(3aR,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 0a995aed-8baf-49ba-86ae-58c71ddcac14
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC12CC(CC(=C)C1=CC3C(C2)OC(=O)C3=C)O
• SMILES (Isomeric): C[C@]12C[C@H](CC(=C)C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)O
• InChI: InChI=1S/C15H18O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,10-11,13,16H,1-2,4,6-7H2,3H3/t10-,11+,13+,15+/m0/s1
• InChI Key: RTCBEIZCBZSCEH-FMVNMVDZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.13
• 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	+	0.9958	99.58%
Caco-2	+	0.6956	69.56%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8349	83.49%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9692	96.92%
P-glycoprotein inhibitior	-	0.8995	89.95%
P-glycoprotein substrate	-	0.7952	79.52%
CYP3A4 substrate	+	0.5716	57.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.6776	67.76%
CYP2C9 inhibition	-	0.8593	85.93%
CYP2C19 inhibition	-	0.6708	67.08%
CYP2D6 inhibition	-	0.9419	94.19%
CYP1A2 inhibition	-	0.6540	65.40%
CYP2C8 inhibition	-	0.8194	81.94%
CYP inhibitory promiscuity	-	0.8060	80.60%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.3832	38.32%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.6687	66.87%
Skin irritation	+	0.4930	49.30%
Skin corrosion	-	0.8918	89.18%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6911	69.11%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7869	78.69%
skin sensitisation	-	0.5818	58.18%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.8227	82.27%
Acute Oral Toxicity (c)	III	0.5580	55.80%
Estrogen receptor binding	+	0.6694	66.94%
Androgen receptor binding	-	0.5877	58.77%
Thyroid receptor binding	+	0.5291	52.91%
Glucocorticoid receptor binding	+	0.6633	66.33%
Aromatase binding	+	0.6633	66.33%
PPAR gamma	+	0.5568	55.68%
Honey bee toxicity	-	0.8147	81.47%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9796	97.96%

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	93.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.04%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.89%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.70%	85.14%
CHEMBL2581	P07339	Cathepsin D	83.29%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.07%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.50%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.19%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.90%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.64%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.29%	95.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 57345670
• LOTUS: LTS0088652
• wikiData: Q105245052