Page last updated: 2024-11-06

simalikalactone d

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

Description

simalikalactone D: quassinoid which inhibits protein synthesis & DNA synthesis in cells; RN given refers to ((11beta)-isomer); structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

simalikalactone D : A quassinoid isolated from Quassia amara and Quassia africana. It has been shown to exhibit antimalarial, cytotoxic and antiviral 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
QuassiagenusA plant genus of the family SIMAROUBACEAE. Members contain quassinoids. Quassia simarouba has been reclassified as SIMAROUBA.[MeSH]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]
Quassia amaraspecies[no description available]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]

Cross-References

ID SourceID
PubMed CID65397
MeSH IDM0083785
PubMed CID15161842
CHEMBL ID480882
CHEBI ID66486

Synonyms (12)

Synonym
35321-80-3
simalikalactone d
nsc 266494
picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12-trihydroxy-15-(2-methyl-1-oxobutoxy)-, (11beta)-
[(2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2r)-2-methylbutanoate
chebi:66486 ,
CHEMBL480882
(1beta,11beta,12alpha,15betab)-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-15-yl (2r)-2-methylbutanoate
(+)-simalikalactone
bdbm50478405
Q27135088
[(1r,2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2r)-2-methylbutanoate

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antiviral agentA substance that destroys or inhibits replication of viruses.
antimalarialA drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
[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 (8)

ClassDescription
quassinoidMembers of the class of triterpenoid, mostly isolated as bitter principles of the Simaroubaceae family. They are chemically regarded as degraded triterpenes and can be categorized into groups with C18, C19, C20, C22 and C25 skeletons.
organic heteropentacyclic compound
delta-lactoneA lactone having a six-membered lactone ring.
cyclic etherAny ether in which the oxygen atom forms part of a ring.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
triolA chemical compound containing three hydroxy groups.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
[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 (47)

