ID: ALA27979

Max Phase: Preclinical

Molecular Formula: C26H34N2O3

Molecular Weight: 422.57

Molecule Type: Small molecule

Representations

Synonyms (1): A-349821
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H]1CC[C@H](C)N1CCCOc1ccc(-c2ccc(C(=O)N3CCOCC3)cc2)cc1

Standard InChI:  InChI=1S/C26H34N2O3/c1-20-4-5-21(2)28(20)14-3-17-31-25-12-10-23(11-13-25)22-6-8-24(9-7-22)26(29)27-15-18-30-19-16-27/h6-13,20-21H,3-5,14-19H2,1-2H3/t20-,21-/m0/s1

Standard InChI Key:  CFUHKRLMDNFZED-SFTDATJTSA-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: 422.57

Molecular Weight (Monoisotopic): 422.2569

AlogP: 4.47

#Rotatable Bonds: 7

Polar Surface Area: 42.01

Molecular Species: BASE

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.96

CX LogP: 3.86

CX LogD: 1.35

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: -1.18

References

1. Faghih R, Dwight W, Pan JB, Fox GB, Krueger KM, Esbenshade TA, McVey JM, Marsh K, Bennani YL, Hancock AA..  (2003)  Synthesis and SAR of aminoalkoxy-biaryl-4-carboxamides: novel and selective histamine H3 receptor antagonists.,  13  (7): [PMID:12657274] [10.1016/s0960-894x(03)00118-5]

2. Roche O, Rodríguez Sarmiento RM..  (2007)  A new class of histamine H3 receptor antagonists derived from ligand based design.,  17  (13): [PMID:17498953] [10.1016/j.bmcl.2007.04.056]

3. Roche O, Nettekoven M, Vifian W, Sarmiento RM..  (2008)  Refinement of histamine H3 ligands pharmacophore model leads to a new class of potent and selective naphthalene inverse agonists.,  18  (15): [PMID:18606542] [10.1016/j.bmcl.2008.06.062]

4. Pierson PD, Fettes A, Freichel C, Gatti-McArthur S, Hertel C, Huwyler J, Mohr P, Nakagawa T, Nettekoven M, Plancher JM, Raab S, Richter H, Roche O, Rodríguez Sarmiento RM, Schmitt M, Schuler F, Takahashi T, Taylor S, Ullmer C, Wiegand R..  (2009)  5-hydroxyindole-2-carboxylic acid amides: novel histamine-3 receptor inverse agonists for the treatment of obesity.,  52  (13): [PMID:19456097] [10.1021/jm900409x]

5. Berlin M, Boyce CW, Ruiz Mde L..  (2011)  Histamine H3 receptor as a drug discovery target.,  54  (1): [PMID:21062081] [10.1021/jm100064d]

Source

Source(1):

• Scientific Literature