(-)-(7'S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one

Details

Top
Internal ID 9bfb3d21-1903-49bb-b5c1-42a1ad3aa74f
Taxonomy Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,9-epoxylignans
IUPAC Name (4-hydroxy-3,5-dimethoxyphenyl)-[(3S,4R,5S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methanone
SMILES (Canonical) COC1=CC(=CC(=C1O)OC)C2C(C(CO2)C(=O)C3=CC(=C(C(=C3)OC)O)OC)CO
SMILES (Isomeric) COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]([C@@H](CO2)C(=O)C3=CC(=C(C(=C3)OC)O)OC)CO
InChI InChI=1S/C22H26O9/c1-27-15-5-11(6-16(28-2)20(15)25)19(24)14-10-31-22(13(14)9-23)12-7-17(29-3)21(26)18(8-12)30-4/h5-8,13-14,22-23,25-26H,9-10H2,1-4H3/t13-,14+,22+/m0/s1
InChI Key ANCVHDRNDJRUOT-DJEJFTSGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C22H26O9
Molecular Weight 434.40 g/mol
Exact Mass 434.15768240 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 2.31
H-Bond Acceptor 9
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

Top
(-)-(7'S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one
CHEMBL1797772
Q27136095
(4-hydroxy-3,5-dimethoxyphenyl)[(3S,4R,5S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl]methanone

2D Structure

Top
2D Structure of (-)-(7'S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9417 94.17%
Caco-2 + 0.5117 51.17%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.9052 90.52%
OATP2B1 inhibitior - 0.8585 85.85%
OATP1B1 inhibitior + 0.7939 79.39%
OATP1B3 inhibitior + 0.9259 92.59%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6211 62.11%
P-glycoprotein inhibitior + 0.6473 64.73%
P-glycoprotein substrate - 0.6720 67.20%
CYP3A4 substrate + 0.5224 52.24%
CYP2C9 substrate - 0.8063 80.63%
CYP2D6 substrate - 0.7556 75.56%
CYP3A4 inhibition + 0.7065 70.65%
CYP2C9 inhibition + 0.6351 63.51%
CYP2C19 inhibition + 0.7734 77.34%
CYP2D6 inhibition - 0.9020 90.20%
CYP1A2 inhibition + 0.5334 53.34%
CYP2C8 inhibition + 0.6579 65.79%
CYP inhibitory promiscuity + 0.9088 90.88%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.6148 61.48%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.8064 80.64%
Skin irritation - 0.8569 85.69%
Skin corrosion - 0.9707 97.07%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.5100 51.00%
Hepatotoxicity - 0.6625 66.25%
skin sensitisation - 0.8615 86.15%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.8730 87.30%
Acute Oral Toxicity (c) III 0.6248 62.48%
Estrogen receptor binding + 0.8648 86.48%
Androgen receptor binding + 0.7554 75.54%
Thyroid receptor binding + 0.6884 68.84%
Glucocorticoid receptor binding + 0.8019 80.19%
Aromatase binding - 0.6035 60.35%
PPAR gamma - 0.5333 53.33%
Honey bee toxicity - 0.8902 89.02%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity - 0.7933 79.33%
Fish aquatic toxicity + 0.9701 97.01%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.49% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.04% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.91% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.81% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.02% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.26% 85.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.11% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.08% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.48% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.31% 97.09%
CHEMBL2535 P11166 Glucose transporter 81.86% 98.75%
CHEMBL2581 P07339 Cathepsin D 81.41% 98.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.11% 92.94%
CHEMBL340 P08684 Cytochrome P450 3A4 81.08% 91.19%

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 53356211
LOTUS LTS0272838
wikiData Q27136095