(+)-(7S,8S)-1',4-dihydroxy-3,3',5'-trimethoxy-7',8',9'-trinor-8,4'-oxyneolignan-7,9-diol

Details

Top
Internal ID ca2c5fc0-e38d-4e56-bf1d-9c1167654722
Taxonomy Lignans, neolignans and related compounds
IUPAC Name (1S,2S)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
SMILES (Canonical) COC1=CC(=CC(=C1OC(CO)C(C2=CC(=C(C=C2)O)OC)O)OC)O
SMILES (Isomeric) COC1=CC(=CC(=C1O[C@@H](CO)[C@H](C2=CC(=C(C=C2)O)OC)O)OC)O
InChI InChI=1S/C18H22O8/c1-23-13-6-10(4-5-12(13)21)17(22)16(9-19)26-18-14(24-2)7-11(20)8-15(18)25-3/h4-8,16-17,19-22H,9H2,1-3H3/t16-,17-/m0/s1
InChI Key LFLJRVPKZONUDD-IRXDYDNUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C18H22O8
Molecular Weight 366.40 g/mol
Exact Mass 366.13146766 g/mol
Topological Polar Surface Area (TPSA) 118.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.60
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

Top
(+)-(7S,8S)-1',4-dihydroxy-3,3',5'-trimethoxy-7',8',9'-trinor-8,4'-oxyneolignan-7,9-diol
CHEMBL1797767
Q27136090
(1S,2S)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol

2D Structure

Top
2D Structure of (+)-(7S,8S)-1',4-dihydroxy-3,3',5'-trimethoxy-7',8',9'-trinor-8,4'-oxyneolignan-7,9-diol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9362 93.62%
Caco-2 + 0.6246 62.46%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7486 74.86%
OATP2B1 inhibitior - 0.8570 85.70%
OATP1B1 inhibitior + 0.9085 90.85%
OATP1B3 inhibitior + 0.8787 87.87%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.8155 81.55%
P-glycoprotein inhibitior - 0.5087 50.87%
P-glycoprotein substrate - 0.7792 77.92%
CYP3A4 substrate - 0.5782 57.82%
CYP2C9 substrate - 0.8074 80.74%
CYP2D6 substrate + 0.3769 37.69%
CYP3A4 inhibition - 0.5958 59.58%
CYP2C9 inhibition - 0.7780 77.80%
CYP2C19 inhibition - 0.5233 52.33%
CYP2D6 inhibition - 0.8884 88.84%
CYP1A2 inhibition + 0.5866 58.66%
CYP2C8 inhibition - 0.5735 57.35%
CYP inhibitory promiscuity - 0.5072 50.72%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8723 87.23%
Carcinogenicity (trinary) Non-required 0.7412 74.12%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.7392 73.92%
Skin irritation - 0.8631 86.31%
Skin corrosion - 0.9576 95.76%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5996 59.96%
Micronuclear - 0.5941 59.41%
Hepatotoxicity - 0.6000 60.00%
skin sensitisation - 0.7310 73.10%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity - 0.6125 61.25%
Nephrotoxicity - 0.7547 75.47%
Acute Oral Toxicity (c) III 0.7437 74.37%
Estrogen receptor binding + 0.6692 66.92%
Androgen receptor binding + 0.5590 55.90%
Thyroid receptor binding + 0.7815 78.15%
Glucocorticoid receptor binding + 0.6717 67.17%
Aromatase binding - 0.5745 57.45%
PPAR gamma - 0.6150 61.50%
Honey bee toxicity - 0.9211 92.11%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.7650 76.50%

Targets

Top

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.70% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.06% 91.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 94.22% 99.15%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 93.56% 89.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.07% 99.17%
CHEMBL2581 P07339 Cathepsin D 89.91% 98.95%
CHEMBL4208 P20618 Proteasome component C5 89.46% 90.00%
CHEMBL1255126 O15151 Protein Mdm4 87.90% 90.20%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.64% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.46% 95.56%
CHEMBL2535 P11166 Glucose transporter 87.02% 98.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.91% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.26% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.57% 96.00%

Plants that contains it

Top
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

Top
PubChem 53356207
LOTUS LTS0164403
wikiData Q27136090