gentamicin C
ID: ALA384124
PubChem CID: 44416734
Max Phase: Preclinical
Molecular Formula: C19H39N5O7
Molecular Weight: 449.55
Molecule Type: Small molecule
Associated Items:
This compound is not in our inventory system
Names and Identifiers
Synonyms: Gentamicin C | Gentamicin C|CHEMBL384124
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](CN)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O
Standard InChI: InChI=1S/C19H39N5O7/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/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13-,14+,15-,16+,17+,18+,19-/m0/s1
Standard InChI Key: VEGXETMJINRLTH-HKHRZCBZSA-N
Molfile:
RDKit 2D
31 33 0 0 1 0 0 0 0 0999 V2000
-2.0527 -18.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3431 -19.2388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.6308 -18.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6265 -18.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3408 -17.5898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0594 -18.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6250 -20.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6250 -21.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0870 -21.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7990 -21.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7990 -20.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0870 -20.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0870 -19.2458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.5147 -20.0771 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.0870 -22.5458 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.3422 -21.7221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.3407 -20.0771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.3407 -22.5471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0544 -22.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0549 -23.7797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3415 -24.1947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6259 -23.7822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6238 -22.9546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.0879 -24.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7685 -22.5452 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.8030 -23.7845 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.0895 -17.5947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.3380 -16.7648 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.7747 -17.5893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.6222 -16.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7792 -18.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8 16 1 1
1 6 1 0
7 17 1 6
2 3 1 0
18 16 1 1
18 19 1 0
3 4 1 0
4 5 1 0
7 12 1 0
8 9 1 0
9 10 1 0
18 23 1 0
19 20 1 0
20 21 1 0
21 22 1 0
22 23 1 0
10 11 1 0
22 24 1 6
11 12 1 0
19 25 1 1
5 6 1 0
24 26 1 0
3 13 1 1
12 13 1 1
4 27 1 6
7 8 1 0
5 28 1 6
11 14 1 6
6 29 1 6
1 2 1 0
28 30 1 0
9 15 1 6
6 31 1 0
M ENDAlternative Forms
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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Calculated Properties
| Molecular Weight: 449.55 | Molecular Weight (Monoisotopic): 449.2849 | AlogP: -3.98 | #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: 9.90 | CX LogP: -3.99 | CX LogD: -11.77 |
| Aromatic Rings: ┄ | Heavy Atoms: 31 | QED Weighted: 0.19 | Np Likeness Score: 1.53 |
References
| 1. Yang G, Trylska J, Tor Y, McCammon JA.. (2006) Binding of aminoglycosidic antibiotics to the oligonucleotide A-site model and 30S ribosomal subunit: Poisson-Boltzmann model, thermal denaturation, and fluorescence studies., 49 (18): [PMID:16942021] [10.1021/jm060288o] |
Source
Source(1):