[(5R,5aR,8aS)-8a-hydroxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate

Details

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Internal ID 7487890d-ac5c-46af-9682-08a72125f669
Taxonomy Lignans, neolignans and related compounds > Lignan lactones
IUPAC Name [(5R,5aR,8aS)-8a-hydroxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate
SMILES (Canonical) CC(=O)OC12C(C3=CC4=C(C=C3CC1(COC2=O)O)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
SMILES (Isomeric) CC(=O)O[C@]12[C@@H](C3=CC4=C(C=C3C[C@@]1(COC2=O)O)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
InChI InChI=1S/C24H24O10/c1-12(25)34-24-20(13-5-18(28-2)21(30-4)19(6-13)29-3)15-8-17-16(32-11-33-17)7-14(15)9-23(24,27)10-31-22(24)26/h5-8,20,27H,9-11H2,1-4H3/t20-,23+,24+/m1/s1
InChI Key POIAZYKALWSBHF-QDSKXPNFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C24H24O10
Molecular Weight 472.40 g/mol
Exact Mass 472.13694696 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 1.72
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(5R,5aR,8aS)-8a-hydroxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9826 98.26%
Caco-2 + 0.6032 60.32%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.7265 72.65%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9249 92.49%
OATP1B3 inhibitior + 0.9378 93.78%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9380 93.80%
P-glycoprotein inhibitior + 0.7812 78.12%
P-glycoprotein substrate - 0.7614 76.14%
CYP3A4 substrate + 0.6499 64.99%
CYP2C9 substrate - 0.7923 79.23%
CYP2D6 substrate - 0.8454 84.54%
CYP3A4 inhibition + 0.6915 69.15%
CYP2C9 inhibition + 0.5113 51.13%
CYP2C19 inhibition - 0.7107 71.07%
CYP2D6 inhibition - 0.8959 89.59%
CYP1A2 inhibition - 0.9523 95.23%
CYP2C8 inhibition + 0.4500 45.00%
CYP inhibitory promiscuity - 0.6876 68.76%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.3740 37.40%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.8656 86.56%
Skin irritation - 0.8319 83.19%
Skin corrosion - 0.9504 95.04%
Ames mutagenesis - 0.5000 50.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4354 43.54%
Micronuclear + 0.7733 77.33%
Hepatotoxicity + 0.5052 50.52%
skin sensitisation - 0.7520 75.20%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.7467 74.67%
Acute Oral Toxicity (c) III 0.5694 56.94%
Estrogen receptor binding + 0.9027 90.27%
Androgen receptor binding + 0.6795 67.95%
Thyroid receptor binding + 0.7012 70.12%
Glucocorticoid receptor binding + 0.8202 82.02%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.7636 76.36%
Honey bee toxicity - 0.7153 71.53%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9115 91.15%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.72% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.84% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.59% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.57% 91.11%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 97.32% 96.77%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 92.96% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.33% 89.00%
CHEMBL2581 P07339 Cathepsin D 90.92% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.11% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.38% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.07% 95.56%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 86.84% 94.80%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.22% 97.09%
CHEMBL2413 P32246 C-C chemokine receptor type 1 86.03% 89.50%
CHEMBL4208 P20618 Proteasome component C5 85.86% 90.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.81% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 84.15% 91.19%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.61% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.58% 100.00%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 81.99% 82.67%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 81.06% 80.96%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 80.46% 96.86%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.24% 94.00%

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.
Commiphora erlangeriana

Cross-Links

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PubChem 10863670
LOTUS LTS0017878
wikiData Q105212418