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(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

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 e071a9c7-1fb9-4d5a-9051-3c10a7b3af60
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)O)O)O
InChI InChI=1S/C27H28O17/c28-7-16-18(33)20(35)24(44-26-22(37)19(34)21(36)23(43-26)25(38)39)27(42-16)40-9-4-12(31)17-13(32)6-14(41-15(17)5-9)8-1-2-10(29)11(30)3-8/h1-6,16,18-24,26-31,33-37H,7H2,(H,38,39)/t16-,18-,19+,20+,21+,22-,23+,24-,26+,27-/m1/s1
InChI Key WVVPBKNYYORVPY-RKYLLTSBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H28O17
Molecular Weight 624.50 g/mol
Exact Mass 624.13264942 g/mol
Topological Polar Surface Area (TPSA) 283.00 Ų
XlogP -0.80
Atomic LogP (AlogP) -2.33
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 7

Synonyms

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2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-[2-O-(beta-D-glucopyranuronosyl)-beta-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

2D Structure

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2D Structure of (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic 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 - 0.9245 92.45%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.5589 55.89%
OATP2B1 inhibitior - 0.5600 56.00%
OATP1B1 inhibitior + 0.9439 94.39%
OATP1B3 inhibitior + 0.9680 96.80%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior - 0.5258 52.58%
P-glycoprotein inhibitior - 0.6335 63.35%
P-glycoprotein substrate - 0.7551 75.51%
CYP3A4 substrate + 0.6244 62.44%
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 + 0.7992 79.92%
CYP inhibitory promiscuity - 0.8782 87.82%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7263 72.63%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.9132 91.32%
Skin irritation - 0.8274 82.74%
Skin corrosion - 0.9638 96.38%
Ames mutagenesis + 0.5336 53.36%
Human Ether-a-go-go-Related Gene inhibition + 0.6584 65.84%
Micronuclear + 0.6633 66.33%
Hepatotoxicity - 0.8341 83.41%
skin sensitisation - 0.9201 92.01%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.9326 93.26%
Acute Oral Toxicity (c) IV 0.4205 42.05%
Estrogen receptor binding + 0.7904 79.04%
Androgen receptor binding + 0.6602 66.02%
Thyroid receptor binding + 0.5363 53.63%
Glucocorticoid receptor binding - 0.4908 49.08%
Aromatase binding + 0.6338 63.38%
PPAR gamma + 0.7781 77.81%
Honey bee toxicity - 0.6424 64.24%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6500 65.00%
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 99.68% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.59% 91.49%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.11% 89.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.31% 99.15%
CHEMBL3194 P02766 Transthyretin 95.12% 90.71%
CHEMBL2581 P07339 Cathepsin D 93.91% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.12% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.82% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.72% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.67% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.55% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 87.14% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.10% 94.45%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.26% 97.36%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 84.67% 83.57%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 83.83% 91.71%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 83.00% 95.78%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.50% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.90% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.00% 95.50%

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.
Elsholtzia ciliata
Stratiotes aloides

Cross-Links

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PubChem 44139740
NPASS NPC253685
LOTUS LTS0118839
wikiData Q105313812