Geneticin

ID: ALA575707

Chembl Id: CHEMBL575707

PubChem CID: 447379

Max Phase: Preclinical

Molecular Formula: C20H40N4O10

Molecular Weight: 496.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@H](C)O)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7-,8+,9+,10+,11-,12-,13+,14+,15+,16-,17+,18+,19+,20-/m0/s1

Standard InChI Key:  BRZYSWJRSDMWLG-KVXRWBJUSA-N

Alternative Forms

1. Parent:

   

   ALA575707

   (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-[(1S)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 496.56

Molecular Weight (Monoisotopic): 496.2744

AlogP: -5.61

#Rotatable Bonds: 6

Polar Surface Area: 248.39

Molecular Species: BASE

HBA: 14

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.39

CX Basic pKa: 9.59

CX LogP: -5.30

CX LogD: -10.24

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.16

Np Likeness Score: 1.62

References

1. Jayanetti DR, Braun DR, Barns KJ, Rajski SR, Bugni TS..  (2019)  Bulbiferates A and B: Antibacterial Acetamidohydroxybenzoates from a Marine Proteobacterium, Microbulbifer sp.,  82  (7): [PMID:31181927] [10.1021/acs.jnatprod.9b00312]

2. Ng MY, Zhang H, Weil A, Singh V, Jamiolkowski R, Baradaran-Heravi A, Roberge M, Jacobson A, Friesen W, Welch E, Goldman YE, Cooperman BS..  (2018)  New in Vitro Assay Measuring Direct Interaction of Nonsense Suppressors with the Eukaryotic Protein Synthesis Machinery.,  9  (12): [PMID:30613341] [10.1021/acsmedchemlett.8b00472]

3. Morrill C, Friesen WJ, Babu S, Baiazitov RY, Du W, Karloff DB, Lee CS, Moon YC, Ren H, Sierra J, Tomizawa Y, Vazirani P, Welch EM, Xue X, Zhuo J..  (2022)  Guanidino quinazolines and pyrimidines promote readthrough of premature termination codons in cells with native nonsense mutations.,  76  [PMID:36150638] [10.1016/j.bmcl.2022.128989]

4. Guchhait S, Khononov A, Pieńko T, Belakhov V, Baasov T..  (2023)  Balancing Nonsense Mutation Readthrough and Toxicity of Designer Aminoglycosides for Treatment of Genetic Diseases.,  14  (6): [PMID:37312846] [10.1021/acsmedchemlett.3c00089]

Source

Source(1):

• Scientific Literature