Gentamicin

ID: ALA1254452

Chembl Id: CHEMBL1254452

Cas Number: 25876-11-3

PubChem CID: 72397

Max Phase: Preclinical

Molecular Formula: C20H41N5O7

Molecular Weight: 463.58

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)N)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C20H41N5O7/c1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19/h8-19,25-28H,4-7,21-24H2,1-3H3/t8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+/m1/s1

Standard InChI Key:  XUFIWSHGXVLULG-IDLVJFIQSA-N

Alternative Forms

1. Parent:

   

   ALA1254452

   Gentamicin C2

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: 463.58

Molecular Weight (Monoisotopic): 463.3006

AlogP: -3.59

#Rotatable Bonds: 6

Polar Surface Area: 213.72

Molecular Species: BASE

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.55

CX Basic pKa: 10.01

CX LogP: -3.57

CX LogD: -11.56

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: 1.67

References

1. Joshi S, Fedoseyenko D, Mahanta N, Ducati RG, Feng M, Schramm VL, Begley TP..  (2019)  Antibacterial Strategy against H. pylori: Inhibition of the Radical SAM Enzyme MqnE in Menaquinone Biosynthesis.,  10  (3): [PMID:30891141] [10.1021/acsmedchemlett.8b00649]

2. Shahin IG,Abutaleb NS,Alhashimi M,Kassab AE,Mohamed KO,Taher AT,Seleem MN,Mayhoub AS.  (2020)  Evaluation of N-phenyl-2-aminothiazoles for treatment of multi-drug resistant and intracellular Staphylococcus aureus infections.,  202  [PMID:32707373] [10.1016/j.ejmech.2020.112497]

3. 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