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

Details

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Internal ID c98ca2ef-830f-46f2-99b6-82bdb209bb43
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
IUPAC Name 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]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)OC5C(C(C(C(O5)CO)O)O)O)O)O)OC6C(C(C(C(O6)CO)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[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C33H40O21/c34-6-16-23(42)27(46)31(54-33-29(48)26(45)22(41)18(8-36)53-33)30(50-16)20-12(39)5-15-19(24(20)43)11(38)4-14(49-15)9-1-2-13(10(37)3-9)51-32-28(47)25(44)21(40)17(7-35)52-32/h1-5,16-18,21-23,25-37,39-48H,6-8H2/t16-,17-,18-,21-,22-,23-,25+,26+,27+,28-,29-,30+,31-,32-,33+/m1/s1
InChI Key RQSYXJLWNNTQIE-QPCXLFDESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H40O21
Molecular Weight 772.70 g/mol
Exact Mass 772.20620828 g/mol
Topological Polar Surface Area (TPSA) 356.00 Ų
XlogP -3.50
Atomic LogP (AlogP) -4.91
H-Bond Acceptor 21
H-Bond Donor 14
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]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 - 0.9014 90.14%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5848 58.48%
OATP2B1 inhibitior - 0.7064 70.64%
OATP1B1 inhibitior + 0.8998 89.98%
OATP1B3 inhibitior + 0.9434 94.34%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6486 64.86%
P-glycoprotein inhibitior + 0.5735 57.35%
P-glycoprotein substrate - 0.6444 64.44%
CYP3A4 substrate + 0.6319 63.19%
CYP2C9 substrate - 0.6643 66.43%
CYP2D6 substrate - 0.8569 85.69%
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 + 0.7224 72.24%
CYP inhibitory promiscuity - 0.7526 75.26%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6848 68.48%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.8987 89.87%
Skin irritation - 0.8255 82.55%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis + 0.5299 52.99%
Human Ether-a-go-go-Related Gene inhibition + 0.7564 75.64%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.8696 86.96%
skin sensitisation - 0.9132 91.32%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.9018 90.18%
Acute Oral Toxicity (c) IV 0.4763 47.63%
Estrogen receptor binding + 0.8188 81.88%
Androgen receptor binding + 0.6770 67.70%
Thyroid receptor binding - 0.4911 49.11%
Glucocorticoid receptor binding - 0.5728 57.28%
Aromatase binding + 0.5907 59.07%
PPAR gamma + 0.7383 73.83%
Honey bee toxicity - 0.6585 65.85%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6600 66.00%
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
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 99.26% 83.57%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.19% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.80% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 96.28% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.12% 89.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 92.69% 96.21%
CHEMBL1951 P21397 Monoamine oxidase A 92.21% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.85% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.39% 86.92%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.08% 99.15%
CHEMBL3194 P02766 Transthyretin 86.96% 90.71%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 86.66% 95.78%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.43% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.04% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 85.14% 94.73%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.35% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.20% 97.09%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 82.74% 83.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.80% 94.45%

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 asclepiadea

Cross-Links

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PubChem 162888575
LOTUS LTS0042840
wikiData Q105243564