(3aR,4aS,8R,8aS,9aR)-4a,8-dihydroxy-8a-methyl-3,5-dimethylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: 95b689f4-8852-4d80-a6bd-0a9a2c4221e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aS,8R,8aS,9aR)-4a,8-dihydroxy-8a-methyl-3,5-dimethylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione
• SMILES (Canonical): CC12CC3C(CC1(C(=C)CC(=O)C2O)O)C(=C)C(=O)O3
• SMILES (Isomeric): C[C@@]12C[C@@H]3[C@H](C[C@@]1(C(=C)CC(=O)[C@@H]2O)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O5/c1-7-4-10(16)12(17)14(3)6-11-9(5-15(7,14)19)8(2)13(18)20-11/h9,11-12,17,19H,1-2,4-6H2,3H3/t9-,11-,12+,14+,15+/m1/s1
• InChI Key: JHZROJQAJIWOAB-FWTMIXAASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 5
• 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	+	0.9735	97.35%
Caco-2	-	0.6683	66.83%
Blood Brain Barrier	+	0.6527	65.27%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6418	64.18%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.9291	92.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9792	97.92%
P-glycoprotein inhibitior	-	0.9373	93.73%
P-glycoprotein substrate	-	0.8275	82.75%
CYP3A4 substrate	+	0.5633	56.33%
CYP2C9 substrate	-	0.7939	79.39%
CYP2D6 substrate	-	0.8850	88.50%
CYP3A4 inhibition	-	0.7871	78.71%
CYP2C9 inhibition	-	0.9096	90.96%
CYP2C19 inhibition	-	0.8887	88.87%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	-	0.8405	84.05%
CYP2C8 inhibition	-	0.8492	84.92%
CYP inhibitory promiscuity	-	0.9297	92.97%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4787	47.87%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8339	83.39%
Skin irritation	+	0.5354	53.54%
Skin corrosion	-	0.8918	89.18%
Ames mutagenesis	-	0.5724	57.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5682	56.82%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7969	79.69%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6784	67.84%
Acute Oral Toxicity (c)	I	0.3546	35.46%
Estrogen receptor binding	+	0.7760	77.60%
Androgen receptor binding	+	0.6065	60.65%
Thyroid receptor binding	-	0.5571	55.71%
Glucocorticoid receptor binding	+	0.7036	70.36%
Aromatase binding	+	0.5343	53.43%
PPAR gamma	-	0.6364	63.64%
Honey bee toxicity	-	0.7730	77.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	95.16%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.67%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.38%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.39%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.95%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.45%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.80%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.68%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	81.68%	90.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.60%	92.94%

Plants that contains it

• Telekia speciosa

Cross-Links

• PubChem: 163041728
• LOTUS: LTS0100317
• wikiData: Q105128841