Kasugamycin (sulfate)

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Description

Kasugamycin (Ksg) hydrochloride hydrate is an antibiotic that binds to 30s and 70s ribosomes but not to the 50s subunit, and has anti-infective activity. Kasugamycin hydrochloride hydrate mimics mRNA nucleotides, disrupts tRNA binding and inhibits canonical translation initiation. Kasugamycin hydrochloride hydrate increases the sensitivity of mycobacteria to Rifampicin in vitro and in mouse infection models[1][2][3].

CAS Number

78822-08-9

Product Name Alternative

Ksg (sulfate)

UNSPSC

12352005

Target

Antibiotic; Bacterial

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/kasugamycin-sulfate.html

Smiles

OS(=O)(O)=O.OC(C(N[C@@H](C[C@@H]1N)[C@@H](C)O[C@]1([H])O[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]2O)=N)=O.[1/2]

Molecular Formula

C14H25N3O9.1/2H2O4S

Molecular Weight

428.40

References & Citations

[1]Schluenzen F, et al. The antibiotic kasugamycin mimics mRNA nucleotides to destabilize tRNA binding and inhibit canonical translation initiation. Nat Struct Mol Biol. 2006 Oct;13 (10) :871-8.|[2]Schuwirth BS, et al. Structural analysis of kasugamycin inhibition of translation. Nat Struct Mol Biol. 2006 Oct;13 (10) :879-86.|[3]Chaudhuri S, et al. Kasugamycin potentiates rifampicin and limits emergence of resistance in Mycobacterium tuberculosis by specifically decreasing mycobacterial mistranslation. Elife. 2018 Aug 28;7:e36782.

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Chemical Information

Kasugamycin sulfate

CAS Number	78822-08-9
PubChem CID	3061202
IUPAC Name	bis(2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid);sulfuric acid
Molecular Formula	C28H52N6O22S
Molecular Weight	856.8
Topological Polar Surface Area	526
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	26
Rotatable Bond Count	8
Heavy Atom Count	57
Formal Charge	0
Complexity	613

SMILES

C[C@@H]1[C@H](C[C@@H]([C@H](O1)OC2[C@@H]([C@H](C([C@@H]([C@@H]2O)O)O)O)O)N)N=C(C(=O)O)N.C[C@@H]1[C@H](C[C@@H]([C@H](O1)OC2[C@@H]([C@H](C([C@@H]([C@@H]2O)O)O)O)O)N)N=C(C(=O)O)N.OS(=O)(=O)O

InChI

InChI=1S/2C14H25N3O9.H2O4S/c2*1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22;1-5(2,3)4/h2*3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24);(H2,1,2,3,4)/t2*3-,4+,5+,6?,7+,8+,9-,10+,11?,14-;/m11./s1

InChIKey

NAPCRKAUXHXHCU-JLNGJXGCSA-N

Chemical Structure

2D Structure

CAS: 78822-08-9

CID: 3061202

Formula: C28H52N6O22S

MW: 856.8

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	856.8
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	26
Rotatable Bond Count	8
Exact Mass	856.28553848
Monoisotopic Mass	856.28553848
Topological Polar Surface Area	526 Å²
Heavy Atom Count	57
Formal Charge	0
Complexity	613
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	3
Compound Is Canonicalized	Yes

Related Products

Catalog	Name
HY-B1864-01	Kasugamycin
HY-B1864A-01	Kasugamycin (hydrochloride)
HY-B1864AR	Kasugamycin (hydrochloride) (Standard)
HY-B1864B-01	Kasugamycin (hydrochloride hydrate)
HY-B1864BR-01	Kasugamycin (hydrochloride hydrate) (Standard)
HY-116282J-01	Dextran sulfate, low sulfate (MW 5000)
HY-116282P-01	Dextran sulfate, high sulfate (MW 5000)
HY-116282M-01	Dextran sulfate, low sulfate (MW 40000)
HY-16955A-01	Plazomicin (sulfate)
HY-111355-01	Cholesterol sulfate

Alternative Products

Catalog	Name
MBS5796696	Kasugamycin sulfate
AK183886-01	Kasugamycin
K005-50G	Kasugamycin hydrochloride
281134-01	Kasugamycin HCl
452998-01	Kasugamycin (~70%)
C5503-5000	Kasugamycin (hydrochloride)

Kasugamycin (sulfate)

Chemical Information

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