ChemSpider 2D Image | cylindrospermopsin | C15H21N5O7S

cylindrospermopsin

  • Molecular FormulaC15H21N5O7S
  • Average mass415.422 Da
  • Monoisotopic mass415.116180 Da
  • ChemSpider ID26396261

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2aS,3R,4S,5aS,7R)-7-[(R)-(2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)(hydroxy)methyl]-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate [ACD/IUPAC Name]
(2aS,3R,4S,5aS,7R)-7-[(R)-(2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)(hydroxy)methyl]-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylen-4-ylhydrogensulfat [German] [ACD/IUPAC Name]
143545-90-8 [RN]
2,4(1H,3H)-Pyrimidinedione, 6-[(R)-hydroxy[(2aS,3R,4S,5aS,7R)-2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy)-1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]- [ACD/Index Name]
2JIZ556BA3
cylindrospermopsin [Wiki]
Hydrogénosulfate de (2aS,3R,4S,5aS,7R)-7-[(R)-(2,6-dioxo-1,2,3,6-tétrahydro-4-pyrimidinyl)(hydroxy)méthyl]-3-méthyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacénaphtylén-4-yle [French] [ACD/IUPAC Name]
(-)-cylindrospermopsin
(2aS,3R,4S,5aS,7R)-7-[(R)-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl]-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-8,8b-diaza-1-azoniaacenaphthylen-4-yl sulfate
(2aS,3R,4S,5aS,7R)-7-[(R)-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CYN [DBID]
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Amide; Ester; Marine Toxin; Bacterial Toxin; Natural Compound Toxin, Toxin-Target Database T3D4232

    • Chemical Class:

      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1<element>H</element>-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-t etrahydropyrimidin-4-yl)(hydroxy)methyl groups, respectively (the 2a<stereo>S</stereo>,3<stereo>R</stereo>,4<stereo>S</stereo>,5a<stereo>S</stereo>,7<stereo>R</stereo> stereoisomer in which the carbon bearing the hydroxy group has <stereo>R</stereo> configuration). It is a cyanotoxin produced by several species of freshwater cyanobacteria, such as <ital>Aphanizomenon ovalisporum</ital>. ChEBI CHEBI:88044, CHEBI:88046
      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-t; etrahydropyrimidi n-4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon; bearing the hydroxy group has R configuration). It is a cyanotoxin produced by several species of f reshwater cyanobacteria, such as Aphanizomenon ovalisporum. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88044, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88046
      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon bearing the hydroxy group has R configuration). It is a cyanotoxin produced by several species of fresh water cyanobacteria, such as Aphanizomenon ovalisporum. ChEBI CHEBI:88044, CHEBI:88046
      A zwitterion resulting from the transfer of a proton from the sulfooxy group to one of the nitrogens of the guanidine group of cylindrospermopsin. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88044, CHEBI:88044, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88046, CHEBI:88046

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 2.0±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.858
Molar Refractivity: 92.0±0.5 cm3
#H bond acceptors: 12
#H bond donors: 5
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: -1.22
ACD/LogD (pH 5.5): -4.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.30
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 178 Å2
Polarizability: 36.5±0.5 10-24cm3
Surface Tension: 97.5±7.0 dyne/cm
Molar Volume: 204.6±7.0 cm3

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