Compounds > azadirone
Page last updated: 2024-11-12

azadirone

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

Description

azadirone: from Azadirachta indica A. Juss; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

azadirone : A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by an oxo group at position 3, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antiplasmodial and antineoplastic activities. [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]

FloraRankFlora DefinitionFamilyFamily Definition
AzadirachtagenusA plant genus of the family MELIACEAE. Members contain azadirachtin A (a limonoid commonly referred to as azadirachtin) and other TRITERPENES. They have been used in PESTICIDES. The old name of Melia azadirachta is very similar to a related plant, MELIA AZEDARACH.[MeSH]MeliaceaeThe mahogany plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida.[MeSH]
Azadirachta indicaspecies[no description available]MeliaceaeThe mahogany plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID10906239
CHEMBL ID1215753
CHEBI ID76293
SCHEMBL ID2145948
MeSH IDM0468477

Synonyms (9)

Synonym
25279-67-8
chebi:76293 ,
azadirone
CHEMBL1215753
SCHEMBL2145948
(5alpha,7alpha,13alpha,17alpha)-17-(furan-3-yl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl acetate
(5alpha,7alpha,13alpha,17alpha)-7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24- norchola-1,14,20,22-tetraen-3-one
Q27145858
DTXSID501036746
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antiplasmodial drugAn antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (5)

ClassDescription
acetate esterAny carboxylic ester where the carboxylic acid component is acetic acid.
cyclic terpene ketoneAn alicyclic ketone in which the carbocyclic ring structure forms part of a terpene skeleton.
furansCompounds containing at least one furan ring.
limonoidAny triterpenoid that is highly oxygenated and has a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. The term 'limonoid' comes from limonin, the first tetranortriterpenoid obtained from citrus bitter principles.
tetracyclic triterpenoidAny triterpenoid consisting of a tetracyclic skeleton.
[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]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID499797Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D10 after 72 hrs by LDH assay2010Journal of natural products, Aug-27, Volume: 73, Issue:8
Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica.
AID1311320Osteogenic activity in rat primary calvarial osteoblasts at 100 pM after 48 hrs by ALP-based colorimetric assay2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
AID499798Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hrs by LDH assay2010Journal of natural products, Aug-27, Volume: 73, Issue:8
Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica.
AID1110753Antifeedant activity against larvae of Spodoptera litura in castor leaves relative to control2002Journal of agricultural and food chemistry, Jul-31, Volume: 50, Issue:16
Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structural relations.
AID1311327Upregulation of ALP mRNA expression in rat primary calvarial osteoblasts at 100 pM by RT-PCR analysis relative to control2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
AID1311322Induction of cell proliferation in rat primary calvarial osteoblasts at 0.1 to 10 nM after 48 hrs by BrDU-staining based assay relative to control2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
AID1311325Upregulation of RunX-2 mRNA expression in rat primary calvarial osteoblasts at 100 pM by RT-PCR analysis relative to control2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
AID1311323Induction of mineralization in rat primary calvarial osteoblasts assessed as mineralized nodule formation at 10 to 1000 nM after 12 days by alizarin red S-staining based assay relative to control2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
AID1311326Upregulation of OCN mRNA expression in rat primary calvarial osteoblasts at 100 pM by RT-PCR analysis relative to control2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's4 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.95

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 Index22.95 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.95)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.0510aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
nimbin
nimbin: from Neem seed (Azadirachta indica). nimbin : A limonoid found in Azadirachta indica.		2.0110acetate ester;
cyclic terpene ketone;
enone;
furans;
limonoid;
methyl ester;
tetracyclic triterpenoid		pesticide;
plant metabolite
7-deacetylgedunin
7-deacetylgedunin : A limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica.		2.0510cyclic terpene ketone;
delta-lactone;
enone;
epoxide;
furans;
limonoid;
pentacyclic triterpenoid		anti-inflammatory agent;
antimalarial;
metabolite;
plant metabolite
azadirachtin
azadirachtin A : A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica).. azadirachtin : A family of terpenoids isolated from the neem tree (Azadirachta indica).		2.0110acetate ester;
azadirachtin;
cyclic hemiketal;
enoate ester;
epoxide;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol;
tertiary alcohol		hepatoprotective agent
gedunin
gedunin: isolated from neem (Azadirachta indica); structure in first source. gedunin : A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata.		2.0510limonoid
salannin
salannin: from seeds of neem tree, Azadirachta indica; inhibits 20-monooxygenase; structure given in first source. salannin : A limonoid with insecticidal activity isolated from Azadirachta indica.		2.1310acetate ester;
furans;
limonoid;
methyl ester;
organic heteropentacyclic compound		antifeedant;
insect growth regulator;
plant metabolite
mexicanolide
mexicanolide: from the seeds of a Godavari mangrove, Xylocarpus moluccensis; exhibits marked antifeedant activity against the third-instar larvae of Brontispa longissima (Gestro); structure in first source		2.1710
6-deacetylnimbin
6-deacetylnimbin: structure in first source. 6-deacetylnimbin : A limonoid that is nimbin in which the acetyloxy group at position 6 is replaced by a hydroxy hroup. It has been isolated from Azadirachta indica.		2.0110cyclic terpene ketone;
diester;
enone;
furans;
limonoid;
methyl ester;
tetracyclic triterpenoid		antifeedant;
insect growth regulator;
plant metabolite
gedunin
[no description available]		2.4320acetate ester;
enone;
epoxide;
furans;
lactone;
limonoid;
organic heteropentacyclic compound;
pentacyclic triterpenoid		antimalarial;
antineoplastic agent;
Hsp90 inhibitor;
plant metabolite
azadiradione
azadiradione: structure in first source. azadiradione : A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities.		2.4320acetate ester;
cyclic terpene ketone;
furans;
limonoid;
tetracyclic triterpenoid		anti-inflammatory agent;
antimycobacterial drug;
plant metabolite
swietenine
swietenine: hypoglycemic from Swietenia macrophylla seeds; structure in first source		2.0110
cedrelone
cedrelone: from Toona ciliata; structure in first source		2.0110limonoid
azadirachtin b
azadirachtin B: structure in first source. azadirachtin B : A member of the class of azadirachtin found in the neem tree, Azadirachta indica.		2.1310
epoxyazadiradione
epoxyazadiradione: limonoid from neem tree Azadirachta indica; RN given for (5alpha,7alpha,13alpha,14beta,15beta,17alpha)-isomer; structure in first source. epoxyazadiradione : A limonoid that is azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes.		2.7430acetate ester;
cyclic terpene ketone;
epoxide;
furans;
limonoid;
pentacyclic triterpenoid		anti-inflammatory agent;
insecticide;
plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.0810
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0810