(2Z)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-6-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one

Details

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Internal ID b6978048-ce8c-4e45-8100-f245a33ac7ea
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
IUPAC Name (2Z)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-6-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC4=CC=C(C=C4)O)C3=O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC2=CC(=C3C(=C2)O/C(=C\C4=CC=C(C=C4)O)/C3=O)O)O)O)O
InChI InChI=1S/C21H20O9/c1-9-17(24)19(26)20(27)21(28-9)29-12-7-13(23)16-14(8-12)30-15(18(16)25)6-10-2-4-11(22)5-3-10/h2-9,17,19-24,26-27H,1H3/b15-6-/t9-,17+,19-,20-,21+/m0/s1
InChI Key ZWKNCUQZWIAEDC-AXOKKZEJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H20O9
Molecular Weight 416.40 g/mol
Exact Mass 416.11073221 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 0.92
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2Z)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-6-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9415 94.15%
Caco-2 - 0.8597 85.97%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6796 67.96%
OATP2B1 inhibitior + 0.5772 57.72%
OATP1B1 inhibitior + 0.9205 92.05%
OATP1B3 inhibitior + 0.9546 95.46%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 1.0000 100.00%
BSEP inhibitior + 0.7223 72.23%
P-glycoprotein inhibitior - 0.7269 72.69%
P-glycoprotein substrate - 0.8620 86.20%
CYP3A4 substrate + 0.5623 56.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8613 86.13%
CYP3A4 inhibition + 0.5843 58.43%
CYP2C9 inhibition - 0.6446 64.46%
CYP2C19 inhibition + 0.7067 70.67%
CYP2D6 inhibition - 0.8246 82.46%
CYP1A2 inhibition + 0.6762 67.62%
CYP2C8 inhibition + 0.4812 48.12%
CYP inhibitory promiscuity + 0.8312 83.12%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Danger 0.5152 51.52%
Eye corrosion - 0.9860 98.60%
Eye irritation - 0.8060 80.60%
Skin irritation - 0.6386 63.86%
Skin corrosion - 0.9368 93.68%
Ames mutagenesis - 0.5000 50.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5899 58.99%
Micronuclear + 0.9000 90.00%
Hepatotoxicity - 0.7662 76.62%
skin sensitisation - 0.6772 67.72%
Respiratory toxicity - 0.5556 55.56%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.5734 57.34%
Acute Oral Toxicity (c) III 0.3841 38.41%
Estrogen receptor binding + 0.6882 68.82%
Androgen receptor binding + 0.5801 58.01%
Thyroid receptor binding + 0.5902 59.02%
Glucocorticoid receptor binding + 0.6991 69.91%
Aromatase binding + 0.6182 61.82%
PPAR gamma + 0.7781 77.81%
Honey bee toxicity - 0.7130 71.30%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9845 98.45%

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
CHEMBL1951 P21397 Monoamine oxidase A 99.65% 91.49%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.10% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.87% 89.00%
CHEMBL2581 P07339 Cathepsin D 95.44% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.20% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 93.51% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.44% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 90.62% 97.36%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 88.42% 94.80%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 88.12% 90.71%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.03% 99.23%
CHEMBL3194 P02766 Transthyretin 85.76% 90.71%
CHEMBL4208 P20618 Proteasome component C5 85.36% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.94% 95.89%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 84.87% 93.40%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.82% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.73% 96.09%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.12% 95.89%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 83.23% 99.15%

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.
Pterocarpus marsupium

Cross-Links

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PubChem 163193979
LOTUS LTS0050318
wikiData Q105384998