[(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

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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

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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

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There are no found synonyms.

2D Structure

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2D Structure of [(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

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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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 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

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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.
Verbena brasiliensis

Cross-Links

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PubChem 162821198
LOTUS LTS0067076
wikiData Q105124183