3a-Hydroxy-5,8a-dimethyl-3-methylidene-4,4a,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: ee9441ce-0fbe-4444-aeda-684b5cf29d09
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 3a-hydroxy-5,8a-dimethyl-3-methylidene-4,4a,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCCC2(C1CC3(C(C2)OC(=O)C3=C)O)C
• SMILES (Isomeric): CC1=CCCC2(C1CC3(C(C2)OC(=O)C3=C)O)C
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-12-15(17,7-11(9)14)10(2)13(16)18-12/h5,11-12,17H,2,4,6-8H2,1,3H3
• InChI Key: AHJCRWCLIOTZDF-UHFFFAOYSA-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: 2.10
• 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	+	0.9967	99.67%
Caco-2	+	0.7934	79.34%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6414	64.14%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9318	93.18%
OATP1B3 inhibitior	+	0.9105	91.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5651	56.51%
BSEP inhibitior	-	0.9525	95.25%
P-glycoprotein inhibitior	-	0.9332	93.32%
P-glycoprotein substrate	-	0.8802	88.02%
CYP3A4 substrate	+	0.5693	56.93%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.5572	55.72%
CYP2C9 inhibition	-	0.9192	91.92%
CYP2C19 inhibition	-	0.7890	78.90%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.5944	59.44%
CYP2C8 inhibition	-	0.8572	85.72%
CYP inhibitory promiscuity	-	0.9451	94.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4888	48.88%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.6130	61.30%
Skin irritation	+	0.5822	58.22%
Skin corrosion	-	0.8921	89.21%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5230	52.30%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6557	65.57%
skin sensitisation	-	0.7124	71.24%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6162	61.62%
Acute Oral Toxicity (c)	IV	0.4711	47.11%
Estrogen receptor binding	-	0.5816	58.16%
Androgen receptor binding	-	0.6527	65.27%
Thyroid receptor binding	-	0.5382	53.82%
Glucocorticoid receptor binding	+	0.6037	60.37%
Aromatase binding	-	0.5997	59.97%
PPAR gamma	+	0.5702	57.02%
Honey bee toxicity	-	0.9143	91.43%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.29%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.84%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.38%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.05%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.35%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.08%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.97%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.46%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.07%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.48%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.11%	94.45%

Plants that contains it

• Chiloscyphus polyanthos

Cross-Links

• PubChem: 163049583
• LOTUS: LTS0190252
• wikiData: Q104912271