(3aR,4aR,8aS,9aR)-4a-hydroxy-5,8a-dimethyl-3-methylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: 62af0774-e717-466e-ae16-517df2acf340
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aR,8aS,9aR)-4a-hydroxy-5,8a-dimethyl-3-methylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione
• InChI: InChI=1S/C15H18O4/c1-8-4-10(16)5-14(3)7-12-11(6-15(8,14)18)9(2)13(17)19-12/h4,11-12,18H,2,5-7H2,1,3H3/t11-,12-,14-,15+/m1/s1
• InChI Key: QGERVCWHOOSNLS-GBOPCIDUSA-N
• Popularity: 2 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): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 4
• 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	+	0.9948	99.48%
Caco-2	+	0.6467	64.67%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6975	69.75%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8847	88.47%
OATP1B3 inhibitior	+	0.9014	90.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9620	96.20%
P-glycoprotein inhibitior	-	0.9450	94.50%
P-glycoprotein substrate	-	0.8145	81.45%
CYP3A4 substrate	+	0.5781	57.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9102	91.02%
CYP3A4 inhibition	+	0.5259	52.59%
CYP2C9 inhibition	-	0.9279	92.79%
CYP2C19 inhibition	-	0.9285	92.85%
CYP2D6 inhibition	-	0.9543	95.43%
CYP1A2 inhibition	-	0.8397	83.97%
CYP2C8 inhibition	-	0.8525	85.25%
CYP inhibitory promiscuity	-	0.9310	93.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5063	50.63%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.7888	78.88%
Skin irritation	+	0.5267	52.67%
Skin corrosion	-	0.8589	85.89%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6424	64.24%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6224	62.24%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5874	58.74%
Acute Oral Toxicity (c)	III	0.5408	54.08%
Estrogen receptor binding	+	0.5443	54.43%
Androgen receptor binding	+	0.5588	55.88%
Thyroid receptor binding	-	0.5751	57.51%
Glucocorticoid receptor binding	+	0.5468	54.68%
Aromatase binding	-	0.5703	57.03%
PPAR gamma	-	0.6316	63.16%
Honey bee toxicity	-	0.8602	86.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9959	99.59%

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	95.97%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.64%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.52%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.71%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.79%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.76%	99.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.73%	83.57%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.47%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.38%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.16%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.69%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.26%	96.09%

Plants that contains it

• Greenmaniella resinosa

Cross-Links

• PubChem: 162864296
• LOTUS: LTS0162906
• wikiData: Q105219988