(3aR,4aR,8S,8aS,9aR)-4a,8-dihydroxy-8a-methyl-3,5-dimethylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: e8987e00-28eb-49d2-8e02-57073c3de25c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aR,8S,8aS,9aR)-4a,8-dihydroxy-8a-methyl-3,5-dimethylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H18O4/c1-8-4-5-12(16)14(3)7-11-10(6-15(8,14)18)9(2)13(17)19-11/h4-5,10-12,16,18H,1-2,6-7H2,3H3/t10-,11-,12+,14+,15-/m1/s1
• InChI Key: PBSYVAMQYVABDV-RKEKIRQTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.10
• 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	+	0.9854	98.54%
Caco-2	-	0.5412	54.12%
Blood Brain Barrier	-	0.5723	57.23%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5381	53.81%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9057	90.57%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9384	93.84%
P-glycoprotein inhibitior	-	0.9315	93.15%
P-glycoprotein substrate	-	0.8452	84.52%
CYP3A4 substrate	+	0.5834	58.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.7656	76.56%
CYP2C9 inhibition	-	0.8836	88.36%
CYP2C19 inhibition	-	0.8387	83.87%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.7876	78.76%
CYP2C8 inhibition	-	0.8843	88.43%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4477	44.77%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.8030	80.30%
Skin irritation	-	0.5193	51.93%
Skin corrosion	-	0.8760	87.60%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6228	62.28%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7337	73.37%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6996	69.96%
Acute Oral Toxicity (c)	I	0.3417	34.17%
Estrogen receptor binding	+	0.6387	63.87%
Androgen receptor binding	-	0.5059	50.59%
Thyroid receptor binding	+	0.5499	54.99%
Glucocorticoid receptor binding	+	0.6116	61.16%
Aromatase binding	-	0.5929	59.29%
PPAR gamma	-	0.5603	56.03%
Honey bee toxicity	-	0.8663	86.63%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	95.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.71%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.72%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.71%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.51%	97.25%
CHEMBL2581	P07339	Cathepsin D	84.80%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.45%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.48%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.21%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.79%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.46%	100.00%

Plants that contains it

• Ferreyranthus fruticosus

Cross-Links

• PubChem: 163009560
• LOTUS: LTS0135284
• wikiData: Q105205417