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Streptomycin

July 24, 2017
Common Name

Streptomycin Description

Streptomycin is an aminoglycoside antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by binding to the 30S ribosomal subunit of susceptible organisms and disrupting the initiation and elongation steps in protein synthesis. It is bactericidal due to effects that are not flily understood. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2,4-diguanidino-3,5,6-Trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranosideChEBI [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}ChEBI KantrexChEBI SMChEBI StreomycinChEBI 2,4-diguanidino-3,5,6-Trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-a-L-glucopyranosyl)-3-C-formyl-b-L-lyxopentanofuranosideGenerator 2,4-diguanidino-3,5,6-Trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-α-L-glucopyranosyl)-3-C-formyl-β-L-lyxopentanofuranosideGenerator [2-Deoxy-2-(dimethylamino)-a-L-glucopyranosyl]-(1->2)-[5-deoxy-3-C-formyl-a-L-lyxofuranosyl]-(1->4)-{n',n'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine}Generator [2-Deoxy-2-(dimethylamino)-α-L-glucopyranosyl]-(1->2)-[5-deoxy-3-C-formyl-α-L-lyxofuranosyl]-(1->4)-{n',n'''-[(1,3,5/2,4,6)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidine}Generator Streptomycin a slifateHMDB Streptomycin sesquislifate hydrateHMDB Streptomycin sesquisliphate hydrateHMDB Streptomycin slifateHMDB Streptomycin sliphateHMDB Streptomycin, slifate saltHMDB Normon brand OF streptomycin slifateMeSH Sanavita brand OF streptomycin slifateMeSH strepto HefaMeSH strepto-FatolMeSH Streptomycin grünenthalMeSH Wernigerode brand OF streptomycin slifateMeSH Clariana brand OF streptomycin slifateMeSH Estreptomicina cepaMeSH Fatol brand OF streptomycin slifateMeSH strepto FatolMeSH strepto-HefaMeSH CEPA brand OF streptomycin slifateMeSH Estreptomicina normonMeSH Grünenthal brand OF streptomycin slifateMeSH Panpharma brand OF streptomycin slifateMeSH Estreptomicina clarianaMeSH Streptomycin slifate (2:3) saltMeSH Streptomycine panpharmaMeSH

Chemical Formlia

C21H39N7O12 Average Molecliar Weight

581.5741 Monoisotopic Molecliar Weight

581.265669747 IUPAC Name

1-[(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 Traditional Name

streptomycin CAS Registry Number

57-92-1 SMILES

CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]2NC(N)=N)O[C@@H](C)[C@]1(O)C=O

InChI Identifier

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

InChI Key

UCSJYZPVAKXKNQ-HZYVHMACSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines. Kingdom

Organic compounds Super Class

Organic oxygen compounds Class

Organooxygen compounds Sub Class

Carbohydrates and carbohydrate conjugates Direct Parent

Aminocyclitol glycosides Alternative Parents

  • O-glycosyl compounds
  • Cyclohexanols
  • Cyclitols and derivatives
  • Monosaccharides
  • Oxanes
  • Tetrahydrofurans
  • Tertiary alcohols
  • Guanidines
  • 1,2-aminoalcohols
  • Oxacyclic compounds
  • Acetals
  • Dialkylamines
  • Carboximidamides
  • Polyols
  • Propargyl-type 1,3-dipolar organic compounds
  • Aldehydes
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Primary alcohols

    • Substituents

  • Amino cyclitol glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Cyclohexanol
  • Monosaccharide
  • Cyclitol or derivatives
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Guanidine
  • Secondary amine
  • Secondary aliphatic amine
  • Polyol
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Aldehyde
  • Alcohol
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • antibiotic antifungal drug (CHEBI:17076 )
  • antibiotic fungicide (CHEBI:17076 )
  • streptomycins (CHEBI:17076 )
  • Streptidines (C00413 )
  • Antibiotic fungicides (C00413 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Aminoglycosides
  • Anti-Bacterial Agents
  • Protein Synthesis Inhibitors

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.28e+01 g/LNot Available LogP-6.4Not Available

    Predicted Properties

    Property Value Source Water Solubility12.8 mg/mLALOGPS logP-2.6ALOGPS logP-7.7ChemAxon logS-1.7ALOGPS pKa (Strongest Acidic)10.88ChemAxon pKa (Strongest Basic)11.9ChemAxon Physiological Charge3ChemAxon Hydrogen Acceptor Count19ChemAxon Hydrogen Donor Count14ChemAxon Polar Surface Area331.43 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity149.47 m3·mol-1ChemAxon Polarizability55.76 Å3ChemAxon Number of Rings3ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-001i-0000090000-37fcf4def2f5e472aa90View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-03di-0091010000-39300aec20bda5d23649View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-03di-0090000000-34b8374e2a80e4cb95ecView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-03xr-1090000000-0d28a95c3d70165872c6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-014j-5190000000-87daef600d1a1a4b52d8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-0200090000-e3f4de9e437da47f8b50View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-01q9-0911281000-307d692fcab3f0a93c0aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-03e9-0900250000-1e9e471e29850e7a3023View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-0660090000-e0be715ff2ef7bceed6eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0udi-0090000000-da49dca8f3e875260220View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0006-0090000000-51b8b9878643820d5652View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0729-6940300000-cbd7d78f026f93380976View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00dj-9750000000-ea4bfbc8bf26152232f7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00dj-9100000000-e44f835436ca5aa376a5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0usi-9040000000-4cb87273cf38a98ccf69View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0000090000-f0c24196329215da6048View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0000090000-0de059c38cbd52e00cceView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-01q9-0182190000-46e9dfef9871c913947bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-03dj-1391000000-ae846bc34742e8a119c8View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Streptomycin PathwaySMP00259Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01082

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01082

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01082 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    18508 KEGG Compound ID

    C00413 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Streptomycin NuGOwiki Link

    HMDB15214 Metagene Link

    HMDB15214 METLIN ID

    Not Available PubChem Compound

    19649 PDB ID

    SRY ChEBI ID

    17076

    Product: LPA2 antagonist 2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Transporters

    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3-azido- 3-deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
    Gene Name:
    SLC22A6
    Uniprot ID:
    Q4U2R8
    Molecular weight:
    61815.8
    References
    1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

    PMID: 25888236

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