1-[(1S,4S,6S)-3-carbamimidamido-6-{[(2R,3S,5S)-3-{[(3S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine

• ChemBase ID: 167711
• Molecular Formular: C21H41N7O12
• Molecular Mass: 583.58994
• Monoisotopic Mass: 583.28131979
• SMILES: C1([C@@H]([C@@H](C([C@H](C1NC(=N)N)O)O)O[C@H]1[C@H](C(O)(CO)[C@@H](O1)C)OC1O[C@H]([C@@H](C([C@@H]1NC)O)O)CO)NC(=N)N)O
• Canonical SMILES: OC[C@@H]1OC(O[C@@H]2[C@H](O[C@@H]3C(O)[C@@H](O)C(C([C@@H]3NC(=N)N)O)NC(=N)N)O[C@H](C2(O)CO)C)[C@H](C([C@H]1O)O)NC
• InChI: InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7?,8-,9-,10+,11?,12-,13?,14?,15-,16+,17?,18-,21?/m0/s1
• InChIKey: ASXBYYWOLISCLQ-FQARQEHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,4S,6S)-3-carbamimidamido-6-{[(2R,3S,5S)-3-{[(3S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine
• IUPAC Traditional name: 1-[(1S,4S,6S)-3-carbamimidamido-6-{[(2R,3S,5S)-3-{[(3S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine
• Synonyms: O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-(hydroxymethyl)-α-L-lyxofuranosyl-(1→4)-N1,N3-bis(aminoiminomethyl)-D-Streptamine Sulfate; Didromycin; Didromycine; Dihydrostreptomycin Sulfate; Double-mycin; Panstreptin; Sol-Mycin; Streptomagna; Dihydrostreptomycin Sesquisulfate

Database IDs

• CAS Number: 5490-27-7
• PubChem SID: 162261844
• PubChem CID: 71316194

CALCULATED PROPERTIES

• Acid pKa: 12.219626
• H Acceptors: 19
• H Donor: 15
• LogD (pH = 5.5): -14.309652
• LogD (pH = 7.4): -12.557682
• Log P: -7.4748745
• Molar Refractivity: 150.4536 cm^3
• Polarizability: 53.031017 Å^3
• Polar Surface Area: 334.59 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D449535

A derivative of Streptomycin (S687500) with antimicrobial activity. It is used in veterinary medicine to treat bovine infection and also as an effective antibiotic to control pests found in crops.

REFERENCES

• Gradin, J.L. et al.: J. Am. Vet. Med. Assoc., 183, 434 (1983)
• Bishop, J.R. et al.: J. Dairy Sci., 67, 437 (1983)
• Singh, D.R. et al.: Obi. Chik. Daig. Gak. Ken. Hok., 11, 475 (1983)