(3abeta,4R,6abeta,9abeta,9balpha)-3,6,9-Trismethylene-4alpha-(4-hydroxyphenylacetyloxy)-8alpha-(beta-D-glucopyranosyloxy)dodecahydroazuleno[4,5-b]furan-2-one

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	70193f62-e5d9-462f-9443-f6bc2ae5c088
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name	[(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
SMILES (Canonical)	C=C1CC(C2C(C3C1CC(C3=C)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C2=C)OC(=O)CC5=CC=C(C=C5)O
SMILES (Isomeric)	C=C1C[C@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)C2=C)OC(=O)CC5=CC=C(C=C5)O
InChI	InChI=1S/C29H34O11/c1-12-8-19(37-21(32)9-15-4-6-16(31)7-5-15)23-14(3)28(36)40-27(23)22-13(2)18(10-17(12)22)38-29-26(35)25(34)24(33)20(11-30)39-29/h4-7,17-20,22-27,29-31,33-35H,1-3,8-11H2/t17-,18-,19+,20+,22-,23+,24+,25-,26+,27+,29+/m0/s1
InChI Key	GJWZSERDLUJEOD-CLPOWKOCSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₂₉H₃₄O₁₁
Molecular Weight	558.60 g/mol
Exact Mass	558.21011190 g/mol
Topological Polar Surface Area (TPSA)	172.00 Å²
XlogP	0.60
Atomic LogP (AlogP)	0.28
H-Bond Acceptor	11
H-Bond Donor	5
Rotatable Bonds	6

Synonyms

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(3abeta,4R,6abeta,9abeta,9balpha)-3,6,9-Trismethylene-4alpha-(4-hydroxyphenylacetyloxy)-8alpha-(beta-D-glucopyranosyloxy)dodecahydroazuleno[4,5-b]furan-2-one

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7303	73.03%
Caco-2	-	0.8853	88.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6962	69.62%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.7905	79.05%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6065	60.65%
P-glycoprotein inhibitior	-	0.5112	51.12%
P-glycoprotein substrate	-	0.5359	53.59%
CYP3A4 substrate	+	0.6884	68.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.6251	62.51%
CYP2C9 inhibition	-	0.8364	83.64%
CYP2C19 inhibition	-	0.6985	69.85%
CYP2D6 inhibition	-	0.8823	88.23%
CYP1A2 inhibition	-	0.8279	82.79%
CYP2C8 inhibition	+	0.6528	65.28%
CYP inhibitory promiscuity	-	0.7501	75.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6772	67.72%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9029	90.29%
Skin irritation	-	0.7717	77.17%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7360	73.60%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.7992	79.92%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5349	53.49%
Acute Oral Toxicity (c)	III	0.4183	41.83%
Estrogen receptor binding	+	0.7185	71.85%
Androgen receptor binding	+	0.6608	66.08%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5137	51.37%
Aromatase binding	+	0.5951	59.51%
PPAR gamma	+	0.6885	68.85%
Honey bee toxicity	-	0.6124	61.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9888	98.88%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	96.84%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.32%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.90%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.39%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	89.59%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.53%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.57%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.37%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.94%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.85%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.42%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.34%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	86.06%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.04%	95.83%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.01%	95.64%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.94%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.12%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	80.37%	90.17%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Crepis tingitana

Euryale ferox

Ixeridium dentatum subsp. dentatum

Ixeris chinensis

Ixeris japonica