apramycin   Click here for help

GtoPdb Ligand ID: 10760

Synonyms: EL-857 | EL857 | Nebramycin factor 2 | Nebramycin II
PDB Ligand
Compound class: Synthetic organic
Comment: Apramycin is a deoxystreptamine class antibiotic with Gram-negative activity [2-3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 11
Rotatable bonds 6
Topological polar surface area 283.64
Molecular weight 539.28
XLogP -4.99
No. Lipinski's rules broken 2
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Canonical SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
Isomeric SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
InChI InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
1. Almabruk KH, Chang JH, Mahmud T. (2016)
Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin.
J Nat Prod, 79 (9): 2391-6. [PMID:27588436]
2. Kang AD, Smith KP, Eliopoulos GM, Berg AH, McCoy C, Kirby JE. (2017)
Invitro Apramycin Activity against multidrug-resistant Acinetobacter baumannii and Pseudomonas aeruginosa.
Diagn Microbiol Infect Dis, 88 (2): 188-191. [PMID:28341099]
3. Sheng Y, Lam PW, Shahab S, Santosa DA, Proteau PJ, Zabriskie TM, Mahmud T. (2015)
Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297.
J Nat Prod, 78 (11): 2768-75. [PMID:26510047]