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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:11 UTC
HMDB IDHMDB0015214
Secondary Accession Numbers
  • HMDB15214
Metabolite Identification
Common NameStreptomycin
DescriptionStreptomycin, also known as SM or kantrex, belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. It is bactericidal due to effects that are not fully understood. Streptomycin is a drug which is used for the treatment of tuberculosis. may also be used in combination with other drugs to treat tularemia (francisella tularensis), plague (yersia pestis), severe m. avium complex, brucellosis, and enterococcal endocarditis (e.g. e. faecalis, e. faecium). Streptomycin is a very strong basic compound (based on its pKa). Streptomycin exists in all living organisms, ranging from bacteria to humans. In humans, streptomycin is involved in streptomycin action pathway. Aminoglycosides like Streptomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Vestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance. Otoxocity occurs via drug accumulation in the endolymph and perilymph of the inner ear. It acts by binding to the 30S ribosomal subunit of susceptible organisms and disrupting the initiation and elongation steps in protein synthesis.
Structure
Data?1582753271
Synonyms
ValueSource
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 sulfateHMDB
Streptomycin sesquisulfate hydrateHMDB
Streptomycin sesquisulphate hydrateHMDB
Streptomycin sulfateHMDB
Streptomycin sulphateHMDB
Streptomycin, sulfate saltHMDB
Normon brand OF streptomycin sulfateHMDB
Sanavita brand OF streptomycin sulfateHMDB
Strepto hefaHMDB
Strepto-fatolHMDB
Streptomycin grünenthalHMDB
Wernigerode brand OF streptomycin sulfateHMDB
Clariana brand OF streptomycin sulfateHMDB
Estreptomicina cepaHMDB
Fatol brand OF streptomycin sulfateHMDB
Strepto fatolHMDB
Strepto-hefaHMDB
CEPA brand OF streptomycin sulfateHMDB
Estreptomicina normonHMDB
Grünenthal brand OF streptomycin sulfateHMDB
Panpharma brand OF streptomycin sulfateHMDB
Estreptomicina clarianaHMDB
Streptomycin sulfate (2:3) saltHMDB
Streptomycine panpharmaHMDB
Chemical FormulaC21H39N7O12
Average Molecular Weight581.5741
Monoisotopic Molecular Weight581.265669747
IUPAC Name1-[(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 Namestreptomycin
CAS Registry Number57-92-1
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 KeyUCSJYZPVAKXKNQ-HZYVHMACSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentm-Xylenes
Alternative Parents
Substituents
  • M-xylene
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.8 g/LNot Available
LogP-6.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity149.47 m³·mol⁻¹ChemAxon
Polarizability55.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-022c-9721280000-33adb59b689fe303f154Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6932027000-4328f33834faafd2eb44Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Ion Trap , Positivesplash10-00di-2901000023-e1b4c2a4d54a44d851b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Hybrid FT , Positivesplash10-00di-2901000023-e1b4c2a4d54a44d851b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000090000-37fcf4def2f5e472aa90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0091010000-39300aec20bda5d23649Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-34b8374e2a80e4cb95ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03xr-1090000000-0d28a95c3d70165872c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014j-5190000000-87daef600d1a1a4b52d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0200090000-e3f4de9e437da47f8b50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01q9-0911281000-307d692fcab3f0a93c0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03e9-0900250000-1e9e471e29850e7a3023Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0660090000-e0be715ff2ef7bceed6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0090000000-da49dca8f3e875260220Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-51b8b9878643820d5652Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0729-6940300000-cbd7d78f026f93380976Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dj-9750000000-ea4bfbc8bf26152232f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dj-9100000000-e44f835436ca5aa376a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0usi-9040000000-4cb87273cf38a98ccf69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0000090000-f0c24196329215da6048Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0000090000-0de059c38cbd52e00cceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0091070000-296c5d94a93e23c898d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0192010000-cfe46d798a52988c4d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9150000000-86ebcc8e9e8c2cc9bc88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001a-3221790000-e7f17966849ac1d1d793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-074l-4284390000-60cb57ddc35b33627b52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-6290000000-4804cacbeee10336cd4fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01082 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01082 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01082
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18508
KEGG Compound IDC00413
BioCyc IDSTREPTOMYCIN
BiGG IDNot Available
Wikipedia LinkStreptomycin
METLIN IDNot Available
PubChem Compound19649
PDB IDSRY
ChEBI ID17076
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]