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

Details

• Internal ID: fcfb7486-8560-42ee-9c6d-2bf239feec50
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,5R,8R,8aR,9aR)-5,8-dihydroxy-3,5,8a-trimethyl-3a,6,7,8,9,9a-hexahydro-3H-benzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H22O4/c1-8-9-6-11-14(2,7-10(9)19-13(8)17)12(16)4-5-15(11,3)18/h6,8-10,12,16,18H,4-5,7H2,1-3H3/t8-,9+,10+,12+,14+,15+/m0/s1
• InChI Key: KMYZDJARJMLULC-NONPZXNPSA-N
• Popularity: 0 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: 0.90
• 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	+	0.9940	99.40%
Caco-2	+	0.6682	66.82%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7741	77.41%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.9364	93.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5179	51.79%
BSEP inhibitior	-	0.9240	92.40%
P-glycoprotein inhibitior	-	0.8990	89.90%
P-glycoprotein substrate	-	0.7734	77.34%
CYP3A4 substrate	+	0.6108	61.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.5833	58.33%
CYP2C9 inhibition	-	0.9269	92.69%
CYP2C19 inhibition	-	0.9258	92.58%
CYP2D6 inhibition	-	0.9425	94.25%
CYP1A2 inhibition	-	0.7047	70.47%
CYP2C8 inhibition	-	0.8939	89.39%
CYP inhibitory promiscuity	-	0.8945	89.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4979	49.79%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.9666	96.66%
Skin irritation	+	0.6968	69.68%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.8470	84.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6580	65.80%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.7534	75.34%
skin sensitisation	-	0.7733	77.33%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5466	54.66%
Estrogen receptor binding	+	0.5843	58.43%
Androgen receptor binding	-	0.4897	48.97%
Thyroid receptor binding	+	0.6916	69.16%
Glucocorticoid receptor binding	+	0.5627	56.27%
Aromatase binding	-	0.5546	55.46%
PPAR gamma	-	0.6845	68.45%
Honey bee toxicity	-	0.8880	88.80%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.95%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.69%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.65%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.41%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.66%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.46%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.99%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.83%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.98%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.62%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%

Plants that contains it

• Inula thapsoides

Cross-Links

• PubChem: 101936595
• LOTUS: LTS0134844
• wikiData: Q105143275