Assay IDTitleYearJournalArticle
AID401579Inhibition of LFA1/ICAM1-mediated HL60 cell aggregation2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401572Selectivity index, ratio of IC50 for african green monkey (Cercopithecus aethiops) Vero cells to IC50 for chloroquine-sensitive Plasmodium falciparum D62004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401592Inhibition of protein biosynthesis in mouse Krebs cells assessed as renilla luciferase activity at 0.4 uM after 1 hr by translation assay relative to control2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401573Selectivity index, ratio of IC50 for african green monkey (Cercopithecus aethiops) Vero cells to IC50 for chloroquine-resistant Plasmodium falciparum W22004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID358630Cytotoxicity against human HL60 cells assessed as loss of membrane integrity after 4 days by trypan blue exclusion assay2001Journal of natural products, Dec, Volume: 64, Issue:12
Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture.
AID401591Inhibition of protein biosynthesis in mouse Krebs cells assessed as firefly luciferase activity at 0.4 uM after 1 hr by translation assay relative to control2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562541Cytotoxicity against human THP1 cells assessed as incorporation of [3H]hypoxanthine after 48 hrs2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID378656Cytotoxicity against human MCF7 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID358629Induction of cell differentiation in human HL60 cells assessed as superoxide anion production after 4 days by NBT reduction assay2001Journal of natural products, Dec, Volume: 64, Issue:12
Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture.
AID562538Antiplasmodial activity against Plasmodium falciparum W2 assessed as suppression of parasitemia after 4 hrs by Giemsa staining2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID378655Cytotoxicity against human CAKI1 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID401106Cytotoxicity against mouse P388 cells after 3 days by MTT assay1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Cytotoxic quassinoids from Simaba cedron.
AID401593Inhibition of translation in human HeLa cells at 0.4 uM by 35S-methionine metabolic labeling study2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401575Cytotoxicity against human SK-MEL cells after 48 hrs by neutral red staining2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401565Inhibition of protein synthesis in human HeLa cells at 2 uM by [35S]methionine metabolic labeling study2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401574Antileishmanial activity against Leishmania donovani promastigotes after 48 hrs by alamar blue assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562536Antiplasmodial activity against Plasmodium falciparum F32 assessed as suppression of parasitemia after 4 hrs by Giemsa staining2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID401576Cytotoxicity against human KB cells after 48 hrs by neutral red staining2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562537Antiplasmodial activity against Plasmodium falciparum FcB1/Columbia assessed as suppression of parasitemia after 4 hrs by Giemsa staining2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID401571Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 by LDH assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401570Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 by LDH assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID378654Cytotoxicity against human HCT8 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID378657Cytotoxicity against human SK-MEL-2 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID401588Inhibition of protein biosynthesis in mouse Krebs cells assessed as firefly luciferase activity at 2 uM after 1 hr by translation assay relative to control2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401567Inhibition of protein synthesis in human HeLa cells assessed as translation at 2 uM by [35S]methionine metabolic labeling study2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401590Inhibition of protein biosynthesis in mouse Krebs cells assessed as renilla luciferase activity at 2 uM after 1 hr by translation assay relative to control2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401578Cytotoxicity against human SKOV3 cells after 48 hrs by neutral red staining2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID378652Cytotoxicity against human KB cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID562564Antiplasmodial activity against Plasmodium yoelii yoelii infected in po dosed rodents2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID401562Cytotoxicity against african green monkey kidney Vero cells2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401568Inhibition of translation in human HeLa cells at 2 uM by 35S-methionine metabolic labeling study2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401563Cytotoxicity against mouse RAW264.7 cells after 2 days by MTT assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562557Antiplasmodial activity against Plasmodium berghei infected in ip dosed mouse2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID336325Antimalarial activity against mefloquine-resistant Plasmodium falciparum D6 (Sierra Leone) after 24 to 60 hrs by [G-H3]hypoxanthine uptake1993Journal of natural products, Nov, Volume: 56, Issue:11
A new antimalarial quassinoid from Simaba guianensis.
AID401581Specific index, ratio of IC50 for human HL60 cells to MIC for LFA1/ICAM12004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID401580Cytotoxicity against human HL60 cells by XTT assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562542Cytotoxicity against human MCF7 cells assessed as incorporation of [3H]hypoxanthine after 48 hrs2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID378653Cytotoxicity against human A549 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID401585Inhibition of iNOS production in LPS-activated mouse RAW264.7 cells after 20 hrs2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID336324Antimalarial activity against chloroquine-resistant Plasmodium falciparum Indochina W2 after 24 to 60 hrs by [G-H3]hypoxanthine uptake 1993Journal of natural products, Nov, Volume: 56, Issue:11
A new antimalarial quassinoid from Simaba guianensis.
AID401583Cytotoxicity against CHO cells transfected with ICAM1 by MTT assay2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID562539Antiplasmodial activity against Plasmodium falciparum W2 gametocytes assessed as suppression of parasitemia after 4 hrs by Giemsa staining2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID401582Inhibition of LFA1/ICAM1-mediated adhesion of HL60 cells to CHO-ICAM1 cells2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
AID422119Growth inhibition of human NCI60 cells2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition.
AID562540Cytotoxicity against african green monkey Vero cells assessed as incorporation of [3H]hypoxanthine after 48 hrs2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae).
AID358628Antiproliferative activity against human HL60 cells assessed as inhibition of [3H]thymidine incorporation after 4 days by liquid scintillation counter2001Journal of natural products, Dec, Volume: 64, Issue:12
Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture.
AID401577Cytotoxicity against human BT549 cells after 48 hrs by neutral red staining2004Journal of natural products, May, Volume: 67, Issue:5
A new antimalarial quassinoid from Simaba orinocensis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (12.50)18.7374
1990's3 (18.75)18.2507
2000's9 (56.25)29.6817
2010's2 (12.50)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: 17.30

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 Index17.30 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]