[(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

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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

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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,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

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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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 99.80% 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

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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 101412294
LOTUS LTS0152740
wikiData Q105350367