4,6,9-Trihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: 8d894d64-d02a-4367-976a-8d7eddb4255c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 4,6,9-trihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1(CCC(C2(C1C3C(C(C2)O)C(=C)C(=O)O3)C)O)O
• SMILES (Isomeric): CC1(CCC(C2(C1C3C(C(C2)O)C(=C)C(=O)O3)C)O)O
• InChI: InChI=1S/C15H22O5/c1-7-10-8(16)6-14(2)9(17)4-5-15(3,19)12(14)11(10)20-13(7)18/h8-12,16-17,19H,1,4-6H2,2-3H3
• InChI Key: HVEYKPZVVPHBGK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.5476	54.76%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6937	69.37%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.8475	84.75%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6170	61.70%
BSEP inhibitior	-	0.9805	98.05%
P-glycoprotein inhibitior	-	0.9170	91.70%
P-glycoprotein substrate	-	0.8187	81.87%
CYP3A4 substrate	+	0.6350	63.50%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.5612	56.12%
CYP2C9 inhibition	-	0.9247	92.47%
CYP2C19 inhibition	-	0.8848	88.48%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.6883	68.83%
CYP2C8 inhibition	-	0.9032	90.32%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8442	84.42%
Skin irritation	+	0.6326	63.26%
Skin corrosion	-	0.8995	89.95%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7379	73.79%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7462	74.62%
skin sensitisation	-	0.7613	76.13%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7150	71.50%
Acute Oral Toxicity (c)	I	0.5236	52.36%
Estrogen receptor binding	+	0.7002	70.02%
Androgen receptor binding	+	0.5347	53.47%
Thyroid receptor binding	+	0.5740	57.40%
Glucocorticoid receptor binding	+	0.6800	68.00%
Aromatase binding	-	0.5832	58.32%
PPAR gamma	-	0.6047	60.47%
Honey bee toxicity	-	0.8303	83.03%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	95.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.73%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.55%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.19%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.09%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.93%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.62%	85.14%
CHEMBL1871	P10275	Androgen Receptor	85.60%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.76%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.07%	96.61%

Plants that contains it

• Cassinia subtropica
• Cota palaestina
• Ursinia abrotanifolia

Cross-Links

• PubChem: 14191305
• LOTUS: LTS0036454
• wikiData: Q105034207