[(3aR,4R,6Z,10Z,11aR)-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 77d58655-d2fe-4eb0-8bac-4fbb6ffe2350
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6Z,10Z,11aR)-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CC(=CCCC(=CC3C2C(=C)C(=O)O3)C)COC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@](O1)(C)C(=O)O[C@@H]2C/C(=C/CC/C(=C\[C@@H]3[C@@H]2C(=C)C(=O)O3)/C)/COC(=O)C
• InChI: InChI=1S/C22H28O7/c1-12-7-6-8-16(11-26-15(4)23)10-18(28-21(25)22(5)14(3)29-22)19-13(2)20(24)27-17(19)9-12/h8-9,14,17-19H,2,6-7,10-11H2,1,3-5H3/b12-9-,16-8-/t14-,17-,18-,19+,22-/m1/s1
• InChI Key: LEXWUGMNKNPDEI-XKXNFZFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.18350323 g/mol
• Topological Polar Surface Area (TPSA): 91.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.5498	54.98%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7402	74.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8740	87.40%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7063	70.63%
P-glycoprotein inhibitior	+	0.6991	69.91%
P-glycoprotein substrate	-	0.5948	59.48%
CYP3A4 substrate	+	0.6966	69.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8860	88.60%
CYP3A4 inhibition	-	0.8036	80.36%
CYP2C9 inhibition	-	0.8124	81.24%
CYP2C19 inhibition	-	0.8720	87.20%
CYP2D6 inhibition	-	0.9292	92.92%
CYP1A2 inhibition	-	0.6034	60.34%
CYP2C8 inhibition	+	0.4765	47.65%
CYP inhibitory promiscuity	-	0.8959	89.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5700	57.00%
Eye corrosion	-	0.9725	97.25%
Eye irritation	-	0.8957	89.57%
Skin irritation	-	0.5829	58.29%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7352	73.52%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5073	50.73%
skin sensitisation	-	0.7710	77.10%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5906	59.06%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.6972	69.72%
Androgen receptor binding	+	0.5988	59.88%
Thyroid receptor binding	+	0.6042	60.42%
Glucocorticoid receptor binding	+	0.8586	85.86%
Aromatase binding	+	0.6470	64.70%
PPAR gamma	+	0.5513	55.13%
Honey bee toxicity	-	0.6587	65.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9894	98.94%

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	98.31%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.14%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.59%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.97%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.75%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.32%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.78%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	89.60%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.77%	85.14%
CHEMBL4208	P20618	Proteasome component C5	87.35%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.94%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.40%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.94%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.18%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.14%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.80%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.54%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.65%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.59%	97.33%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.49%	96.39%

Plants that contains it

• Aldama robusta

Cross-Links

• PubChem: 162989534
• LOTUS: LTS0032584
• wikiData: Q105150875