(8-Acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl) 2-methylbut-2-enoate

Details

• Internal ID: 6825dae8-66fb-40dc-a94d-53b471cd7f8e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (8-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CC(CC(=CC2C1C(=C)C(=O)O2)C)OC(=O)C)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CC(=CC(CC(=CC2C1C(=C)C(=O)O2)C)OC(=O)C)C
• InChI: InChI=1S/C22H28O6/c1-7-14(4)21(24)27-18-10-12(2)8-17(26-16(6)23)9-13(3)11-19-20(18)15(5)22(25)28-19/h7-8,11,17-20H,5,9-10H2,1-4,6H3
• InChI Key: IICUPNNWEALZTN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.18858861 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	+	0.6005	60.05%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5334	53.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8769	87.69%
OATP1B3 inhibitior	+	0.8627	86.27%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8704	87.04%
P-glycoprotein inhibitior	+	0.7446	74.46%
P-glycoprotein substrate	-	0.7823	78.23%
CYP3A4 substrate	+	0.6085	60.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.7694	76.94%
CYP2C9 inhibition	-	0.8777	87.77%
CYP2C19 inhibition	-	0.7808	78.08%
CYP2D6 inhibition	-	0.9647	96.47%
CYP1A2 inhibition	-	0.5752	57.52%
CYP2C8 inhibition	-	0.7574	75.74%
CYP inhibitory promiscuity	-	0.8325	83.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.5559	55.59%
Eye corrosion	-	0.9229	92.29%
Eye irritation	-	0.8752	87.52%
Skin irritation	-	0.6611	66.11%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3634	36.34%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6428	64.28%
skin sensitisation	-	0.6214	62.14%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8161	81.61%
Acute Oral Toxicity (c)	III	0.4216	42.16%
Estrogen receptor binding	+	0.6074	60.74%
Androgen receptor binding	+	0.5197	51.97%
Thyroid receptor binding	+	0.5577	55.77%
Glucocorticoid receptor binding	+	0.7617	76.17%
Aromatase binding	+	0.5326	53.26%
PPAR gamma	-	0.5055	50.55%
Honey bee toxicity	-	0.6467	64.67%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9838	98.38%

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	95.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.30%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.64%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.69%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.55%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.09%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.11%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	84.07%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.95%	95.50%

Plants that contains it

• Eupatorium chinense

Cross-Links

• PubChem: 162856409
• LOTUS: LTS0068382
• wikiData: Q105113411