[(1S,2R,4S,6R,8S,9R,11R)-8,9-dihydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradecan-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: d5923b19-f3b7-421c-9d1d-b0440dd25cdc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1S,2R,4S,6R,8S,9R,11R)-8,9-dihydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradecan-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2(C(O2)CC(C(CC3C1C(=C)C(=O)O3)(CO)O)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C[C@]2([C@H](O2)C[C@@H]([C@@](C[C@@H]3[C@@H]1C(=C)C(=O)O3)(CO)O)O)C
• InChI: InChI=1S/C20H28O8/c1-5-10(2)17(23)26-12-7-19(4)15(28-19)6-14(22)20(25,9-21)8-13-16(12)11(3)18(24)27-13/h5,12-16,21-22,25H,3,6-9H2,1-2,4H3/b10-5-/t12-,13-,14+,15-,16-,19+,20-/m1/s1
• InChI Key: AQWYQKBXSZYHMI-DDMMOONKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₈
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.17841785 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 8
• 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	+	0.8719	87.19%
Caco-2	-	0.6398	63.98%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6283	62.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8993	89.93%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6060	60.60%
P-glycoprotein inhibitior	-	0.6974	69.74%
P-glycoprotein substrate	-	0.5611	56.11%
CYP3A4 substrate	+	0.6854	68.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8806	88.06%
CYP3A4 inhibition	-	0.5359	53.59%
CYP2C9 inhibition	-	0.7636	76.36%
CYP2C19 inhibition	-	0.8601	86.01%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.8017	80.17%
CYP2C8 inhibition	-	0.6726	67.26%
CYP inhibitory promiscuity	-	0.9514	95.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5945	59.45%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9435	94.35%
Skin irritation	-	0.5879	58.79%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6690	66.90%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.8455	84.55%
Acute Oral Toxicity (c)	III	0.4191	41.91%
Estrogen receptor binding	+	0.8008	80.08%
Androgen receptor binding	+	0.6019	60.19%
Thyroid receptor binding	+	0.5895	58.95%
Glucocorticoid receptor binding	+	0.7964	79.64%
Aromatase binding	+	0.6029	60.29%
PPAR gamma	+	0.5595	55.95%
Honey bee toxicity	-	0.5865	58.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9776	97.76%

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	98.09%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.94%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.80%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.88%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.11%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.89%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.10%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.71%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.49%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.75%	91.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.56%	97.21%
CHEMBL2996	Q05655	Protein kinase C delta	85.49%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.45%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.07%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.95%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.86%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.52%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.76%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.55%	94.00%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 163029075
• LOTUS: LTS0015833
• wikiData: Q104917139