(1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^{3,8}]tetradecan-7-one dihydrochloride

• ChemBase ID: 73055
• Molecular Formular: C14H26Cl2N2O7
• Molecular Mass: 405.27144
• Monoisotopic Mass: 404.11170654
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H]2[C@@H]([C@H]1O)O[C@H]1[C@@](O2)(C(=O)C[C@H](O1)C)O)NC)O)NC.Cl.Cl
• Canonical SMILES: CN[C@H]1[C@H](O)[C@H]2O[C@@H]3O[C@H](C)CC(=O)[C@@]3(O[C@@H]2[C@H]([C@H]1O)NC)O.Cl.Cl
• InChI: InChI=1S/C14H24N2O7.2ClH/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14;;/h5,7-13,15-16,18-20H,4H2,1-3H3;2*1H/t5-,7-,8+,9+,10+,11-,12-,13+,14+;;/m1../s1
• InChIKey: FOGDPGQSHLLYIK-XYQGXRRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^{3,8}]tetradecan-7-one dihydrochloride; (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^3,^8]tetradecan-7-one dihydrochloride
• IUPAC Traditional name: spectinomycin dihydrochloride; prospec dihydrochloride
• Synonyms: Spectinomycin hydrochloride; (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^{3,8}]tetradecan-7-one dihydrochloride

Database IDs

• CAS Number: 21736-83-4
• MDL Number: MFCD00070403
• PubChem SID: 162037975
• PubChem CID: 64740

CALCULATED PROPERTIES

• Acid pKa: 8.576982
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.963829
• LogD (pH = 7.4): -3.421742
• Log P: -2.3693373
• Molar Refractivity: 75.4362 cm^3
• Polarizability: 31.587643 Å^3
• Polar Surface Area: 129.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 210 - 212°C
• Hydrophobicity(logP): -2.878

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 95%
• Salt Data: hydrochloride

DETAILS

Selleck Chemicals - S2510

Research Area: Infection
Biological Activity:
Spectinomycin hydrochloride is a new parenteral antibiotic prepared from Streptomyces spectabilis. Spectinomycin (HCl) is structurally related to aminoglycosides. Spectinomycin lacks amino sugar and glycosidic bonds. Spectinomycin has moderate antibacterial activity against many gram positive and gram negative bacteria but Spectinomycin (HCl) is especially effective against Niesseria gonorrhoeae. [1][2]

REFERENCES

• http://en.wikipedia.org/wiki/Spectinomycin