(1R,3S,5R,8R,10R,11R,12S,13S,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

• ChemBase ID: 177713
• Molecular Formular: C14H24N2O7
• Molecular Mass: 332.34956
• Monoisotopic Mass: 332.15835112
• 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
• 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
• InChI: InChI=1S/C14H24N2O7/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/t5-,7+,8-,9+,10+,11-,12-,13+,14+/m1/s1
• InChIKey: UNFWWIHTNXNPBV-UVJBGAKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,8R,10R,11R,12S,13S,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^3,^8]tetradecan-7-one
• IUPAC Traditional name: (1R,3S,5R,8R,10R,11R,12S,13S,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^3,^8]tetradecan-7-one
• Synonyms: (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-pyrano[2,3-b][1,4]benzodioxin-4-one Hydrochloride; (+)-Spectinomycin Dihydrochloride; NSC 248616; Spectinomycin Hydrochloride; Stanilo; Spectinomycin Dihydrochloride

Database IDs

• CAS Number: 21736-83-4
• PubChem SID: 164233623
• PubChem CID: 71752167

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

DETAILS

Toronto Research Chemicals - S680250

An antibiotic used in the treatment and control of infectious bacterial enteritis in animals. Used in drug testing against nonreplicating mycobacterium tuberculosis.

REFERENCES

• Sala, C. et al.: Antimicrob. Agents Chemother., 54, 4150 (2010)
• Food and Drug Admin.: Fed. Reg., 69, 52815 (2010)