ID: ALA483406

Max Phase: Preclinical

Molecular Formula: C17H23N5O

Molecular Weight: 313.40

Molecule Type: Small molecule

Representations

Synonyms (1): UR-AK24
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(CC(=O)/N=C(\N)NCCCc1c[nH]cn1)c1ccccc1

Standard InChI:  InChI=1S/C17H23N5O/c1-13(14-6-3-2-4-7-14)10-16(23)22-17(18)20-9-5-8-15-11-19-12-21-15/h2-4,6-7,11-13H,5,8-10H2,1H3,(H,19,21)(H3,18,20,22,23)

Standard InChI Key:  NTHUVTORAXKPJS-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: 313.40

Molecular Weight (Monoisotopic): 313.1903

AlogP: 1.97

#Rotatable Bonds: 7

Polar Surface Area: 96.16

Molecular Species: BASE

HBA: 2

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.97

CX LogP: 1.36

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: -0.55

References

1. Igel P, Schneider E, Schnell D, Elz S, Seifert R, Buschauer A..  (2009)  N(G)-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent.,  52  (8): [PMID:19317445] [10.1021/jm9000693]

2. Ghorai P, Kraus A, Keller M, Götte C, Igel P, Schneider E, Schnell D, Bernhardt G, Dove S, Zabel M, Elz S, Seifert R, Buschauer A..  (2008)  Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists.,  51  (22): [PMID:18950149] [10.1021/jm800841w]

3. Igel P, Dove S, Buschauer A..  (2010)  Histamine H4 receptor agonists.,  20  (24): [PMID:21044842] [10.1016/j.bmcl.2010.10.041]

4. Geyer R, Igel P, Kaske M, Elz S, Buschauer A.  (2014)  Synthesis, SAR and selectivity of 2-acyl- and 2-cyano-1-hetarylalkyl-guanidines at the four histamine receptor subtypes: a bioisosteric approach,  5  (1): [10.1039/C3MD00245D]

Source

Source(1):

• Scientific Literature