Page last updated: 2024-11-08

spinosyn a

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

Description

spinosyn A: a macrolide ; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

spinosyn A : A spinosyn in which the sugar amino and hydroxy groups are globally methylated. One of the two active ingredients of spinosad. [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]

Cross-References

ID SourceID
PubMed CID443059
CHEMBL ID501411
CHEBI ID9230
SCHEMBL ID465876
MeSH IDM0296061

Synonyms (32)

Synonym
spinosyn-a
hsdb 7006
(-)-spinosyn a
1h-as-indaceno(3,2-d)oxacyclododecin-7,15-dione, 2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-2-((6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl)oxy)- 13-((5-dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)oxy)-9-ethyl-14-methyl-, (2r-(2r*,3a
131929-60-7
spinosyn a
spinosad factor a
2r,3as,5ar,5bs,9s,13s,14r,16as,16br)-2-(6-deoxy-2,3,4-tri-o-methyl-?-l-mannopyranosyloxy)-13-(4-dimethylamino-2,3,4,6-tetradeoxy-?-d-erythropyranosyloxy)-9-ethyl-2,3,3a,5a,5b,6,7,9,10,11,12,13,14,15,16a,16b-hexadecahydro-14-methyl-1h-as-indaceno[3,2-d]oxa
a 83543a
lepicidin a
CHEBI:9230 ,
(2r,3as,5ar,5bs,9s,13s,14r,16as,16br)-13-{[(2r,5s,6r)-5-(dimethylamino)-6-methyltetrahydro-2h-pyran-2-yl]oxy}-9-ethyl-14-methyl-7,15-dioxo-2,3,3a,5a,5b,6,7,9,10,11,12,13,14,15,16a,16b-hexadecahydro-1h-as-indaceno[3,2-d]oxacyclododecin-2-yl 6-deoxy-2,3,4-t
CHEMBL501411
oy0l59v61n ,
ccris 8937
(2r,3as,5ar,5bs,9s,13s,14r,16as,16br)-2-((6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl)oxy)-13-(((2r,5s,6r)-5-(dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)oxy)-9-ethyl-14-methyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1h-as-indacen
1h-as-indaceno(3,2-d)oxacyclododecin-7,15-dione, 2-((6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl)oxy)-13-(((2r,5s,6r)-5-(dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)oxy)-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-,
unii-oy0l59v61n
spinosad factor a [usan]
spinosyns [mi]
spinosad factor a [hsdb]
SCHEMBL465876
DTXSID8037598
AKOS032946512
(1s,2r,5s,7r,9r,10s,14r,15s,19s)-15-[(2r,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-19-ethyl-14-methyl-7-[(2r,3r,4r,5s,6s)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione
SRJQTHAZUNRMPR-UYQKXTDMSA-N
Q27108323
(2r,3as,5ar,5bs,9s,13s,14r,16as,16br)-2-[(6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl)oxy]-13-[[(2r,5s,6r)-5-(dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl]oxy]-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-1h-as-indacen
benzenesulfinicacidsodiumsalt
CS-0009656
HY-B0767
1ST20443

Research Excerpts

Overview

Spinosyn A is a polyketide-derived macrolide produced by Saccharopolyspora spinosa. It is an active ingredient in several commercial insecticides.

ExcerptReferenceRelevance
"Spinosyn A is a polyketide-derived macrolide produced by Saccharopolyspora spinosa and is an active ingredient in several commercial insecticides. "( Biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of permethylated rhamnose and characterization of the functions of SpnH, SpnI, and SpnK.
Isiorho, EA; Kim, HJ; Liu, HW; Ogasawara, Y; Shin, N; White-Phillip, JA, 2010
)
1.8

Dosage Studied

ExcerptRelevanceReference
" Dairy cows were dosed for 28 days with spinosad at rates equivalent to 0, 1, 3, and 10 microg/g in the diet."( Residues of spinosad in meat, milk, and eggs.
Dolder, SC; Gardner, RC; Robb, CK; Rutherford, BS; West, SD, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
pediculicideSubstance used to treat lice (genus Pediculus) infestation.
[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 (2)

ClassDescription
spinosynA family of macrolide natural products produced by the soil microorganism Saccharopolyspora spinosa.
spinosyn insecticide
[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 (30)

