ID: ALA2396664

Max Phase: Preclinical

Molecular Formula: C20H23N3O2

Molecular Weight: 337.42

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC(=O)[C@@H]1[C@H](c2ccccc2)CCN1C(=O)[C@@H](N)Cc1ccccc1

Standard InChI:  InChI=1S/C20H23N3O2/c21-17(13-14-7-3-1-4-8-14)20(25)23-12-11-16(18(23)19(22)24)15-9-5-2-6-10-15/h1-10,16-18H,11-13,21H2,(H2,22,24)/t16-,17-,18-/m0/s1

Standard InChI Key:  MDHXNDICWFLLQE-BZSNNMDCSA-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: 337.42

Molecular Weight (Monoisotopic): 337.1790

AlogP: 1.43

#Rotatable Bonds: 5

Polar Surface Area: 89.42

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.70

CX LogP: 1.51

CX LogD: 1.03

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.03

References

1. Fransson R, Sköld C, Kratz JM, Svensson R, Artursson P, Nyberg F, Hallberg M, Sandström A..  (2013)  Constrained H-Phe-Phe-NH2 analogues with high affinity to the substance P 1-7 binding site and with improved metabolic stability and cell permeability.,  56  (12): [PMID:23735006] [10.1021/jm400209h]

2. Fransson R, Nordvall G, Bylund J, Carlsson-Jonsson A, Kratz JM, Svensson R, Artursson P, Hallberg M, Sandström A..  (2014)  Exploration and pharmacokinetic profiling of phenylalanine based carbamates as novel substance p 1-7 analogues.,  5  (12): [PMID:25516784] [10.1021/ml5002954]

3. Skogh A, Lesniak A, Sköld C, Karlgren M, Gaugaz FZ, Svensson R, Diwakarla S, Jonsson A, Fransson R, Nyberg F, Hallberg M, Sandström A..  (2018)  An imidazole based H-Phe-Phe-NH2 peptidomimetic with anti-allodynic effect in spared nerve injury mice.,  28  (14): [PMID:29929882] [10.1016/j.bmcl.2018.06.009]

Source

Source(1):

• Scientific Literature