,10a-bis(methylsulanyl)-3,5a,6,10-tetrahydropyrazino[1,2-a]indole-1,4-dione |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8911 | 89.11% |
| Caco-2 | - | 0.5433 | 54.33% |
| Blood Brain Barrier | - | 0.5750 | 57.50% |
| Human oral bioavailability | + | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.5204 | 52.04% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9118 | 91.18% |
| OATP1B3 inhibitior | + | 0.9394 | 93.94% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.7899 | 78.99% |
| BSEP inhibitior | - | 0.8211 | 82.11% |
| P-glycoprotein inhibitior | - | 0.9217 | 92.17% |
| P-glycoprotein substrate | - | 0.6337 | 63.37% |
| CYP3A4 substrate | + | 0.5784 | 57.84% |
| CYP2C9 substrate | - | 0.8038 | 80.38% |
| CYP2D6 substrate | - | 0.8291 | 82.91% |
| CYP3A4 inhibition | - | 0.7791 | 77.91% |
| CYP2C9 inhibition | - | 0.5619 | 56.19% |
| CYP2C19 inhibition | - | 0.5984 | 59.84% |
| CYP2D6 inhibition | - | 0.8375 | 83.75% |
| CYP1A2 inhibition | - | 0.5986 | 59.86% |
| CYP2C8 inhibition | - | 0.8671 | 86.71% |
| CYP inhibitory promiscuity | + | 0.6032 | 60.32% |
| UGT catelyzed | + | 1.0000 | 100.00% |
| Carcinogenicity (binary) | - | 0.9100 | 91.00% |
| Carcinogenicity (trinary) | Non-required | 0.5388 | 53.88% |
| Eye corrosion | - | 0.9840 | 98.40% |
| Eye irritation | - | 0.9896 | 98.96% |
| Skin irritation | - | 0.7418 | 74.18% |
| Skin corrosion | - | 0.9102 | 91.02% |
| Ames mutagenesis | - | 0.5700 | 57.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4620 | 46.20% |
| Micronuclear | + | 0.6600 | 66.00% |
| Hepatotoxicity | + | 0.6952 | 69.52% |
| skin sensitisation | - | 0.8523 | 85.23% |
| Respiratory toxicity | + | 0.7000 | 70.00% |
| Reproductive toxicity | + | 0.8111 | 81.11% |
| Mitochondrial toxicity | + | 0.8500 | 85.00% |
| Nephrotoxicity | + | 0.6118 | 61.18% |
| Acute Oral Toxicity (c) | III | 0.5077 | 50.77% |
| Estrogen receptor binding | - | 0.7034 | 70.34% |
| Androgen receptor binding | + | 0.6017 | 60.17% |
| Thyroid receptor binding | + | 0.5506 | 55.06% |
| Glucocorticoid receptor binding | - | 0.5706 | 57.06% |
| Aromatase binding | - | 0.6865 | 68.65% |
| PPAR gamma | - | 0.6442 | 64.42% |
| Honey bee toxicity | - | 0.8270 | 82.70% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | + | 0.5200 | 52.00% |
| Fish aquatic toxicity | + | 0.8301 | 83.01% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 97.42% | 83.82% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 96.68% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.23% | 98.95% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 89.49% | 91.11% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 89.45% | 90.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.91% | 95.56% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 83.10% | 93.40% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 83.08% | 86.33% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 146683985 |
| LOTUS | LTS0257328 |
| wikiData | Q104912299 |