[(E)-2-[[(1R,2R,4R,6R,8S,9Z,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl]oxycarbonyl]but-2-enyl] (E)-2-(acetyloxymethyl)-4-hydroxybut-2-enoate

Details

• Internal ID: 2e6100d5-627b-4e83-bed9-415884f3d5d5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(E)-2-[[(1R,2R,4R,6R,8S,9Z,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl]oxycarbonyl]but-2-enyl] (E)-2-(acetyloxymethyl)-4-hydroxybut-2-enoate
• SMILES (Canonical): CC=C(COC(=O)C(=CCO)COC(=O)C)C(=O)OC1CC2(C(O2)CC(C(=CC3C1C(=C)C(=O)O3)C)O)C
• SMILES (Isomeric): C/C=C(\COC(=O)/C(=C/CO)/COC(=O)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)/C)O)C
• InChI: InChI=1S/C27H34O11/c1-6-17(12-35-25(32)18(7-8-28)13-34-16(4)29)26(33)37-21-11-27(5)22(38-27)10-19(30)14(2)9-20-23(21)15(3)24(31)36-20/h6-7,9,19-23,28,30H,3,8,10-13H2,1-2,4-5H3/b14-9-,17-6+,18-7+/t19-,20+,21+,22+,23-,27+/m0/s1
• InChI Key: RKZPYMCRHSHNPN-PMCIHPDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₁
• Molecular Weight: 534.60 g/mol
• Exact Mass: 534.21011190 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9404	94.04%
Caco-2	-	0.8071	80.71%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6193	61.93%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.8591	85.91%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9026	90.26%
P-glycoprotein inhibitior	+	0.7519	75.19%
P-glycoprotein substrate	+	0.6027	60.27%
CYP3A4 substrate	+	0.7009	70.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8957	89.57%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8330	83.30%
CYP2C19 inhibition	-	0.8529	85.29%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.7594	75.94%
CYP2C8 inhibition	+	0.5227	52.27%
CYP inhibitory promiscuity	-	0.9289	92.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4936	49.36%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9360	93.60%
Skin irritation	-	0.5850	58.50%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3954	39.54%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5072	50.72%
skin sensitisation	-	0.8265	82.65%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6121	61.21%
Acute Oral Toxicity (c)	III	0.3614	36.14%
Estrogen receptor binding	+	0.7438	74.38%
Androgen receptor binding	+	0.6522	65.22%
Thyroid receptor binding	-	0.5258	52.58%
Glucocorticoid receptor binding	+	0.7791	77.91%
Aromatase binding	+	0.6334	63.34%
PPAR gamma	+	0.5632	56.32%
Honey bee toxicity	-	0.6245	62.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9773	97.73%

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	97.74%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.73%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.08%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.33%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.98%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	88.26%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.52%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.69%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.64%	97.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.30%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.22%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.99%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.66%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.50%	94.62%
CHEMBL1951	P21397	Monoamine oxidase A	81.68%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.38%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.27%	95.89%

Plants that contains it

• Mikania haenkeana

Cross-Links

• PubChem: 162924026
• LOTUS: LTS0239148
• wikiData: Q105239670