ID: ALA461553

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 372.43

Molecule Type: Small molecule

Representations

Synonyms (2): Dihydroxypentamidine | Pentamidine DAO
Synonyms from Alternative Forms(2):

Canonical SMILES:  N/C(=N\O)c1ccc(OCCCCCOc2ccc(/C(N)=N/O)cc2)cc1

Standard InChI:  InChI=1S/C19H24N4O4/c20-18(22-24)14-4-8-16(9-5-14)26-12-2-1-3-13-27-17-10-6-15(7-11-17)19(21)23-25/h4-11,24-25H,1-3,12-13H2,(H2,20,22)(H2,21,23)

Standard InChI Key:  UVADNHMLTJNGDH-UHFFFAOYSA-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: 372.43

Molecular Weight (Monoisotopic): 372.1798

AlogP: 2.50

#Rotatable Bonds: 10

Polar Surface Area: 135.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.64

CX Basic pKa: 5.65

CX LogP: 2.32

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.17

Np Likeness Score: -0.39

References

1. Gruenewald S, Wahl B, Bittner F, Hungeling H, Kanzow S, Kotthaus J, Schwering U, Mendel RR, Clement B..  (2008)  The fourth molybdenum containing enzyme mARC: cloning and involvement in the activation of N-hydroxylated prodrugs.,  51  (24): [PMID:19053771] [10.1021/jm8010417]

2. Kahvedžić A, Nathwani SM, Zisterer DM, Rozas I..  (2013)  Aromatic bis-N-hydroxyguanidinium derivatives: synthesis, biophysical, and biochemical evaluations.,  56  (2): [PMID:23252648] [10.1021/jm301358s]

3. Berger O, Ortial S, Wein S, Denoyelle S, Bressolle F, Durand T, Escale R, Vial HJ, Vo-Hoang Y..  (2019)  Evaluation of amidoxime derivatives as prodrug candidates of potent bis-cationic antimalarials.,  29  (16): [PMID:31255483] [10.1016/j.bmcl.2019.06.045]

Source

Source(1):

• Scientific Literature