(1R,7S,8R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione

Details

• Internal ID: e9fff925-48a9-430a-9c51-3d35eae2c336
• Taxonomy: Organoheterocyclic compounds > Diazinanes > Piperazines > Thiodioxopiperazines > Epipolythiodioxopiperazines > Gliotoxins
• IUPAC Name: (1R,7S,8R,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione
• SMILES (Canonical): CN1C(=O)C23CC4=CC=CC(C4N2C(=O)C1(SS3)CO)O
• SMILES (Isomeric): CN1C(=O)[C@]23CC4=CC=C[C@@H]([C@@H]4N2C(=O)[C@]1(SS3)CO)O
• InChI: InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9+,12+,13+/m0/s1
• InChI Key: FIVPIPIDMRVLAY-HIAZDOBYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄N₂O₄S₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.03949928 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.30
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• SCHEMBL14514067

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8547	85.47%
Caco-2	-	0.5125	51.25%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5981	59.81%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7707	77.07%
P-glycoprotein inhibitior	-	0.9655	96.55%
P-glycoprotein substrate	-	0.6794	67.94%
CYP3A4 substrate	+	0.6139	61.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.8511	85.11%
CYP2C9 inhibition	-	0.6673	66.73%
CYP2C19 inhibition	-	0.7174	71.74%
CYP2D6 inhibition	-	0.8572	85.72%
CYP1A2 inhibition	-	0.7229	72.29%
CYP2C8 inhibition	-	0.9143	91.43%
CYP inhibitory promiscuity	-	0.6994	69.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5677	56.77%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.9915	99.15%
Skin irritation	-	0.7477	74.77%
Skin corrosion	-	0.9122	91.22%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4612	46.12%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.8362	83.62%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6710	67.10%
Acute Oral Toxicity (c)	III	0.5146	51.46%
Estrogen receptor binding	-	0.5475	54.75%
Androgen receptor binding	+	0.6797	67.97%
Thyroid receptor binding	+	0.5263	52.63%
Glucocorticoid receptor binding	+	0.6436	64.36%
Aromatase binding	-	0.5912	59.12%
PPAR gamma	+	0.5276	52.76%
Honey bee toxicity	-	0.8815	88.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8203	82.03%

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	96.21%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.28%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	93.04%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.71%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.22%	96.77%
CHEMBL4208	P20618	Proteasome component C5	84.74%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.33%	86.33%

Plants that contains it

• Artemisia gilvescens
• Datura stramonium
• Oenanthe fistulosa

Cross-Links

• PubChem: 6713040
• NPASS: NPC43642
• LOTUS: LTS0273138
• wikiData: Q104995889