(5R,6S,8S,10R)-10-[(S)-hydroxy(2-hydroxy-6-oxo-1,6-dihydropyrimidin-4-yl)methyl]-5-methyl-6-(sulfooxy)-2,11,12-triazatricyclo[6.3.1.04,12]dodec-1-en-2-ium

• ChemBase ID: 126829
• Molecular Formular: C15H22N5O7S+
• Molecular Mass: 416.42948
• Monoisotopic Mass: 416.12399407
• SMILES: O=c1cc(nc(O)[nH]1)[C@@H](O)[C@H]1C[C@H]2C[C@H](OS(=O)(=O)O)[C@H](C)C3C[NH+]=C(N1)N23
• Canonical SMILES: C[C@H]1[C@H](C[C@H]2N3C1C[NH+]=C3N[C@H](C2)[C@@H](c1cc(=O)[nH]c(n1)O)O)OS(=O)(=O)O
• InChI: InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/p+1/t6-,7+,8-,10?,11+,13+/m1/s1
• InChIKey: LHJPHMKIGRLKDR-NPSYHWQSSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S,8S,10R)-10-[(S)-hydroxy(2-hydroxy-6-oxo-1,6-dihydropyrimidin-4-yl)methyl]-5-methyl-6-(sulfooxy)-2,11,12-triazatricyclo[6.3.1.0^4,^1^2]dodec-1-en-2-ium
• IUPAC Traditional name: cylindrospermopsin
• Synonyms: Cylindrospermopsine; Cylindrospermopsin

Database IDs

• CAS Number: 143545-90-8
• PubChem SID: 162221156
• PubChem CID: 57459020
• Chemspider ID: 21106433
• Wikipedia Title: Cylindrospermopsin

CALCULATED PROPERTIES

• Acid pKa: -1.4064043
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.8437405
• LogD (pH = 7.4): -2.3454676
• Log P: -1.8315843
• Molar Refractivity: 106.0249 cm^3
• Polarizability: 37.180527 Å^3
• Polar Surface Area: 174.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: High in water
• Apperance: White solid