[2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-(3-hydroxyphenyl)methanone

Details

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Internal ID 83c3bf78-e23b-4587-adbf-8d827f1b220d
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name [2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-(3-hydroxyphenyl)methanone
SMILES (Canonical) COC1=CC(=C(C(=C1)OC2C(C(C(C(O2)CO)O)O)O)C(=O)C3=CC(=CC=C3)O)O
SMILES (Isomeric) COC1=CC(=C(C(=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)C3=CC(=CC=C3)O)O
InChI InChI=1S/C20H22O10/c1-28-11-6-12(23)15(16(24)9-3-2-4-10(22)5-9)13(7-11)29-20-19(27)18(26)17(25)14(8-21)30-20/h2-7,14,17-23,25-27H,8H2,1H3/t14-,17-,18+,19-,20-/m1/s1
InChI Key QYORVZINCMRBMV-LWUBGYQZSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H22O10
Molecular Weight 422.40 g/mol
Exact Mass 422.12129689 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP 0.70
Atomic LogP (AlogP) -0.48
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-(3-hydroxyphenyl)methanone

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7178 71.78%
Caco-2 - 0.8694 86.94%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.6648 66.48%
OATP2B1 inhibitior - 0.5606 56.06%
OATP1B1 inhibitior + 0.9120 91.20%
OATP1B3 inhibitior + 0.9525 95.25%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.6581 65.81%
P-glycoprotein inhibitior - 0.7518 75.18%
P-glycoprotein substrate - 0.7684 76.84%
CYP3A4 substrate + 0.5568 55.68%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8454 84.54%
CYP3A4 inhibition - 0.8632 86.32%
CYP2C9 inhibition - 0.8775 87.75%
CYP2C19 inhibition - 0.9154 91.54%
CYP2D6 inhibition - 0.9346 93.46%
CYP1A2 inhibition - 0.8980 89.80%
CYP2C8 inhibition + 0.5386 53.86%
CYP inhibitory promiscuity - 0.7229 72.29%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7412 74.12%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.8400 84.00%
Skin irritation - 0.8333 83.33%
Skin corrosion - 0.9617 96.17%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4910 49.10%
Micronuclear + 0.5733 57.33%
Hepatotoxicity - 0.7476 74.76%
skin sensitisation - 0.9027 90.27%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.7629 76.29%
Acute Oral Toxicity (c) III 0.7844 78.44%
Estrogen receptor binding + 0.6812 68.12%
Androgen receptor binding + 0.5197 51.97%
Thyroid receptor binding + 0.5317 53.17%
Glucocorticoid receptor binding + 0.7272 72.72%
Aromatase binding + 0.6675 66.75%
PPAR gamma + 0.6987 69.87%
Honey bee toxicity - 0.9013 90.13%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.7155 71.55%
Fish aquatic toxicity + 0.6638 66.38%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.37% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.07% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.63% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.13% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.11% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.32% 94.00%
CHEMBL3401 O75469 Pregnane X receptor 91.07% 94.73%
CHEMBL2535 P11166 Glucose transporter 89.93% 98.75%
CHEMBL4208 P20618 Proteasome component C5 88.40% 90.00%
CHEMBL2581 P07339 Cathepsin D 87.86% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 87.45% 95.93%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.90% 95.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.39% 96.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.47% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.82% 91.07%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 83.34% 99.15%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.68% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.60% 89.00%

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 163076314
LOTUS LTS0169572
wikiData Q105230301