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Brucine

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 8678d8fe-f8fc-4602-8d72-c97bb527c5d6
Taxonomy Alkaloids and derivatives > Strychnos alkaloids
IUPAC Name (4aR,5aS,8aR,13aS,15aS,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
SMILES (Canonical) COC1=C(C=C2C(=C1)C34CCN5C3CC6C7C4N2C(=O)CC7OCC=C6C5)OC
SMILES (Isomeric) COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7[C@@H]4N2C(=O)C[C@@H]7OCC=C6C5)OC
InChI InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
InChI Key RRKTZKIUPZVBMF-IBTVXLQLSA-N
Popularity 394 references in papers

Physical and Chemical Properties

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Molecular Formula C23H26N2O4
Molecular Weight 394.50 g/mol
Exact Mass 394.18925731 g/mol
Topological Polar Surface Area (TPSA) 51.20 Ų
XlogP 1.00
Atomic LogP (AlogP) 2.11
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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357-57-3
10,11-Dimethoxystrychnine
Brucinum
2,3-Dimethoxystrychnine
(-)-Brucine
l-Brucine
Brucina
Bruzin
2,3-Dimethoxystrychnidin-10-one
Brucine, Anhydrous
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Brucine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9902 99.02%
Caco-2 + 0.9312 93.12%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7403 74.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9413 94.13%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior + 0.9189 91.89%
P-glycoprotein inhibitior + 0.6464 64.64%
P-glycoprotein substrate + 0.6250 62.50%
CYP3A4 substrate + 0.6589 65.89%
CYP2C9 substrate - 0.7869 78.69%
CYP2D6 substrate + 0.4541 45.41%
CYP3A4 inhibition - 0.8308 83.08%
CYP2C9 inhibition - 0.9220 92.20%
CYP2C19 inhibition - 0.9223 92.23%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.7105 71.05%
CYP2C8 inhibition - 0.5654 56.54%
CYP inhibitory promiscuity - 0.8433 84.33%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.5286 52.86%
Eye corrosion - 0.9848 98.48%
Eye irritation - 0.9562 95.62%
Skin irritation - 0.7913 79.13%
Skin corrosion - 0.9378 93.78%
Ames mutagenesis - 0.9200 92.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8760 87.60%
Micronuclear + 0.7100 71.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.8381 83.81%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.7839 78.39%
Acute Oral Toxicity (c) III 0.4746 47.46%
Estrogen receptor binding + 0.8008 80.08%
Androgen receptor binding + 0.7125 71.25%
Thyroid receptor binding - 0.8320 83.20%
Glucocorticoid receptor binding + 0.7345 73.45%
Aromatase binding + 0.5854 58.54%
PPAR gamma + 0.7221 72.21%
Honey bee toxicity - 0.7510 75.10%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.8800 88.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 44668.36 nM
 Ki
 PMID: 22329602
CHEMBL1293232 Q16637 Survival motor neuron protein 794.3 nM
794.3 nM
 Potency
Potency
 via Super-PRED
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.33% 96.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 98.06% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.11% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.73% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.86% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.88% 94.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 91.78% 97.14%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.35% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.20% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.03% 95.89%
CHEMBL2581 P07339 Cathepsin D 88.22% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.28% 91.11%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 83.37% 90.24%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 82.49% 91.03%
CHEMBL217 P14416 Dopamine D2 receptor 82.13% 95.62%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 82.08% 82.38%
CHEMBL284 P27487 Dipeptidyl peptidase IV 81.77% 95.69%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 81.48% 93.40%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.42% 100.00%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 81.17% 96.86%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 81.06% 95.53%

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 javanica
Festuca pratensis
Strychnos ignatii
Strychnos lucida
Strychnos nux-vomica
Strychnos wallichiana

Cross-Links

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PubChem 442021
NPASS NPC159815
ChEMBL CHEMBL501756
LOTUS LTS0141958
wikiData Q411022