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

Details

• Internal ID: 7da97f9a-1464-4077-8f61-8a2e0bcdba8d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,5R,6Z,8S,10Z,11aR)-5,8-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H26O6/c1-6-11(3)19(23)26-18-16-13(5)20(24)25-15(16)8-10(2)7-14(21)9-12(4)17(18)22/h6,8-9,14-18,21-22H,5,7H2,1-4H3/b10-8-,11-6+,12-9-/t14-,15+,16+,17+,18+/m0/s1
• InChI Key: YAXKSMGYDCTPBJ-ORNCTXMDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.5681	56.81%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5157	51.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8533	85.33%
OATP1B3 inhibitior	+	0.9090	90.90%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4937	49.37%
P-glycoprotein inhibitior	-	0.5294	52.94%
P-glycoprotein substrate	-	0.7391	73.91%
CYP3A4 substrate	+	0.5956	59.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.7323	73.23%
CYP2C9 inhibition	-	0.9051	90.51%
CYP2C19 inhibition	-	0.8633	86.33%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.7616	76.16%
CYP2C8 inhibition	-	0.8169	81.69%
CYP inhibitory promiscuity	-	0.9280	92.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4415	44.15%
Eye corrosion	-	0.9621	96.21%
Eye irritation	-	0.8888	88.88%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5607	56.07%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.6051	60.51%
skin sensitisation	-	0.7155	71.55%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5929	59.29%
Acute Oral Toxicity (c)	III	0.3445	34.45%
Estrogen receptor binding	+	0.5463	54.63%
Androgen receptor binding	-	0.6113	61.13%
Thyroid receptor binding	+	0.5311	53.11%
Glucocorticoid receptor binding	+	0.5837	58.37%
Aromatase binding	-	0.6048	60.48%
PPAR gamma	-	0.4929	49.29%
Honey bee toxicity	-	0.6544	65.44%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9213	92.13%

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	92.36%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.92%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.80%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.57%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.33%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.56%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.75%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.33%	93.03%
CHEMBL4040	P28482	MAP kinase ERK2	84.05%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.71%	96.09%
CHEMBL2581	P07339	Cathepsin D	81.49%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.44%	95.89%

Plants that contains it

• Montanoa frutescens

Cross-Links

• PubChem: 163006549
• LOTUS: LTS0271228
• wikiData: Q105345656