(2R,3R,4R,5S,6R)-5-[[(3S,3aR,4S,6R,6aS)-3,6-bis(1,3-benzodioxol-5-yl)-6a-hydroxy-3,3a,4,6-tetrahydro-1H-furo[3,4-c]furan-4-yl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol

Details

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Internal ID 4e85de6e-f2f0-49d1-8835-03c9e5301e76
Taxonomy Lignans, neolignans and related compounds > Furanoid lignans
IUPAC Name (2R,3R,4R,5S,6R)-5-[[(3S,3aR,4S,6R,6aS)-3,6-bis(1,3-benzodioxol-5-yl)-6a-hydroxy-3,3a,4,6-tetrahydro-1H-furo[3,4-c]furan-4-yl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol
SMILES (Canonical) C1C2(C(C(O1)C3=CC4=C(C=C3)OCO4)C(OC2C5=CC6=C(C=C5)OCO6)OC7C(OC(C(C7O)O)O)CO)O
SMILES (Isomeric) C1[C@]2([C@@H]([C@H](O1)C3=CC4=C(C=C3)OCO4)[C@H](O[C@@H]2C5=CC6=C(C=C5)OCO6)O[C@@H]7[C@H](O[C@H]([C@@H]([C@H]7O)O)O)CO)O
InChI InChI=1S/C26H28O13/c27-7-17-22(19(28)20(29)24(30)37-17)38-25-18-21(11-1-3-13-15(5-11)35-9-33-13)32-8-26(18,31)23(39-25)12-2-4-14-16(6-12)36-10-34-14/h1-6,17-25,27-31H,7-10H2/t17-,18+,19-,20-,21-,22-,23-,24-,25+,26-/m1/s1
InChI Key OLWYIRWEJGBJFE-JNBNCJMSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H28O13
Molecular Weight 548.50 g/mol
Exact Mass 548.15299094 g/mol
Topological Polar Surface Area (TPSA) 175.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -0.52
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4R,5S,6R)-5-[[(3S,3aR,4S,6R,6aS)-3,6-bis(1,3-benzodioxol-5-yl)-6a-hydroxy-3,3a,4,6-tetrahydro-1H-furo[3,4-c]furan-4-yl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5469 54.69%
Caco-2 - 0.8646 86.46%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.5485 54.85%
OATP2B1 inhibitior - 0.8550 85.50%
OATP1B1 inhibitior + 0.8892 88.92%
OATP1B3 inhibitior + 0.9447 94.47%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.6368 63.68%
P-glycoprotein inhibitior - 0.4689 46.89%
P-glycoprotein substrate - 0.8096 80.96%
CYP3A4 substrate + 0.6136 61.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8258 82.58%
CYP3A4 inhibition - 0.5305 53.05%
CYP2C9 inhibition - 0.8689 86.89%
CYP2C19 inhibition - 0.7405 74.05%
CYP2D6 inhibition - 0.7222 72.22%
CYP1A2 inhibition - 0.8837 88.37%
CYP2C8 inhibition - 0.6369 63.69%
CYP inhibitory promiscuity - 0.5146 51.46%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4794 47.94%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9154 91.54%
Skin irritation - 0.7923 79.23%
Skin corrosion - 0.9421 94.21%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7868 78.68%
Micronuclear + 0.6659 66.59%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.8622 86.22%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.6305 63.05%
Acute Oral Toxicity (c) III 0.5908 59.08%
Estrogen receptor binding + 0.7895 78.95%
Androgen receptor binding + 0.7154 71.54%
Thyroid receptor binding + 0.5382 53.82%
Glucocorticoid receptor binding - 0.5316 53.16%
Aromatase binding + 0.6061 60.61%
PPAR gamma + 0.7365 73.65%
Honey bee toxicity - 0.7084 70.84%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.6835 68.35%

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 99.36% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.92% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 95.45% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.75% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.28% 94.45%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 92.57% 96.77%
CHEMBL2581 P07339 Cathepsin D 91.20% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.15% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.76% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.50% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.02% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.59% 100.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 83.68% 89.67%
CHEMBL1951 P21397 Monoamine oxidase A 82.42% 91.49%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.43% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.40% 94.00%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 80.71% 85.49%

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.
Gmelina arborea

Cross-Links

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PubChem 162858102
LOTUS LTS0101148
wikiData Q105194171