2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid

Details

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Internal ID 763ad82b-f39e-469e-8ffa-dba74b1464f1
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-8-O-glucuronides
IUPAC Name (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-8-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
InChI InChI=1S/C27H28O19/c28-5-11-13(33)15(35)18(38)26(42-11)45-23-14(34)12-9(31)4-10(32)21(22(12)43-20(23)6-1-2-7(29)8(30)3-6)44-27-19(39)16(36)17(37)24(46-27)25(40)41/h1-4,11,13,15-19,24,26-33,35-39H,5H2,(H,40,41)/t11-,13-,15+,16+,17+,18-,19-,24+,26+,27-/m1/s1
InChI Key YGWFDAMCHDILHX-JQHPUGQPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H28O19
Molecular Weight 656.50 g/mol
Exact Mass 656.12247866 g/mol
Topological Polar Surface Area (TPSA) 323.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -3.27
H-Bond Acceptor 18
H-Bond Donor 12
Rotatable Bonds 7

Synonyms

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135010-45-6
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid

2D Structure

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2D Structure of 2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6249 62.49%
Caco-2 - 0.9198 91.98%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.5589 55.89%
OATP2B1 inhibitior - 0.5562 55.62%
OATP1B1 inhibitior + 0.9218 92.18%
OATP1B3 inhibitior + 0.9680 96.80%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior - 0.5974 59.74%
P-glycoprotein inhibitior - 0.4753 47.53%
P-glycoprotein substrate - 0.8259 82.59%
CYP3A4 substrate + 0.5934 59.34%
CYP2C9 substrate - 0.8147 81.47%
CYP2D6 substrate - 0.8766 87.66%
CYP3A4 inhibition - 0.9184 91.84%
CYP2C9 inhibition - 0.9174 91.74%
CYP2C19 inhibition - 0.9299 92.99%
CYP2D6 inhibition - 0.9641 96.41%
CYP1A2 inhibition - 0.9320 93.20%
CYP2C8 inhibition + 0.7669 76.69%
CYP inhibitory promiscuity - 0.8782 87.82%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7263 72.63%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.8719 87.19%
Skin irritation - 0.8274 82.74%
Skin corrosion - 0.9638 96.38%
Ames mutagenesis + 0.5246 52.46%
Human Ether-a-go-go-Related Gene inhibition + 0.6768 67.68%
Micronuclear + 0.6633 66.33%
Hepatotoxicity - 0.5625 56.25%
skin sensitisation - 0.9201 92.01%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.8846 88.46%
Acute Oral Toxicity (c) IV 0.4205 42.05%
Estrogen receptor binding + 0.7778 77.78%
Androgen receptor binding + 0.6606 66.06%
Thyroid receptor binding - 0.5568 55.68%
Glucocorticoid receptor binding - 0.5617 56.17%
Aromatase binding - 0.5587 55.87%
PPAR gamma + 0.6440 64.40%
Honey bee toxicity - 0.7607 76.07%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 0.8695 86.95%

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%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.61% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 94.17% 91.49%
CHEMBL2581 P07339 Cathepsin D 93.50% 98.95%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 92.92% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.69% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.65% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.49% 86.33%
CHEMBL3194 P02766 Transthyretin 88.24% 90.71%
CHEMBL3401 O75469 Pregnane X receptor 86.57% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.99% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.52% 94.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.67% 95.50%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.02% 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.
Cota coelopoda
Malva sylvestris

Cross-Links

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PubChem 14887603
LOTUS LTS0052793
wikiData Q104990253