(3aR,5S,7S,8aR,9aS)-7-hydroxy-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 1b846e29-b453-4cf6-8f95-51d619b6b11f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,5S,7S,8aR,9aS)-7-hydroxy-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CC(CC2(C1=CC3C(C2)OC(=O)C3=C)C)O
• SMILES (Isomeric): C[C@H]1C[C@@H](C[C@]2(C1=C[C@H]3[C@H](C2)OC(=O)C3=C)C)O
• InChI: InChI=1S/C15H20O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,10-11,13,16H,2,4,6-7H2,1,3H3/t8-,10-,11+,13-,15+/m0/s1
• InChI Key: FZSKLHDEGWSLTB-DBIGVJDZSA-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): 46.50 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7997	79.97%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6121	61.21%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9546	95.46%
P-glycoprotein inhibitior	-	0.8758	87.58%
P-glycoprotein substrate	-	0.8275	82.75%
CYP3A4 substrate	+	0.5787	57.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5705	57.05%
CYP2C9 inhibition	-	0.8750	87.50%
CYP2C19 inhibition	-	0.7632	76.32%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.7183	71.83%
CYP2C8 inhibition	-	0.8159	81.59%
CYP inhibitory promiscuity	-	0.7810	78.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4113	41.13%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8093	80.93%
Skin irritation	+	0.4934	49.34%
Skin corrosion	-	0.9023	90.23%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7755	77.55%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7658	76.58%
skin sensitisation	-	0.5507	55.07%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5118	51.18%
Acute Oral Toxicity (c)	III	0.5520	55.20%
Estrogen receptor binding	+	0.6519	65.19%
Androgen receptor binding	+	0.5253	52.53%
Thyroid receptor binding	+	0.5676	56.76%
Glucocorticoid receptor binding	+	0.5674	56.74%
Aromatase binding	+	0.5828	58.28%
PPAR gamma	-	0.5169	51.69%
Honey bee toxicity	-	0.8419	84.19%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9829	98.29%

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	94.72%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.22%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.83%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.30%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.33%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.80%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.53%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	85.90%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.66%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	85.63%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.91%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.22%	99.23%

Plants that contains it

• Inula helenium

Cross-Links

• PubChem: 162931767
• LOTUS: LTS0083463
• wikiData: Q105005148