(R)-1-(8-chloro-2-(trifluoromethyl)benzofuro[3,2-d]pyrimidin-4-yl)-N-methylpyrrolidin-3-amine

ID: ALA1092543

PubChem CID: 46885241

Max Phase: Preclinical

Molecular Formula: C16H14ClF3N4O

Molecular Weight: 370.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H]1CCN(c2nc(C(F)(F)F)nc3c2oc2ccc(Cl)cc23)C1

Standard InChI:  InChI=1S/C16H14ClF3N4O/c1-21-9-4-5-24(7-9)14-13-12(22-15(23-14)16(18,19)20)10-6-8(17)2-3-11(10)25-13/h2-3,6,9,21H,4-5,7H2,1H3/t9-/m1/s1

Standard InChI Key:  WBBJYCNZUHEQHO-SECBINFHSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   16.7928   -8.4893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7786   -7.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7774   -8.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4918   -8.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4900   -7.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2049   -7.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2098   -8.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0013   -8.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9934   -7.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4832   -7.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3048   -7.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6376   -7.0661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1427   -6.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3228   -6.4921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0644   -7.1001    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.4709   -5.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5413   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2108   -9.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8755   -9.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6167   -8.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6609   -9.5157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8364  -10.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2900   -5.5474    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9800   -4.9790    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.8776   -4.9221    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  3  4  1  0
 13 14  2  0
 14  9  1  0
 11  1  1  0
  4  7  2  0
  2 15  1  0
  7  8  1  0
 13 16  1  0
  1 17  1  0
  8 10  1  0
  9  6  1  0
  2  3  2  0
  6  5  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  1  1  0
  9 10  2  0
 19 21  1  6
  5  2  1  0
 21 22  1  0
 10 11  1  0
 16 23  1  0
  6  7  1  0
 16 24  1  0
 11 12  2  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092543

   (R)-1-(8-chloro-2-(trifluoromethyl)benzofuro[3,2-d]pyrimidin-4-yl)-N-methylpyrrolidin-3-amine

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

Calculated Properties

Molecular Weight: 370.76

Molecular Weight (Monoisotopic): 370.0808

AlogP: 3.85

#Rotatable Bonds: 2

Polar Surface Area: 54.19

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.49

CX LogP: 4.32

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.26

References

1. Cramp S, Dyke HJ, Higgs C, Clark DE, Gill M, Savy P, Jennings N, Price S, Lockey PM, Norman D, Porres S, Wilson F, Jones A, Ramsden N, Mangano R, Leggate D, Andersson M, Hale R..  (2010)  Identification and hit-to-lead exploration of a novel series of histamine H4 receptor inverse agonists.,  20  (8): [PMID:20299215] [10.1016/j.bmcl.2010.02.097]

Source

Source(1):

• Scientific Literature