7-(5-(4-carbamimidoylphenyl)furan-2-yl)-2-naphthimidamide

ID: ALA1650568

PubChem CID: 53320552

Max Phase: Preclinical

Molecular Formula: C22H18N4O

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DB1173 | CHEMBL1650568|DB1173

Canonical SMILES:  N=C(N)c1ccc(-c2ccc(-c3ccc4ccc(C(=N)N)cc4c3)o2)cc1

Standard InChI:  InChI=1S/C22H18N4O/c23-21(24)15-5-3-14(4-6-15)19-9-10-20(27-19)16-7-1-13-2-8-17(22(25)26)12-18(13)11-16/h1-12H,(H3,23,24)(H3,25,26)

Standard InChI Key:  KEWJKDDWQUBRDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -3.4625   -2.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638   -3.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -3.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294   -3.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0325   -2.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1799   -3.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948   -3.5578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1811   -4.7982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3194   -2.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504   -2.7984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196   -2.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -1.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0593   -1.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7298   -2.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -3.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -2.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -3.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350   -3.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331   -4.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -5.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564   -4.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8547   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -6.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -6.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  2  7  1  0
 12 15  1  0
  3  4  2  0
 15 16  2  0
 16 20  1  0
  7  8  2  0
 19 17  1  0
 17 18  2  0
 18 15  1  0
  7  9  1  0
  4  5  1  0
 19 20  2  0
  5 10  1  0
 20 21  1  0
 10 11  1  0
 21 22  2  0
  2  3  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
  6  1  1  0
 22 25  1  0
  1  2  2  0
 25 26  1  0
 11 12  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650568

   7-[5-(4-Carbamimidoylphenyl)furan-2-yl]naphthalene-2-carboximidamide

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: 354.41

Molecular Weight (Monoisotopic): 354.1481

AlogP: 4.33

#Rotatable Bonds: 4

Polar Surface Area: 112.88

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.52

CX LogP: 3.08

CX LogD: -1.72

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.05

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R..  (2009)  In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.,  53  (12): [PMID:19786604] [10.1128/aac.00422-09]

Source

Source(1):

• Scientific Literature