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

Details

• Internal ID: ff17357e-db98-4e6f-8e45-10a1f47467ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 7-hydroxy-3,8a-dimethyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3C(=C)CC(CC3(CC2OC1=O)C)O
• SMILES (Isomeric): CC1C2CC3C(=C)CC(CC3(CC2OC1=O)C)O
• InChI: InChI=1S/C15H22O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h9-13,16H,1,4-7H2,2-3H3
• InChI Key: FPEGOJNBPHXMRU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.29
• 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	+	0.9960	99.60%
Caco-2	+	0.7211	72.11%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5969	59.69%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.8728	87.28%
OATP1B3 inhibitior	+	0.9252	92.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9240	92.40%
P-glycoprotein inhibitior	-	0.9085	90.85%
P-glycoprotein substrate	-	0.7316	73.16%
CYP3A4 substrate	+	0.6022	60.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	+	0.5308	53.08%
CYP2C9 inhibition	-	0.9276	92.76%
CYP2C19 inhibition	-	0.7422	74.22%
CYP2D6 inhibition	-	0.9533	95.33%
CYP1A2 inhibition	-	0.6941	69.41%
CYP2C8 inhibition	-	0.9312	93.12%
CYP inhibitory promiscuity	-	0.8496	84.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4898	48.98%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8066	80.66%
Skin irritation	+	0.5600	56.00%
Skin corrosion	-	0.9134	91.34%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7021	70.21%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.5968	59.68%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.7185	71.85%
Acute Oral Toxicity (c)	III	0.5649	56.49%
Estrogen receptor binding	+	0.6855	68.55%
Androgen receptor binding	+	0.6054	60.54%
Thyroid receptor binding	+	0.5894	58.94%
Glucocorticoid receptor binding	+	0.7153	71.53%
Aromatase binding	-	0.5459	54.59%
PPAR gamma	-	0.6810	68.10%
Honey bee toxicity	-	0.7174	71.74%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6113	61.13%
Fish aquatic toxicity	+	0.9960	99.60%

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	95.67%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.38%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.21%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	88.88%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.70%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.45%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.03%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.71%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.79%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.71%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.89%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.73%	100.00%

Plants that contains it

• Carpesium macrocephalum
• Dittrichia graveolens

Cross-Links

• PubChem: 13944073
• LOTUS: LTS0117593
• wikiData: Q104999126