8-Hydroxy-5,8a-dimethyl-3-methylidene-3a,4,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 993863cb-2bd6-4c82-8af1-0355d61c56ad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 8-hydroxy-5,8a-dimethyl-3-methylidene-3a,4,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1=C2CC3C(CC2(C(CC1=O)O)C)OC(=O)C3=C
• SMILES (Isomeric): CC1=C2CC3C(CC2(C(CC1=O)O)C)OC(=O)C3=C
• InChI: InChI=1S/C15H18O4/c1-7-9-4-10-8(2)11(16)5-13(17)15(10,3)6-12(9)19-14(7)18/h9,12-13,17H,1,4-6H2,2-3H3
• InChI Key: KJSSILWQFKEAFM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.7299	72.99%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7347	73.47%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.8637	86.37%
OATP1B3 inhibitior	+	0.8843	88.43%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9472	94.72%
P-glycoprotein inhibitior	-	0.8925	89.25%
P-glycoprotein substrate	-	0.8441	84.41%
CYP3A4 substrate	+	0.5710	57.10%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8955	89.55%
CYP3A4 inhibition	-	0.5649	56.49%
CYP2C9 inhibition	-	0.8937	89.37%
CYP2C19 inhibition	-	0.8925	89.25%
CYP2D6 inhibition	-	0.9615	96.15%
CYP1A2 inhibition	-	0.8056	80.56%
CYP2C8 inhibition	-	0.8091	80.91%
CYP inhibitory promiscuity	-	0.9414	94.14%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4871	48.71%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.7588	75.88%
Skin irritation	+	0.5783	57.83%
Skin corrosion	-	0.8929	89.29%
Ames mutagenesis	-	0.6524	65.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5242	52.42%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.8051	80.51%
skin sensitisation	-	0.7641	76.41%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.7445	74.45%
Acute Oral Toxicity (c)	I	0.3969	39.69%
Estrogen receptor binding	-	0.5321	53.21%
Androgen receptor binding	+	0.5519	55.19%
Thyroid receptor binding	-	0.6646	66.46%
Glucocorticoid receptor binding	-	0.5576	55.76%
Aromatase binding	-	0.7587	75.87%
PPAR gamma	+	0.5399	53.99%
Honey bee toxicity	-	0.7256	72.56%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.07%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.49%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.19%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.83%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.77%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.19%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.18%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	82.90%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.65%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.15%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.00%	96.09%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 75581906
• LOTUS: LTS0204622
• wikiData: Q105141951