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Streptomycin

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Identification
Molecular formula
C21H39N7O12
CAS number
57-92-1
IUPAC name
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
State
State

At room temperature, streptomycin is in a solid state, typically existing as a fine, crystalline powder that can be hygroscopic in nature, meaning it can absorb water from the atmosphere.

Melting point (Celsius)
0.00
Melting point (Kelvin)
273.15
Boiling point (Celsius)
200.00
Boiling point (Kelvin)
473.15
General information
Molecular weight
581.57g/mol
Molar mass
581.5710g/mol
Density
1.3700g/cm3
Appearence

Streptomycin appears as a white or off-white, crystalline powder that is hygroscopic. It is usually provided as a sulfate salt, meaning the powder is often slightly acidic.

Comment on solubility

Solubility Characteristics of 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

The solubility of the compound 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 is influenced by a number of structural factors. Due to the presence of multiple hydroxyl groups along with aminated sites, this compound is expected to exhibit high solubility in polar solvents such as water. Here are some key points regarding its solubility:

  • Hydrophilic Nature: The numerous hydroxyl (-OH) and amino (-NH2) groups contribute significantly to its hydrophilicity.
  • Solvent Interaction: The capacity for hydrogen bonding with water molecules enhances its solubility.
  • Polarity: The overall polarity of the structure suggests solubility in aqueous systems, making it less likely to dissolve in nonpolar organic solvents.
  • Potential Complexation: This compound could potentially form complexes with ions or other polar molecules, further affecting its solubility profile.

In conclusion, the solubility of this complex guanidine derivative in aqueous media can be visually represented as "very soluble," effectively illustrating its interaction dynamics thanks to the polyfunctional character of its molecular structure. Understanding these characteristics is crucial for applications in pharmaceuticals and biochemistry where solubility plays a fundamental role.

Interesting facts

Interesting Facts about 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

This complex compound is a fascinating example of intricate organic chemistry. It showcases the beautiful complexity and diversity of molecular structures found within biological systems. Here are some notable aspects of this compound:

  • Stereochemistry: This compound contains multiple stereocenters, which means its spatial arrangement is crucial to its function. The specific configuration at these centers can greatly influence the compound's biological activity.
  • Biological Importance: Compounds like this one are often studied for their potential roles in medicine, particularly as therapeutic agents. The multiple hydroxyl and aminoguanidino functionalities may contribute to their interaction with biological systems.
  • Natural Products: The structure suggests that it may be derived from natural products or could mimic them, indicating potential applications in drug design or synthetic biology.
  • Metabolic Pathways: Understanding the metabolic pathways involving such compounds can provide insights into the mechanisms of action, allowing scientists to manipulate these pathways for beneficial outcomes.

As a chemistry student or scientist, you might find it thrilling to explore the myriad of interactions this molecule can have. It is a prime example of how complex organic structures can be formed and how they might relate to biological functions. The potential implications of research into such compounds can lead to groundbreaking discoveries in pharmaceuticals and biotechnology.

In the words of a famous chemist, “The beauty of chemistry is not in its equations, but in its creative possibilities.” Keep exploring the creative dimensions of chemical compounds!

Synonyms
streptomycin
57-92-1
Strepcen
Gerox
Streptomycine
Estreptomicina
Agrimycin
Agrept
Neodiestreptopab
Streptomicina
Streptomycinum
Streptomyzin
Hokko-mycin
CHEBI:17076
Caswell No. 804
NSC-14083
streomycin
UNII-Y45QSO73OB
Y45QSO73OB
CCRIS 5730
HSDB 1768
EINECS 200-355-3
EPA Pesticide Chemical Code 006306
BRN 0074498
Estreptomicina [INN-Spanish]
4-18-00-07540 (Beilstein Handbook Reference)
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)-
STREPTOMYCIN (MART.)
STREPTOMYCIN [MART.]
Estreptomicina (INN-Spanish)
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)-
A07AA04
J01GA01
200-355-3
Streptomycin A
Streptomycin sulphate
Chemform
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
Streptomycin A sulfate
2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside
Streptomycin (INN)
2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-glucopyranosyl)-3-formylpentofuranoside
STREPTOMYCIN [INN]
NSC 14083
[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}
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
SRY
Streptomycin Sesquisulfate Hydrate
Streptomyzin [German]
Streptomicina [Italian]
NCGC00159339-02
Streptomycin [INN:BAN]
Streptomycin, Sulfate Salt
streptomycin?
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
Streptomycin (TN)
Streptomycin & EEP
Liposomal Streptomycin
Streptomycin & Propolis
STREPTOMYCIN [MI]
Agrimycin; Streptomycin A
Epitope ID:224553
STREPTOMYCIN [HSDB]
SCHEMBL3276
STREPTOMYCIN [VANDF]
STREPTOMYCIN [WHO-DD]
CHEMBL372795
DTXSID4023597
GTPL10923
STREPTOMYCIN [GREEN BOOK]
Streptomycin Sesquisulphate Hydrate
HY-B1906
BDBM50103513
AKOS015969759
DB01082
AS-35042
DA-78060
CS-0013964
C00413
D08531
AB00443813_02
EN300-7481099
Q192717
BRD-K07166362-330-02-8
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
2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-|A-glucopyranosyl)-3-formylpentofuranoside
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-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-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
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