Page last updated: 2024-09-27

komaroviquinone

Description

komaroviquinone: trypanocidal agent that fosters generation of reactive oxygen species via semiquinone radical produced by old yellow enzyme; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

komaroviquinone : A tetracyclic diterpenoid isolated from Dracocephalum komarovii and has been shown to exhibit trypanocidal activity. [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
Dracocephalumgenus[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
Dracocephalum komaroviispecies[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID637171
CHEMBL ID463213
CHEBI ID66148
SCHEMBL ID5308872
MeSH IDM0495879

Synonyms (11)

Synonym
rel-(4ar,10r,11ar)-10-hydroxy-8-isopropyl-7-methoxy-1,1-dimethyl-1,2,3,4,5,10,11,11a-octahydro-4a,10-epoxydibenzo[a,d][7]annulene-6,9-dione
4a,10-epoxy-4ah-dibenzo[a,d]cycloheptene-6,9-dione, 1,2,3,4,5,10,11,11a-octahydro-10-hydroxy-7-methoxy-1,1-dimethyl-8-(1-methylethyl)-, (4as,10s,11as)-
inchi=1/c21h28o5/c1-11(2)14-17(23)15-12(16(22)18(14)25-5)9-20-8-6-7-19(3,4)13(20)10-21(15,24)26-20/h11,13,24h,6-10h2,1-5h3/t13-,20-,21-/m0/s
komaroviquinone
chebi:66148 ,
CHEMBL463213
(+)-komaroviquinone
(4as,10s,11as)-10-hydroxy-7-methoxy-1,1-dimethyl-8-(propan-2-yl)-1,2,3,4,5,10,11,11a-octahydro-4a,10-epoxydibenzo[a,d][7]annulene-6,9-dione
SCHEMBL5308872
(1s,9s,11s)-9-hydroxy-5-methoxy-12,12-dimethyl-6-propan-2-yl-16-oxatetracyclo[7.6.1.01,11.03,8]hexadeca-3(8),5-diene-4,7-dione
Q27134670

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
trypanocidal drugA drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
[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 (4)

ClassDescription
tetracyclic diterpenoidA diterpenoid with a tetracyclic skeleton.
bridged compoundA polycyclic compound in which two rings have two or more atoms in common.
lactolCyclic hemiacetals formed by intramolecular addition of a hydroxy group to an aldehydic or ketonic carbonyl group. They are thus 1-oxacycloalkan-2-ols or unsaturated analogues.
p-quinonesA quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid 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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1236977Antitrypanosomal activity against trypomastigotes stage of Trypanosoma cruzi infected in human HT1080 cells assessed as inhibition of parasite growth at 1 uM after 24 hrs by microscopic analysis2015Bioorganic & medicinal chemistry letters, Aug-01, Volume: 25, Issue:15
Synthesis and biological evaluation of quinones derived from natural product komaroviquinone as anti-Trypanosoma cruzi agents.
AID1236976Antitrypanosomal activity against trypomastigotes stage of Trypanosoma cruzi infected in human HT1080 cells assessed as inhibition of parasite growth at 10 uM after 24 hrs by microscopic analysis2015Bioorganic & medicinal chemistry letters, Aug-01, Volume: 25, Issue:15
Synthesis and biological evaluation of quinones derived from natural product komaroviquinone as anti-Trypanosoma cruzi agents.
AID1236979Induction of reactive oxygen species formation in human HT1080 cells at 10 to 50 M by fluorometric analysis2015Bioorganic & medicinal chemistry letters, Aug-01, Volume: 25, Issue:15
Synthesis and biological evaluation of quinones derived from natural product komaroviquinone as anti-Trypanosoma cruzi agents.
AID334202Trypanocidal activity against Trypanosoma cruzi epimastigotes2003Journal of natural products, Jan, Volume: 66, Issue:1
New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi.
AID1236978Antitrypanosomal activity against trypomastigotes stage of Trypanosoma cruzi infected in human HT1080 cells assessed as inhibition of parasite growth after 24 hrs by microscopic analysis2015Bioorganic & medicinal chemistry letters, Aug-01, Volume: 25, Issue:15
Synthesis and biological evaluation of quinones derived from natural product komaroviquinone as anti-Trypanosoma cruzi agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's4 (33.33)24.3611
2020's3 (25.00)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%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]