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

Details

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Internal ID ed9f3f7f-b7b2-44f0-96de-e2ceb112c232
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
IUPAC Name 3-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-5-methoxy-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) CC(=CCC1=C(C(=CC(=C1)C2=COC3=C(C2=O)C(=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)O)OC)C
SMILES (Isomeric) CC(=CCC1=C(C(=CC(=C1)C2=COC3=C(C2=O)C(=CC(=C3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)OC)O)OC)C
InChI InChI=1S/C28H32O11/c1-13(2)5-6-14-7-15(8-18(30)27(14)36-4)17-12-37-20-10-16(9-19(35-3)22(20)23(17)31)38-28-26(34)25(33)24(32)21(11-29)39-28/h5,7-10,12,21,24-26,28-30,32-34H,6,11H2,1-4H3/t21-,24+,25+,26-,28-/m1/s1
InChI Key DWLRNWOJJADWTC-KJTTYUBRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H32O11
Molecular Weight 544.50 g/mol
Exact Mass 544.19446183 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 1.87
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-5-methoxy-7-[(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 + 0.8416 84.16%
Caco-2 - 0.8309 83.09%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.6475 64.75%
OATP2B1 inhibitior - 0.8484 84.84%
OATP1B1 inhibitior + 0.9317 93.17%
OATP1B3 inhibitior + 0.9353 93.53%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9486 94.86%
P-glycoprotein inhibitior + 0.6477 64.77%
P-glycoprotein substrate - 0.6616 66.16%
CYP3A4 substrate + 0.6505 65.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8283 82.83%
CYP3A4 inhibition - 0.9029 90.29%
CYP2C9 inhibition - 0.6680 66.80%
CYP2C19 inhibition - 0.6897 68.97%
CYP2D6 inhibition - 0.8239 82.39%
CYP1A2 inhibition - 0.6676 66.76%
CYP2C8 inhibition + 0.6182 61.82%
CYP inhibitory promiscuity - 0.5550 55.50%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7266 72.66%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9157 91.57%
Skin irritation - 0.7986 79.86%
Skin corrosion - 0.9489 94.89%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7832 78.32%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.6342 63.42%
skin sensitisation - 0.8681 86.81%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.5743 57.43%
Acute Oral Toxicity (c) III 0.6108 61.08%
Estrogen receptor binding + 0.8233 82.33%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.5174 51.74%
Glucocorticoid receptor binding + 0.6913 69.13%
Aromatase binding + 0.5914 59.14%
PPAR gamma + 0.7088 70.88%
Honey bee toxicity - 0.6766 67.66%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9678 96.78%

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 99.75% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.78% 85.14%
CHEMBL2581 P07339 Cathepsin D 95.13% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.34% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.21% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.61% 96.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.50% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.84% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.35% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 86.61% 94.73%
CHEMBL3922 P50579 Methionine aminopeptidase 2 85.96% 97.28%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.62% 92.62%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.44% 99.15%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.75% 95.56%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.14% 96.21%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.03% 97.09%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 83.80% 96.09%
CHEMBL4208 P20618 Proteasome component C5 82.32% 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.
Sphaeranthus indicus

Cross-Links

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PubChem 163103903
LOTUS LTS0237898
wikiData Q104990608