4a,8-dihydroxy-3,5,8a-trimethyl-3a,4,5,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: f3d2fd68-1c38-44fe-bc69-9a6d08eaa488
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 4a,8-dihydroxy-3,5,8a-trimethyl-3a,4,5,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCC(C2(C1(CC3C(C(=O)OC3C2)C)O)C)O
• SMILES (Isomeric): CC1CCC(C2(C1(CC3C(C(=O)OC3C2)C)O)C)O
• InChI: InChI=1S/C15H24O4/c1-8-4-5-12(16)14(3)7-11-10(6-15(8,14)18)9(2)13(17)19-11/h8-12,16,18H,4-7H2,1-3H3
• InChI Key: NXVLBVXAFDLCSI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.49
• 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	+	0.9633	96.33%
Caco-2	+	0.5060	50.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6097	60.97%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.9401	94.01%
OATP1B3 inhibitior	+	0.9169	91.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.9119	91.19%
P-glycoprotein inhibitior	-	0.9209	92.09%
P-glycoprotein substrate	-	0.7298	72.98%
CYP3A4 substrate	+	0.6006	60.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8405	84.05%
CYP3A4 inhibition	-	0.6564	65.64%
CYP2C9 inhibition	-	0.8681	86.81%
CYP2C19 inhibition	-	0.9089	90.89%
CYP2D6 inhibition	-	0.9676	96.76%
CYP1A2 inhibition	-	0.7350	73.50%
CYP2C8 inhibition	-	0.9400	94.00%
CYP inhibitory promiscuity	-	0.9584	95.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6130	61.30%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9773	97.73%
Skin irritation	+	0.6177	61.77%
Skin corrosion	-	0.8601	86.01%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6438	64.38%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.6524	65.24%
skin sensitisation	-	0.8707	87.07%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7599	75.99%
Acute Oral Toxicity (c)	I	0.3832	38.32%
Estrogen receptor binding	+	0.7396	73.96%
Androgen receptor binding	-	0.5066	50.66%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.7065	70.65%
Aromatase binding	+	0.5624	56.24%
PPAR gamma	-	0.5407	54.07%
Honey bee toxicity	-	0.8988	89.88%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9596	95.96%

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	93.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.58%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.70%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.22%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.80%	85.14%
CHEMBL1871	P10275	Androgen Receptor	85.31%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.58%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.13%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.71%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.05%	92.94%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 75581808
• LOTUS: LTS0159027
• wikiData: Q105187344