4-(3-(Pyrrolidin-1-yl)azetidin-1-yl)pyrimidin-2-amine Fumarate

ID: ALA4539015

PubChem CID: 155544432

Max Phase: Preclinical

Molecular Formula: C15H21N5O4

Molecular Weight: 219.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nccc(N2CC(N3CCCC3)C2)n1.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C11H17N5.C4H4O4/c12-11-13-4-3-10(14-11)16-7-9(8-16)15-5-1-2-6-15;5-3(6)1-2-4(7)8/h3-4,9H,1-2,5-8H2,(H2,12,13,14);1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  WRBOQUAJZDAMRY-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    8.8111   -2.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0831   -3.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2939   -2.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0536   -3.5665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8428   -3.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3256   -3.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254   -3.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975   -3.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8697   -4.7312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700   -5.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421   -5.9920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2979   -4.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5475   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1199   -2.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7317   -1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9195   -1.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7731   -7.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7835   -6.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1534   -7.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5700   -7.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7939   -5.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5908   -5.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5804   -6.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2106   -4.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  4  3  1  0
  4  5  1  0
  5  2  1  0
  6  4  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10  9  2  0
 10 11  1  0
 10 12  1  0
 12  6  2  0
  1 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16  1  1  0
 21 24  2  0
 21 22  1  0
 20 17  1  0
 23 18  2  0
 21 23  1  0
 18 20  1  0
 20 19  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 219.29

Molecular Weight (Monoisotopic): 219.1484

AlogP: 0.34

#Rotatable Bonds: 2

Polar Surface Area: 58.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.12

CX LogP: 0.91

CX LogD: 0.05

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.78

Np Likeness Score: -1.23

References

1. Wágner G, Mocking TAM, Arimont M, Provensi G, Rani B, Silva-Marques B, Latacz G, Da Costa Pereira D, Karatzidou C, Vischer HF, Wijtmans M, Kieć-Kononowicz K, de Esch IJP, Leurs R..  (2019)  4-(3-Aminoazetidin-1-yl)pyrimidin-2-amines as High-Affinity Non-imidazole Histamine H3 Receptor Agonists with in Vivo Central Nervous System Activity.,  62  (23): [PMID:31675226] [10.1021/acs.jmedchem.9b01462]

Source

Source(1):

• Scientific Literature