1-acetyloxy-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylic acid

Details

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Internal ID 4e98f512-1092-4cca-963a-0767cf8287c1
Taxonomy Organoheterocyclic compounds > Benzofurans > Flavaglines
IUPAC Name 1-acetyloxy-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylic acid
SMILES (Canonical) CC(=O)OC1C(C(C2(C1(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5)C(=O)O
SMILES (Isomeric) CC(=O)OC1C(C(C2(C1(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5)C(=O)O
InChI InChI=1S/C29H28O9/c1-16(30)37-26-23(27(31)32)24(17-8-6-5-7-9-17)29(18-10-12-19(34-2)13-11-18)28(26,33)25-21(36-4)14-20(35-3)15-22(25)38-29/h5-15,23-24,26,33H,1-4H3,(H,31,32)
InChI Key XGFHSPORRWHGPC-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H28O9
Molecular Weight 520.50 g/mol
Exact Mass 520.17333247 g/mol
Topological Polar Surface Area (TPSA) 121.00 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.62
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 1-acetyloxy-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9777 97.77%
Caco-2 - 0.5808 58.08%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7889 78.89%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8798 87.98%
OATP1B3 inhibitior - 0.2591 25.91%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9253 92.53%
P-glycoprotein inhibitior + 0.8689 86.89%
P-glycoprotein substrate - 0.7721 77.21%
CYP3A4 substrate + 0.6508 65.08%
CYP2C9 substrate + 0.6069 60.69%
CYP2D6 substrate - 0.8388 83.88%
CYP3A4 inhibition - 0.7104 71.04%
CYP2C9 inhibition - 0.6344 63.44%
CYP2C19 inhibition - 0.9277 92.77%
CYP2D6 inhibition - 0.9337 93.37%
CYP1A2 inhibition - 0.8991 89.91%
CYP2C8 inhibition + 0.7909 79.09%
CYP inhibitory promiscuity - 0.5796 57.96%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9443 94.43%
Carcinogenicity (trinary) Danger 0.3592 35.92%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.7669 76.69%
Skin irritation - 0.8028 80.28%
Skin corrosion - 0.9596 95.96%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4421 44.21%
Micronuclear + 0.8000 80.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.9354 93.54%
Respiratory toxicity - 0.6000 60.00%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity + 0.7436 74.36%
Acute Oral Toxicity (c) III 0.4441 44.41%
Estrogen receptor binding + 0.7309 73.09%
Androgen receptor binding + 0.7868 78.68%
Thyroid receptor binding + 0.5676 56.76%
Glucocorticoid receptor binding + 0.6918 69.18%
Aromatase binding - 0.6008 60.08%
PPAR gamma + 0.6583 65.83%
Honey bee toxicity - 0.8293 82.93%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5249 52.49%
Fish aquatic toxicity + 0.9841 98.41%

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 98.36% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.46% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.57% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.15% 86.33%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 90.34% 89.44%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 90.33% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 90.00% 91.19%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.57% 97.14%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 89.37% 94.08%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.23% 85.14%
CHEMBL2581 P07339 Cathepsin D 87.55% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.62% 92.62%
CHEMBL4208 P20618 Proteasome component C5 86.42% 90.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.53% 94.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.26% 96.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 84.60% 94.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.51% 99.23%
CHEMBL2535 P11166 Glucose transporter 82.40% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.45% 91.07%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 80.99% 100.00%

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.
Aglaia rubiginosa

Cross-Links

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PubChem 75048987
LOTUS LTS0254991
wikiData Q105327567