2-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Details

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Internal ID c006b2f4-2327-4088-95fe-5edd6f3dbbe5
Taxonomy Lignans, neolignans and related compounds > Coumarinolignans
IUPAC Name 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
SMILES (Canonical) COC1=CC(=CC(=C1O)OC)C2C(OC3=C(C=C4C=CC(=O)OC4=C3O2)OC)CO
SMILES (Isomeric) COC1=CC(=CC(=C1O)OC)C2C(OC3=C(C=C4C=CC(=O)OC4=C3O2)OC)CO
InChI InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-20-14(27-3)6-10-4-5-16(23)29-19(10)21(20)30-18/h4-8,15,18,22,24H,9H2,1-3H3
InChI Key IXSZNNRKGDOXQI-UHFFFAOYSA-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) 113.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.40
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9099 90.99%
Caco-2 - 0.5763 57.63%
Blood Brain Barrier - 0.8750 87.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7924 79.24%
OATP2B1 inhibitior - 0.8613 86.13%
OATP1B1 inhibitior + 0.8062 80.62%
OATP1B3 inhibitior - 0.4172 41.72%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.8174 81.74%
P-glycoprotein inhibitior + 0.8443 84.43%
P-glycoprotein substrate - 0.8029 80.29%
CYP3A4 substrate - 0.5000 50.00%
CYP2C9 substrate - 0.8212 82.12%
CYP2D6 substrate - 0.8135 81.35%
CYP3A4 inhibition - 0.9029 90.29%
CYP2C9 inhibition - 0.7504 75.04%
CYP2C19 inhibition - 0.8518 85.18%
CYP2D6 inhibition - 0.9343 93.43%
CYP1A2 inhibition - 0.9270 92.70%
CYP2C8 inhibition - 0.5729 57.29%
CYP inhibitory promiscuity + 0.5000 50.00%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6663 66.63%
Eye corrosion - 0.9866 98.66%
Eye irritation - 0.7973 79.73%
Skin irritation - 0.8543 85.43%
Skin corrosion - 0.9774 97.74%
Ames mutagenesis - 0.6914 69.14%
Human Ether-a-go-go-Related Gene inhibition - 0.7625 76.25%
Micronuclear + 0.6733 67.33%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.9235 92.35%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.7562 75.62%
Acute Oral Toxicity (c) III 0.6358 63.58%
Estrogen receptor binding + 0.8911 89.11%
Androgen receptor binding + 0.7369 73.69%
Thyroid receptor binding + 0.5524 55.24%
Glucocorticoid receptor binding + 0.8926 89.26%
Aromatase binding - 0.5071 50.71%
PPAR gamma + 0.6480 64.80%
Honey bee toxicity - 0.8384 83.84%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.7363 73.63%

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 98.78% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.09% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 93.26% 94.00%
CHEMBL2581 P07339 Cathepsin D 92.13% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.68% 95.56%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.47% 86.92%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.78% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.83% 99.23%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.36% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.86% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.47% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 82.20% 94.73%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.69% 99.15%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.44% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.42% 97.09%

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.
Aquilaria malaccensis
Cleome viscosa
Daphne mucronata
Grewia bilamellata
Hibiscus syriacus
Zanthoxylum avicennae

Cross-Links

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PubChem 13965873
LOTUS LTS0025912
wikiData Q105122464