(3S,5aR,9bS)-3,5a,9-trimethyl-3a,4,5,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2,6-dione

Details

• Internal ID: d81f7458-43a9-44b2-aff6-ca6a9d54f652
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,5aR,9bS)-3,5a,9-trimethyl-3a,4,5,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C2CCC3(C(=O)CCC(=C3C2OC1=O)C)C
• SMILES (Isomeric): C[C@H]1C2CC[C@]3(C(=O)CCC(=C3[C@H]2OC1=O)C)C
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-10,13H,4-7H2,1-3H3/t9-,10?,13-,15-/m0/s1
• InChI Key: RSDQBPGKMDFRHH-RWGQQCCOSA-N
• Popularity: 0 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: 1.40
• Atomic LogP (AlogP): 2.64
• 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	+	0.9973	99.73%
Caco-2	+	0.8549	85.49%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7141	71.41%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9735	97.35%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.8900	89.00%
P-glycoprotein inhibitior	-	0.8310	83.10%
P-glycoprotein substrate	-	0.8918	89.18%
CYP3A4 substrate	+	0.5629	56.29%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.6958	69.58%
CYP2C9 inhibition	-	0.9335	93.35%
CYP2C19 inhibition	-	0.7760	77.60%
CYP2D6 inhibition	-	0.9565	95.65%
CYP1A2 inhibition	-	0.5226	52.26%
CYP2C8 inhibition	-	0.9041	90.41%
CYP inhibitory promiscuity	-	0.8616	86.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5076	50.76%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.7810	78.10%
Skin irritation	+	0.5968	59.68%
Skin corrosion	-	0.8860	88.60%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6083	60.83%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.6583	65.83%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6688	66.88%
Acute Oral Toxicity (c)	III	0.7818	78.18%
Estrogen receptor binding	-	0.6343	63.43%
Androgen receptor binding	-	0.4827	48.27%
Thyroid receptor binding	+	0.5325	53.25%
Glucocorticoid receptor binding	-	0.5607	56.07%
Aromatase binding	-	0.8446	84.46%
PPAR gamma	-	0.6860	68.60%
Honey bee toxicity	-	0.7980	79.80%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.22%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.48%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.00%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.27%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.10%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.08%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.02%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.69%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.17%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.06%	91.49%
CHEMBL2581	P07339	Cathepsin D	82.76%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	81.42%	89.63%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	81.02%	95.55%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.63%	93.04%

Plants that contains it

• Artemisia vestita
• Seriphidium lessingianum

Cross-Links

• PubChem: 9816345
• NPASS: NPC157436