Compounds > Koenimbine
Page last updated: 2024-12-07

Koenimbine

Description

koenimbin: has antineoplastic activity; isolated from curry leaf, Murraya koenigii; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID97487
CHEMBL ID2323768
CHEBI ID169698

Synonyms (20)

Synonym
8-methoxy-3,3,5-trimethyl-11h-pyrano[3,2-a]carbazole
koenimbine
CHEBI:169698
nsc127152
koenimbin
21087-98-9
nsc-127152
3,11-dihydro-8-methoxy-3,3,5-trimethylpyrano(3,2-a)carbazole
pyrano(3,2-a)carbazole, 3,11-dihydro-8-methoxy-3,3,5-trimethyl-
nsc 127152
CHEMBL2323768
kenimbine
DTXSID90175317
13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1,3,7,9,11,13,15-heptaene
AKOS030537929
koenimbine, analytical standard
3,11-dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci
bdbm50207384
8-methoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole
OSERHKINMDLESD-UHFFFAOYSA-N
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Pancreatic triacylglycerol lipaseHomo sapiens (human)IC50 (µMol)168.60000.00600.32530.7800AID1333884
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
lipid metabolic processPancreatic triacylglycerol lipaseHomo sapiens (human)
intestinal cholesterol absorptionPancreatic triacylglycerol lipaseHomo sapiens (human)
retinol metabolic processPancreatic triacylglycerol lipaseHomo sapiens (human)
positive regulation of triglyceride lipase activityPancreatic triacylglycerol lipaseHomo sapiens (human)
lipid catabolic processPancreatic triacylglycerol lipaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
triglyceride lipase activityPancreatic triacylglycerol lipaseHomo sapiens (human)
lipase activityPancreatic triacylglycerol lipaseHomo sapiens (human)
metal ion bindingPancreatic triacylglycerol lipaseHomo sapiens (human)
all-trans-retinyl-palmitate hydrolase, all-trans-retinol forming activityPancreatic triacylglycerol lipaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
extracellular regionPancreatic triacylglycerol lipaseHomo sapiens (human)
extracellular spacePancreatic triacylglycerol lipaseHomo sapiens (human)
extracellular spacePancreatic triacylglycerol lipaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID727894Cytotoxicity against mouse theophylline-induced B16-4A5 cells assessed as cell viability at 1 uM after 72 hrs by WST8 assay relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727898Inhibition of theophylline-induced melanogenesis in mouse B16-4A5 cells after 72 hrs by spectrophotometric analysis relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727901Inhibition of theophylline-induced melanogenesis in mouse B16-4A5 cells at 1 uM after 72 hrs by spectrophotometric analysis relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1315294Half life in rat liver microsomes in presence of NADPH by HPLC analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1315289Activation of Akt-dependent signalling pathway in rat L6 myotubes assessed as increase in myc-tagged GLUT4-mediated 2-[3H]-deoxyglucose uptake at 25 uM incubated for 16 hrs measured for 5 mins by beta scintillation counting relative to control2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1871701Antiproliferative activity against human HepG2 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID727886Inhibition of mushroom tyrosinase using L-DOPA as substrate after at 100 uM after 5 mins relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1871700Antiproliferative activity against human OVCAR-3 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID1315292Activation of Akt-dependent signalling pathway in rat L6 myotubes assessed as induction of myc-tagged GLUT4 translocation to cell surface at 25 uM incubated for 16 hrs by O-phenylenediamide based colorimetric assay relative to control2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1315288Activation of Akt-dependent signalling pathway in rat L6 myotubes assessed as increase in insulin-stimulated myc-tagged GLUT4-mediated 2-[3H]-deoxyglucose uptake at 25 uM incubated for 16 hrs followed by insulin stimulation for 20 mins measured for 5 mins2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1871699Antiproliferative activity against human PA-1 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID727893Cytotoxicity against mouse theophylline-induced B16-4A5 cells assessed as cell viability at 3 uM after 72 hrs by WST8 assay relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1315295Antidiabetic activity in overnight fasted STZ-induced albino Sprague-Dawley rat diabetic model assessed as decrease in blood glucose level at 100 mg/kg, po measured up to 5 hrs2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1871702Antiproliferative activity against human DU-145 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID1315310Cmax in Sprague-Dawley rat plasma at 100 mg/kg, po administered as single dose measured up to 48 hrs post dose by LC-MS/MS analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID727888Inhibition of mushroom tyrosinase using L-DOPA as substrate after at 10 uM after 5 mins relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1315309AUC (0 to infinity) in Sprague-Dawley rat plasma at 100 mg/kg, po administered as single dose measured up to 48 hrs post dose by LC-MS/MS analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1333884Inhibition of pancreatic lipase (unknown origin)2017Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2
Synthesis, evaluation and molecular modelling studies of 2-(carbazol-3-yl)-2-oxoacetamide analogues as a new class of potential pancreatic lipase inhibitors.
