(2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

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Internal ID d9bb456c-cc90-4973-8ac8-c5dc6431a561
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name (2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
SMILES (Canonical) C1C(OC2=CC(=C(C(=C2C1=O)O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=CC(=C4)O)O
SMILES (Isomeric) C1[C@H](OC2=CC(=C(C(=C2C1=O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC(=CC(=C4)O)O
InChI InChI=1S/C21H22O12/c22-6-14-17(27)19(29)20(30)21(33-14)32-13-5-12-15(18(28)16(13)26)10(25)4-11(31-12)7-1-8(23)3-9(24)2-7/h1-3,5,11,14,17,19-24,26-30H,4,6H2/t11-,14+,17+,19-,20+,21+/m0/s1
InChI Key DUGVPRQGQKRYOM-LBNJVWSVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H22O12
Molecular Weight 466.40 g/mol
Exact Mass 466.11112613 g/mol
Topological Polar Surface Area (TPSA) 207.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.61
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-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 - 0.5116 51.16%
Caco-2 - 0.9361 93.61%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.8857 88.57%
Subcellular localzation Mitochondria 0.6068 60.68%
OATP2B1 inhibitior - 0.5565 55.65%
OATP1B1 inhibitior + 0.8997 89.97%
OATP1B3 inhibitior + 0.9265 92.65%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.6468 64.68%
P-glycoprotein inhibitior - 0.7384 73.84%
P-glycoprotein substrate - 0.8617 86.17%
CYP3A4 substrate + 0.5803 58.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8398 83.98%
CYP3A4 inhibition - 0.9193 91.93%
CYP2C9 inhibition - 0.9296 92.96%
CYP2C19 inhibition - 0.9289 92.89%
CYP2D6 inhibition - 0.9513 95.13%
CYP1A2 inhibition - 0.9084 90.84%
CYP2C8 inhibition - 0.5983 59.83%
CYP inhibitory promiscuity - 0.7728 77.28%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7144 71.44%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.8373 83.73%
Skin irritation - 0.8036 80.36%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3883 38.83%
Micronuclear + 0.6533 65.33%
Hepatotoxicity - 0.7750 77.50%
skin sensitisation - 0.9122 91.22%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.5776 57.76%
Acute Oral Toxicity (c) III 0.4045 40.45%
Estrogen receptor binding + 0.7864 78.64%
Androgen receptor binding - 0.4896 48.96%
Thyroid receptor binding + 0.5705 57.05%
Glucocorticoid receptor binding + 0.5703 57.03%
Aromatase binding + 0.5638 56.38%
PPAR gamma + 0.7837 78.37%
Honey bee toxicity - 0.7228 72.28%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6249 62.49%
Fish aquatic toxicity + 0.8218 82.18%

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 99.30% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.91% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.49% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.95% 89.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 91.16% 96.21%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.33% 94.45%
CHEMBL2581 P07339 Cathepsin D 89.47% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.63% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.42% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.24% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.58% 95.56%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.22% 86.92%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.12% 95.89%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 84.28% 95.64%
CHEMBL4208 P20618 Proteasome component C5 83.78% 90.00%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 82.14% 95.78%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.74% 90.71%
CHEMBL3401 O75469 Pregnane X receptor 81.40% 94.73%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.08% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.78% 99.23%

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.
Lippia origanoides

Cross-Links

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PubChem 163014749
LOTUS LTS0163520
wikiData Q104989222