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
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
Synthesis of biomimetic analogs of neomycin B: potential inhibitors of the HIV RNA Rev response element.	2000 Jan-Feb	10772716
Study of aminoglycoside-nucleic acid interactions by an HPLC method.	2001 Apr 23	11327578
Aminoglycoside antibiotics, neamine and its derivatives as potent inhibitors for the RNA-protein interactions derived from HIV-1 activators.	2001 Feb 26	11229778
An efficient synthesis of mimetics of neamine for RNA recognition.	2001 May 31	11405670
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.	2003 Feb 28	12589761
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.	2003 Nov	14638394
Fluorinated aminoglycosides and their mechanistic implication for aminoglycoside 3'-phosphotransferases from Gram-negative bacteria.	2004 Mar 9	14992574
Voltage-dependent inhibition of rat skeletal muscle sodium channels by aminoglycoside antibiotics.	2004 May	14963710
Determination of tobramycin and impurities using high-performance anion exchange chromatography with integrated pulsed amperometric detection.	2006 Mar 3	16243470
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease.	2006 Oct 1	16870442
Nucleobase modified neamines, their synthesis and binding specificity for HIV TAR RNA.	2007	18029660
Structure-function relationship of novel X4 HIV-1 entry inhibitors - L- and D-arginine peptide-aminoglycoside conjugates.	2007 Dec	18028446
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2007 Jan 4	16860963
Unique O-ribosylation in the biosynthesis of butirosin.	2007 Jul 1	17482823
Aminoglycoside antibiotic derivatives: preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity.	2007 Jun 1	17416529
Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching.	2007 Jun 1	17399988
Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery.	2007 Mar 21	17319662
Two-dimensional combinatorial screening identifies specific aminoglycoside-RNA internal loop partners.	2008 Aug 20	18652457
Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA.	2008 Oct 15	18829307
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.	2009 Apr 28	19812740
Enantioseparation by MEKC using a ligand exchange-based chiral pseudostationary phase.	2009 Aug	19637217
Search for novel aminoglycosides by combining fragment-based virtual screening and 3D-QSAR scoring.	2009 Feb	19434840
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.	2009 Oct 21	19795065
Neamine inhibits cell proliferation, migration, and invasion in H7402 human hepatoma cells.	2010 Dec	21135992
Aminoglycoside binding to Oxytricha nova telomeric DNA.	2010 Nov 16	20886815

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