sisomicin   Click here for help

GtoPdb Ligand ID: 10858

Synonyms: Antibiotic 66-40 | Antibiotic 6640 | Sch-13475 | Sch13475 | sisomycin | Sissomicin
PDB Ligand
Comment: Sisomicin is a naturally occurring aminoglycoside antibiotic that has activity against Gram-positive and Gram-negative bacteria [1-2]. It is produced by Micromonospora inyoensis.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 12
Hydrogen bond donors 8
Rotatable bonds 6
Topological polar surface area 213.72
Molecular weight 447.27
XLogP -3.63
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
Isomeric SMILES NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
InChI InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
InChI Key URWAJWIAIPFPJE-YFMIWBNJSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
3027 sisomicin
Synonyms Click here for help
Antibiotic 66-40 | Antibiotic 6640 | Sch-13475 | Sch13475 | sisomycin | Sissomicin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1021
Other databases
CAS Registry No. 32385-11-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL221886
DrugBank Ligand DB12604
DrugCentral Ligand 2447
GtoPdb PubChem SID 405560299
PubChem CID 36119
RCSB PDB Ligand SIS
Search Google for chemical match using the InChIKey URWAJWIAIPFPJE-YFMIWBNJSA-N
Search Google for chemicals with the same backbone URWAJWIAIPFPJE
Search PubMed clinical trials sisomicin
Search PubMed titles sisomicin
Search PubMed titles/abstracts sisomicin
Search UniChem for chemical match using the InChIKey URWAJWIAIPFPJE-YFMIWBNJSA-N
Search UniChem for chemicals with the same backbone URWAJWIAIPFPJE