[(2R,3S,4S,5R,6R)-6-[[(3S,3aS,4R,5S,6aS)-4-(hydroxymethyl)-5-methyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-3-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: fdbdd3ce-0f4a-4707-953b-c5b2695a8a8d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3S,3aS,4R,5S,6aS)-4-(hydroxymethyl)-5-methyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-3-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1CC2C(C1CO)C(C(=O)O2)COC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@@H]([C@@H]1CO)[C@H](C(=O)O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C25H32O12/c1-11-6-17-20(13(11)8-26)14(24(33)36-17)9-35-25-23(32)22(31)21(30)18(37-25)10-34-19(29)5-3-12-2-4-15(27)16(28)7-12/h2-5,7,11,13-14,17-18,20-23,25-28,30-32H,6,8-10H2,1H3/b5-3+/t11-,13+,14+,17-,18+,20-,21+,22-,23+,25+/m0/s1
• InChI Key: JBANWRRXNAVXHA-MZGZSVKJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₂
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.18937645 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7733	77.33%
Caco-2	-	0.8949	89.49%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9579	95.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6884	68.84%
P-glycoprotein inhibitior	-	0.6716	67.16%
P-glycoprotein substrate	-	0.6805	68.05%
CYP3A4 substrate	+	0.6512	65.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.8547	85.47%
CYP2C9 inhibition	-	0.8916	89.16%
CYP2C19 inhibition	-	0.7337	73.37%
CYP2D6 inhibition	-	0.8985	89.85%
CYP1A2 inhibition	-	0.7932	79.32%
CYP2C8 inhibition	+	0.5851	58.51%
CYP inhibitory promiscuity	-	0.7793	77.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6269	62.69%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9346	93.46%
Skin irritation	-	0.7974	79.74%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5510	55.10%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7199	71.99%
skin sensitisation	-	0.8311	83.11%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8247	82.47%
Acute Oral Toxicity (c)	III	0.5422	54.22%
Estrogen receptor binding	+	0.7662	76.62%
Androgen receptor binding	+	0.6063	60.63%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6356	63.56%
PPAR gamma	+	0.6211	62.11%
Honey bee toxicity	-	0.7683	76.83%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9919	99.19%

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	99.67%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.51%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.81%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.43%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.21%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.33%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.40%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.95%	80.78%
CHEMBL5255	O00206	Toll-like receptor 4	86.98%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.34%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.87%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.80%	94.80%
CHEMBL226	P30542	Adenosine A1 receptor	83.88%	95.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.42%	96.95%
CHEMBL3194	P02766	Transthyretin	83.17%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	82.12%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.32%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.99%	94.45%
CHEMBL2581	P07339	Cathepsin D	80.61%	98.95%

Plants that contains it

• Verbena brasiliensis

Cross-Links

• PubChem: 162821198
• LOTUS: LTS0067076
• wikiData: Q105124183