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

Details

• Internal ID: 98ce500e-689e-48e5-8a6c-9b2e96e251fd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,5R,6E,8S,10E,11aR)-4,8-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-5-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H26O6/c1-6-11(3)19(23)26-18-12(4)9-14(21)7-10(2)8-15-16(17(18)22)13(5)20(24)25-15/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: GXJIVHRXEGIYKR-MMUAQWFJSA-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	+	0.6121	61.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5157	51.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8736	87.36%
OATP1B3 inhibitior	+	0.9090	90.90%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5143	51.43%
P-glycoprotein inhibitior	-	0.5634	56.34%
P-glycoprotein substrate	-	0.7211	72.11%
CYP3A4 substrate	+	0.6170	61.70%
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	-	0.7638	76.38%
CYP inhibitory promiscuity	-	0.9280	92.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4415	44.15%
Eye corrosion	-	0.9621	96.21%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5360	53.60%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7155	71.55%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6181	61.81%
Acute Oral Toxicity (c)	III	0.3445	34.45%
Estrogen receptor binding	+	0.5766	57.66%
Androgen receptor binding	-	0.6106	61.06%
Thyroid receptor binding	-	0.5655	56.55%
Glucocorticoid receptor binding	+	0.5480	54.80%
Aromatase binding	-	0.6560	65.60%
PPAR gamma	+	0.5442	54.42%
Honey bee toxicity	-	0.6643	66.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
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	94.87%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.01%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.74%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.50%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.49%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.86%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.07%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.57%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.37%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.04%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	82.32%	90.17%

Plants that contains it

• Balsamorhiza sagittata

Cross-Links

• PubChem: 163032679
• LOTUS: LTS0004597
• wikiData: Q105023095