Compounds > mahanimbine
Page last updated: 2024-12-08

mahanimbine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

mahanimbine: from Murraya koenigii leaves; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
MurrayagenusA plant genus of the family RUTACEAE. Members contain murrayanine, koenine, isomahanine, kwangsine, siamenol, murrayafoline A, murrayaquinone A and other cytotoxic carbazolequinones.[MeSH]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]
Murraya koenigiispecies[no description available]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID167963
CHEMBL ID495873
CHEBI ID6646
SCHEMBL ID2991765
MeSH IDM0556080

Synonyms (31)

Synonym
nsc-186884
nsc186884
3,5-dimethyl-3-(4-methylpent-3-enyl)-11h-pyrano[3,2-a]carbazole
3,5-dimethyl-3-(4-methyl-pent-3-enyl)-3,11-dihydro-4-oxa-11-aza-benzo[a]fluorene
ACON1_002475
MEGXP0_002025
C09220 ,
(+)-3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)pyrano[3,2-a]carbazole
mahanimbine
21104-28-9
NCGC00160181-01
NCGC00160181-02
3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazole
CHEMBL495873
chebi:6646 ,
rel-(+)-mahanimbine
mahanimbin
pyrano(3,2-a)carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)-, (+)-
(+)-3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)pyrano(3,2-a)carbazole
SCHEMBL2991765
5,8-dimethyl-5-(4-methylpent-3-en-1-yl)-6-oxa-17-azatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1,3,7,9,11,13,15-heptaene
(+)-mahanimbine
mahanimbine, analytical standard
NCGC00160181-03
bdbm50207385
HTNVFUBCWIYPJN-UHFFFAOYSA-N
Q27107290
24948-14-9
pyrano[3,2-a]carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)-
DTXSID601035072
FS-7575

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency5.08790.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency15.84890.180013.557439.8107AID1460
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Pancreatic triacylglycerol lipaseHomo sapiens (human)IC50 (µMol)17.90000.00600.32530.7800AID1333884
[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 (22)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID379657Antiviral activity against HIV2000Journal of natural products, Mar, Volume: 63, Issue:3
Siamenol, a new carbazole alkaloid from Murraya siamensis.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (6.25)29.6817
2010's10 (62.50)24.3611
2020's5 (31.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.57

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.57 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.79 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbazole
carbazole: structure in first source		2.4820carbazole
Koenimbine
koenimbin: has antineoplastic activity; isolated from curry leaf, Murraya koenigii; structure in first source		2.5220carbazoles
4-hydroxycarbazole
4-hydroxycarbazole: structure in first source		2.0810
gefitinib
[no description available]		2.4110aromatic ether;
monochlorobenzenes;
monofluorobenzenes;
morpholines;
quinazolines;
secondary amino compound;
tertiary amino compound		antineoplastic agent;
epidermal growth factor receptor antagonist
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
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
mahanine
mahanine: structure in first source		7.4720
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.5820
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Cancer of Lung
[description not available]		02.4110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.4110
Cancer of Pancreas
[description not available]		02.1710
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.1710
Hyperlipemia
[description not available]		02.1510
Innate Inflammatory Response
[description not available]		02.1510
Insulin Sensitivity
[description not available]		02.1510
Hyperlipidemias
Conditions with excess LIPIDS in the blood.		02.1510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.1510
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.		07.1510
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		07.4920
Weight Gain
Increase in BODY WEIGHT over existing weight.		02.1510
Anxiety
Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.		02.1310