(3R,3aS,5aS,9S,9aS,9bS)-3,5a,9-trimethyl-3a,4,5,9,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2,8-dione

Details

• Internal ID: 4ae4e29f-7106-4e67-bb11-3c0c834efcae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aS,5aS,9S,9aS,9bS)-3,5a,9-trimethyl-3a,4,5,9,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2,8-dione
• InChI: InChI=1S/C15H20O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-10,12-13H,4,6H2,1-3H3/t8-,9-,10+,12-,13+,15+/m1/s1
• InChI Key: QKFUYQHESIDKSK-HIEKWVOZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.8077	80.77%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5700	57.00%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8613	86.13%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8735	87.35%
P-glycoprotein inhibitior	-	0.8528	85.28%
P-glycoprotein substrate	-	0.8062	80.62%
CYP3A4 substrate	+	0.5880	58.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8965	89.65%
CYP3A4 inhibition	-	0.7943	79.43%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.8753	87.53%
CYP2D6 inhibition	-	0.9529	95.29%
CYP1A2 inhibition	+	0.6390	63.90%
CYP2C8 inhibition	-	0.9177	91.77%
CYP inhibitory promiscuity	-	0.8303	83.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4572	45.72%
Eye corrosion	-	0.9730	97.30%
Eye irritation	-	0.9123	91.23%
Skin irritation	+	0.5920	59.20%
Skin corrosion	-	0.5711	57.11%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4685	46.85%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.5517	55.17%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5166	51.66%
Acute Oral Toxicity (c)	III	0.6629	66.29%
Estrogen receptor binding	+	0.6994	69.94%
Androgen receptor binding	+	0.6212	62.12%
Thyroid receptor binding	-	0.5788	57.88%
Glucocorticoid receptor binding	-	0.5772	57.72%
Aromatase binding	-	0.8000	80.00%
PPAR gamma	-	0.7365	73.65%
Honey bee toxicity	-	0.7733	77.33%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.31%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.28%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.10%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.80%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.64%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.24%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.53%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.83%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.59%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.00%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.45%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.58%	99.23%

Plants that contains it

• Dicoma anomala

Cross-Links

• PubChem: 162929212
• LOTUS: LTS0191660
• wikiData: Q105223080