ID: ALA2431743

Max Phase: Preclinical

Molecular Formula: C40H54N4O6

Molecular Weight: 686.89

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](OCCCCc3ccc4ccccc4c3)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](OCCCCc2ccc3ccccc3c2)[C@@H]1O

Standard InChI:  InChI=1S/C40H54N4O6/c41-24-33-35(45)39(48-20-8-6-10-26-16-18-28-12-2-4-14-30(28)22-26)34(44)40(49-33)50-38-32(43)23-31(42)37(36(38)46)47-19-7-5-9-25-15-17-27-11-1-3-13-29(27)21-25/h1-4,11-18,21-22,31-40,45-46H,5-10,19-20,23-24,41-44H2/t31-,32+,33-,34-,35-,36-,37+,38-,39-,40-/m1/s1

Standard InChI Key:  QKYDVHKVFANLIK-HFUCYITCSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 686.89

Molecular Weight (Monoisotopic): 686.4043

AlogP: 3.29

#Rotatable Bonds: 15

Polar Surface Area: 181.46

Molecular Species: BASE

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.81

CX Basic pKa: 9.54

CX LogP: 3.78

CX LogD: -0.94

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.10

Np Likeness Score: 0.76

References

1. Zimmermann L, Bussière A, Ouberai M, Baussanne I, Jolivalt C, Mingeot-Leclercq MP, Décout JL..  (2013)  Tuning the antibacterial activity of amphiphilic neamine derivatives and comparison to paromamine homologues.,  56  (19): [PMID:24083676] [10.1021/jm401148j]

2. Mingeot-Leclercq M, Decout J.  (2016)  Bacterial lipid membranes as promising targets to fight antimicrobial resistance, molecular foundations and illustration through the renewal of aminoglycoside antibiotics and emergence of amphiphilic aminoglycosides,  7  (4): [10.1039/C5MD00503E]

3. Zimmermann L, Kempf J, Briée F, Swain J, Mingeot-Leclercq MP, Décout JL..  (2018)  Broad-spectrum antibacterial amphiphilic aminoglycosides: A new focus on the structure of the lipophilic groups extends the series of active dialkyl neamines.,  157  [PMID:30282323] [10.1016/j.ejmech.2018.08.022]

Source

Source(1):

• Scientific Literature