Structure via PubChem · Public domain (PubChem)
spinosad
Sign in to saveAlso known as LY-232105, PP-105, XDE-105, NAF-144, Natroba
Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in th
Chemical data
- Formula
- C83H132N2O20
- Molecular weight
- 1477.9 g/mol
- IUPAC name
- (1S,2S,5R,7S,9S,10S,14R,15S,19S)-15-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-19-ethyl-4,14-dimethyl-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;(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
- SMILES
- CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3[C@@H]2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C
- InChIKey
- JFLRKDZMHNBDQS-SGSTVUCESA-N
- Polar surface area
- 222 Ų
- H-bond donors
- 0
- H-bond acceptors
- 22
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,225 papers- Spinosad: in pediculosis capitis.American journal of clinical dermatology · 2011
- Spinosad for the treatment of head lice infestations.Drugs of today (Barcelona, Spain : 1998) · 2012
- Spinosad (Natroba) topical suspension for head lice.The Medical letter on drugs and therapeutics · 2011
- Properties, toxicity and current applications of the biolarvicide spinosad.Journal of toxicology and environmental health. Part B, Critical reviews · 2020
- The spinosyns, spinosad, spinetoram, and synthetic spinosyn mimics - discovery, exploration, and evolution of a natural product chemistry and the impact of computational tools.Pest management science · 2021
via PubMed
Wikidata facts
- Subclass of
- mixture
- Mass
- 1476.937345
- Has use
- insecticide
Show 5 more facts
- Commons category
- Spinosyns
- chemical formula
- C₈₃H₁₃₂N₂O₂₀
- isomeric SMILES
- CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3[C@@H]2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C
- canonical SMILES
- CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C=CC3C2CC(=O)O1)OC5C(C(C(C(O5)C)OC)OC)OC)C)OC6CCC(C(O6)C)N(C)C.CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C(=CC3C2CC(=O)O1)C)OC5C(C(C(C(O5)C)OC)OC)OC)C)OC6CCC(C(O6)C)N(C)C
- medical condition treated
- lice infestation
via Wikidata · CC0
~6 min read
Encyclopedic overview
7 sectionsContents
- Mode of action
- Uses
- Spinosyn A
- Resistance
- Safety and ecotoxicology
- References
- Further reading
Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water.
Spinosad is a novel-mode-of-action insecticide derived from a family of natural products obtained by fermentation of S. spinosa. Spinosyns occur in over 20 natural forms, and over 200 synthetic forms (spinosoids) have been produced in the lab. Spinosad contains a mix of two spinosoids, spinosyn A, the major component, and spinosyn D (the minor component), in a roughly 17:3 ratio.
Excerpted from Wikipedia’s “spinosad” article, available under the CC BY-SA 4.0 licence.