Page last updated: 2024-09-27

graveoline

Description

graveoline: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID353825
CHEMBL ID1371756
CHEBI ID5541
MeSH IDM0468704

Synonyms (51)

Synonym
BRD-K92683369-001-03-6
alkaloid from ruta angustifolia plant
nsc-603064
graveolin
NSC603064 ,
MLS001048950
smr000386974
PRESTWICK_165
cas-485-61-0
NCGC00016465-01
BSPBIO_000767
PRESTWICK3_000674
NCGC00179443-01
OPREA1_746980
PRESTWICK2_000674
BPBIO1_000845
485-61-0
graveoline
PRESTWICK0_000674
PRESTWICK1_000674
SPBIO_002688
2-(1,3-benzodioxol-5-yl)-1-methylquinolin-4-one
AKOS002141814
HMS1570G09
HMS2097G09
chebi:5541 ,
CHEMBL1371756
HMS2268L04
NCGC00016465-02
CCG-208356
2-(1,3-benzodioxol-5-yl)-1-methyl-4(1h)-quinolinone (graveoline)
COBBNRKBTCBWQP-UHFFFAOYSA-N
DTXSID80326593
2-(2h-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one
4(1h)-quinolinone, 2-(1,3-benzodioxol-5-yl)-1-methyl-
SR-01000737557-3
sr-01000737557
2-(1,3-benzodioxol-5-yl)-1-methyl-4(1h)-quinolinone, 9ci
1-methyl-2-(3,4-methylenedioxyphenyl)-4(1h)-quinolinone
rutamine
foliosine
2-(benzo[d][1,3]dioxol-5-yl)-1-methylquinolin-4(1h)-one
graveoline (4-chinolon)
ZB1720
DS-19520
Q27106801
STL565967
2-(1,3-benzodioxol-5-yl)-1-methylquinolin-4(1h)-one
C75292
SB71513
CS-0011994

Research Excerpts

Overview

ExcerptReference
"Graveoline is a biologically active ingredient extracted from Ruta graveolens. "( Guo, S; Liu, H; Xi, S, 2023)

Drug Classes (1)

ClassDescription
quinolinesA class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
[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 (30)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency12.58930.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency12.58930.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency22.10610.177814.390939.8107AID2147
Chain A, Ferritin light chainEquus caballus (horse)Potency11.22025.623417.292931.6228AID485281
glp-1 receptor, partialHomo sapiens (human)Potency3.54810.01846.806014.1254AID624417
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency27.82980.011212.4002100.0000AID1030
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency7.94330.00137.762544.6684AID914; AID915
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency1.58490.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency1.99530.00255.840031.6228AID899
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency11.22020.001815.663839.8107AID894
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency100.00003.548119.542744.6684AID743266
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency10.00000.031610.279239.8107AID884; AID885
lamin isoform A-delta10Homo sapiens (human)Potency3.16230.891312.067628.1838AID1487
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Rap guanine nucleotide exchange factor 4Homo sapiens (human)Potency3.16233.981146.7448112.2020AID720708
GABA theta subunitRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
adaptive immune responseRap guanine nucleotide exchange factor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
calcium-ion regulated exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
positive regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of synaptic vesicle cycleRap guanine nucleotide exchange factor 4Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein-macromolecule adaptor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
small GTPase bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
cytosolRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
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.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1103220Phytotoxicity against Lactuca sativa cv. Burpee's Iceberg (lettuce) assessed as cellular leakage at 100 uM measured after incubation over 18 hr in darkness and 24 hr in light by spectrophotometry relative to control2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1503775Antichlamydial activity against Chlamydia pneumoniae K7 infected in HL cells assessed as chlamydial inhibition at 50 uM after 70 hrs by fluorescent microscopic analysis2017Journal of natural products, 10-27, Volume: 80, Issue:10
Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.
AID1102095Stimulation of Diaporthe ampelina growth at 30 to 300 uM after 120 hr by microplate photometric analysis2003Journal of agricultural and food chemistry, Feb-12, Volume: 51, Issue:4
Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID1103224Phytotoxicity against Lactuca sativa cv. Burpee's Iceberg (lettuce) assessed as reduction in chlorophyll content compound treated at 100 uM in darkness after 7 days followed by exposure to white light by spectrophotometry2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1102101Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 100 uM after 120 hr by microplate photometric analysis2003Journal of agricultural and food chemistry, Feb-12, Volume: 51, Issue:4
Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
AID1103225Phytotoxicity against Lactuca sativa cv. Burpee's Iceberg (lettuce) assessed as reduction in chlorophyll content at 100 uM after 7 days by spectrophotometry2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1102115Antifungal activity against Colletotrichum fragariae assessed as growth inhibition at 30 to 300 uM after 48 hr by microplate photometric analysis2003Journal of agricultural and food chemistry, Feb-12, Volume: 51, Issue:4
Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
AID1503774Cytotoxicity against human HL cells assessed as cell viability at 50 uM after 72 hrs by resazurin dye based fluorescence assay relative to control2017Journal of natural products, 10-27, Volume: 80, Issue:10
Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.
AID1102109Antifungal activity against Fusarium oxysporum assessed as growth inhibition at 300 uM after 48 hr by microplate photometric analysis2003Journal of agricultural and food chemistry, Feb-12, Volume: 51, Issue:4
Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
AID1103219Phytotoxicity against Agrostis stolonifera assessed as mortality at 333 uM after 12 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1103216Phytotoxicity against Allium cepa (onion) assessed as inhibition of mitosis in root tips at 100 uM measured on day 7 of compound treatment by microscopy2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1102104Stimulation of Botryotinia fuckeliana growth at 30 uM after 48 hr by microplate photometric analysis2003Journal of agricultural and food chemistry, Feb-12, Volume: 51, Issue:4
Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
AID1103218Phytotoxicity against Lemna paucicostata assessed as growth inhibition at 100 uM after 4 to 5 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1103217Phytotoxicity against Lemna paucicostata assessed as tissue degradation at 250 uM after 4 to 5 days2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Phytotoxins from the leaves of Ruta graveolens.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (13.64)29.6817
2010's13 (59.09)24.3611
2020's6 (27.27)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%
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]