Assay IDTitleYearJournalArticle
AID379890Insecticidal activity against beet armyworm assessed as mortality per larva after 5 days2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1420891Induction of apoptosis in human NCI-H460 cells assessed as necrotic cells at 64 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 2.11%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420889Induction of apoptosis in human NCI-H460 cells assessed as early apoptotic cells at 32 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 2.17%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420886Antiproliferative activity against human U87MG cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID379172Insecticidal activity against beet armyworm eggs assessed as inhibition of insect growth at 28 degC after 6 days by lepidopteran diet assay2006Journal of natural products, Oct, Volume: 69, Issue:10
Discovery, synthesis, and insecticidal activity of cycloaspeptide E.
AID1420894Induction of apoptosis in human NCI-H460 cells assessed as viable cells at 64 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 93.9%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420904Inhibition of oxygen consumption rate in human NCI-H460 cells at 32 uM after 1 hr2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID379886Insecticidal activity against cotton aphid assessed as count of nonwinged stage live aphid after 72 hrs with 24 hrs of photoperiod prior to grading2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1420883Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420893Induction of apoptosis in human NCI-H460 cells assessed as early apoptotic cells at 64 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 2.17%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420905Growth inhibition of human NCI-H460 cells at 32 uM after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420884Antiproliferative activity against human HCT116 cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420887Induction of apoptosis in human NCI-H460 cells assessed as necrotic cells at 32 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 2.11%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID379887Insecticidal activity against green peach aphid assessed as count of nonwinged stage live aphid after 72 hrs with 24 hrs of photoperiod prior to grading2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID379892Insecticidal activity against two-spotted spinder mites assessed as count of live mites after 4 days with low light condition2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1667599Antiproliferative activity against human U87MG cells incubated for 48 hrs2020Bioorganic & medicinal chemistry letters, 05-01, Volume: 30, Issue:9
Synthesis and anti-OXPHOS, antitumor activities of DLC modified spinosyn derivatives.
AID1420890Induction of apoptosis in human NCI-H460 cells assessed as viable cells at 32 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 93.9%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1420892Induction of apoptosis in human NCI-H460 cells assessed as late apoptotic cells at 64 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 1.80%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1667597Antiproliferative activity against human HCT116 cells incubated for 48 hrs2020Bioorganic & medicinal chemistry letters, 05-01, Volume: 30, Issue:9
Synthesis and anti-OXPHOS, antitumor activities of DLC modified spinosyn derivatives.
AID1420888Induction of apoptosis in human NCI-H460 cells assessed as late apoptotic cells at 32 uM after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 1.80%)2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID334207Antilepidopteran activity against tobacco budworm eggs assessed as minimum emergent larvicide concentration after 6 to 7 days2003Journal of natural products, Jan, Volume: 66, Issue:1
Tartrolone C: a novel insecticidal macrodiolide produced by Streptomyces sp. CP1130.
AID334206Antilepidopteran activity against beet armyworm eggs assessed as minimum emergent larvicide concentration after 6 to 7 days2003Journal of natural products, Jan, Volume: 66, Issue:1
Tartrolone C: a novel insecticidal macrodiolide produced by Streptomyces sp. CP1130.
AID1420882Antiproliferative activity against human MCF7 cells at 50 uM after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID1667596Antiproliferative activity against human MCF7 cells incubated for 48 hrs2020Bioorganic & medicinal chemistry letters, 05-01, Volume: 30, Issue:9
Synthesis and anti-OXPHOS, antitumor activities of DLC modified spinosyn derivatives.
AID379889Insecticidal activity against tobacco budworm assessed per larva2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1420885Antiproliferative activity against human NCI-H460 cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID379891Insecticidal activity against cabbage looper assessed as mortality per larva after 5 days2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1420906Induction of apoptosis in human NCI-H460 cells after 48 hrs by Annexin V-FITC/propidium iodide staining-based flow cytometric analysis2018Bioorganic & medicinal chemistry letters, 11-01, Volume: 28, Issue:20
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
AID379888Insecticidal activity against sweet potato whitefly assessed as larval survival after 13 days2006Journal of natural products, Dec, Volume: 69, Issue:12
Engineering of the spinosyn PKS: directing starter unit incorporation.
AID1667598Antiproliferative activity against human NCI-H460 cells incubated for 48 hrs2020Bioorganic & medicinal chemistry letters, 05-01, Volume: 30, Issue:9
Synthesis and anti-OXPHOS, antitumor activities of DLC modified spinosyn derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (56)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (3.57)18.2507
2000's26 (46.43)29.6817
2010's22 (39.29)24.3611
2020's6 (10.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.42

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index40.42 (24.57)
Research Supply Index4.04 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index50.53 (26.88)
Search Engine Supply Index2.62 (0.95)

This Compound (40.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (96.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]