[(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] (2S,3S)-2,3-dihydroxy-2-methylbutanoate

Details

• Internal ID: c3b802cc-6861-4f1a-9fea-793ca2c2c9cc
• 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] (2S,3S)-2,3-dihydroxy-2-methylbutanoate
• InChI: InChI=1S/C20H28O7/c1-10-6-14(22)7-11(2)9-16(27-19(24)20(5,25)13(4)21)17-12(3)18(23)26-15(17)8-10/h7-8,13-17,21-22,25H,3,6,9H2,1-2,4-5H3/b10-8+,11-7+/t13-,14+,15+,16+,17-,20-/m0/s1
• InChI Key: ZHUKVZKTDPGGMP-GUFDMYATSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9277	92.77%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5580	55.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8681	86.81%
OATP1B3 inhibitior	+	0.8986	89.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6662	66.62%
P-glycoprotein inhibitior	-	0.5969	59.69%
P-glycoprotein substrate	-	0.6781	67.81%
CYP3A4 substrate	+	0.6102	61.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.6885	68.85%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.7988	79.88%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.7011	70.11%
CYP2C8 inhibition	-	0.7754	77.54%
CYP inhibitory promiscuity	-	0.9505	95.05%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4768	47.68%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9342	93.42%
Skin irritation	-	0.5626	56.26%
Skin corrosion	-	0.9122	91.22%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4204	42.04%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7481	74.81%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6076	60.76%
Acute Oral Toxicity (c)	III	0.3205	32.05%
Estrogen receptor binding	+	0.6540	65.40%
Androgen receptor binding	-	0.5125	51.25%
Thyroid receptor binding	+	0.5714	57.14%
Glucocorticoid receptor binding	+	0.7272	72.72%
Aromatase binding	+	0.5682	56.82%
PPAR gamma	+	0.5411	54.11%
Honey bee toxicity	-	0.7350	73.50%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9621	96.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.09%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.23%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.27%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.11%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.95%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	90.20%	97.79%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.19%	97.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.25%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.93%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	87.61%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.87%	97.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.70%	90.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.58%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.47%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.06%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.58%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.39%	94.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%
CHEMBL5028	O14672	ADAM10	80.17%	97.50%

Plants that contains it

• Eupatorium chinense

Cross-Links

• PubChem: 163087830
• LOTUS: LTS0274049
• wikiData: Q105376019