(4-Hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl) 2-(acetyloxymethyl)but-2-enoate

Details

• Internal ID: a5ca84e3-e6ec-4fac-bb81-75d7decc05a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl) 2-(acetyloxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(COC(=O)C)C(=O)OC1CCC2(CO2)C3C1(CC(C4C3OC(=O)C4=C)O)C
• SMILES (Isomeric): CC=C(COC(=O)C)C(=O)OC1CCC2(CO2)C3C1(CC(C4C3OC(=O)C4=C)O)C
• InChI: InChI=1S/C22H28O8/c1-5-13(9-27-12(3)23)20(26)29-15-6-7-22(10-28-22)18-17-16(11(2)19(25)30-17)14(24)8-21(15,18)4/h5,14-18,24H,2,6-10H2,1,3-4H3
• InChI Key: ICJKWZPWHNFBRJ-UHFFFAOYSA-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): 112.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9793	97.93%
Caco-2	-	0.7233	72.33%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7452	74.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8582	85.82%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5021	50.21%
BSEP inhibitior	+	0.7166	71.66%
P-glycoprotein inhibitior	+	0.6023	60.23%
P-glycoprotein substrate	-	0.5667	56.67%
CYP3A4 substrate	+	0.6886	68.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8932	89.32%
CYP3A4 inhibition	-	0.5604	56.04%
CYP2C9 inhibition	-	0.7823	78.23%
CYP2C19 inhibition	-	0.8582	85.82%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.8118	81.18%
CYP2C8 inhibition	-	0.6310	63.10%
CYP inhibitory promiscuity	-	0.9349	93.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5105	51.05%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9138	91.38%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7368	73.68%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5842	58.42%
skin sensitisation	-	0.8220	82.20%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8520	85.20%
Acute Oral Toxicity (c)	I	0.4680	46.80%
Estrogen receptor binding	+	0.7482	74.82%
Androgen receptor binding	+	0.6656	66.56%
Thyroid receptor binding	-	0.5571	55.71%
Glucocorticoid receptor binding	+	0.8552	85.52%
Aromatase binding	+	0.6442	64.42%
PPAR gamma	+	0.6592	65.92%
Honey bee toxicity	-	0.6989	69.89%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9933	99.33%

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	98.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.32%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.94%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.09%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.22%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.16%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.49%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.23%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.52%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.23%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.15%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.02%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.00%	97.28%
CHEMBL2581	P07339	Cathepsin D	84.05%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.34%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.84%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.71%	91.07%
CHEMBL5028	O14672	ADAM10	81.69%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.05%	92.62%
CHEMBL2996	Q05655	Protein kinase C delta	80.66%	97.79%
CHEMBL226	P30542	Adenosine A1 receptor	80.61%	95.93%

Plants that contains it

• Dimerostemma brasilianum

Cross-Links

• PubChem: 163045381
• LOTUS: LTS0003188
• wikiData: Q105111021