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Voaluteine

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 98ab3b18-a59d-47ad-b15d-a7c2f7f38c0d
Taxonomy Organoheterocyclic compounds > Quinolizidines
IUPAC Name methyl 9'-ethyl-5-methoxy-3-oxospiro[1H-indole-2,6'-3-azatricyclo[5.3.1.03,8]undecane]-7'-carboxylate
SMILES (Canonical) CCC1CC2CC3(C1N(C2)CCC34C(=O)C5=C(N4)C=CC(=C5)OC)C(=O)OC
SMILES (Isomeric) CCC1CC2CC3(C1N(C2)CCC34C(=O)C5=C(N4)C=CC(=C5)OC)C(=O)OC
InChI InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(26)28-3)18(14)24(12-13)8-7-22(21)19(25)16-10-15(27-2)5-6-17(16)23-22/h5-6,10,13-14,18,23H,4,7-9,11-12H2,1-3H3
InChI Key ZZJBUKQZGMCYEE-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28N2O4
Molecular Weight 384.50 g/mol
Exact Mass 384.20490738 g/mol
Topological Polar Surface Area (TPSA) 67.90 Ų
XlogP 2.90
Atomic LogP (AlogP) 2.73
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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Rupicoline
Voaluleine
Voluteine
Voacangine pseudoindoxyl
ZZJBUKQZGMCYEE-UHFFFAOYSA-N
Spiro[2H-indole-2,4'-[4H-1,6]methanoquinoline]-4'a(5'H)-carboxylic acid, 8'-ethyl-1,2',3,3',6',7',8',8'a-octahydro-5-methoxy-3-oxo-, methyl ester
Spiro[2H-indole-2,4'-[4H-1,6]methanoquinoline]-4'a(5'H)-carboxylic acid, 8'-ethyl-1,2',3,3',6',7',8',8'a-octahydro-5-methoxy-3-oxo-, methyl ester, [1'R-(1'.alpha.,4'.alpha.,4'a.beta.,6'.alpha.,8'.alpha.,8'a.beta.)]-

2D Structure

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2D Structure of Voaluteine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9747 97.47%
Caco-2 + 0.7363 73.63%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Lysosomes 0.4964 49.64%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9122 91.22%
OATP1B3 inhibitior + 0.9254 92.54%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.5788 57.88%
P-glycoprotein inhibitior - 0.4701 47.01%
P-glycoprotein substrate + 0.7031 70.31%
CYP3A4 substrate + 0.6652 66.52%
CYP2C9 substrate + 0.8081 80.81%
CYP2D6 substrate - 0.7381 73.81%
CYP3A4 inhibition - 0.7372 73.72%
CYP2C9 inhibition - 0.9052 90.52%
CYP2C19 inhibition - 0.8292 82.92%
CYP2D6 inhibition - 0.6077 60.77%
CYP1A2 inhibition - 0.7804 78.04%
CYP2C8 inhibition - 0.7364 73.64%
CYP inhibitory promiscuity - 0.8485 84.85%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6544 65.44%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9877 98.77%
Skin irritation - 0.8052 80.52%
Skin corrosion - 0.9463 94.63%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8534 85.34%
Micronuclear + 0.6500 65.00%
Hepatotoxicity + 0.5309 53.09%
skin sensitisation - 0.8768 87.68%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity - 0.7580 75.80%
Acute Oral Toxicity (c) III 0.6065 60.65%
Estrogen receptor binding + 0.7027 70.27%
Androgen receptor binding + 0.7896 78.96%
Thyroid receptor binding + 0.6578 65.78%
Glucocorticoid receptor binding + 0.6091 60.91%
Aromatase binding + 0.7071 70.71%
PPAR gamma - 0.6177 61.77%
Honey bee toxicity - 0.8523 85.23%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9262 92.62%

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 99.42% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.31% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.57% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.69% 94.45%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 94.69% 82.69%
CHEMBL2581 P07339 Cathepsin D 93.71% 98.95%
CHEMBL4208 P20618 Proteasome component C5 93.58% 90.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.60% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.44% 95.56%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 90.12% 90.71%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.97% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.50% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.12% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.95% 96.77%
CHEMBL4588 P22894 Matrix metalloproteinase 8 86.09% 94.66%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.66% 97.25%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 85.61% 91.03%
CHEMBL2535 P11166 Glucose transporter 84.72% 98.75%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.47% 93.03%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.36% 97.28%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.66% 97.14%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.58% 86.92%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.28% 92.62%

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.
Tabernaemontana pandacaqui

Cross-Links

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PubChem 633439
LOTUS LTS0189180
wikiData Q105386857