Compound: Pederin
SMILES: O=C(N[C@@H](OC)[C@H]1O[C@@H](C(C)(C)[C@@H](C1)O)C[C@H](OC)COC)[C@@H](O)[C@@]2(O[C@@H]([C@H](C)C(C2)=C)C)OC
InChIKey: ZNEZZONMADKYTB-VRCUBXEUSA-N
Synonyms: Pederin, Pederine, 27973-72-4, (+)-pederine, (+)-pederin, paederine, B8F7J348GJ, NSC-114781, CHEBI:78591, DTXSID90182248, (2S)-N-[(S)-[(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl]-methoxymethyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide, N-((6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)methoxymethyl)tetrahydro-alpha-hydroxy-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-acetamide, (2S)-N-((S)-((2S,4R,6R)-6-((2S)-2,3-dimethoxypropyl)-4-hydroxy-5,5-dimethyloxan-2-yl)-methoxymethyl)-2-hydroxy-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl)acetamide, RefChem:170656, DTXCID00104739, NSC 114781, UNII-B8F7J348GJ, NSC114781, PEDERIN [MI], PEDERIN, (+)-, SCHEMBL452974, 2H-Pyran-2-acetamide, N-(6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)tetrahydro-alpha-hydroxy-2-methoxy-5,6-dimethyl-4-methylene-, (2S-(2alpha(R*(R* (2S*,5S*,6S*))),4beta,6beta(R*)))-, 2H-Pyran-2-glycolamide, N-((6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)methoxymethyl)tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-, D-manno-Nonitol, 2,6-anhydro-3,5,7-trideoxy-1-C-(((2S)-hydroxy((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetyl)amino)-5,5-dimethyl-1,8,9-tri-O-methyl-, (1S)-, Q8214251, (2S)-N-[(S)-{(2S,4R,6R)-6-[(2S)-2,3-Dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide, (2S)-N-[(S)-{(2S,4R,6R)-6-[(2S)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2H-pyran-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl]acetamide, 2H-Puran-2-acetamide,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5- dimethyl-2H-pyran-2-yl]tetrahydro-.alpha.-hydroxy-2- methoxy-5,6-dimethyl-4-methylene-, [2S-[2.alpha.[R*[R* (2S*,5S*,6S*)]],4.beta.,6.beta.(R*)]]-, 2H-Pyran-2-glycolamide,3-dimethoxypropyl0tetrahydro-3-hydroxy-5,5- dimethyl-2H-pyran-2-yl]methoxymethyl]tetrahydro-2-methoxy- 5,6-dimethyl-4-methylene-, D-MANNO-NONITOL, 2,6-ANHYDRO-3,5,7-TRIDEOXY-1-C-(((2S)-2-HYDROXY-2-((2R,5R,6R)-TETRAHYDRO-2-METHOXY-5,6-DIMETHYL-4-METHYLENE-2H-PYRAN-2-YL)ACETYL)AMINO)-5,5-DIMETHYL-1,8,9-TRI-O-METHYL-, (1S)-
Theoretical properties:
molecular_formula: C25H45NO9
molecular_weight: 503.6 g/mol
exact_mass: 503.30943201 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 11
heavy_atom_count: 35
topological_polar_surface_area: 125 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Pederin is a polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent. It has a role as an antineoplastic agent, an antimitotic, a bacterial metabolite and a vesicant. It is a secondary carboxamide, a diol, a polyketide, a secondary alcohol, a member of oxanes and a cyclic ketal.
chebi: A polyketide and carboxamide produced by a (<em>Pseudomonas</em>) bacterial endosymbiont of certain rove beetles (genus <em>Paederus</em>). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent.
wikipedia: Pederin is a vesicant toxic amide with two tetrahydropyran rings, found in the haemolymph of the beetle genus Paederus, including the Nairobi fly, belonging to the family Staphylinidae. It was first characterized by processing 25 million field-collected P. fuscipes.  It makes up approximately 0.025% of an insect's weight (for P. fuscipes).
It has been demonstrated that the production of pederin relies on the activities of an endosymbiont (Pseudomonas ssp.) within Paederus.
The manufacture of pederin is largely confined to adult female beetles—larvae and males only store pederin acquired maternally (i.e., through eggs) or by ingestion.