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[(1S,2S,5S,6S,7R,8S,9S,12R)-5-acetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-8-[(Z)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate

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 5c550c81-1603-4990-833b-608df71b1236
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
IUPAC Name [(1S,2S,5S,6S,7R,8S,9S,12R)-5-acetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-8-[(Z)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate
SMILES (Canonical) CC(=O)OC1CCC(C23C1(C(C(C(C2O)C(O3)(C)C)OC(=O)C=CC4=CC=CC=C4)OC(=O)C5=CC=CC=C5)C)(C)O
SMILES (Isomeric) CC(=O)O[C@H]1CC[C@]([C@]23[C@@]1([C@H]([C@H]([C@H]([C@H]2O)C(O3)(C)C)OC(=O)/C=C\C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)C)(C)O
InChI InChI=1S/C33H38O9/c1-20(34)39-23-18-19-31(4,38)33-27(36)25(30(2,3)42-33)26(40-24(35)17-16-21-12-8-6-9-13-21)28(32(23,33)5)41-29(37)22-14-10-7-11-15-22/h6-17,23,25-28,36,38H,18-19H2,1-5H3/b17-16-/t23-,25+,26-,27+,28-,31-,32-,33-/m0/s1
InChI Key KAPQKCUDPVRZEX-TUCWLARQSA-N
Popularity 1 reference 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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[Acetoxy-dihydroxy-tetramethyl-[(Z)-3-phenylprop-2-enoyl]oxy-[?]yl] benzoate

2D Structure

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2D Structure of [(1S,2S,5S,6S,7R,8S,9S,12R)-5-acetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-8-[(Z)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9561 95.61%
Caco-2 - 0.7765 77.65%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.5895 58.95%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8366 83.66%
OATP1B3 inhibitior + 0.8675 86.75%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8071 80.71%
BSEP inhibitior + 0.9664 96.64%
P-glycoprotein inhibitior + 0.8737 87.37%
P-glycoprotein substrate - 0.5973 59.73%
CYP3A4 substrate + 0.6960 69.60%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8778 87.78%
CYP3A4 inhibition + 0.6877 68.77%
CYP2C9 inhibition - 0.7152 71.52%
CYP2C19 inhibition - 0.7904 79.04%
CYP2D6 inhibition - 0.9227 92.27%
CYP1A2 inhibition - 0.7503 75.03%
CYP2C8 inhibition + 0.8424 84.24%
CYP inhibitory promiscuity - 0.8344 83.44%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4936 49.36%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9134 91.34%
Skin irritation - 0.6367 63.67%
Skin corrosion - 0.8721 87.21%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8292 82.92%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.6291 62.91%
skin sensitisation - 0.8310 83.10%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6649 66.49%
Acute Oral Toxicity (c) III 0.4426 44.26%
Estrogen receptor binding + 0.7990 79.90%
Androgen receptor binding + 0.7131 71.31%
Thyroid receptor binding + 0.6678 66.78%
Glucocorticoid receptor binding + 0.7218 72.18%
Aromatase binding + 0.6278 62.78%
PPAR gamma + 0.7347 73.47%
Honey bee toxicity - 0.7718 77.18%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5045 50.45%
Fish aquatic toxicity + 0.9921 99.21%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4302 P08183 P-glycoprotein 1 280 nM
 Ki
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.69% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.15% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.99% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 94.15% 90.17%
CHEMBL3192 Q9BY41 Histone deacetylase 8 93.29% 93.99%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.45% 95.56%
CHEMBL2581 P07339 Cathepsin D 90.87% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.54% 89.00%
CHEMBL4040 P28482 MAP kinase ERK2 89.28% 83.82%
CHEMBL5028 O14672 ADAM10 88.69% 97.50%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 88.59% 89.44%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.41% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.55% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.39% 99.23%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 86.12% 83.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.36% 95.89%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.34% 81.11%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.29% 93.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.40% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.36% 92.62%
CHEMBL340 P08684 Cytochrome P450 3A4 83.28% 91.19%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.10% 97.14%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.30% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.00% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.83% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.34% 85.14%

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.
There are no matching plants.

Cross-Links

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PubChem 44598213
NPASS NPC70403
LOTUS LTS0016503
wikiData Q105137948