Page last updated: 2024-12-07

girinimbine

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

Description

girinimbine: carbazole alkaloid [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID96943
CHEMBL ID1477760
CHEBI ID69926
SCHEMBL ID4132680
MeSH IDM0105202

Synonyms (35)

Synonym
girinimbine
23095-44-5
nsc94932
nsc-94932
ACON1_001999
MEGXP0_000255
MLS000863568 ,
smr000440762
BRD-K08091267-001-01-2
3,3,5-trimethyl-11h-pyrano[3,2-a]carbazole
3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole
chebi:69926 ,
CHEMBL1477760
wh639v7qsf ,
pyrano(3,2-a)carbazole, 3,11-dihydro-3,3,5-trimethyl-
girinimbin
unii-wh639v7qsf
nsc 94932
HMS2270D17
SCHEMBL4132680
bdbm68168
cid_96943
c18h17no
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
3,11-dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci
3,11-dihydro-3,3,5-trimethyl-pyrano(3,2-a)carbazole
CS-0181880
GAEQWKVGMHUUKO-UHFFFAOYSA-N
Q25104278
MS-23714
DTXSID90945774
HY-N9488
3,11-dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole
pyrano[3,2-a]carbazole, 3,11-dihydro-3,3,5-trimethyl-
AKOS040763158

Research Excerpts

Overview

Girinimbine is a carbazole alkaloid isolated from Murraya koenigii (the curry tree) It is used in Chinese herbal medicine.

ExcerptReferenceRelevance
"Girinimbine is a carbazole alkaloid isolated from Murraya koenigii (the curry tree) and is used in Chinese herbal medicine."( Girinimbine Inhibits the Proliferation of Human Ovarian Cancer Cells In Vitro via the Phosphatidylinositol-3-Kinase (PI3K)/Akt and the Mammalian Target of Rapamycin (mTOR) and Wnt/β-Catenin Signaling Pathways.
Muer, A; Xin, Q, 2018
)
2.64
"Girinimbine is a carbazole alkaloid isolated from the stem bark and root of Murraya koenigii. "( In vitro and in vivo anti-angiogenic activity of girinimbine isolated from Murraya koenigii.
Hobani, YH; Iman, V; Karimian, H; Mohan, S; Mustafa, MR; Noor, SM; Noordin, MI, 2015
)
2.11
"Girinimbine is an antiplatelet agent isolated from Murraya euchrestifolia. "( Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia.
Ko, FN; Lee, YS; Teng, CM; Wu, TS, 1994
)
1.96

Effects

ExcerptReferenceRelevance
"Girinimbine has induced potent chromatin condensation and nuclear fragmentation."( Naturally occurring Girinimbine alkaloid inhibits the proliferation, migration, and invasion of human breast cancer cells via induction of apoptosis and inhibition of MEK/ERK and STAT3 signalling pathways.
Yang, L; Yu, X, 2021
)
1.67

Actions

ExcerptReferenceRelevance
"Girinimbine can inhibit both cancer cell migration as well as invasion."( Naturally occurring Girinimbine alkaloid inhibits the proliferation, migration, and invasion of human breast cancer cells via induction of apoptosis and inhibition of MEK/ERK and STAT3 signalling pathways.
Yang, L; Yu, X, 2021
)
1.67

Treatment

ExcerptReferenceRelevance
"Girinimbine-treated HepG2 cells showed typical morphological features of apoptosis, as observed from normal inverted microscopy and Hoechst 33342 assay."( The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest.
Abdelwahab, SI; Abdul, AB; Mohan, S; Sukari, MA; Syam, S; Wah, TS, 2011
)
1.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

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 (21)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency56.23410.631035.7641100.0000AID504339
LuciferasePhotinus pyralis (common eastern firefly)Potency10.69100.007215.758889.3584AID588342
glp-1 receptor, partialHomo sapiens (human)Potency28.18380.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency19.46830.004110.890331.5287AID504466; AID504467
TDP1 proteinHomo sapiens (human)Potency26.10110.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency17.78280.180013.557439.8107AID1460
Smad3Homo sapiens (human)Potency22.38720.00527.809829.0929AID588855
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency50.11870.707936.904389.1251AID504333
P53Homo sapiens (human)Potency10.00000.07319.685831.6228AID504706
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency3.16230.01262.451825.0177AID485313
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency29.09290.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency39.81073.548119.542744.6684AID743266
transcriptional regulator ERG isoform 3Homo sapiens (human)Potency22.38720.794321.275750.1187AID624246
DNA polymerase betaHomo sapiens (human)Potency89.12510.022421.010289.1251AID485314
ras-related protein Rab-9AHomo sapiens (human)Potency3.16230.00022.621531.4954AID485297
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency89.12510.425612.059128.1838AID504891
gemininHomo sapiens (human)Potency22.14270.004611.374133.4983AID624296; AID624297
VprHuman immunodeficiency virus 1Potency25.11891.584919.626463.0957AID651644
TAR DNA-binding protein 43Homo sapiens (human)Potency28.18381.778316.208135.4813AID652104
[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)
XBP1Homo sapiens (human)IC50 (µMol)10.00000.16005.404910.0000AID504313
DNA damage-inducible transcript 3 proteinMus musculus (house mouse)IC50 (µMol)10.00000.16003.995910.0000AID504322
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID587892Cytotoxicity against human KB cells by resazurin microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID1684495Anticancer activity against human SW1990 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID1684490Anticancer activity against human MCF7 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID664539Cytotoxicity against human NCI-H187 cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1684492Anticancer activity against human H7402 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID664538Cytotoxicity against human MCF7 cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID587893Cytotoxicity against human NCI-H187 by resazurin microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID1684497Anticancer activity against human HeLa cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID587894Cytotoxicity against african green monkey Vero cells by green fluorescent protein microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID664536Antibacterial activity against Salmonella typhimurium TISTR 292 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID664535Antibacterial activity against Escherichia coli TISTR 780 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1684491Anticancer activity against human HCT-8 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID664534Antibacterial activity against Staphylococcus aureus TISTR 1466 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1684499Anticancer activity against human A431 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID634796Growth inhibition of human HepG2 cells after 48 hrs by WST-8 based CCK8 assay2012European journal of medicinal chemistry, Jan, Volume: 47, Issue:1
Induction of cell cycle arrest by the carbazole alkaloid Clauszoline-I from Clausena vestita D. D. Tao via inhibition of the PKCδ phosphorylation.
AID1684494Anticancer activity against human BGC-823 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID1684493Anticancer activity against human H460 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID1684498Anticancer activity against human A2780 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
AID664537Cytotoxicity against human KB cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID664533Antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1684496Anticancer activity against human KETR3 cells by MTT assay2021Bioorganic & medicinal chemistry letters, 02-01, Volume: 33Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.55)18.7374
1990's2 (9.09)18.2507
2000's1 (4.55)29.6817
2010's14 (63.64)24.3611
2020's4 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.60

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 Index22.60 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.55%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (95.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]