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5,7-dihydroxy-2-[3-hydroxy-4-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]phenyl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

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 fb5efdd1-f8e5-48a0-be80-fb795c885e9c
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
IUPAC Name 5,7-dihydroxy-2-[3-hydroxy-4-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]phenyl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
SMILES (Canonical) C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O)OCC5C(C(C(C(O5)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)OC[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)O)O)O)O
InChI InChI=1S/C27H30O16/c28-6-15-19(32)22(35)24(37)26(42-15)18-11(31)5-14-17(21(18)34)10(30)4-13(41-14)8-1-2-12(9(29)3-8)40-7-16-20(33)23(36)25(38)27(39)43-16/h1-5,15-16,19-20,22-29,31-39H,6-7H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
InChI Key JZDOUTSJNGBWOR-KETMJRJWSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H30O16
Molecular Weight 610.50 g/mol
Exact Mass 610.15338487 g/mol
Topological Polar Surface Area (TPSA) 277.00 Ų
XlogP -2.50
Atomic LogP (AlogP) -2.73
H-Bond Acceptor 16
H-Bond Donor 11
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5,7-dihydroxy-2-[3-hydroxy-4-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]phenyl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5736 57.36%
Caco-2 - 0.9197 91.97%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5848 58.48%
OATP2B1 inhibitior - 0.5504 55.04%
OATP1B1 inhibitior + 0.8515 85.15%
OATP1B3 inhibitior + 0.9434 94.34%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.5715 57.15%
P-glycoprotein inhibitior - 0.4878 48.78%
P-glycoprotein substrate - 0.6299 62.99%
CYP3A4 substrate + 0.6314 63.14%
CYP2C9 substrate - 0.6534 65.34%
CYP2D6 substrate - 0.8464 84.64%
CYP3A4 inhibition - 0.9390 93.90%
CYP2C9 inhibition - 0.9315 93.15%
CYP2C19 inhibition - 0.9047 90.47%
CYP2D6 inhibition - 0.9458 94.58%
CYP1A2 inhibition - 0.9180 91.80%
CYP2C8 inhibition + 0.7789 77.89%
CYP inhibitory promiscuity - 0.7526 75.26%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6848 68.48%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.8834 88.34%
Skin irritation - 0.8255 82.55%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis + 0.6399 63.99%
Human Ether-a-go-go-Related Gene inhibition + 0.7306 73.06%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.7821 78.21%
skin sensitisation - 0.9132 91.32%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.8914 89.14%
Acute Oral Toxicity (c) IV 0.4763 47.63%
Estrogen receptor binding + 0.7846 78.46%
Androgen receptor binding + 0.6892 68.92%
Thyroid receptor binding - 0.4932 49.32%
Glucocorticoid receptor binding - 0.5171 51.71%
Aromatase binding + 0.5618 56.18%
PPAR gamma + 0.7378 73.78%
Honey bee toxicity - 0.7136 71.36%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.7958 79.58%

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 99.13% 91.11%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 98.82% 83.57%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 96.97% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.85% 89.00%
CHEMBL2581 P07339 Cathepsin D 96.07% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 93.54% 86.92%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 92.76% 99.15%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.27% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 89.64% 94.73%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 88.84% 95.78%
CHEMBL1075162 Q13304 Uracil nucleotide/cysteinyl leukotriene receptor 87.72% 80.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.58% 97.09%
CHEMBL3194 P02766 Transthyretin 86.34% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.81% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.90% 99.17%
CHEMBL1951 P21397 Monoamine oxidase A 84.02% 91.49%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.98% 95.83%
CHEMBL5284 Q96RR4 CaM-kinase kinase beta 82.44% 89.23%
CHEMBL1937 Q92769 Histone deacetylase 2 80.70% 94.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.09% 85.14%

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.
Gentiana verna

Cross-Links

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PubChem 162969375
LOTUS LTS0020583
wikiData Q105137351