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

Details

• Internal ID: 8227d4bf-49d1-456c-90a7-45109b4a7c83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (5aR)-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCCC2(C1C3C(CC2)C(=C)C(=O)O3)C
• SMILES (Isomeric): CC1=CCC[C@]2(C1C3C(CC2)C(=C)C(=O)O3)C
• InChI: InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h5,11-13H,2,4,6-8H2,1,3H3/t11?,12?,13?,15-/m1/s1
• InChI Key: UHODXTMZSDNATP-CDKPOMLUSA-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: 3.30
• Atomic LogP (AlogP): 3.24
• 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	+	0.8753	87.53%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4444	44.44%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.8772	87.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.9699	96.99%
P-glycoprotein inhibitior	-	0.8783	87.83%
P-glycoprotein substrate	-	0.9038	90.38%
CYP3A4 substrate	+	0.5874	58.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	+	0.7392	73.92%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	+	0.8538	85.38%
CYP2C8 inhibition	-	0.5847	58.47%
CYP inhibitory promiscuity	-	0.6910	69.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4867	48.67%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.6860	68.60%
Skin irritation	-	0.5244	52.44%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4180	41.80%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6555	65.55%
skin sensitisation	+	0.5706	57.06%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7097	70.97%
Acute Oral Toxicity (c)	III	0.7166	71.66%
Estrogen receptor binding	-	0.5437	54.37%
Androgen receptor binding	+	0.6568	65.68%
Thyroid receptor binding	-	0.6265	62.65%
Glucocorticoid receptor binding	-	0.4673	46.73%
Aromatase binding	-	0.7284	72.84%
PPAR gamma	-	0.6255	62.55%
Honey bee toxicity	-	0.8123	81.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.18%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.25%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.13%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.79%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.97%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.97%	97.09%
CHEMBL4530	P00488	Coagulation factor XIII	86.33%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.73%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.94%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.81%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.43%	95.89%

Plants that contains it

• Aucklandia costus

Cross-Links

• PubChem: 5316245
• NPASS: NPC246393