(3aR,4aS,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 3bff06fc-7398-40a1-9581-2d3e0980f73b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aS,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H18O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h4-5,10-13,16H,1-2,6-7H2,3H3/t10-,11+,12-,13+,15-/m1/s1
• InChI Key: GUEMUJOVYAQBRL-GEJOOGBSSA-N
• Popularity: 0 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): 46.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 3
• 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	+	0.9971	99.71%
Caco-2	+	0.6088	60.88%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6417	64.17%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8688	86.88%
OATP1B3 inhibitior	+	0.9289	92.89%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9568	95.68%
P-glycoprotein inhibitior	-	0.9380	93.80%
P-glycoprotein substrate	-	0.8383	83.83%
CYP3A4 substrate	+	0.6027	60.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.6300	63.00%
CYP2C9 inhibition	-	0.8596	85.96%
CYP2C19 inhibition	-	0.6373	63.73%
CYP2D6 inhibition	-	0.9438	94.38%
CYP1A2 inhibition	-	0.6334	63.34%
CYP2C8 inhibition	-	0.9199	91.99%
CYP inhibitory promiscuity	-	0.7550	75.50%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4470	44.70%
Eye corrosion	-	0.9748	97.48%
Eye irritation	-	0.7641	76.41%
Skin irritation	+	0.4899	48.99%
Skin corrosion	-	0.8686	86.86%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4592	45.92%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6961	69.61%
skin sensitisation	-	0.5822	58.22%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7191	71.91%
Acute Oral Toxicity (c)	III	0.5612	56.12%
Estrogen receptor binding	+	0.5523	55.23%
Androgen receptor binding	+	0.5510	55.10%
Thyroid receptor binding	-	0.5242	52.42%
Glucocorticoid receptor binding	+	0.5525	55.25%
Aromatase binding	-	0.7450	74.50%
PPAR gamma	-	0.5929	59.29%
Honey bee toxicity	-	0.7950	79.50%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	94.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.12%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.67%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.72%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	89.08%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.28%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.91%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.19%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	82.69%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.89%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.30%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.19%	100.00%

Plants that contains it

• Ferreyranthus fruticosus

Cross-Links

• PubChem: 14021274
• LOTUS: LTS0036700
• wikiData: Q105020058