(1R,2S)-1-(3,4-dihydroxyphenyl)-3-[[(2R,3R,4R,5R)-5-(2,3-dihydroxypropyl)-3,4-dihydroxyoxolan-2-yl]methoxycarbonyl]-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid

Details

Top
Internal ID 5c1b7732-7709-40db-9d07-5d64a862dd3e
Taxonomy Lignans, neolignans and related compounds > Lignan glycosides
IUPAC Name (1R,2S)-1-(3,4-dihydroxyphenyl)-3-[[(2R,3R,4R,5R)-5-(2,3-dihydroxypropyl)-3,4-dihydroxyoxolan-2-yl]methoxycarbonyl]-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
SMILES (Canonical) C1=CC(=C(C=C1C2C(C(=CC3=CC(=C(C=C23)O)O)C(=O)OCC4C(C(C(O4)CC(CO)O)O)O)C(=O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1[C@H]2[C@@H](C(=CC3=CC(=C(C=C23)O)O)C(=O)OC[C@@H]4[C@@H]([C@H]([C@H](O4)CC(CO)O)O)O)C(=O)O)O)O
InChI InChI=1S/C26H28O13/c27-8-12(28)6-19-23(33)24(34)20(39-19)9-38-26(37)14-3-11-5-17(31)18(32)7-13(11)21(22(14)25(35)36)10-1-2-15(29)16(30)4-10/h1-5,7,12,19-24,27-34H,6,8-9H2,(H,35,36)/t12?,19-,20-,21-,22-,23+,24+/m1/s1
InChI Key SPXXGPHPASGHLM-DHYIGXGMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C26H28O13
Molecular Weight 548.50 g/mol
Exact Mass 548.15299094 g/mol
Topological Polar Surface Area (TPSA) 235.00 Ų
XlogP -0.60
Atomic LogP (AlogP) -0.49
H-Bond Acceptor 12
H-Bond Donor 9
Rotatable Bonds 8

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1R,2S)-1-(3,4-dihydroxyphenyl)-3-[[(2R,3R,4R,5R)-5-(2,3-dihydroxypropyl)-3,4-dihydroxyoxolan-2-yl]methoxycarbonyl]-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9509 95.09%
Caco-2 - 0.9304 93.04%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.7506 75.06%
OATP2B1 inhibitior - 0.7026 70.26%
OATP1B1 inhibitior + 0.8681 86.81%
OATP1B3 inhibitior + 0.9539 95.39%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.8269 82.69%
P-glycoprotein inhibitior - 0.5649 56.49%
P-glycoprotein substrate - 0.7237 72.37%
CYP3A4 substrate + 0.6216 62.16%
CYP2C9 substrate - 0.7958 79.58%
CYP2D6 substrate - 0.8530 85.30%
CYP3A4 inhibition - 0.8844 88.44%
CYP2C9 inhibition - 0.6452 64.52%
CYP2C19 inhibition - 0.5966 59.66%
CYP2D6 inhibition - 0.8682 86.82%
CYP1A2 inhibition - 0.5530 55.30%
CYP2C8 inhibition + 0.6245 62.45%
CYP inhibitory promiscuity - 0.6833 68.33%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6246 62.46%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.8961 89.61%
Skin irritation - 0.8126 81.26%
Skin corrosion - 0.9521 95.21%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4183 41.83%
Micronuclear + 0.5974 59.74%
Hepatotoxicity - 0.7375 73.75%
skin sensitisation - 0.7895 78.95%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.9009 90.09%
Acute Oral Toxicity (c) III 0.4513 45.13%
Estrogen receptor binding + 0.8176 81.76%
Androgen receptor binding + 0.5976 59.76%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.5728 57.28%
Aromatase binding - 0.5383 53.83%
PPAR gamma + 0.6743 67.43%
Honey bee toxicity - 0.7942 79.42%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.7550 75.50%
Fish aquatic toxicity + 0.9897 98.97%

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 99.53% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.47% 96.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.44% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.97% 94.45%
CHEMBL1951 P21397 Monoamine oxidase A 91.73% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.92% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 89.83% 95.93%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.43% 86.92%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.54% 99.17%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 87.19% 89.67%
CHEMBL2581 P07339 Cathepsin D 86.83% 98.95%
CHEMBL3194 P02766 Transthyretin 85.82% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.35% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.78% 85.14%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 82.80% 83.00%
CHEMBL3401 O75469 Pregnane X receptor 81.25% 94.73%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.95% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.22% 86.33%

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.
Bazzania trilobata

Cross-Links

Top
PubChem 100918689
LOTUS LTS0016362
wikiData Q105257670