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

Details

• Internal ID: 65a6dc4d-6914-4a0c-a663-245a3e59205c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,8R,10E,11aR)-8-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
• InChI: InChI=1S/C22H28O8/c1-12-7-17(28-15(4)25)8-13(2)10-19(30-22(27)16(11-24)5-6-23)20-14(3)21(26)29-18(20)9-12/h5,8-9,17-20,23-24H,3,6-7,10-11H2,1-2,4H3/b12-9+,13-8+,16-5+/t17-,18-,19-,20+/m1/s1
• InChI Key: DLSZRADAIUXWLF-OCEDBXPTSA-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: 0.60
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9221	92.21%
Caco-2	-	0.6557	65.57%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6907	69.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8845	88.45%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7272	72.72%
P-glycoprotein inhibitior	-	0.4481	44.81%
P-glycoprotein substrate	-	0.6613	66.13%
CYP3A4 substrate	+	0.6352	63.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.5156	51.56%
CYP2C9 inhibition	-	0.8403	84.03%
CYP2C19 inhibition	-	0.7806	78.06%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.6545	65.45%
CYP2C8 inhibition	-	0.6875	68.75%
CYP inhibitory promiscuity	-	0.8254	82.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5914	59.14%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.6707	67.07%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6279	62.79%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8295	82.95%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7550	75.50%
Acute Oral Toxicity (c)	III	0.4856	48.56%
Estrogen receptor binding	+	0.6699	66.99%
Androgen receptor binding	+	0.5695	56.95%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7438	74.38%
Aromatase binding	+	0.5588	55.88%
PPAR gamma	+	0.5619	56.19%
Honey bee toxicity	-	0.7085	70.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9778	97.78%

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	96.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.10%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.77%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.02%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.65%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.15%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.13%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.63%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.97%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.76%	97.09%

Plants that contains it

• Chaenactis douglasii

Cross-Links

• PubChem: 163039376
• LOTUS: LTS0001271
• wikiData: Q104984689