ID: ALA387573

Max Phase: Preclinical

Molecular Formula: C34H46N10O3

Molecular Weight: 642.81

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)[C@@H](N)CCCNC(=N)N)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C34H46N10O3/c35-27(13-7-19-40-33(36)37)30(45)44-29(21-23-15-17-26(18-16-23)25-11-5-2-6-12-25)32(47)43-28(14-8-20-41-34(38)39)31(46)42-22-24-9-3-1-4-10-24/h1-6,9-12,15-18,27-29H,7-8,13-14,19-22,35H2,(H,42,46)(H,43,47)(H,44,45)(H4,36,37,40)(H4,38,39,41)/t27-,28-,29-/m0/s1

Standard InChI Key:  IIUQVWAODMBQQA-AWCRTANDSA-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: 642.81

Molecular Weight (Monoisotopic): 642.3754

AlogP: 1.04

#Rotatable Bonds: 18

Polar Surface Area: 237.12

Molecular Species: BASE

HBA: 6

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.31

CX Basic pKa: 11.87

CX LogP: 0.39

CX LogD: -4.37

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.05

Np Likeness Score: -0.07

References

1. Svenson J, Brandsdal BO, Stensen W, Svendsen JS..  (2007)  Albumin binding of short cationic antimicrobial micropeptides and its influence on the in vitro bactericidal effect.,  50  (14): [PMID:17569519] [10.1021/jm0703542]

2. Karstad R, Isaksen G, Brandsdal BO, Svendsen JS, Svenson J..  (2010)  Unnatural amino acid side chains as S1, S1', and S2' probes yield cationic antimicrobial peptides with stability toward chymotryptic degradation.,  53  (15): [PMID:20608742] [10.1021/jm1006337]

3. Flaten GE, Kottra G, Stensen W, Isaksen G, Karstad R, Svendsen JS, Daniel H, Svenson J..  (2011)  In vitro characterization of human peptide transporter hPEPT1 interactions and passive permeation studies of short cationic antimicrobial peptides.,  54  (7): [PMID:21401113] [10.1021/jm1015704]

4. Karstad R, Isaksen G, Wynendaele E, Guttormsen Y, De Spiegeleer B, Brandsdal BO, Svendsen JS, Svenson J..  (2012)  Targeting the S1 and S3 subsite of trypsin with unnatural cationic amino acids generates antimicrobial peptides with potential for oral administration.,  55  (14): [PMID:22720778] [10.1021/jm3002058]

Source

Source(1):

• Scientific Literature