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(3R,9aR)-5alpha-[(E)-3-Phenylpropenoyloxy]-6beta-(benzoyloxy)-7alpha-acetoxy-3,4,5,5a,6,7,8,9-octahydro-2,2,5abeta,9-tetramethyl-8alpha,9alpha-dihydroxy-2H-3,9a-methano-1-benzooxepin

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 9651ae59-5fe7-4fba-9e00-fecccc985dcd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
IUPAC Name [(1R,2S,3S,4R,5R,6R,7S,9R)-4-acetyloxy-2,3-dihydroxy-2,6,10,10-tetramethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] benzoate
SMILES (Canonical) CC(=O)OC1C(C(C23CC(CC(C2(C1OC(=O)C4=CC=CC=C4)C)OC(=O)C=CC5=CC=CC=C5)C(O3)(C)C)(C)O)O
SMILES (Isomeric) CC(=O)O[C@@H]1[C@@H]([C@]([C@@]23C[C@@H](C[C@@H]([C@@]2([C@H]1OC(=O)C4=CC=CC=C4)C)OC(=O)/C=C/C5=CC=CC=C5)C(O3)(C)C)(C)O)O
InChI InChI=1S/C33H38O9/c1-20(34)39-26-27(36)32(5,38)33-19-23(30(2,3)42-33)18-24(40-25(35)17-16-21-12-8-6-9-13-21)31(33,4)28(26)41-29(37)22-14-10-7-11-15-22/h6-17,23-24,26-28,36,38H,18-19H2,1-5H3/b17-16+/t23-,24+,26-,27+,28+,31-,32+,33-/m1/s1
InChI Key VGUVQKDLHHRXNF-SQFMQKTMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H38O9
Molecular Weight 578.60 g/mol
Exact Mass 578.25158279 g/mol
Topological Polar Surface Area (TPSA) 129.00 Ų
XlogP 4.10
Atomic LogP (AlogP) 3.86
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,9aR)-5alpha-[(E)-3-Phenylpropenoyloxy]-6beta-(benzoyloxy)-7alpha-acetoxy-3,4,5,5a,6,7,8,9-octahydro-2,2,5abeta,9-tetramethyl-8alpha,9alpha-dihydroxy-2H-3,9a-methano-1-benzooxepin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9582 95.82%
Caco-2 - 0.7769 77.69%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.7117 71.17%
OATP2B1 inhibitior - 0.8585 85.85%
OATP1B1 inhibitior + 0.8491 84.91%
OATP1B3 inhibitior - 0.2386 23.86%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9620 96.20%
P-glycoprotein inhibitior + 0.8491 84.91%
P-glycoprotein substrate - 0.5389 53.89%
CYP3A4 substrate + 0.6739 67.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8777 87.77%
CYP3A4 inhibition - 0.7653 76.53%
CYP2C9 inhibition - 0.8048 80.48%
CYP2C19 inhibition - 0.7322 73.22%
CYP2D6 inhibition - 0.9419 94.19%
CYP1A2 inhibition - 0.7266 72.66%
CYP2C8 inhibition + 0.8024 80.24%
CYP inhibitory promiscuity - 0.8852 88.52%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5140 51.40%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9125 91.25%
Skin irritation - 0.7249 72.49%
Skin corrosion - 0.9229 92.29%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8204 82.04%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.5791 57.91%
skin sensitisation - 0.8043 80.43%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.7102 71.02%
Acute Oral Toxicity (c) III 0.3629 36.29%
Estrogen receptor binding + 0.7602 76.02%
Androgen receptor binding + 0.6789 67.89%
Thyroid receptor binding + 0.6479 64.79%
Glucocorticoid receptor binding + 0.6900 69.00%
Aromatase binding + 0.6224 62.24%
PPAR gamma + 0.7081 70.81%
Honey bee toxicity - 0.8050 80.50%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5255 52.55%
Fish aquatic toxicity + 0.9974 99.74%

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
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.85% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.24% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 95.69% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.83% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.79% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.22% 96.00%
CHEMBL1951 P21397 Monoamine oxidase A 90.53% 91.49%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 89.88% 95.50%
CHEMBL3192 Q9BY41 Histone deacetylase 8 88.88% 93.99%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 88.74% 94.08%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.61% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.11% 99.23%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 86.65% 94.62%
CHEMBL4208 P20618 Proteasome component C5 86.46% 90.00%
CHEMBL5028 O14672 ADAM10 86.41% 97.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.32% 97.14%
CHEMBL2581 P07339 Cathepsin D 85.85% 98.95%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 84.20% 83.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.15% 97.09%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 83.76% 89.44%
CHEMBL340 P08684 Cytochrome P450 3A4 82.07% 91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 46185592
LOTUS LTS0041239
wikiData Q105286088