[(1R,3R,4R,6S,8E,11S)-9-(acetyloxymethyl)-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-8-en-4-yl]methyl 3-methylbutanoate

Details

• Internal ID: 7cdce721-9f24-467e-9604-e9af7ef8af31
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,3R,4R,6S,8E,11S)-9-(acetyloxymethyl)-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-8-en-4-yl]methyl 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OCC12C(O1)CC=C(CC3C(CC2O)C(=C)C(=O)O3)COC(=O)C
• SMILES (Isomeric): CC(C)CC(=O)OC[C@@]12[C@@H](O1)C/C=C(\C[C@H]3[C@H](C[C@H]2O)C(=C)C(=O)O3)/COC(=O)C
• InChI: InChI=1S/C22H30O8/c1-12(2)7-20(25)28-11-22-18(24)9-16-13(3)21(26)29-17(16)8-15(10-27-14(4)23)5-6-19(22)30-22/h5,12,16-19,24H,3,6-11H2,1-2,4H3/b15-5+/t16-,17+,18-,19+,22-/m1/s1
• InChI Key: ALKJEOWDCFQCTJ-DGRDYZOHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19406791 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9710	97.10%
Caco-2	-	0.6882	68.82%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7313	73.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8120	81.20%
OATP1B3 inhibitior	+	0.9270	92.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5964	59.64%
P-glycoprotein inhibitior	-	0.4947	49.47%
P-glycoprotein substrate	+	0.5161	51.61%
CYP3A4 substrate	+	0.6711	67.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.7450	74.50%
CYP2C9 inhibition	-	0.7044	70.44%
CYP2C19 inhibition	-	0.7801	78.01%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.8150	81.50%
CYP2C8 inhibition	+	0.5424	54.24%
CYP inhibitory promiscuity	-	0.9415	94.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5499	54.99%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.8711	87.11%
Skin irritation	-	0.6396	63.96%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6732	67.32%
skin sensitisation	-	0.7729	77.29%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8405	84.05%
Acute Oral Toxicity (c)	I	0.3788	37.88%
Estrogen receptor binding	+	0.8363	83.63%
Androgen receptor binding	+	0.6141	61.41%
Thyroid receptor binding	-	0.5088	50.88%
Glucocorticoid receptor binding	+	0.8250	82.50%
Aromatase binding	+	0.7036	70.36%
PPAR gamma	+	0.5427	54.27%
Honey bee toxicity	-	0.6794	67.94%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9884	98.84%

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	97.93%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	96.32%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	95.99%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.48%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.38%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.81%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.78%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.32%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.20%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.14%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.41%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.88%	99.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.58%	95.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.12%	83.10%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.96%	96.61%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.67%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	81.61%	91.49%
CHEMBL5028	O14672	ADAM10	81.24%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.20%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.84%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%

Plants that contains it

• Mikania thapsoides

Cross-Links

• PubChem: 10862750
• LOTUS: LTS0005806
• wikiData: Q104914175