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Nortrilobolide

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 2ddf74b8-d1fd-4228-bff8-82ffe66f6339
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
IUPAC Name [(3S,3aR,4S,6S,6aS,8R,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-8-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CCCC(=O)OC1CC(C2CC(C(=C2C3C1(C(C(=O)O3)(C)O)O)C)OC(=O)C(=CC)C)(C)OC(=O)C
SMILES (Isomeric) CCCC(=O)O[C@H]1C[C@]([C@H]2C[C@H](C(=C2[C@H]3[C@]1([C@](C(=O)O3)(C)O)O)C)OC(=O)/C(=C\C)/C)(C)OC(=O)C
InChI InChI=1S/C26H36O10/c1-8-10-19(28)34-18-12-24(6,36-15(5)27)16-11-17(33-22(29)13(3)9-2)14(4)20(16)21-26(18,32)25(7,31)23(30)35-21/h9,16-18,21,31-32H,8,10-12H2,1-7H3/b13-9-/t16-,17+,18-,21-,24-,25+,26+/m0/s1
InChI Key WEJWYRUDUWBNIB-YQMCDBNQSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C26H36O10
Molecular Weight 508.60 g/mol
Exact Mass 508.23084734 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 2.05
H-Bond Acceptor 10
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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136051-63-3
[(3S,3aR,4S,6S,6aS,8R,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-8-yl] (Z)-2-methylbut-2-enoate
(-)-Nortrilobolide
SCHEMBL17380888
2-Butenoic acid, 2-methyl-, 6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-2-oxo-4-(1-oxobutoxy)azuleno(4,5-b)furan-8-yl ester, (3S-(3alpha,3abeta,4alpha,6beta,6abeta,8alpha(Z),9balpha))-

2D Structure

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2D Structure of Nortrilobolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9737 97.37%
Caco-2 - 0.6832 68.32%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7331 73.31%
OATP2B1 inhibitior - 0.8576 85.76%
OATP1B1 inhibitior + 0.8223 82.23%
OATP1B3 inhibitior + 0.8700 87.00%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9474 94.74%
P-glycoprotein inhibitior + 0.7736 77.36%
P-glycoprotein substrate + 0.7683 76.83%
CYP3A4 substrate + 0.6793 67.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9059 90.59%
CYP3A4 inhibition + 0.7960 79.60%
CYP2C9 inhibition + 0.8537 85.37%
CYP2C19 inhibition + 0.8601 86.01%
CYP2D6 inhibition - 0.9228 92.28%
CYP1A2 inhibition + 0.9106 91.06%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.8693 86.93%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5505 55.05%
Eye corrosion - 0.9871 98.71%
Eye irritation - 0.9024 90.24%
Skin irritation + 0.5425 54.25%
Skin corrosion - 0.9194 91.94%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6883 68.83%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.5375 53.75%
skin sensitisation - 0.8656 86.56%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.5100 51.00%
Acute Oral Toxicity (c) II 0.4100 41.00%
Estrogen receptor binding + 0.7534 75.34%
Androgen receptor binding + 0.6775 67.75%
Thyroid receptor binding + 0.5546 55.46%
Glucocorticoid receptor binding + 0.7188 71.88%
Aromatase binding + 0.7277 72.77%
PPAR gamma + 0.6707 67.07%
Honey bee toxicity - 0.6212 62.12%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.6700 67.00%
Fish aquatic toxicity + 0.9925 99.25%

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 96.42% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.67% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.52% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.61% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.98% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.14% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.85% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.32% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.42% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.39% 99.23%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.85% 95.50%
CHEMBL221 P23219 Cyclooxygenase-1 86.45% 90.17%
CHEMBL2996 Q05655 Protein kinase C delta 85.96% 97.79%
CHEMBL340 P08684 Cytochrome P450 3A4 84.58% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.18% 99.17%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.18% 97.14%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.42% 97.28%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.38% 92.94%
CHEMBL5255 O00206 Toll-like receptor 4 81.13% 92.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.03% 94.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.65% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.39% 93.00%

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.
Thapsia garganica
Thapsia gymnesica

Cross-Links

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PubChem 10097774
LOTUS LTS0145790
wikiData Q104391853