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

Details

• Internal ID: 8f43d894-caee-44c9-8a33-ed42777bcb80
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(2R,3S,4R,5R,6R)-6-[[(3R,3aS,4R,5S,6aS)-4-(hydroxymethyl)-5-methyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-3-yl]methoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1CC2C(C1CO)C(C(=O)O2)COC3C(C(C(C(O3)CO)OC(=O)C=CC4=CC(=C(C=C4)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)CO)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O
• InChI: InChI=1S/C25H32O12/c1-11-6-17-20(13(11)8-26)14(24(33)35-17)10-34-25-22(32)21(31)23(18(9-27)36-25)37-19(30)5-3-12-2-4-15(28)16(29)7-12/h2-5,7,11,13-14,17-18,20-23,25-29,31-32H,6,8-10H2,1H3/b5-3+/t11-,13+,14-,17-,18+,20-,21+,22+,23+,25+/m0/s1
• InChI Key: YLXHBUXEDMVNGL-KVWIEXSUSA-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	+	0.8748	87.48%
Caco-2	-	0.8970	89.70%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8055	80.55%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8268	82.68%
P-glycoprotein inhibitior	-	0.6941	69.41%
P-glycoprotein substrate	-	0.6269	62.69%
CYP3A4 substrate	+	0.6628	66.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.8255	82.55%
CYP2C9 inhibition	-	0.8300	83.00%
CYP2C19 inhibition	-	0.5827	58.27%
CYP2D6 inhibition	-	0.8676	86.76%
CYP1A2 inhibition	-	0.7025	70.25%
CYP2C8 inhibition	+	0.5786	57.86%
CYP inhibitory promiscuity	-	0.7213	72.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5706	57.06%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9301	93.01%
Skin irritation	-	0.7908	79.08%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5961	59.61%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6699	66.99%
skin sensitisation	-	0.7976	79.76%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8700	87.00%
Acute Oral Toxicity (c)	III	0.5611	56.11%
Estrogen receptor binding	+	0.7470	74.70%
Androgen receptor binding	+	0.6031	60.31%
Thyroid receptor binding	-	0.5160	51.60%
Glucocorticoid receptor binding	-	0.5126	51.26%
Aromatase binding	+	0.6633	66.33%
PPAR gamma	+	0.5844	58.44%
Honey bee toxicity	-	0.7381	73.81%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	99.80%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.79%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.05%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.07%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.81%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.76%	94.80%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.38%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.44%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.70%	80.78%
CHEMBL5255	O00206	Toll-like receptor 4	87.08%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	85.90%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.55%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.54%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.23%	99.17%
CHEMBL3194	P02766	Transthyretin	83.18%	90.71%
CHEMBL2581	P07339	Cathepsin D	82.65%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	81.62%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.41%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.16%	91.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.49%	100.00%

Plants that contains it

• Verbena brasiliensis

Cross-Links

• PubChem: 101412294
• LOTUS: LTS0152740
• wikiData: Q105350367