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

• ChemBase ID: 177885
• Molecular Formular: C21H39N7O12
• Molecular Mass: 581.57406
• Monoisotopic Mass: 581.26566972
• SMILES: [C@H]1([C@@H]([C@H]([C@H]([C@H]([C@@H]1NC(=N)N)O)O)O[C@H]1[C@@H](C(O)([C@@H](O1)C)C=O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](O1)CO)O)O)NC)NC(=N)N)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@@H](O)[C@@H](O)[C@@H]([C@@H]([C@@H]3NC(=N)N)O)NC(=N)N)O[C@H](C2(O)C=O)C)[C@@H]([C@@H]([C@H]1O)O)NC
• InChI: InChI=1S/C21H39N7O12/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/h4-18,26,29,31-36H,3H2,1-2H3,(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: UCSJYZPVAKXKNQ-HZYVHMACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine
• IUPAC Traditional name: 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-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-formyl-α-L-lyxofura nosyl-(1-4)-N1,N3-bis(aminoiminomethyl)-D-streptamine Disulfate; Agrept; Agrimycin; NSC 14083; Neodiestreptopab; Streptomycin A; Vetstrep; Streptomycin Sulfate

Database IDs

• CAS Number: 3810-74-0
• PubChem SID: 164233795
• PubChem CID: 19649

CALCULATED PROPERTIES

• Acid pKa: 10.877018
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -13.912841
• LogD (pH = 7.4): -12.161263
• Log P: -7.651423
• Molar Refractivity: 149.4707 cm^3
• Polarizability: 52.500404 Å^3
• Polar Surface Area: 331.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Crystalline Powder

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S687500

Antibiotic substance produced by aerobic fermentation. Antibacterial (tuberculostatic).

REFERENCES

• Weiss, et al.: Antibiot. Chemother., 7, 374 (1957)
• Umezawa, et al.: J. Antibiot., 27, 997 (1957)
• Mossa, J., et al.: Anal. Profiles Drug Subs., 16, 507 (1957)