Sisomicin

HCID 36119
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Basic information

CAS
32385-11-8
Standard SMILES
CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CN)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O
InChIKey
URWAJWIAIPFPJE-YFMIWBNJSA-N
Molecular formula
C19H37N5O7
Average molar mass
447.5 g/mol

Overview

Sisomycin is an amino cyclitol glycoside, an aminoglycoside antibiotic, a beta-L-arabinoside and a monosaccharide derivative.

Names & identifiers

Preferred name
Sisomicin
IUPAC
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

Names & synonyms

sisomicinRickamicin32385-11-8SisomycinSissomicinAntibiotic 66-40SisomicinaSisomicineAntibiotic 6640SisomicinumSch 13475Dehydrogentamicin Cla
Show more names
X55XSL74YQ4,5 DehydrogentamicinSch13475CHEBI:9169(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diolD-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-Sizomycin(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside

Database identifiers

CAS
32385-11-8
PubChem CID
36119
ChEMBL
CHEMBL221886
ChEBI
CHEBI:9169
UNII
X55XSL74YQ
EC Number
251-018-2
Nikkaji
J342.544D

Properties

Computed structural propertiesFilling in

XLogP
-5.1
Topological polar surface area
214 Ų
Hydrogen bond donors
8
Hydrogen bond acceptors
12
Rotatable bonds
6
Heavy atoms
31

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]

P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationREACH registered substance: Sisomicin (EC: 251-018-2)
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

MeSH Pharmacological Classification · 2 items

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

Substances that inhibit the growth or reproduction of BACTERIA.

Related reactions

2 records
New reaction record

Compound notes

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