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Bruceanol B

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 7dde34b2-7a66-4d5b-b7e1-bf0b1de318d3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
IUPAC Name methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-hexanoyloxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
SMILES (Canonical) CCCCCC(=O)OC1C2C34COC2(C(C(C3C5(C(CC4OC1=O)C(=CC(=O)C5O)C)C)O)O)C(=O)OC
SMILES (Isomeric) CCCCCC(=O)O[C@@H]1[C@H]2[C@@]3([C@H]([C@@H]([C@H]4C2(CO3)[C@@H](C[C@@H]5[C@@]4([C@@H](C(=O)C=C5C)O)C)OC1=O)O)O)C(=O)OC
InChI InChI=1S/C27H36O11/c1-5-6-7-8-16(29)38-18-20-26-11-36-27(20,24(34)35-4)22(32)17(30)19(26)25(3)13(10-15(26)37-23(18)33)12(2)9-14(28)21(25)31/h9,13,15,17-22,30-32H,5-8,10-11H2,1-4H3/t13-,15+,17+,18+,19+,20+,21+,22-,25-,26?,27+/m0/s1
InChI Key NZDAVMOPAYYVCK-FIUJHEBUSA-N
Popularity 1 reference 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 1.00
Atomic LogP (AlogP) 0.22
H-Bond Acceptor 11
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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101391-05-3
methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-hexanoyloxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
DTXSID90906123
Picras-3-en-21-oic acid, 13,20-epoxy-1,11,12-trihydroxy-2,16-dioxo-15-((1-oxopentyl)oxy)-, methyl ester, (1beta,11beta,12alpha,15beta)-

2D Structure

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2D Structure of Bruceanol B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9215 92.15%
Caco-2 - 0.7769 77.69%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.7807 78.07%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8104 81.04%
OATP1B3 inhibitior + 0.9589 95.89%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.8131 81.31%
P-glycoprotein inhibitior + 0.7011 70.11%
P-glycoprotein substrate + 0.9302 93.02%
CYP3A4 substrate + 0.7111 71.11%
CYP2C9 substrate - 0.8253 82.53%
CYP2D6 substrate - 0.8954 89.54%
CYP3A4 inhibition - 0.7794 77.94%
CYP2C9 inhibition - 0.8166 81.66%
CYP2C19 inhibition - 0.8293 82.93%
CYP2D6 inhibition - 0.9289 92.89%
CYP1A2 inhibition - 0.7908 79.08%
CYP2C8 inhibition + 0.5160 51.60%
CYP inhibitory promiscuity - 0.8261 82.61%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4731 47.31%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9289 92.89%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9242 92.42%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5264 52.64%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.5672 56.72%
skin sensitisation - 0.8925 89.25%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.7049 70.49%
Acute Oral Toxicity (c) III 0.6064 60.64%
Estrogen receptor binding + 0.7682 76.82%
Androgen receptor binding + 0.6824 68.24%
Thyroid receptor binding - 0.5692 56.92%
Glucocorticoid receptor binding + 0.7331 73.31%
Aromatase binding + 0.6634 66.34%
PPAR gamma + 0.6269 62.69%
Honey bee toxicity - 0.7664 76.64%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.7063 70.63%
Fish aquatic toxicity + 0.9716 97.16%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.12% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.14% 96.09%
CHEMBL2581 P07339 Cathepsin D 97.97% 98.95%
CHEMBL230 P35354 Cyclooxygenase-2 97.91% 89.63%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.35% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 95.28% 97.79%
CHEMBL299 P17252 Protein kinase C alpha 95.20% 98.03%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.60% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.34% 96.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 91.81% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 90.81% 92.50%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 90.61% 96.95%
CHEMBL221 P23219 Cyclooxygenase-1 88.94% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.80% 99.23%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 88.59% 97.21%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.30% 96.77%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 87.08% 96.38%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.53% 86.33%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 84.83% 95.71%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.43% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.88% 97.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.53% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.98% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.82% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.34% 95.89%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.15% 82.69%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 81.10% 95.17%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.93% 100.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 80.78% 96.47%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.73% 95.56%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.28% 98.75%

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.
Brucea antidysenterica

Cross-Links

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PubChem 127804
LOTUS LTS0203997
wikiData Q82874790