(3S,3aR,6R,8R,8aR,9aR)-6,8-dihydroxy-3,5,8a-trimethyl-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 8d773469-f4ef-489e-b4e0-8840d2d8e1e6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,6R,8R,8aR,9aR)-6,8-dihydroxy-3,5,8a-trimethyl-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3=C(C(CC(C3(CC2OC1=O)C)O)O)C
• SMILES (Isomeric): C[C@H]1[C@H]2CC3=C([C@@H](C[C@H]([C@@]3(C[C@H]2OC1=O)C)O)O)C
• InChI: InChI=1S/C15H22O4/c1-7-9-4-10-8(2)11(16)5-13(17)15(10,3)6-12(9)19-14(7)18/h7,9,11-13,16-17H,4-6H2,1-3H3/t7-,9+,11+,12+,13+,15+/m0/s1
• InChI Key: JIBCHCJSBYLSTP-XOGYVCSVSA-N
• Popularity: 1 reference 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: 0.70
• Atomic LogP (AlogP): 1.41
• 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	+	0.9905	99.05%
Caco-2	+	0.6308	63.08%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6336	63.36%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.9163	91.63%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8235	82.35%
P-glycoprotein inhibitior	-	0.9149	91.49%
P-glycoprotein substrate	-	0.6954	69.54%
CYP3A4 substrate	+	0.5828	58.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.6920	69.20%
CYP2C9 inhibition	-	0.9028	90.28%
CYP2C19 inhibition	-	0.9151	91.51%
CYP2D6 inhibition	-	0.9579	95.79%
CYP1A2 inhibition	-	0.8035	80.35%
CYP2C8 inhibition	-	0.9217	92.17%
CYP inhibitory promiscuity	-	0.8519	85.19%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4332	43.32%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8874	88.74%
Skin irritation	+	0.5943	59.43%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6098	60.98%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.7658	76.58%
skin sensitisation	-	0.7896	78.96%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.7180	71.80%
Acute Oral Toxicity (c)	I	0.5757	57.57%
Estrogen receptor binding	+	0.5978	59.78%
Androgen receptor binding	-	0.6016	60.16%
Thyroid receptor binding	+	0.5463	54.63%
Glucocorticoid receptor binding	-	0.5400	54.00%
Aromatase binding	-	0.6526	65.26%
PPAR gamma	-	0.5787	57.87%
Honey bee toxicity	-	0.7495	74.95%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	94.70%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.94%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.54%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.14%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.28%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	86.69%	91.49%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.92%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.05%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.11%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.87%	86.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.78%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.29%	96.77%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 50917930
• LOTUS: LTS0270774
• wikiData: Q105128884