AID1315290Activation of Akt-dependent signalling pathway in rat L6 myotubes assessed as increase in myc-tagged GLUT4-mediated 2-[3H]-deoxyglucose uptake incubated for 16 hrs measured for 5 mins by beta scintillation counting2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1871703Antiproliferative activity against human HCT-116 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID727890Inhibition of mushroom tyrosinase using L-DOPA as substrate after at 1 uM after 5 mins relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727902Inhibition of theophylline-induced melanogenesis in mouse B16-4A5 cells at 3 uM after 72 hrs by spectrophotometric analysis relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727887Inhibition of mushroom tyrosinase using L-DOPA as substrate after at 30 uM after 5 mins relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727891Cytotoxicity against mouse theophylline-induced B16-4A5 cells assessed as cell viability at 10 uM after 72 hrs by WST8 assay relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1315296Antidiabetic activity in overnight fasted STZ-induced albino Sprague-Dawley rat diabetic model assessed as decrease in blood glucose level at 100 mg/kg, po measured up to 24 hrs2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID727892Cytotoxicity against mouse theophylline-induced B16-4A5 cells assessed as cell viability at 30 uM after 72 hrs by WST8 assay relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1315307Metabolic stability in rat liver microsomes assessed as drug degradation rate constant incubated for 90 mins by HPLC analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID1315311Tmax in Sprague-Dawley rat plasma at 100 mg/kg, po administered as single dose by LC-MS/MS analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
AID727899Inhibition of theophylline-induced melanogenesis in mouse B16-4A5 cells at 10 uM after 72 hrs by spectrophotometric analysis relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID727889Inhibition of mushroom tyrosinase using L-DOPA as substrate after at 3 uM after 5 mins relative to control2013Bioorganic & medicinal chemistry, Mar-01, Volume: 21, Issue:5
Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.
AID1871704Antiproliferative activity against human HeLa cells assessed as cell growth inhibition measured after 48 hrs by MTT assay2022European journal of medicinal chemistry, Feb-05, Volume: 229Current status of carbazole hybrids as anticancer agents.
AID1315293Metabolic stability in rat liver microsomes assessed as parent compound remaining after 90 mins in presence of NADPH by HPLC analysis2016Journal of natural products, 05-27, Volume: 79, Issue:5
Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (75.00)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (25.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (75.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ellipticine
ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.		3.5110indole alkaloid;
organic heterotetracyclic compound;
organonitrogen heterocyclic compound;
polycyclic heteroarene		antineoplastic agent;
plant metabolite
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		3.5110nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
metformin
Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.		2.1310guanidinesenvironmental contaminant;
geroprotector;
hypoglycemic agent;
xenobiotic
pioglitazone
Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.		2.1310aromatic ether;
pyridines;
thiazolidinediones		antidepressant;
cardioprotective agent;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hypoglycemic agent;
insulin-sensitizing drug;
PPARgamma agonist;
xenobiotic
carbazole
carbazole: structure in first source		2.5320carbazole
etoposide
[no description available]		3.5110beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		3.5110organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
rosiglitazone
[no description available]		2.1310aminopyridine;
thiazolidinediones		EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug
4-hydroxycarbazole
4-hydroxycarbazole: structure in first source		2.0810
mahanimbine
mahanimbine: from Murraya koenigii leaves; structure in first source		2.5220carbazoles
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		2.0810beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
curcumin
Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.		3.2710aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger
orlistat
Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.		2.1510beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative		anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
ellagic acid
[no description available]		3.2710catechols;
cyclic ketone;
lactone;
organic heterotetracyclic compound;
polyphenol		antioxidant;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor;
EC 2.4.1.1 (glycogen phosphorylase) inhibitor;
EC 2.5.1.18 (glutathione transferase) inhibitor;
EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor;
EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor;
EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
food additive;
fungal metabolite;
geroprotector;
plant metabolite;
skin lightening agent
fosbretabulin
fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source		3.5110
o-methylmurrayamine a
O-methylmurrayamine A: structure in first source		3.7120
ConditionIndicatedRelationship StrengthStudiesTrials
Alloxan Diabetes
[description not available]		02.1310
Insulin Sensitivity
[description not available]		02.1310
Insulin Resistance
Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.		02.1310
Cancer of Colon
[description not available]		02.2510
Colonic Neoplasms
Tumors or cancer of the COLON.		02.2510
Benign Neoplasms
[description not available]		03.0910
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0910
Breast Cancer
[description not available]		02.5520
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.5520
chemdatabank.com