flindersine profile

Flindersine is a natural alkaloid isolated from the Australian plant *Flindersia australis*. It has shown promising biological activities, including anti-inflammatory, anticancer, and antioxidant properties. Research into flindersine has focused on its potential therapeutic applications, particularly in the treatment of inflammatory diseases and cancer. Its unique structural features and biological activities make it a valuable target for further investigation in medicinal chemistry and drug discovery.'

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

ID Source	ID
PubMed CID	68230
CHEMBL ID	1507844
CHEBI ID	5094
SCHEMBL ID	3125149
MeSH ID	M0534255

Synonym
2,2-dimethyl-2,6-dihydro-5h-pyrano[3,2-c]quinolin-5-one
STK722191
MLS000071803
smr000009047
2,2-dimethyl-2,6-dihydro-pyrano[3,2-c]quinolin-5-one
OPREA1_138192
OPREA1_017316
5h-pyrano[3, 2,6-dihydro-2,2-dimethyl-
nsc-94655
nsc94655
523-64-8
flindersine
inchi=1/c14h13no2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8h,1-2h3,(h,15,16)
pxnmnablqwumcx-uhfffaoysa-
HMS1648O08
2,2-dimethyl-6h-pyrano[3,2-c]quinolin-5-one
2h-pyrano[3,2-c]quinolin-5-ol, 2,2-dimethyl-
AKOS000635152
ST044783 ,
2,2-dimethyl-6-hydro-2h-pyrano[5,6-c]quinolin-5-one
nsc 94655
unii-6a8pd12ckp
5h-pyrano(3,2-c)quinolin-5-one, 2,6-dihydro-2,2-dimethyl-
6a8pd12ckp ,
HMS2303K10
2,6-dihydro-2,2-dimethyl-5h-pyrano(3,2-c)quinolin-5-one
flindersine [mi]
2,2'-dimethyl-.alpha.-pyrano(5',6',3,4)-2(1h)-quinolone
CHEMBL1507844
chebi:5094 ,
PXNMNABLQWUMCX-UHFFFAOYSA-N
2,6-dihydro-2,2-dimethyl-5h-pyrano[3,2-c]-quinolin-5-one
SCHEMBL3125149
DTXSID80200324
Q5862594
F0722-8699
2,2-dimethyl-2h,5h,6h-pyrano[3,2-c]quinolin-5-one
5h-pyrano[3,2-c]quinolin-5-one,2,6-dihydro-2,2-dimethyl-
STARBLD0041951

Excerpt	Relevance	Reference
" acutatum, Botrytis cinerea, Fusarium oxysporum, and Phomopsis obscurans in a dose-response growth-inhibitory bioassay at 50."	( Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii. Cantrell, CL; Dunbar, C; Kustova, TS; Mamonov, LK; Schrader, KK; Sitpaeva, GT; Wedge, DE, 2005)	0.33

Class	Description
oxacycle	Any organic heterocyclic compound containing at least one ring oxygen atom.
organonitrogen heterocyclic compound	Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms.
organic heterotricyclic compound	An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
[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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Beta-lactamase	Escherichia coli K-12	Potency	112.2020	0.0447	17.8581	100.0000	AID485294
Chain A, HADH2 protein	Homo sapiens (human)	Potency	19.9526	0.0251	20.2376	39.8107	AID886
Chain B, HADH2 protein	Homo sapiens (human)	Potency	19.9526	0.0251	20.2376	39.8107	AID886
TDP1 protein	Homo sapiens (human)	Potency	16.3601	0.0008	11.3822	44.6684	AID686978
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (42)

