[(1R,1'S,3aR,4S,6'S,7R,7aS,9'R)-1-acetyloxy-3a-methyl-10'-methylidene-2',11'-dioxospiro[1,3,4,5,6,7a-hexahydro-2-benzofuran-7,5'-3-oxatricyclo[7.2.1.01,6]dodecane]-4-yl] acetate

Details

• Internal ID: e6274a0c-d722-4d07-8104-7e05e35ef6db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,1'S,3aR,4S,6'S,7R,7aS,9'R)-1-acetyloxy-3a-methyl-10'-methylidene-2',11'-dioxospiro[1,3,4,5,6,7a-hexahydro-2-benzofuran-7,5'-3-oxatricyclo[7.2.1.01,6]dodecane]-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1CCC2(COC(=O)C34C2CCC(C3)C(=C)C4=O)C5C1(COC5OC(=O)C)C
• SMILES (Isomeric): CC(=O)O[C@H]1CC[C@]2(COC(=O)[C@]34[C@H]2CC[C@H](C3)C(=C)C4=O)[C@H]5[C@@]1(CO[C@@H]5OC(=O)C)C
• InChI: InChI=1S/C24H30O8/c1-12-15-5-6-16-23(11-30-21(28)24(16,9-15)19(12)27)8-7-17(31-13(2)25)22(4)10-29-20(18(22)23)32-14(3)26/h15-18,20H,1,5-11H2,2-4H3/t15-,16+,17+,18-,20-,22-,23-,24+/m1/s1
• InChI Key: FCLJXTKZNMUCAS-FKBPKVMUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.34
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9747	97.47%
Caco-2	-	0.5556	55.56%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7438	74.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8857	88.57%
OATP1B3 inhibitior	+	0.8825	88.25%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8135	81.35%
P-glycoprotein inhibitior	+	0.6848	68.48%
P-glycoprotein substrate	-	0.6667	66.67%
CYP3A4 substrate	+	0.6826	68.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.7789	77.89%
CYP2C9 inhibition	-	0.8876	88.76%
CYP2C19 inhibition	-	0.8353	83.53%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.6852	68.52%
CYP2C8 inhibition	+	0.5384	53.84%
CYP inhibitory promiscuity	-	0.9039	90.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5852	58.52%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.8833	88.33%
Skin irritation	-	0.5980	59.80%
Skin corrosion	-	0.9109	91.09%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5447	54.47%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5895	58.95%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7779	77.79%
Acute Oral Toxicity (c)	III	0.3763	37.63%
Estrogen receptor binding	+	0.8729	87.29%
Androgen receptor binding	+	0.6607	66.07%
Thyroid receptor binding	+	0.5950	59.50%
Glucocorticoid receptor binding	+	0.8627	86.27%
Aromatase binding	+	0.7447	74.47%
PPAR gamma	+	0.7055	70.55%
Honey bee toxicity	-	0.7689	76.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5750	57.50%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.72%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.24%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.84%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.55%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.47%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.15%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.76%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.44%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.86%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.74%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	84.16%	92.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.79%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.51%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.60%	96.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.69%	92.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.21%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.00%	95.89%

Plants that contains it

• Isodon trichocarpus

Cross-Links

• PubChem: 13314595
• LOTUS: LTS0184510
• wikiData: Q104993206