(3aR,5aR,9R,9aS,9bR)-3a,9-dihydroxy-5a,9-dimethyl-3-methylidene-5,6,7,8,9a,9b-hexahydro-4H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 655103cb-604c-4446-b42e-dadfc2b027db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,5aR,9R,9aS,9bR)-3a,9-dihydroxy-5a,9-dimethyl-3-methylidene-5,6,7,8,9a,9b-hexahydro-4H-benzo[g][1]benzofuran-2-one
• InChI: InChI=1S/C15H22O4/c1-9-12(16)19-11-10-13(2,7-8-15(9,11)18)5-4-6-14(10,3)17/h10-11,17-18H,1,4-8H2,2-3H3/t10-,11-,13-,14-,15-/m1/s1
• InChI Key: NZLXVTHNPSCQMS-OKNSCYNVSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9874	98.74%
Caco-2	+	0.7170	71.70%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7026	70.26%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.9282	92.82%
OATP1B3 inhibitior	+	0.8780	87.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6170	61.70%
BSEP inhibitior	-	0.9668	96.68%
P-glycoprotein inhibitior	-	0.9053	90.53%
P-glycoprotein substrate	-	0.9251	92.51%
CYP3A4 substrate	+	0.5431	54.31%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.6317	63.17%
CYP2C9 inhibition	-	0.9144	91.44%
CYP2C19 inhibition	-	0.8446	84.46%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.6544	65.44%
CYP2C8 inhibition	-	0.9422	94.22%
CYP inhibitory promiscuity	-	0.9284	92.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4853	48.53%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.6965	69.65%
Skin irritation	+	0.6584	65.84%
Skin corrosion	-	0.8962	89.62%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5486	54.86%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6678	66.78%
skin sensitisation	-	0.7996	79.96%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5279	52.79%
Acute Oral Toxicity (c)	I	0.4246	42.46%
Estrogen receptor binding	+	0.6805	68.05%
Androgen receptor binding	-	0.5701	57.01%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5449	54.49%
Aromatase binding	-	0.5135	51.35%
PPAR gamma	-	0.6102	61.02%
Honey bee toxicity	-	0.9395	93.95%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9936	99.36%

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	94.82%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.01%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.27%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	90.19%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.42%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.36%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	85.46%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.46%	92.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.96%	93.03%
CHEMBL230	P35354	Cyclooxygenase-2	83.93%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.59%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.68%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.53%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.25%	92.62%

Plants that contains it

• Podachaenium eminens

Cross-Links

• PubChem: 15828228
• LOTUS: LTS0025641
• wikiData: Q105188259