Assay ID	Title	Year	Journal	Article
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. 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.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. 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.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. 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.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & 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.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1103422	Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 50 measured at 48 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103423	Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 50 uM measured at 144 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103411	Antialgal activity against Selenastrum capricornutum assessed as lowest observed effect concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103421	Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 50 measured at 72 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103414	Antialgal activity against Pseudanabaena sp. LW397 assessed as lowest observed effect concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1328348	Antifungal activity against Candida albicans DSY2621 by MTT assay	2016	Journal of natural products, 09-23, Volume: 79, Issue:9	Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks.
AID1103416	Antialgal activity against Planktothrix agardhii assessed as lowest complete inhibition concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103427	Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 50 to 150 uM measured up to 72 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103428	Antifungal activity against Diaporthe ampelina assessed as growth inhibition at 50 to 150 uM measured up to 120 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103409	Antialgal activity against Selenastrum capricornutum assessed as inhibition measured for 96 hr	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103417	Antialgal activity against Planktothrix agardhii assessed as lowest observed effect concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103415	Antialgal activity against Planktothrix agardhii assessed as inhibition measured for 96 hr	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103418	Antialgal activity against Oscillatoria perornata assessed as inhibition measured for 96 hr	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103424	Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 50 uM measured at 120 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103429	Antifungal activity against Colletotrichum fragariae assessed as growth inhibition at 50 to 150 uM measured up to 72 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103419	Antialgal activity against Oscillatoria perornata assessed as lowest observed effect concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103426	Antifungal activity against Colletotrichum acutatum assessed as growth inhibition at 50 to 150 uM measured up to 72 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103431	Antifungal activity against Fusarium oxysporum assessed as growth inhibition at 50 to 150 uM measured up to 72 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103413	Antialgal activity against Pseudanabaena sp. LW397 assessed as lowest complete inhibition concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103410	Antialgal activity against Selenastrum capricornutum assessed as lowest complete inhibition concentration measured for 4 days	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103420	Antialgal activity against Oscillatoria perornata assessed as lowest complete inhibition concentration measured for 4 daysos	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1103430	Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 50 to 150 uM measured up to 120 hr by 96-well microtiter assay	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
AID1328349	Antifungal activity against wild type Candida albicans CAF2-1 by MTT assay	2016	Journal of natural products, 09-23, Volume: 79, Issue:9	Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks.
AID1103412	Antialgal activity against Pseudanabaena sp. LW397 assessed as inhibition measured for 96 hr	2005	Journal of agricultural and food chemistry, Oct-05, Volume: 53, Issue:20	Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	4 (26.67)	29.6817
2010's	7 (46.67)	24.3611
2020's	4 (26.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	15 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.13	1	dichlorobenzene; ether; imidazoles
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.25	1	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	7.04	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
quinoline [no description available]	2.25	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
(+)-Eudesmin [no description available]	2.02	1	lignan
haplamine haplamine: isolated from Haplophyllum acutifolium; structure in first source	2.02	1	organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.07	1	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.05	1
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.	2.05	1
Encephalitis, Polio [description not available]	2.06	1
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	2.06	1
Alloxan Diabetes [description not available]	2.41	1
Diabetes Mellitus, Adult-Onset [description not available]	2.41	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.41	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Leishmaniasis, American [description not available]	2.25	1
Leishmaniasis, Cutaneous An endemic disease that is characterized by the development of single or multiple localized lesions on exposed areas of skin that typically ulcerate. The disease has been divided into Old and New World forms. Old World leishmaniasis is separated into three distinct types according to epidemiology and clinical manifestations and is caused by species of the L. tropica and L. aethiopica complexes as well as by species of the L. major genus. New World leishmaniasis, also called American leishmaniasis, occurs in South and Central America and is caused by species of the L. mexicana or L. braziliensis complexes.	2.25	1

flindersine

Description

Cross-References

Synonyms (39)

Research Excerpts

Dosage Studied

Drug Classes (3)

Protein Targets (4)

Potency Measurements

Bioassays (42)

Research

Studies (15)

Market Indicators

Research Demand Index: 11.71

Study Types

flindersine

Description

Cross-References

Synonyms (39)

Research Excerpts

Dosage Studied

Drug Classes (3)

Protein Targets (4)

Potency Measurements

Bioassays (42)

Research

Studies (15)

Market Indicators

Research Demand Index: 11.71

Study Types

Related Drugs (7)

Related Conditions (10)