[(3aR,4R,6E,8S,9S,10E,11aR)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-4-acetyloxy-2-methylbut-2-enoate

Details

• Internal ID: 9bfc94ed-cafc-4f43-9ba1-49f7b16991df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,8S,9S,10E,11aR)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-4-acetyloxy-2-methylbut-2-enoate
• InChI: InChI=1S/C22H28O8/c1-11-8-16(24)20(25)13(3)10-18-19(14(4)22(27)30-18)17(9-11)29-21(26)12(2)6-7-28-15(5)23/h6,8,10,16-20,24-25H,4,7,9H2,1-3,5H3/b11-8+,12-6-,13-10+/t16-,17+,18+,19+,20-/m0/s1
• InChI Key: RTTZVQOUFITRBN-FOBGNBPUSA-N
• Popularity: 2 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: 0.70
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9311	93.11%
Caco-2	-	0.7085	70.85%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6537	65.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8768	87.68%
OATP1B3 inhibitior	+	0.9132	91.32%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7341	73.41%
P-glycoprotein inhibitior	+	0.6245	62.45%
P-glycoprotein substrate	-	0.6271	62.71%
CYP3A4 substrate	+	0.6255	62.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8985	89.85%
CYP3A4 inhibition	-	0.8123	81.23%
CYP2C9 inhibition	-	0.7974	79.74%
CYP2C19 inhibition	-	0.7951	79.51%
CYP2D6 inhibition	-	0.9171	91.71%
CYP1A2 inhibition	-	0.6042	60.42%
CYP2C8 inhibition	-	0.6348	63.48%
CYP inhibitory promiscuity	-	0.8949	89.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6299	62.99%
Eye corrosion	-	0.9759	97.59%
Eye irritation	-	0.8923	89.23%
Skin irritation	-	0.6524	65.24%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6549	65.49%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5551	55.51%
skin sensitisation	-	0.8143	81.43%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7868	78.68%
Acute Oral Toxicity (c)	III	0.4511	45.11%
Estrogen receptor binding	+	0.7258	72.58%
Androgen receptor binding	-	0.4889	48.89%
Thyroid receptor binding	-	0.5154	51.54%
Glucocorticoid receptor binding	+	0.6290	62.90%
Aromatase binding	-	0.6340	63.40%
PPAR gamma	-	0.4934	49.34%
Honey bee toxicity	-	0.6811	68.11%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9712	97.12%

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	94.33%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.72%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.44%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.85%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.94%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	87.76%	90.17%
CHEMBL2581	P07339	Cathepsin D	86.68%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.59%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.21%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	83.62%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.31%	100.00%

Plants that contains it

• Eupatorium chinense

Cross-Links

• PubChem: 162911694
• LOTUS: LTS0251951
• wikiData: Q105245401