[4-(Acetyloxymethyl)-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] 2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 8d06e9ea-298f-4da9-b047-fe1141cc5525
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [4-(acetyloxymethyl)-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] 2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CC3(C(O3)CCC(=CC4C2C(=C)C(=O)O4)C)COC(=O)C
• SMILES (Isomeric): CC1C(O1)(C)C(=O)OC2CC3(C(O3)CCC(=CC4C2C(=C)C(=O)O4)C)COC(=O)C
• InChI: InChI=1S/C22H28O8/c1-11-6-7-17-22(30-17,10-26-14(4)23)9-16(28-20(25)21(5)13(3)29-21)18-12(2)19(24)27-15(18)8-11/h8,13,15-18H,2,6-7,9-10H2,1,3-5H3
• InChI Key: FAUMCPFTDXKTHJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.17841785 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 8
• 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	-	0.5423	54.23%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7402	74.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8630	86.30%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.5628	56.28%
P-glycoprotein inhibitior	+	0.6396	63.96%
P-glycoprotein substrate	-	0.5882	58.82%
CYP3A4 substrate	+	0.6869	68.69%
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	+	0.4655	46.55%
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	-	0.8806	88.06%
Skin irritation	-	0.5829	58.29%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4220	42.20%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5270	52.70%
skin sensitisation	-	0.7710	77.10%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6156	61.56%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.8409	84.09%
Androgen receptor binding	+	0.6528	65.28%
Thyroid receptor binding	+	0.6367	63.67%
Glucocorticoid receptor binding	+	0.8593	85.93%
Aromatase binding	+	0.6926	69.26%
PPAR gamma	+	0.6894	68.94%
Honey bee toxicity	-	0.7435	74.35%
Biodegradation	-	0.7750	77.50%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.51%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	94.57%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.90%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.57%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.27%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.00%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.82%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.16%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.99%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.95%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.21%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.82%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	83.59%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.38%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.81%	94.80%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.62%	91.07%
CHEMBL230	P35354	Cyclooxygenase-2	80.75%	89.63%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.66%	98.75%
CHEMBL5028	O14672	ADAM10	80.14%	97.50%

Plants that contains it

• Gonzalezia hypargyrea
• Helianthus tuberosus
• Tithonia rotundifolia

Cross-Links

• PubChem: 162961077
• LOTUS: LTS0254930
• wikiData: Q104992438