(3aS,5aS,7S,9bR)-7-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: fb28bae8-840a-4413-ba61-fc7df1c8f1de
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aS,7S,9bR)-7-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(CCC2(CC(C1)O)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@H]3[C@@H](CC[C@]2(C[C@H](C1)O)C)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O3/c1-8-6-10(16)7-15(3)5-4-11-9(2)14(17)18-13(11)12(8)15/h10-11,13,16H,2,4-7H2,1,3H3/t10-,11-,13+,15-/m0/s1
• InChI Key: IBYCSUBEDIAOOY-MEDZGJRSSA-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: 1.70
• Atomic LogP (AlogP): 2.36
• 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	+	0.9955	99.55%
Caco-2	+	0.7607	76.07%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6678	66.78%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8454	84.54%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6401	64.01%
BSEP inhibitior	-	0.9509	95.09%
P-glycoprotein inhibitior	-	0.8669	86.69%
P-glycoprotein substrate	-	0.8398	83.98%
CYP3A4 substrate	+	0.6199	61.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5114	51.14%
CYP2C9 inhibition	-	0.9267	92.67%
CYP2C19 inhibition	-	0.7458	74.58%
CYP2D6 inhibition	-	0.9300	93.00%
CYP1A2 inhibition	+	0.5108	51.08%
CYP2C8 inhibition	-	0.7955	79.55%
CYP inhibitory promiscuity	-	0.8909	89.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4928	49.28%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.5467	54.67%
Skin irritation	+	0.6180	61.80%
Skin corrosion	-	0.9080	90.80%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6116	61.16%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.6950	69.50%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.6840	68.40%
Acute Oral Toxicity (c)	III	0.6157	61.57%
Estrogen receptor binding	+	0.5281	52.81%
Androgen receptor binding	-	0.6109	61.09%
Thyroid receptor binding	-	0.5669	56.69%
Glucocorticoid receptor binding	-	0.5607	56.07%
Aromatase binding	-	0.5779	57.79%
PPAR gamma	-	0.6669	66.69%
Honey bee toxicity	-	0.7771	77.71%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	91.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.36%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.02%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.38%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.21%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.92%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	82.18%	97.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.88%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.15%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.23%	100.00%

Plants that contains it

• Sphaeranthus suaveolens

Cross-Links

• PubChem: 14589092
• LOTUS: LTS0250631
• wikiData: Q105110834