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

Details

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Internal ID fb5dc98b-7639-4317-b357-dc18548f379e
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
IUPAC Name 5-hydroxy-3-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
InChI InChI=1S/C27H30O16/c28-6-16-20(33)22(35)24(37)26(42-16)40-10-4-13(31)18-15(5-10)39-8-11(19(18)32)9-1-2-12(30)14(3-9)41-27-25(38)23(36)21(34)17(7-29)43-27/h1-5,8,16-17,20-31,33-38H,6-7H2/t16-,17-,20-,21-,22+,23+,24-,25-,26+,27+/m1/s1
InChI Key WBUYXWBGDDXLJL-XHYOFSJDSA-N
Popularity 0 references 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) 266.00 Ų
XlogP -1.30
Atomic LogP (AlogP) -2.77
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5-hydroxy-3-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2R,3R,4S,5S,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 - 0.5736 57.36%
Caco-2 - 0.9102 91.02%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.5848 58.48%
OATP2B1 inhibitior - 0.5514 55.14%
OATP1B1 inhibitior + 0.9524 95.24%
OATP1B3 inhibitior + 0.9434 94.34%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.7273 72.73%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.8722 87.22%
CYP3A4 substrate + 0.6038 60.38%
CYP2C9 substrate - 0.6762 67.62%
CYP2D6 substrate - 0.8575 85.75%
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 + 0.6656 66.56%
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 - 0.8826 88.26%
Skin irritation - 0.8255 82.55%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis - 0.5182 51.82%
Human Ether-a-go-go-Related Gene inhibition + 0.7020 70.20%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.7071 70.71%
skin sensitisation - 0.9132 91.32%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.5561 55.61%
Acute Oral Toxicity (c) IV 0.4763 47.63%
Estrogen receptor binding + 0.7492 74.92%
Androgen receptor binding + 0.5523 55.23%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.5627 56.27%
Aromatase binding + 0.5554 55.54%
PPAR gamma + 0.7907 79.07%
Honey bee toxicity - 0.7236 72.36%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5299 52.99%
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 98.77% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.51% 98.95%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 94.74% 99.15%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.64% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.41% 94.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 92.96% 96.21%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 92.85% 95.78%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 92.55% 86.92%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.72% 99.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.00% 97.09%
CHEMBL3194 P02766 Transthyretin 87.68% 90.71%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.35% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.88% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.39% 95.56%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.08% 97.28%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.21% 95.89%
CHEMBL220 P22303 Acetylcholinesterase 82.14% 94.45%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.43% 90.71%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 80.76% 95.53%
CHEMBL4208 P20618 Proteasome component C5 80.52% 90.00%

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.
Perilla frutescens

Cross-Links

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PubChem 99653118
NPASS NPC89845