7-methyl-3-methylidene-6-(3-oxobut-1-enyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: 8a45c779-50a9-44cc-9ee7-4d1c8080c9f7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: 7-methyl-3-methylidene-6-(3-oxobut-1-enyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3
• InChI Key: RBRPTFMVULVGIC-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CHEBI:180746
• NCI60_000832
• PD124314
• FT-0775577
• 7-methyl-3-methylidene-6-(3-oxobut-1-enyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]uran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.5764	57.64%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5898	58.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9316	93.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7399	73.99%
P-glycoprotein inhibitior	-	0.8964	89.64%
P-glycoprotein substrate	-	0.8186	81.86%
CYP3A4 substrate	+	0.5508	55.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8362	83.62%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.8082	80.82%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.5647	56.47%
CYP2C8 inhibition	-	0.6805	68.05%
CYP inhibitory promiscuity	-	0.8819	88.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9260	92.60%
Carcinogenicity (trinary)	Non-required	0.5801	58.01%
Eye corrosion	-	0.9068	90.68%
Eye irritation	-	0.5694	56.94%
Skin irritation	-	0.5988	59.88%
Skin corrosion	-	0.9158	91.58%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6727	67.27%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	+	0.5312	53.12%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7075	70.75%
Acute Oral Toxicity (c)	III	0.4874	48.74%
Estrogen receptor binding	-	0.5732	57.32%
Androgen receptor binding	-	0.6405	64.05%
Thyroid receptor binding	-	0.6409	64.09%
Glucocorticoid receptor binding	-	0.4796	47.96%
Aromatase binding	-	0.7387	73.87%
PPAR gamma	-	0.7902	79.02%
Honey bee toxicity	-	0.8521	85.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.05%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.45%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.47%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.40%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.94%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.88%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.05%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.86%	97.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.54%	97.09%

Plants that contains it

• Xanthium spinosum
• Xanthium spinosum subsp. spinosum
• Xanthium strumarium

Cross-Links

• PubChem: 282783
• LOTUS: LTS0040201
• wikiData: Q105233303