(2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

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Internal ID 545149b8-9ca3-44d1-b99e-5d03239e96d6
Taxonomy Lignans, neolignans and related compounds > Lignan glycosides
IUPAC Name (2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(CC3=CC(=C(C(=C3C2C4=CC(=C(C=C4)O)OC)OC)O)OC)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@H]2[C@@H](CC3=CC(=C(C(=C3[C@@H]2C4=CC(=C(C=C4)O)OC)OC)O)OC)CO)O)O)O
InChI InChI=1S/C27H36O11/c1-12-22(30)24(32)25(33)27(38-12)37-11-16-15(10-28)7-14-9-19(35-3)23(31)26(36-4)21(14)20(16)13-5-6-17(29)18(8-13)34-2/h5-6,8-9,12,15-16,20,22,24-25,27-33H,7,10-11H2,1-4H3/t12-,15-,16-,20+,22-,24+,25+,27+/m0/s1
InChI Key NAPVUVFFKYNLSM-CLQINZGASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H36O11
Molecular Weight 536.60 g/mol
Exact Mass 536.22576196 g/mol
Topological Polar Surface Area (TPSA) 168.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 0.88
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5461 54.61%
Caco-2 - 0.7905 79.05%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.5570 55.70%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8715 87.15%
OATP1B3 inhibitior + 0.9588 95.88%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.5347 53.47%
P-glycoprotein inhibitior - 0.5570 55.70%
P-glycoprotein substrate - 0.5435 54.35%
CYP3A4 substrate + 0.6148 61.48%
CYP2C9 substrate - 0.7915 79.15%
CYP2D6 substrate - 0.7682 76.82%
CYP3A4 inhibition - 0.8845 88.45%
CYP2C9 inhibition - 0.8487 84.87%
CYP2C19 inhibition - 0.7730 77.30%
CYP2D6 inhibition - 0.9155 91.55%
CYP1A2 inhibition - 0.6768 67.68%
CYP2C8 inhibition + 0.6703 67.03%
CYP inhibitory promiscuity - 0.5472 54.72%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6722 67.22%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.9365 93.65%
Skin irritation - 0.8341 83.41%
Skin corrosion - 0.9556 95.56%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6995 69.95%
Micronuclear + 0.6300 63.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.9218 92.18%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.9571 95.71%
Acute Oral Toxicity (c) III 0.6180 61.80%
Estrogen receptor binding + 0.7592 75.92%
Androgen receptor binding + 0.6486 64.86%
Thyroid receptor binding + 0.5977 59.77%
Glucocorticoid receptor binding + 0.6495 64.95%
Aromatase binding - 0.4845 48.45%
PPAR gamma + 0.5740 57.40%
Honey bee toxicity - 0.8312 83.12%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9110 91.10%

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 99.84% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.60% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.67% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.49% 86.33%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 91.26% 89.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.14% 94.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.47% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.11% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.42% 99.17%
CHEMBL2581 P07339 Cathepsin D 88.14% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 86.49% 94.73%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.05% 92.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.89% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.67% 95.89%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.23% 99.15%
CHEMBL1951 P21397 Monoamine oxidase A 85.13% 91.49%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.76% 85.14%
CHEMBL4208 P20618 Proteasome component C5 84.48% 90.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 84.36% 97.36%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.43% 96.00%
CHEMBL4306 P22460 Voltage-gated potassium channel subunit Kv1.5 81.24% 94.03%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.41% 95.56%

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.
Aconitum burnatii

Cross-Links

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PubChem 101245340
NPASS NPC148643