4a,8-Dihydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 2e008f60-64fc-4d01-b53c-f64637643712
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 4a,8-dihydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3(C(=C)CCC(C3(CC2OC1=O)C)O)O
• SMILES (Isomeric): CC1C2CC3(C(=C)CCC(C3(CC2OC1=O)C)O)O
• InChI: InChI=1S/C15H22O4/c1-8-4-5-12(16)14(3)7-11-10(6-15(8,14)18)9(2)13(17)19-11/h9-12,16,18H,1,4-7H2,2-3H3
• InChI Key: SBMVCYUMWSRJRE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	+	0.5708	57.08%
Blood Brain Barrier	+	0.5027	50.27%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6356	63.56%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.8524	85.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6170	61.70%
BSEP inhibitior	-	0.8604	86.04%
P-glycoprotein inhibitior	-	0.9364	93.64%
P-glycoprotein substrate	-	0.8600	86.00%
CYP3A4 substrate	+	0.6194	61.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.6026	60.26%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.8920	89.20%
CYP2D6 inhibition	-	0.9461	94.61%
CYP1A2 inhibition	-	0.7294	72.94%
CYP2C8 inhibition	-	0.8927	89.27%
CYP inhibitory promiscuity	-	0.8869	88.69%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5319	53.19%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9634	96.34%
Skin irritation	+	0.5944	59.44%
Skin corrosion	-	0.8980	89.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5483	54.83%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6982	69.82%
skin sensitisation	-	0.7751	77.51%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6467	64.67%
Acute Oral Toxicity (c)	I	0.5393	53.93%
Estrogen receptor binding	+	0.7892	78.92%
Androgen receptor binding	+	0.5789	57.89%
Thyroid receptor binding	+	0.6353	63.53%
Glucocorticoid receptor binding	+	0.8412	84.12%
Aromatase binding	-	0.4912	49.12%
PPAR gamma	-	0.6005	60.05%
Honey bee toxicity	-	0.8534	85.34%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	92.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.58%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.71%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.43%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.61%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	88.93%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.18%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.63%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.65%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.14%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL1871	P10275	Androgen Receptor	80.85%	96.43%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 75581809
• LOTUS: LTS0187679
• wikiData: Q105249555