(3aR,4R,5aR,6R,8R,9bS)-4,6,8-trihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: b340904d-51a4-4f26-961d-86528c4b23f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4R,5aR,6R,8R,9bS)-4,6,8-trihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(C(CC2(C(CC1O)O)C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H]([C@@H](C[C@]2([C@@H](C[C@H]1O)O)C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O5/c1-6-8(16)4-10(18)15(3)5-9(17)11-7(2)14(19)20-13(11)12(6)15/h8-11,13,16-18H,2,4-5H2,1,3H3/t8-,9-,10-,11-,13+,15+/m1/s1
• InChI Key: OGIJYJZISLQTBF-LVKXLNOLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.30
• 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	+	0.9911	99.11%
Caco-2	+	0.5602	56.02%
Blood Brain Barrier	+	0.6277	62.77%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5695	56.95%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9699	96.99%
P-glycoprotein inhibitior	-	0.8579	85.79%
P-glycoprotein substrate	-	0.7584	75.84%
CYP3A4 substrate	+	0.5826	58.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.6033	60.33%
CYP2C9 inhibition	-	0.8903	89.03%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	-	0.7570	75.70%
CYP2C8 inhibition	-	0.8788	87.88%
CYP inhibitory promiscuity	-	0.8406	84.06%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4376	43.76%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.6922	69.22%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8872	88.72%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6384	63.84%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7658	76.58%
skin sensitisation	-	0.7141	71.41%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6793	67.93%
Acute Oral Toxicity (c)	I	0.3995	39.95%
Estrogen receptor binding	+	0.5726	57.26%
Androgen receptor binding	-	0.5589	55.89%
Thyroid receptor binding	-	0.4948	49.48%
Glucocorticoid receptor binding	+	0.5670	56.70%
Aromatase binding	-	0.7134	71.34%
PPAR gamma	-	0.5827	58.27%
Honey bee toxicity	-	0.6532	65.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9927	99.27%

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	91.85%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.35%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.04%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.51%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.48%	95.58%
CHEMBL221	P23219	Cyclooxygenase-1	86.79%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.99%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.97%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.57%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.79%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.12%	99.23%

Plants that contains it

• Cassinia subtropica

Cross-Links

• PubChem: 14191311
• LOTUS: LTS0005736
• wikiData: Q105191633