[(1S,1'S,3aR,4S,6'S,7R,7'R,7aS,9'S)-1,7'-dihydroxy-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: eded9748-a57a-4f79-b3a1-787077215396
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,1'S,3aR,4S,6'S,7R,7'R,7aS,9'S)-1,7'-dihydroxy-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)C34C2C(CC(C3)C(=C)C4=O)O)C5C1(COC5O)C
• SMILES (Isomeric): CC(=O)O[C@H]1CC[C@]2(COC(=O)[C@]34[C@H]2[C@@H](C[C@H](C3)C(=C)C4=O)O)[C@H]5[C@@]1(CO[C@@H]5O)C
• InChI: InChI=1S/C22H28O8/c1-10-12-6-13(24)15-21(9-29-19(27)22(15,7-12)17(10)25)5-4-14(30-11(2)23)20(3)8-28-18(26)16(20)21/h12-16,18,24,26H,1,4-9H2,2-3H3/t12-,13-,14+,15+,16-,18+,20-,21-,22+/m1/s1
• InChI Key: SEHPAYZBNFCEKJ-WCFVHXTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.17841785 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.74
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9541	95.41%
Caco-2	-	0.6044	60.44%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8101	81.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8275	82.75%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7120	71.20%
BSEP inhibitior	-	0.6089	60.89%
P-glycoprotein inhibitior	-	0.6026	60.26%
P-glycoprotein substrate	-	0.5986	59.86%
CYP3A4 substrate	+	0.7027	70.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.7848	78.48%
CYP2C9 inhibition	-	0.8776	87.76%
CYP2C19 inhibition	-	0.8969	89.69%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.8496	84.96%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9535	95.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5525	55.25%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.5497	54.97%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4853	48.53%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8650	86.50%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7463	74.63%
Acute Oral Toxicity (c)	I	0.5075	50.75%
Estrogen receptor binding	+	0.8470	84.70%
Androgen receptor binding	+	0.6867	68.67%
Thyroid receptor binding	-	0.5130	51.30%
Glucocorticoid receptor binding	+	0.7804	78.04%
Aromatase binding	+	0.7146	71.46%
PPAR gamma	+	0.5184	51.84%
Honey bee toxicity	-	0.7457	74.57%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	96.44%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.72%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.46%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.84%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.64%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.00%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.69%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.25%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.14%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.69%	98.95%
CHEMBL1871	P10275	Androgen Receptor	85.91%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.79%	97.25%
CHEMBL259	P32245	Melanocortin receptor 4	84.81%	95.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.11%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.01%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.68%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.03%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.94%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.00%	92.50%
CHEMBL5028	O14672	ADAM10	80.89%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.52%	92.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.11%	97.28%

Plants that contains it

• Isodon trichocarpus

Cross-Links

• PubChem: 162973796
• LOTUS: LTS0006186
• wikiData: Q105251173