NEAMINE SULFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H26N4O6.H2O4S
Molecular Weight	420.437
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=UPUAISIJDDQCRN-SQAHNGQVSA-N

InChI=1S/C12H26N4O6.H2O4S/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20;1-5(2,3)4/h3-12,17-20H,1-2,13-16H2;(H2,1,2,3,4)/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C12H26N4O6
Molecular Weight	322.358
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Neamine inhibits cell proliferation, migration, and invasion in H7402 human hepatoma cells.	2010-12	21135992
Aminoglycoside binding to Oxytricha nova telomeric DNA.	2010-11-16	20886815
Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines.	2010-08-05	20700526
Antibacterial activities of aminoglycoside antibiotics-derived cationic amphiphiles. Polyol-modified neomycin B-, kanamycin A-, amikacin-, and neamine-based amphiphiles with potent broad spectrum antibacterial activity.	2010-05-13	20373816
Two-dimensional combinatorial screening of a bacterial rRNA A-site-like motif library: defining privileged asymmetric internal loops that bind aminoglycosides.	2010-03-09	20108982
The nebramycin aminoglycoside profiles of Streptomyces tenebrarius and their characterization using an integrated liquid chromatography-electrospray ionization-tandem mass spectrometric analysis.	2010-02-19	20113718
Synthesis and antimicrobial evaluation of amphiphilic neamine derivatives.	2010-01-14	20000576
Synthesis and transfection properties of a series of lipidic neamine derivatives.	2009-11	19848402
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.	2009-10-21	19795065
Enantioseparation by MEKC using a ligand exchange-based chiral pseudostationary phase.	2009-08	19637217
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.	2009-04-28	19812740
Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA.	2009-04-15	19327991
Neamine inhibits prostate cancer growth by suppressing angiogenin-mediated rRNA transcription.	2009-03-15	19276260
Search for novel aminoglycosides by combining fragment-based virtual screening and 3D-QSAR scoring.	2009-02	19434840
Chiral ligand-exchange chromatography of amino acids using porous graphitic carbon coated with a dinaphthyl derivative of neamine.	2009-01	18998115
Synthesis of a phosphonate-linked aminoglycoside-coenzyme a bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance.	2009	19152351
Two-dimensional combinatorial screening identifies specific 6'-acylated kanamycin A- and 6'-acylated neamine-RNA hairpin interactions.	2008-12-02	18991404
Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA.	2008-10-15	18829307
Two-dimensional combinatorial screening identifies specific aminoglycoside-RNA internal loop partners.	2008-08-20	18652457
Identification of tobramycin impurities for quality control process monitoring using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2008-08-05	18486398
Copper(II) complexes of lipophilic aminoglycoside derivatives for the amino acid enantiomeric separation by ligand-exchange liquid chromatography.	2008-03-28	18295773
Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption.	2008-02	18408324
Fluorescence correlation spectroscopy at single molecule level on the Tat-TAR complex and its inhibitors.	2008-01	17764074
Structure-function relationship of novel X4 HIV-1 entry inhibitors - L- and D-arginine peptide-aminoglycoside conjugates.	2007-12	18028446
Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA.	2007-10-25	17915882
Design and synthesis of a structurally constrained aminoglycoside.	2007-07-06	17579461
Unique O-ribosylation in the biosynthesis of butirosin.	2007-07-01	17482823
Aminoglycoside antibiotic derivatives: preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity.	2007-06-01	17416529
Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching.	2007-06-01	17399988
Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery.	2007-03-21	17319662
Elaboration of neosamine rings in the biosynthesis of neomycin and butirosin.	2007-02-12	17206729
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2007-01-04	16860963
Nucleobase modified neamines, their synthesis and binding specificity for HIV TAR RNA.	2007	18029660
Mechanism of RNA cleavage catalyzed by sequence specific polyamide nucleic acid-neamine conjugate.	2007	17854270
Synthesis and antibacterial activity of novel neamine derivatives.	2006-12-15	16997557
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease.	2006-10-01	16870442
A molecular dynamics simulation study of an aminoglycoside/A-site RNA complex: conformational and hydration patterns.	2006-08	16824662
Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides.	2006-07	16817854
Cationic polyamines inhibit anthrax lethal factor protease.	2006-06-08	16762077
Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR-Tat.	2006-04-15	16413787
Determination of tobramycin and impurities using high-performance anion exchange chromatography with integrated pulsed amperometric detection.	2006-03-03	16243470
Interactions of designer antibiotics and the bacterial ribosomal aminoacyl-tRNA site.	2006-02	16492561
Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice.	2005-12-15	16361562
Neamine dimers targeting the HIV-1 TAR RNA.	2005-11-01	16153833
The RNA-bound conformation of neamine as determined by transferred NOE experiments.	2005-07	15937986
Structure-activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities.	2005-04-15	15808482
Structure-activity relationships of aminoglycoside-arginine conjugates that bind HIV-1 RNAs as determined by fluorescence and NMR spectroscopy.	2004-11-19	15556620
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004-10-06	15453764
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993-09-24	8402886
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:19:37 GMT 2025` Edited by `admin` on `Mon Mar 31 20:19:37 GMT 2025`
Record UNII	XYP2JD4C64
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

D-STREPTAMINE, 4-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL)-2-DEOXY-, SULFATE (SALT)

Preferred Name

English

NEAMINE SULFATE

Common Name

English

NEOMYCIN A SULFATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID50188726