15-O-(3-Methylbutanoyl)-3-O-beta-D-glucopyranosylbruceolide

Details

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Internal ID 7add384d-5ee9-4fa3-8c9a-0d344ccf287a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
IUPAC Name methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
SMILES (Canonical) CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)OC)O)O)C)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)OC)O)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C32H44O16/c1-11(2)6-17(35)47-23-25-31-10-44-32(25,29(42)43-5)26(40)21(39)24(31)30(4)8-14(34)22(12(3)13(30)7-16(31)46-27(23)41)48-28-20(38)19(37)18(36)15(9-33)45-28/h11,13,15-16,18-21,23-26,28,33,36-40H,6-10H2,1-5H3/t13-,15+,16+,18+,19-,20+,21+,23+,24+,25+,26-,28-,30-,31+,32-/m0/s1
InChI Key VNXFGKATJSGRMH-PKMWWCJOSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C32H44O16
Molecular Weight 684.70 g/mol
Exact Mass 684.26293531 g/mol
Topological Polar Surface Area (TPSA) 245.00 Ų
XlogP -1.10
Atomic LogP (AlogP) -2.14
H-Bond Acceptor 16
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 15-O-(3-Methylbutanoyl)-3-O-beta-D-glucopyranosylbruceolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7682 76.82%
Caco-2 - 0.8750 87.50%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7661 76.61%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8286 82.86%
OATP1B3 inhibitior + 0.9135 91.35%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.4800 48.00%
P-glycoprotein inhibitior + 0.7077 70.77%
P-glycoprotein substrate + 0.8097 80.97%
CYP3A4 substrate + 0.7177 71.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8895 88.95%
CYP3A4 inhibition - 0.8843 88.43%
CYP2C9 inhibition - 0.8215 82.15%
CYP2C19 inhibition - 0.8570 85.70%
CYP2D6 inhibition - 0.9403 94.03%
CYP1A2 inhibition - 0.8924 89.24%
CYP2C8 inhibition + 0.5291 52.91%
CYP inhibitory promiscuity - 0.9127 91.27%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6114 61.14%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9144 91.44%
Skin irritation - 0.6906 69.06%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis - 0.5177 51.77%
Human Ether-a-go-go-Related Gene inhibition + 0.6851 68.51%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.5625 56.25%
skin sensitisation - 0.8716 87.16%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.7545 75.45%
Acute Oral Toxicity (c) I 0.4259 42.59%
Estrogen receptor binding + 0.7305 73.05%
Androgen receptor binding + 0.7117 71.17%
Thyroid receptor binding - 0.5745 57.45%
Glucocorticoid receptor binding + 0.6469 64.69%
Aromatase binding + 0.6358 63.58%
PPAR gamma + 0.6681 66.81%
Honey bee toxicity - 0.6132 61.32%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9727 97.27%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.59% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.82% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.60% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.07% 96.09%
CHEMBL299 P17252 Protein kinase C alpha 96.82% 98.03%
CHEMBL2581 P07339 Cathepsin D 96.74% 98.95%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 96.12% 96.47%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.26% 96.00%
CHEMBL2996 Q05655 Protein kinase C delta 95.19% 97.79%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 95.07% 96.21%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.01% 96.77%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 89.49% 98.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.91% 97.09%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 88.30% 91.24%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 88.14% 96.95%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 87.74% 95.71%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.07% 91.07%
CHEMBL5028 O14672 ADAM10 87.05% 97.50%
CHEMBL220 P22303 Acetylcholinesterase 86.99% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.99% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.58% 94.45%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.45% 95.50%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.05% 97.21%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 85.55% 94.33%
CHEMBL1993 P26358 DNA (cytosine-5)-methyltransferase 1 84.39% 95.44%
CHEMBL5255 O00206 Toll-like receptor 4 84.32% 92.50%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 84.25% 89.34%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.92% 97.14%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 83.63% 81.11%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.44% 99.17%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 83.42% 97.47%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.06% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.05% 89.00%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 82.91% 95.17%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 81.11% 90.93%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.63% 93.56%

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.
Asplenium normale
Brucea javanica
Carpobrotus edulis
Castanea crenata
Centrolobium tomentosum
Ceratophyllum submersum
Dracocephalum kotschyi
Lippia carviodora
Myrica nana
Psilostrophe cooperi
Sideritis tragoriganum
Solanum jamaicense
Trifolium alexandrinum

Cross-Links

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PubChem 21636147
NPASS NPC54950
LOTUS LTS0265105
wikiData Q105290004