6-o-(4-Methoxybenzoyl)ajugol

Details

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Internal ID 024ec2e3-ef6e-41ac-9640-5a4ae7eb10c4
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-methoxybenzoate
SMILES (Canonical) CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC=C(C=C4)OC)O
SMILES (Isomeric) C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC=C(C=C4)OC)O
InChI InChI=1S/C23H30O11/c1-23(29)9-14(32-20(28)11-3-5-12(30-2)6-4-11)13-7-8-31-21(16(13)23)34-22-19(27)18(26)17(25)15(10-24)33-22/h3-8,13-19,21-22,24-27,29H,9-10H2,1-2H3/t13-,14+,15+,16+,17+,18-,19+,21-,22-,23-/m0/s1
InChI Key TYZRNRJFBKBHEC-ANWGMTKTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H30O11
Molecular Weight 482.50 g/mol
Exact Mass 482.17881177 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.71
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 6

Synonyms

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146564-46-7
4-Methoxybenzoic acid (1S)-1alpha-(beta-D-glucopyranosyloxy)-7alpha-hydroxy-7-methyl-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-yl ester

2D Structure

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2D Structure of 6-o-(4-Methoxybenzoyl)ajugol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7166 71.66%
Caco-2 - 0.8499 84.99%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.5490 54.90%
OATP2B1 inhibitior - 0.8611 86.11%
OATP1B1 inhibitior + 0.8451 84.51%
OATP1B3 inhibitior + 0.9482 94.82%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.5168 51.68%
P-glycoprotein inhibitior - 0.6425 64.25%
P-glycoprotein substrate - 0.6696 66.96%
CYP3A4 substrate + 0.6852 68.52%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8503 85.03%
CYP3A4 inhibition - 0.8048 80.48%
CYP2C9 inhibition - 0.9389 93.89%
CYP2C19 inhibition - 0.9036 90.36%
CYP2D6 inhibition - 0.8755 87.55%
CYP1A2 inhibition - 0.8800 88.00%
CYP2C8 inhibition + 0.5505 55.05%
CYP inhibitory promiscuity - 0.8527 85.27%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5692 56.92%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9613 96.13%
Skin irritation - 0.7630 76.30%
Skin corrosion - 0.9447 94.47%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3621 36.21%
Micronuclear - 0.5526 55.26%
Hepatotoxicity - 0.7564 75.64%
skin sensitisation - 0.8432 84.32%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.7197 71.97%
Acute Oral Toxicity (c) III 0.5395 53.95%
Estrogen receptor binding + 0.8094 80.94%
Androgen receptor binding - 0.5164 51.64%
Thyroid receptor binding + 0.5826 58.26%
Glucocorticoid receptor binding + 0.6108 61.08%
Aromatase binding + 0.6207 62.07%
PPAR gamma + 0.6815 68.15%
Honey bee toxicity - 0.8261 82.61%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.7200 72.00%
Fish aquatic toxicity + 0.7631 76.31%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.09% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.93% 91.11%
CHEMBL4208 P20618 Proteasome component C5 95.25% 90.00%
CHEMBL221 P23219 Cyclooxygenase-1 94.96% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.38% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.05% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.22% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.65% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.48% 99.17%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 87.35% 94.97%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.29% 95.89%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.36% 96.21%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.03% 86.92%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.01% 91.07%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.03% 96.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.86% 95.83%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.66% 96.95%
CHEMBL226 P30542 Adenosine A1 receptor 82.86% 95.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.14% 92.62%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.65% 92.94%
CHEMBL3820 P35557 Hexokinase type IV 81.16% 91.96%
CHEMBL2581 P07339 Cathepsin D 80.62% 98.95%

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.
Handroanthus impetiginosus

Cross-Links

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PubChem 11477204
NPASS NPC235571
LOTUS LTS0243522
wikiData Q105267830