(-)-(7''S,8''S)-4'',5,7-trihydroxy-3',5'-dimethoxy-4',8''-oxyflavonolignan-7'',9''-diol

Details

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Internal ID 24030665-6837-4a0f-9016-f6fee50330a0
Taxonomy Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
IUPAC Name 2-[4-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-5,7-dihydroxychromen-4-one
SMILES (Canonical) COC1=CC(=CC(=C1OC(CO)C(C2=CC=C(C=C2)O)O)OC)C3=CC(=O)C4=C(C=C(C=C4O3)O)O
SMILES (Isomeric) COC1=CC(=CC(=C1O[C@@H](CO)[C@H](C2=CC=C(C=C2)O)O)OC)C3=CC(=O)C4=C(C=C(C=C4O3)O)O
InChI InChI=1S/C26H24O10/c1-33-21-7-14(19-11-18(31)24-17(30)9-16(29)10-20(24)35-19)8-22(34-2)26(21)36-23(12-27)25(32)13-3-5-15(28)6-4-13/h3-11,23,25,27-30,32H,12H2,1-2H3/t23-,25-/m0/s1
InChI Key XWGDMVNWFZRSNF-ZCYQVOJMSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C26H24O10
Molecular Weight 496.50 g/mol
Exact Mass 496.13694696 g/mol
Topological Polar Surface Area (TPSA) 155.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 3.07
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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(-)-(7''S,8''S)-4'',5,7-trihydroxy-3',5'-dimethoxy-4',8''-oxyflavonolignan-7'',9''-diol
CHEMBL1797781
Q27136112
2-(4-{[(1S,2S)-1,3-dihydroxy-1-(4-hydroxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

2D Structure

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2D Structure of (-)-(7''S,8''S)-4'',5,7-trihydroxy-3',5'-dimethoxy-4',8''-oxyflavonolignan-7'',9''-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9207 92.07%
Caco-2 - 0.7815 78.15%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.6395 63.95%
OATP2B1 inhibitior - 0.5638 56.38%
OATP1B1 inhibitior + 0.8939 89.39%
OATP1B3 inhibitior + 0.8001 80.01%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6872 68.72%
P-glycoprotein inhibitior + 0.8757 87.57%
P-glycoprotein substrate + 0.5309 53.09%
CYP3A4 substrate + 0.6015 60.15%
CYP2C9 substrate - 0.8000 80.00%
CYP2D6 substrate - 0.8193 81.93%
CYP3A4 inhibition - 0.5524 55.24%
CYP2C9 inhibition - 0.5942 59.42%
CYP2C19 inhibition - 0.5953 59.53%
CYP2D6 inhibition - 0.9006 90.06%
CYP1A2 inhibition - 0.6120 61.20%
CYP2C8 inhibition + 0.7688 76.88%
CYP inhibitory promiscuity + 0.6697 66.97%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7578 75.78%
Eye corrosion - 0.9851 98.51%
Eye irritation - 0.8623 86.23%
Skin irritation - 0.8192 81.92%
Skin corrosion - 0.9608 96.08%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4175 41.75%
Micronuclear + 0.6959 69.59%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.9046 90.46%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.8033 80.33%
Acute Oral Toxicity (c) III 0.6718 67.18%
Estrogen receptor binding + 0.8256 82.56%
Androgen receptor binding + 0.8456 84.56%
Thyroid receptor binding + 0.6665 66.65%
Glucocorticoid receptor binding + 0.8189 81.89%
Aromatase binding + 0.5385 53.85%
PPAR gamma + 0.6879 68.79%
Honey bee toxicity - 0.7594 75.94%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7700 77.00%
Fish aquatic toxicity - 0.3805 38.05%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.70% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.63% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.56% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.60% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.00% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.92% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 92.77% 99.15%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.86% 96.09%
CHEMBL3194 P02766 Transthyretin 90.74% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.54% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.79% 86.33%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.66% 93.99%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.74% 94.45%
CHEMBL242 Q92731 Estrogen receptor beta 86.14% 98.35%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.54% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 84.54% 94.73%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 84.40% 90.71%
CHEMBL4208 P20618 Proteasome component C5 83.30% 90.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.23% 95.89%
CHEMBL1255126 O15151 Protein Mdm4 80.16% 90.20%

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.
Bambusa emeiensis

Cross-Links

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PubChem 45103834
LOTUS LTS0056844
wikiData Q27136112