ID: ALA2431742

Max Phase: Preclinical

Molecular Formula: C38H50N4O6

Molecular Weight: 658.84

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](OCCCc3ccc4ccccc4c3)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](OCCCc2ccc3ccccc3c2)[C@@H]1O

Standard InChI:  InChI=1S/C38H50N4O6/c39-22-31-33(43)37(46-18-6-8-24-14-16-26-10-2-4-12-28(26)20-24)32(42)38(47-31)48-36-30(41)21-29(40)35(34(36)44)45-17-5-7-23-13-15-25-9-1-3-11-27(25)19-23/h1-4,9-16,19-20,29-38,43-44H,5-8,17-18,21-22,39-42H2/t29-,30+,31-,32-,33-,34-,35+,36-,37-,38-/m1/s1

Standard InChI Key:  KJIYMTGVSPGHNN-UADGBHTGSA-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: 658.84

Molecular Weight (Monoisotopic): 658.3730

AlogP: 2.51

#Rotatable Bonds: 13

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: 2.89

CX LogD: -1.82

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.12

Np Likeness Score: 0.77

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