(1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.17,11.01,6]tetradec-3-ene-5,9,12,13,14-pentol

• ChemBase ID: 129820
• Molecular Formular: C11H17N3O8
• Molecular Mass: 319.26798
• Monoisotopic Mass: 319.10156452
• SMILES: O1[C@@H]2[C@@](O)([C@H]3O[C@@]1(O)[C@@H](O)[C@]1(NC(=N[C@H](O)[C@@H]31)N)[C@@H]2O)CO
• Canonical SMILES: OC[C@@]1(O)[C@H]2O[C@]3(O[C@H]1[C@H]1[C@@]([C@@H]2O)([C@@H]3O)NC(=N[C@@H]1O)N)O
• InChI: InChI=1S/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1
• InChIKey: CFMYXEVWODSLAX-QOZOJKKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^7,^1^1.0^1,^6]tetradec-3-ene-5,9,12,13,14-pentol
• IUPAC Traditional name: (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1^7,^1^1.0^1,^6]tetradec-3-ene-5,9,12,13,14-pentol
• Synonyms: anhydrotetrodotoxin; 4-epitetrodotoxin; tetrodonic acin; TTX; Tetrodotoxin

Database IDs

• CAS Number: 4368-28-9
• PubChem SID: 162224107
• PubChem CID: 11174599
• CHEMBL: 507974
• Chemspider ID: 9349691
• KEGG ID: C11692
• Wikipedia Title: Tetrodotoxin

CALCULATED PROPERTIES

• Acid pKa: 10.397875
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -6.938484
• LogD (pH = 7.4): -6.552516
• Log P: -4.814641
• Molar Refractivity: 64.9705 cm^3
• Polarizability: 26.7011 Å^3
• Polar Surface Area: 190.25 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false