(3R,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidene-3a,4,4a,6,9,9a-hexahydro-3H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: b181c9fb-f90a-412c-b965-7b7d6bba6ee0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidene-3a,4,4a,6,9,9a-hexahydro-3H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3C(=C)CC=CC3(CC2OC1=O)C
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@H]3C(=C)CC=C[C@]3(C[C@H]2OC1=O)C
• InChI: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h4,6,10-13H,1,5,7-8H2,2-3H3/t10-,11-,12+,13-,15+/m1/s1
• InChI Key: VHANAQXZAJSCOS-VVSAWPALSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 2
• 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	+	1.0000	100.00%
Caco-2	+	0.6848	68.48%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4551	45.51%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8800	88.00%
OATP1B3 inhibitior	+	0.8922	89.22%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6835	68.35%
P-glycoprotein inhibitior	-	0.9088	90.88%
P-glycoprotein substrate	-	0.7458	74.58%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	-	0.5081	50.81%
CYP2C9 inhibition	-	0.9508	95.08%
CYP2C19 inhibition	+	0.6905	69.05%
CYP2D6 inhibition	-	0.9595	95.95%
CYP1A2 inhibition	+	0.6071	60.71%
CYP2C8 inhibition	-	0.9001	90.01%
CYP inhibitory promiscuity	-	0.7367	73.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4670	46.70%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.8433	84.33%
Skin irritation	-	0.5286	52.86%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.8802	88.02%
skin sensitisation	+	0.6534	65.34%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6655	66.55%
Acute Oral Toxicity (c)	III	0.7127	71.27%
Estrogen receptor binding	-	0.5292	52.92%
Androgen receptor binding	+	0.5377	53.77%
Thyroid receptor binding	-	0.7000	70.00%
Glucocorticoid receptor binding	+	0.6132	61.32%
Aromatase binding	-	0.7522	75.22%
PPAR gamma	-	0.6596	65.96%
Honey bee toxicity	-	0.7264	72.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	95.02%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.71%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	88.53%	91.49%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.05%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.22%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.41%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.74%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.52%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.08%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.94%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.43%	96.77%

Plants that contains it

• Callitris columellaris

Cross-Links

• PubChem: 163017021
• LOTUS: LTS0265645
• wikiData: Q105286284