2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

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Internal ID 92259484-81a9-43ca-9c06-06b8dbae9512
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name 2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=CC(=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=CC(=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O
InChI InChI=1S/C21H20O12/c22-6-12-14(27)16(29)17(30)21(31-12)33-20-15(28)13-9(24)3-4-10(25)19(13)32-18(20)7-1-2-8(23)11(26)5-7/h1-5,12,14,16-17,21-27,29-30H,6H2/t12-,14+,16+,17-,21+/m1/s1
InChI Key MSBHOJSEFZPTET-LWHUYORISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H20O12
Molecular Weight 464.40 g/mol
Exact Mass 464.09547607 g/mol
Topological Polar Surface Area (TPSA) 207.00 Ų
XlogP 0.40
Atomic LogP (AlogP) -0.54
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 2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-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 - 0.9115 91.15%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6068 60.68%
OATP2B1 inhibitior + 0.5935 59.35%
OATP1B1 inhibitior + 0.9394 93.94%
OATP1B3 inhibitior + 0.9265 92.65%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.6148 61.48%
P-glycoprotein inhibitior - 0.6303 63.03%
P-glycoprotein substrate - 0.8850 88.50%
CYP3A4 substrate + 0.5561 55.61%
CYP2C9 substrate - 0.6709 67.09%
CYP2D6 substrate - 0.8582 85.82%
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 + 0.6570 65.70%
CYP inhibitory promiscuity - 0.7728 77.28%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7144 71.44%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.7642 76.42%
Skin irritation - 0.8036 80.36%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis + 0.7009 70.09%
Human Ether-a-go-go-Related Gene inhibition - 0.4881 48.81%
Micronuclear + 0.6533 65.33%
Hepatotoxicity - 0.6321 63.21%
skin sensitisation - 0.9122 91.22%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.6893 68.93%
Acute Oral Toxicity (c) III 0.4045 40.45%
Estrogen receptor binding + 0.7337 73.37%
Androgen receptor binding + 0.7335 73.35%
Thyroid receptor binding - 0.5106 51.06%
Glucocorticoid receptor binding + 0.7121 71.21%
Aromatase binding + 0.5868 58.68%
PPAR gamma + 0.6998 69.98%
Honey bee toxicity - 0.7473 74.73%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6350 63.50%
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 99.67% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.76% 89.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 93.24% 99.15%
CHEMBL2581 P07339 Cathepsin D 92.59% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.03% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.64% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 88.46% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.72% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.15% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.85% 86.92%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.55% 95.56%
CHEMBL3194 P02766 Transthyretin 81.46% 90.71%

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.
Gutierrezia grandis
Hypericum papuanum

Cross-Links

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PubChem 163189274
LOTUS LTS0121960
wikiData Q104667131