[(3aR,4R,6E,8R,10E,11aR)-8-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-[(1S)-1-hydroxyethyl]oxirane-2-carboxylate

Details

• Internal ID: e22bb647-6618-4840-b884-4e4f2c232d49
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,8R,10E,11aR)-8-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-[(1S)-1-hydroxyethyl]oxirane-2-carboxylate
• InChI: InChI=1S/C20H26O7/c1-10-5-14(22)6-11(2)8-16(17-12(3)18(23)26-15(17)7-10)27-19(24)20(9-25-20)13(4)21/h6-7,13-17,21-22H,3,5,8-9H2,1-2,4H3/b10-7+,11-6+/t13-,14+,15+,16+,17-,20+/m0/s1
• InChI Key: TUBACTXYHYQVHV-WCQDJYQJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	-	0.5612	56.12%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6294	62.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	+	0.8921	89.21%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9364	93.64%
BSEP inhibitior	-	0.7060	70.60%
P-glycoprotein inhibitior	-	0.5497	54.97%
P-glycoprotein substrate	-	0.6894	68.94%
CYP3A4 substrate	+	0.6078	60.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8499	84.99%
CYP3A4 inhibition	-	0.6582	65.82%
CYP2C9 inhibition	-	0.7927	79.27%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.7573	75.73%
CYP2C8 inhibition	-	0.8261	82.61%
CYP inhibitory promiscuity	-	0.9504	95.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5379	53.79%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.5981	59.81%
Skin corrosion	-	0.9241	92.41%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3882	38.82%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5034	50.34%
skin sensitisation	-	0.8164	81.64%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6498	64.98%
Acute Oral Toxicity (c)	III	0.3380	33.80%
Estrogen receptor binding	+	0.6994	69.94%
Androgen receptor binding	+	0.5886	58.86%
Thyroid receptor binding	+	0.5703	57.03%
Glucocorticoid receptor binding	+	0.7789	77.89%
Aromatase binding	+	0.5496	54.96%
PPAR gamma	+	0.6042	60.42%
Honey bee toxicity	-	0.6795	67.95%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9720	97.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.58%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.31%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.73%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.50%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.33%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.81%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.66%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.77%	96.47%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.21%	93.03%
CHEMBL221	P23219	Cyclooxygenase-1	85.66%	90.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.35%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.39%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.54%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.07%	95.89%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.63%	94.08%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.33%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.05%	97.25%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.59%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.34%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.30%	86.33%

Plants that contains it

• Helianthus resinosus

Cross-Links

• PubChem: 163045816
• LOTUS: LTS0259134
• wikiData: Q105264653