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[(2R,3S,4R,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Table of Contents

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 bf19b4e6-87d4-442a-aeab-dedcaeb8ff99
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
IUPAC Name [(2R,3S,4R,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES (Canonical) C1=CC(=C(C=C1C=CC(=O)OCC2C(C(C(C(O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
InChI InChI=1S/C30H26O14/c31-14-4-1-12(7-16(14)33)2-6-23(37)42-11-22-26(38)28(40)29(41)30(44-22)25-19(36)10-21-24(27(25)39)18(35)9-20(43-21)13-3-5-15(32)17(34)8-13/h1-10,22,26,28-34,36,38-41H,11H2/b6-2+/t22-,26-,28+,29-,30+/m1/s1
InChI Key AINXWDZMEIYUSK-PDAWMBKQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C30H26O14
Molecular Weight 610.50 g/mol
Exact Mass 610.13225550 g/mol
Topological Polar Surface Area (TPSA) 244.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.47
H-Bond Acceptor 14
H-Bond Donor 9
Rotatable Bonds 6

Synonyms

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6''-O-(3,4-Dihydroxy-E-cinnamoyl)isoorientin

2D Structure

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2D Structure of [(2R,3S,4R,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-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 - 0.4689 46.89%
Caco-2 - 0.9070 90.70%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.5846 58.46%
OATP2B1 inhibitior - 0.5521 55.21%
OATP1B1 inhibitior + 0.8793 87.93%
OATP1B3 inhibitior + 0.9635 96.35%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior - 0.4849 48.49%
P-glycoprotein inhibitior + 0.6231 62.31%
P-glycoprotein substrate - 0.7107 71.07%
CYP3A4 substrate + 0.6475 64.75%
CYP2C9 substrate - 0.7966 79.66%
CYP2D6 substrate - 0.8683 86.83%
CYP3A4 inhibition - 0.8901 89.01%
CYP2C9 inhibition - 0.8448 84.48%
CYP2C19 inhibition - 0.8659 86.59%
CYP2D6 inhibition - 0.9392 93.92%
CYP1A2 inhibition - 0.9312 93.12%
CYP2C8 inhibition + 0.8417 84.17%
CYP inhibitory promiscuity - 0.7755 77.55%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6770 67.70%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.8807 88.07%
Skin irritation - 0.8069 80.69%
Skin corrosion - 0.9555 95.55%
Ames mutagenesis - 0.5355 53.55%
Human Ether-a-go-go-Related Gene inhibition - 0.4000 40.00%
Micronuclear + 0.7292 72.92%
Hepatotoxicity - 0.7250 72.50%
skin sensitisation - 0.8777 87.77%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.9734 97.34%
Acute Oral Toxicity (c) III 0.4048 40.48%
Estrogen receptor binding + 0.7564 75.64%
Androgen receptor binding + 0.8088 80.88%
Thyroid receptor binding + 0.5379 53.79%
Glucocorticoid receptor binding + 0.6266 62.66%
Aromatase binding + 0.5333 53.33%
PPAR gamma + 0.7169 71.69%
Honey bee toxicity - 0.6995 69.95%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9677 96.77%

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 99.86% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 98.96% 91.49%
CHEMBL1806 P11388 DNA topoisomerase II alpha 98.18% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.98% 86.33%
CHEMBL2581 P07339 Cathepsin D 95.07% 98.95%
CHEMBL3194 P02766 Transthyretin 94.23% 90.71%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 90.92% 99.15%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.70% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.09% 96.00%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 88.18% 80.78%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.09% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 87.64% 94.73%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.04% 91.71%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 85.36% 90.71%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 85.01% 83.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.40% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.30% 99.17%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 82.77% 95.64%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.07% 86.92%

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.
Centaurea hermannii
Crataegus monogyna
Gentiana arisanensis
Prunus arborea var. montana
Vitex agnus-castus

Cross-Links

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PubChem 101687176
NPASS NPC123519
LOTUS LTS0219060
wikiData Q104912874