fagaronine profile

Fagaronine is an alkaloid found in plants of the Rutaceae family, particularly in the genus Fagara. It has been shown to exhibit a range of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. Research on fagaronine has been driven by its potential therapeutic applications, particularly in the treatment of inflammatory diseases and infections. The compound has shown promising activity against various cancer cell lines, prompting further investigation into its potential as an anticancer agent. Its unique chemical structure and biological activity have made it a subject of ongoing research, focusing on its synthesis, mechanism of action, and potential applications in medicine.'

fagaronine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	40305
CHEMBL ID	121087
CHEBI ID	28954
SCHEMBL ID	424549
MeSH ID	M0042531

Synonym
2-hydroxy-3,8,9-trimethoxy-5-methylbenzo[c]phenanthridinium
CHEBI:28954 ,
brn 1554609
benzo(c)phenanthridinium, 2-hydroxy-3,8,9-trimethoxy-5-methyl-
benzo(c)phenanthridinium, 2-hydroxy-5-methyl-3,8,9-trimethoxy-
NEURO_000091
{benzo[c]phenanthridinium,} 2-hydroxy-3,8,9-trimethoxy-5-methyl-, chloride (mf1)
3,8,9-trimethoxy-5-methyl-5lambda~5~-benzo[c]phenanthridin-2-ol
3,8,9-trimethoxy-5-methyl-benzo[c]phenanthridin-5-ium-2-ol
fagaronine
52259-65-1
C09438
NCI60_001154
3,8,9-trimethoxy-5-methylbenzo[c]phenanthridin-5-ium-2-ol
CHEMBL121087
unii-59hne8rjs6
59hne8rjs6 ,
SCHEMBL424549
DTXSID30200298
Q17042674
2-hydroxy-3,8,9-trimethoxy-5-methylbenzo[c]phenanthridin-5-ium
2-hydroxy-3,8,9-trimethoxy-5-methylbenzo(c)phenanthridinium

Excerpt	Reference	Relevance
"Fagaronine (Fine) is a novel antileukemic drug extracted from Fagara xanthoxyloides Lam. "	( Effect of fagaronine on cell cycle progression of human erythroleukemia K562 cells. Carpentier, Y; Comoë, L; Desoize, B; Jardillier, JC, 1988)	2.12

Excerpt	Reference	Relevance
" Both compounds have toxic effects but no statistically significant increase in the frequency of spots was detected with the analogue of nitidine chloride."	( Evaluation of genotoxicity of the indenoisoquinoline analogues of fagaronine and nitidine in Drosophila melanogaster. Narváez, Z; Pérez-Chiesa, Y, 1993)	0.52

Role	Description
mutagen	An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
[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]

Class	Description
benzophenanthridine alkaloid	A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (32.43)	18.7374
1990's	11 (29.73)	18.2507
2000's	11 (29.73)	29.6817
2010's	3 (8.11)	24.3611
2020's	0 (0.00)	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	39 (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
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	1.97	1	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
phenol [no description available]	2.03	1	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	8.38	7	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.07	1	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
nitidine nitidine: RN given refers to parent cpd; synonym NSC 146397 refers to chloride; structure	3.09	5	phenanthridines
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	8.38	7	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
thymidine [no description available]	1.97	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.98	1	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.03	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	1.98	1	ortho-fused polycyclic arene	plant metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	1.98	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
1,7-phenanthroline [no description available]	2.02	1	phenanthroline
3-nitrobenzothiazolo(3,2-a)quinolinium 3-nitrobenzothiazolo(3,2-a)quinolinium: RN given refers to parent cpd; structure given in first source	1.96	1
aclacinomycin aklavin: antibiotic prepared from culture liquids of streptomycete (A 1129); possessing antiphage activity; structure. aclacinomycin T : An anthracycline that is aklavinone having an alpha-L-rhodosaminyl residue attached at position 4 via a glycosidic linkage.	7.38	2	aminoglycoside; anthracycline; deoxy hexoside; methyl ester; monosaccharide derivative; phenols; polyketide; tertiary alcohol; tetracenequinones; zwitterion	antimicrobial agent; antineoplastic agent; metabolite
acronine Acronine: A pyrano-acridone alkaloid found in RUTACEAE plants.. acronycine : An alkaloid antineoplastic agent isolated from Acronychia baueri.	1.99	1	acridone derivatives; alkaloid	antineoplastic agent; metabolite
aclarubicin Aclarubicin: An anthracycline produced by Streptomyces galilaeus. It has potent antineoplastic activity.. aclacinomycin A : An anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity.	2.89	4	aminoglycoside; anthracycline; methyl ester; phenols; polyketide; tetracenequinones; trisaccharide derivative; zwitterion	antimicrobial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
ethoxidine ethoxidine: InChIKey: IIATUSCNYYSFNW-UHFFFAOYSA-N	2.7	3
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.01	1
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	1.97	1

Condition	Relationship Strength	Studies
Leukemia L 1210 [description not available]	2.41	2
Invasiveness, Neoplasm [description not available]	2.06	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.07	1
Glial Cell Tumors [description not available]	2.01	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.01	1
Adenocarcinoma, Basal Cell [description not available]	2.41	2
Cancer of Prostate [description not available]	2.03	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.41	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.03	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.38	2
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	1.98	1
Breast Cancer [description not available]	1.98	1
Breast Neoplasms Tumors or cancer of the human BREAST.	1.98	1
Leucocythaemia [description not available]	2.67	3
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.67	3
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	1.97	1
Di Guglielmo Disease [description not available]	2.88	4
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.88	4
Anasarca [description not available]	1.96	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.96	1
Abnormalities, Autosome [description not available]	2.37	2
Sterility, Male [description not available]	1.96	1
Chromosome Deletion Actual loss of portion of a chromosome.	1.96	1
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	1.96	1
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	1.96	1
Experimental Neoplasms [description not available]	1.96	1
Experimental Leukemia [description not available]	1.94	1

fagaronine

Description

Cross-References

Synonyms (22)

Research Excerpts

Overview

Toxicity

Roles (1)

Drug Classes (1)

Research

Studies (37)

Study Types