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[(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2S)-2-acetyloxy-2-methylbutanoate

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 5846869e-fd49-4f0d-97dc-4d86351985f6
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
IUPAC Name [(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2S)-2-acetyloxy-2-methylbutanoate
SMILES (Canonical) CCC(C)(C(=O)OC1C2C3(C(C(C4C2(CO3)C(CC5C4(C(C(=O)C=C5C)O)C)OC1=O)O)O)C)OC(=O)C
SMILES (Isomeric) CC[C@@](C)(C(=O)O[C@@H]1[C@H]2[C@]3([C@H]([C@@H]([C@H]4[C@@]2(CO3)[C@@H](C[C@@H]5[C@@]4([C@@H](C(=O)C=C5C)O)C)OC1=O)O)O)C)OC(=O)C
InChI InChI=1S/C27H36O11/c1-7-24(4,38-12(3)28)23(34)37-17-19-26(6)21(32)16(30)18-25(5)13(11(2)8-14(29)20(25)31)9-15(36-22(17)33)27(18,19)10-35-26/h8,13,15-21,30-32H,7,9-10H2,1-6H3/t13-,15+,16+,17+,18+,19-,20+,21-,24-,25-,26-,27+/m0/s1
InChI Key FXMIXHYJCNZLFE-ZXNWRKIUSA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C27H36O11
Molecular Weight 536.60 g/mol
Exact Mass 536.22576196 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP 0.20
Atomic LogP (AlogP) 0.21
H-Bond Acceptor 11
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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CHEMBL444177

2D Structure

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2D Structure of [(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2S)-2-acetyloxy-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9444 94.44%
Caco-2 - 0.7855 78.55%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7435 74.35%
OATP2B1 inhibitior - 0.8606 86.06%
OATP1B1 inhibitior + 0.8368 83.68%
OATP1B3 inhibitior + 0.9463 94.63%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9067 90.67%
P-glycoprotein inhibitior + 0.6940 69.40%
P-glycoprotein substrate + 0.8597 85.97%
CYP3A4 substrate + 0.7143 71.43%
CYP2C9 substrate - 0.8253 82.53%
CYP2D6 substrate - 0.8954 89.54%
CYP3A4 inhibition - 0.6906 69.06%
CYP2C9 inhibition - 0.8083 80.83%
CYP2C19 inhibition - 0.8062 80.62%
CYP2D6 inhibition - 0.9432 94.32%
CYP1A2 inhibition - 0.8042 80.42%
CYP2C8 inhibition + 0.6173 61.73%
CYP inhibitory promiscuity - 0.7634 76.34%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4948 49.48%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9109 91.09%
Skin irritation - 0.5155 51.55%
Skin corrosion - 0.9290 92.90%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6547 65.47%
Micronuclear - 0.6500 65.00%
Hepatotoxicity - 0.5202 52.02%
skin sensitisation - 0.8618 86.18%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6152 61.52%
Acute Oral Toxicity (c) III 0.7876 78.76%
Estrogen receptor binding + 0.7693 76.93%
Androgen receptor binding + 0.6836 68.36%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7542 75.42%
Aromatase binding + 0.7312 73.12%
PPAR gamma + 0.6597 65.97%
Honey bee toxicity - 0.7243 72.43%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9893 98.93%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.60% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.86% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.40% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.16% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.41% 86.33%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 89.14% 94.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 88.67% 96.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.20% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.55% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 86.68% 97.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.05% 89.00%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 85.93% 90.93%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.21% 95.56%
CHEMBL3922 P50579 Methionine aminopeptidase 2 84.61% 97.28%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.84% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.33% 91.07%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 83.21% 95.71%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 83.05% 92.68%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.35% 94.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.20% 96.47%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.04% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.76% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.66% 99.23%

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.
Leitneria floridana
Quassia amara

Cross-Links

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PubChem 44566234
LOTUS LTS0057981
wikiData Q105004037