PlantaeDB Logo
Login Sign-up

3-Hydroxyquinine

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

Top
Internal ID ddafbee3-f63e-453a-bbc6-f6da3c4857ca
Taxonomy Alkaloids and derivatives > Cinchona alkaloids
IUPAC Name (3S,4S,6S)-3-ethenyl-6-[(R)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18-,19+,20+/m0/s1
InChI Key BSRUJCFCZKMFMB-YGHPHNMRSA-N
Popularity 85 references in papers

Physical and Chemical Properties

Top
Molecular Formula C20H24N2O3
Molecular Weight 340.40 g/mol
Exact Mass 340.17869263 g/mol
Topological Polar Surface Area (TPSA) 65.80 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.29
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

Top
78549-61-8
Cinchonan-3,9-diol, 6'-methoxy-, (8alpha,9R)-
4D7695509M
CHEBI:17685
DTXSID901316798
(3S,4S,6S)-3-ethenyl-6-[(R)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
(3S,4S,6S)-3-ethenyl-6-((R)-hydroxy-(6-methoxyquinolin-4-yl)methyl)-1-azabicyclo(2.2.2)octan-3-ol
RefChem:94400
DTXCID801746625
(3S,4R,6S)-3-ethenyl-6-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-1-azabicyclo(2.2.2)octan-3-ol
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of 3-Hydroxyquinine

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9739 97.39%
Caco-2 + 0.6957 69.57%
Blood Brain Barrier + 0.6386 63.86%
Human oral bioavailability + 0.6571 65.71%
Subcellular localzation Mitochondria 0.7762 77.62%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9438 94.38%
OATP1B3 inhibitior + 0.9535 95.35%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior + 0.6250 62.50%
BSEP inhibitior + 0.9021 90.21%
P-glycoprotein inhibitior + 0.5884 58.84%
P-glycoprotein substrate + 0.7456 74.56%
CYP3A4 substrate + 0.6908 69.08%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.4528 45.28%
CYP3A4 inhibition - 0.7739 77.39%
CYP2C9 inhibition - 0.8871 88.71%
CYP2C19 inhibition - 0.8000 80.00%
CYP2D6 inhibition + 0.6187 61.87%
CYP1A2 inhibition - 0.9395 93.95%
CYP2C8 inhibition - 0.7937 79.37%
CYP inhibitory promiscuity - 0.8763 87.63%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6125 61.25%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9848 98.48%
Skin irritation - 0.6114 61.14%
Skin corrosion - 0.9283 92.83%
Ames mutagenesis - 0.8370 83.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8974 89.74%
Micronuclear + 0.6300 63.00%
Hepatotoxicity + 0.8000 80.00%
skin sensitisation - 0.8470 84.70%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.8925 89.25%
Acute Oral Toxicity (c) III 0.5025 50.25%
Estrogen receptor binding + 0.6749 67.49%
Androgen receptor binding + 0.7506 75.06%
Thyroid receptor binding + 0.6077 60.77%
Glucocorticoid receptor binding + 0.6888 68.88%
Aromatase binding + 0.6249 62.49%
PPAR gamma - 0.6628 66.28%
Honey bee toxicity - 0.7058 70.58%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity - 0.6567 65.67%

Targets

Top

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.27% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.78% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.59% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 97.10% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.80% 94.45%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 93.38% 91.03%
CHEMBL4208 P20618 Proteasome component C5 92.89% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 92.77% 95.89%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.38% 96.00%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 90.10% 85.49%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.42% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.26% 86.33%
CHEMBL2243 O00519 Anandamide amidohydrolase 88.76% 97.53%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.89% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.73% 97.09%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 87.42% 100.00%
CHEMBL2581 P07339 Cathepsin D 87.39% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 87.17% 91.49%
CHEMBL1868 P17948 Vascular endothelial growth factor receptor 1 87.09% 96.47%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.76% 95.56%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.57% 92.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.54% 94.00%
CHEMBL3492 P49721 Proteasome Macropain subunit 85.15% 90.24%
CHEMBL5203 P33316 dUTP pyrophosphatase 84.44% 99.18%
CHEMBL5747 Q92793 CREB-binding protein 83.94% 95.12%
CHEMBL1795139 Q8IU80 Transmembrane protease serine 6 83.02% 98.33%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.83% 94.97%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.12% 97.36%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.17% 92.94%

Plants that contains it

Top
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.
There are no matching plants.

Cross-Links

Top
PubChem 157225
LOTUS LTS0010336
wikiData Q27102531