ID: ALA9025

Max Phase: Preclinical

Molecular Formula: C25H32N6

Molecular Weight: 416.57

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C(NC1CC1)c1ccc(N2CCCN(c3ccc(C(=N)NC4CC4)cc3)CC2)cc1

Standard InChI:  InChI=1S/C25H32N6/c26-24(28-20-6-7-20)18-2-10-22(11-3-18)30-14-1-15-31(17-16-30)23-12-4-19(5-13-23)25(27)29-21-8-9-21/h2-5,10-13,20-21H,1,6-9,14-17H2,(H2,26,28)(H2,27,29)

Standard InChI Key:  UHYHEMDZZSTUQM-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: 416.57

Molecular Weight (Monoisotopic): 416.2688

AlogP: 3.56

#Rotatable Bonds: 6

Polar Surface Area: 78.24

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 12.35

CX LogP: 3.21

CX LogD: -1.62

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.67

References

1. Donkor IO, Huang TL, Tao B, Rattendi D, Lane S, Vargas M, Goldberg B, Bacchi C..  (2003)  Trypanocidal activity of conformationally restricted pentamidine congeners.,  46  (6): [PMID:12620080] [10.1021/jm020375q]

2. Huang TL, Tao B, Quarshie Y, Queener SF, Donkor IO..  (2001)  N,N'-bis[4-(N-alkylamidino)phenyl]homopiperazines as anti-Pneumocystis carinii agents.,  11  (20): [PMID:11591500] [10.1016/s0960-894x(01)00541-8]

3. Vanden Eynde JJ, Mayence A, Johnson MT, Huang TL, Collins MS, Rebholz S, Walzer PD, Cushion MT, Donkor IO.  (2005)  Antitumor and Anti-Pneumocystis Carinii Activities of Novel Bisbenzamidines,  14  (3): [10.1007/s00044-005-0130-2]

4. Berger ML, Maciejewska D, Vanden Eynde JJ, Mottamal M, Żabiński J, Kaźmierczak P, Rezler M, Jarak I, Piantanida I, Karminski-Zamola G, Mayence A, Rebernik P, Kumar A, Ismail MA, Boykin DW, Huang TL..  (2015)  Pentamidine analogs as inhibitors of [(3)H]MK-801 and [(3)H]ifenprodil binding to rat brain NMDA receptors.,  23  (15): [PMID:26117647] [10.1016/j.bmc.2015.06.012]

5. Beckmann AM, Gilberg E, Gattner S, Huang TL, Vanden Eynde JJ, Mayence A, Bajorath J, Stirnberg M, Gütschow M..  (2016)  Evaluation of bisbenzamidines as inhibitors for matriptase-2.,  26  (15): [PMID:27287367] [10.1016/j.bmcl.2016.05.071]

Source

Source(1):

• Scientific Literature