3-(3,5-dihydroxy-4-methoxyphenyl)-8-hydroxy-7-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

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Internal ID 28d259e5-9baf-45e2-8c9a-88c74299b43e
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
IUPAC Name 3-(3,5-dihydroxy-4-methoxyphenyl)-8-hydroxy-7-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) COC1=C(C=C(C=C1O)C2=COC3=C(C(=C(C=C3C2=O)OC4C(C(C(C(O4)CO)O)O)O)OC)O)O
SMILES (Isomeric) COC1=C(C=C(C=C1O)C2=COC3=C(C(=C(C=C3C2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O)O
InChI InChI=1S/C23H24O13/c1-32-21-11(25)3-8(4-12(21)26)10-7-34-20-9(15(10)27)5-13(22(33-2)19(20)31)35-23-18(30)17(29)16(28)14(6-24)36-23/h3-5,7,14,16-18,23-26,28-31H,6H2,1-2H3/t14-,16-,17+,18-,23-/m1/s1
InChI Key APKDRIMLZJZHKZ-URAQMDAQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H24O13
Molecular Weight 508.40 g/mol
Exact Mass 508.12169082 g/mol
Topological Polar Surface Area (TPSA) 205.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.23
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-(3,5-dihydroxy-4-methoxyphenyl)-8-hydroxy-7-methoxy-6-[(2S,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 - 0.5074 50.74%
Caco-2 - 0.8938 89.38%
Blood Brain Barrier - 0.9000 90.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6238 62.38%
OATP2B1 inhibitior - 0.5615 56.15%
OATP1B1 inhibitior + 0.8813 88.13%
OATP1B3 inhibitior + 0.9678 96.78%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.6523 65.23%
P-glycoprotein inhibitior - 0.5110 51.10%
P-glycoprotein substrate - 0.7998 79.98%
CYP3A4 substrate + 0.6156 61.56%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8324 83.24%
CYP3A4 inhibition - 0.8862 88.62%
CYP2C9 inhibition - 0.9258 92.58%
CYP2C19 inhibition - 0.9329 93.29%
CYP2D6 inhibition - 0.9457 94.57%
CYP1A2 inhibition - 0.9089 90.89%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.7195 71.95%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7238 72.38%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9087 90.87%
Skin irritation - 0.8305 83.05%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis + 0.5409 54.09%
Human Ether-a-go-go-Related Gene inhibition + 0.6610 66.10%
Micronuclear + 0.6733 67.33%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.9389 93.89%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.8518 85.18%
Acute Oral Toxicity (c) III 0.6799 67.99%
Estrogen receptor binding + 0.8401 84.01%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.5529 55.29%
Glucocorticoid receptor binding + 0.6262 62.62%
Aromatase binding + 0.5506 55.06%
PPAR gamma + 0.6515 65.15%
Honey bee toxicity - 0.8021 80.21%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.7522 75.22%

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 99.51% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.85% 89.00%
CHEMBL2581 P07339 Cathepsin D 95.58% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.18% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.15% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.24% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.13% 86.33%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 85.73% 96.21%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.33% 99.15%
CHEMBL1937 Q92769 Histone deacetylase 2 83.88% 94.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.61% 95.56%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.20% 86.92%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.32% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 81.89% 94.73%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.57% 92.62%

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.
Iris potaninii

Cross-Links

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PubChem 11038496
LOTUS LTS0048502
wikiData Q104916367