Compound: streptomycin
SMILES: O=C[C@]1(O)[C@@H](O[C@@H]2O[C@H]([C@H](O)[C@H]([C@@H]2NC)O)CO)[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N=C(N)N)[C@H]([C@@H]3N=C(N)N)O)O[C@H]1C
InChIKey: UCSJYZPVAKXKNQ-HZYVHMACSA-N
Synonyms: streptomycin, 57-92-1, Streptomycine, Agrimycin, Strepcen, Agrept, Gerox, Streptomicina, Streptomycinum, Streptomyzin, Hokko-mycin, Estreptomicina, CHEBI:17076, Y45QSO73OB, 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside, DTXSID4023597, D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-O-5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl-(1-4)-N,N'-bis(aminoiminomethyl)-, NSC-14083, D-Streptamine, O-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1.fwdarw.2)-O-5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl-(1.fwdarw.4)-N,N'-bis(aminoiminomethyl)-, 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(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-2,5,6-trihydroxycyclohexyl]guanidine, Strepto Fatol, Strepto Hefa, 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, 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, RefChem:6500, DTXCID803597, A07AA04, J01GA01, 2-((1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-((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-2,5,6-trihydroxycyclohexyl)guanidine, 200-355-3, Streptomycin A, Streptomycin (INN), Neodiestreptopab, STREPTOMYCIN [INN], C21H39N7O12, 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-glucopyranosyl)-3-formylpentofuranoside, SRY, Streptomycin Sesquisulfate Hydrate, Caswell No. 804, Streptomyzin [German], Streptomicina [Italian], NCGC00159339-02, Streptomycin [INN:BAN], Streptomycin, Sulfate Salt, UNII-Y45QSO73OB, streomycin, Merstep, Estreptomicina [INN-Spanish], Estreptomicina;, Streptomisin;, Agrimycin;, CCRIS 5730, Agrept;, HSDB 1768, 1-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-formyl-4-hydroxy-5-methyl-tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine, EINECS 200-355-3, MFCD00072108, Streptomycin & EEP, EPA Pesticide Chemical Code 006306, Liposomal Streptomycin, BRN 0074498, Streptomycin & Propolis, STREPTOMYCIN [MI], Agrimycin; Streptomycin A, Epitope ID:224553, STREPTOMYCIN [HSDB], STREPTOMYCIN [VANDF], STREPTOMYCIN [MART.], 4-18-00-07540 (Beilstein Handbook Reference), STREPTOMYCIN [WHO-DD], STREPTOMYCIN [GREEN BOOK], Streptomycin Sesquisulphate Hydrate, BDBM50103513, AKOS015969759, DB01082, AS-35042, -trihydroxycyclohexane-1,3-diyl)diguanidine, C00413, D08531, AB00443813_02, BRD-K07166362-330-02-8, [2-deoxy-2-(dimethylamino)-alpha-L-glucopyranosyl]-(1->2)-[5-deoxy-3-C-formyl-alpha-L-lyxofuranosyl]-(1->4)-{N',N'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine}, 1,1'-((1R,2R,3S,4R,5R,6S)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-formyl-4-hydroxy-5-methyltetrahydrofuran-2-yl)oxy)-2,5,6, 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-|_-glucopyranosyl)-3-formylpentofuranoside, 2-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-formyl-4-hydroxy-5-methyl-tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine, D-Streptamine, O-2-deoxy-2-(methylamino)-.alpha.-L-glucopyranosyl-(1->2)-O-5-deoxy-3-C-formyl-.alpha.-L-lyxofuranosyl-(1->4)-N,N'-bis(aminoiminomethyl)-, N,N'''-[(1R,2R,3S,4R,5R,6S)-4-{5-deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-formyl-alpha-L-lyxofuranosyloxy}-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine, N,N'-[(1R,2R,3S,4R,5R,6S)-4-({5-Deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-formyl-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine, O-2-Deoxy-2-(methylamino)-.alpha.-L-glucopyranosyl-(1->2)-O-5-deoxy-3-C-formyl-.alpha.-L-lyxofuranosyl-(1->4)-N,N'-bis(aminoiminomethyl)-D-streptamine and Liposome
Theoretical properties:
molecular_formula: C21H39N7O12
molecular_weight: 581.6 g/mol
exact_mass: 581.26566970 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 12
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 9
heavy_atom_count: 40
topological_polar_surface_area: 336 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Hygroscopic powder
color: Hygroscopic powder
odor: Odorless or nearly so
boiling_point: 872.9∓75.0°C at 760 mmHg
melting_point: MW: 1457.383. Powder. MP: aproximately 230 °C /Streptomycin sulfate; 3810-74-0/
solubility: White to light gray or pale buff powder; faint amine-like odor; solubility in mg/mL at about 28 °C: water greater than 20; methanol 0.85; ethanol 0.30; isopropanol 0.01; petroleum ether 0.015; carbon tetrachloride 0.035; ether 0.035, Practically insoluble in chloroform. /Streptomycin sesquisulfate/
Descriptions:
pubchem: Streptomycin is a amino cyclitol glycoside that consists of streptidine having a disaccharyl moiety attached at the 4-position. The parent of the streptomycin class. It has a role as an antimicrobial agent, an antimicrobial drug, an antibacterial drug, a protein synthesis inhibitor, a bacterial metabolite and an antifungal agrochemical. It is a member of streptomycins, an antibiotic antifungal drug and an antibiotic fungicide. It is functionally related to a streptidine. It is a conjugate base of a streptomycin(3+).
chebi: A amino cyclitol glycoside that consists of streptidine having a disaccharyl moiety attached at the 4-position. The parent of the streptomycin class
chembl: STREPTOMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Streptomycin is an antibiotic medication used to treat a number of bacterial infections, including tuberculosis, Mycobacterium avium complex, endocarditis, brucellosis, Burkholderia infection, plague, tularemia, and rat bite fever. For active tuberculosis it is often given together with isoniazid, rifampicin, and pyrazinamide. It is administered by injection into a vein or muscle.
Common side effects include vertigo, vomiting, numbness of the face, fever, and rash. Use during pregnancy may result in permanent deafness in the developing baby. Use appears to be safe while breastfeeding. It is not recommended in people with myasthenia gravis or other neuromuscular disorders. Streptomycin is an aminoglycoside. It works by blocking the ability of 30S ribosomal subunits to make proteins, which results in bacterial death.
Albert Schatz first isolated streptomycin in 1943 from Streptomyces griseus. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies it as critically important for human medicine.