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Isobrucein 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 35042ddc-0ddf-432b-b391-2abeb2967db2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
IUPAC Name methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-3-acetyloxy-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) CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
SMILES (Isomeric) CC1=CC(=O)[C@H]([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)C)(OC5)C(=O)OC)O)O)C)O
InChI InChI=1S/C23H28O11/c1-8-5-11(25)17(27)21(3)10(8)6-12-22-7-32-23(20(30)31-4,18(28)13(26)15(21)22)16(22)14(19(29)34-12)33-9(2)24/h5,10,12-18,26-28H,6-7H2,1-4H3/t10-,12+,13+,14+,15+,16+,17+,18-,21-,22+,23-/m0/s1
InChI Key WAYNIXHIORQRDI-RWLFMTGCSA-N
Popularity 11 references in papers

Physical and Chemical Properties

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Molecular Formula C23H28O11
Molecular Weight 480.50 g/mol
Exact Mass 480.16316171 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -1.34
H-Bond Acceptor 11
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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ISOBRUCEINE B
53663-03-9
CHEBI:5988
CHEMBL475082
NSC-238181
methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-3-acetyloxy-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
AC1L40YM
NSC 238181
C08770
Q27106964
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Isobrucein B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8980 89.80%
Caco-2 - 0.7361 73.61%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7598 75.98%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8527 85.27%
OATP1B3 inhibitior + 0.9635 96.35%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.6549 65.49%
P-glycoprotein inhibitior + 0.5805 58.05%
P-glycoprotein substrate + 0.8961 89.61%
CYP3A4 substrate + 0.7076 70.76%
CYP2C9 substrate - 0.8253 82.53%
CYP2D6 substrate - 0.8954 89.54%
CYP3A4 inhibition - 0.8162 81.62%
CYP2C9 inhibition - 0.9023 90.23%
CYP2C19 inhibition - 0.8711 87.11%
CYP2D6 inhibition - 0.9371 93.71%
CYP1A2 inhibition - 0.8465 84.65%
CYP2C8 inhibition - 0.6274 62.74%
CYP inhibitory promiscuity - 0.8983 89.83%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4999 49.99%
Eye corrosion - 0.9869 98.69%
Eye irritation - 0.9178 91.78%
Skin irritation - 0.6333 63.33%
Skin corrosion - 0.9235 92.35%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5087 50.87%
Micronuclear - 0.5400 54.00%
Hepatotoxicity + 0.5460 54.60%
skin sensitisation - 0.8458 84.58%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.7949 79.49%
Acute Oral Toxicity (c) III 0.4748 47.48%
Estrogen receptor binding + 0.8290 82.90%
Androgen receptor binding + 0.6624 66.24%
Thyroid receptor binding - 0.5332 53.32%
Glucocorticoid receptor binding + 0.6871 68.71%
Aromatase binding + 0.6102 61.02%
PPAR gamma + 0.6426 64.26%
Honey bee toxicity - 0.6779 67.79%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9451 94.51%

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 98.66% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.37% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.49% 85.14%
CHEMBL2581 P07339 Cathepsin D 93.19% 98.95%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 90.96% 81.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.99% 96.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 88.37% 94.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.14% 96.77%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.32% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.12% 99.23%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 86.20% 95.71%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.81% 96.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.28% 97.21%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.21% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.83% 94.45%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.69% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.03% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.96% 86.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.76% 97.28%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 82.60% 96.38%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.46% 97.25%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 82.22% 98.75%
CHEMBL5028 O14672 ADAM10 81.43% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.24% 97.09%

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
Picrolemma huberi
Picrolemma sprucei
Soulamea amara

Cross-Links

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PubChem 99530
LOTUS LTS0228773
wikiData Q27106964