N''-[(3S)-3-(5-fluoro-2-methylphenyl)-3,4-dihydronaphthalen-1(2H)-ylidene]carbonohydrazonic diamide

ID: ALA3980085

PubChem CID: 134152938

Max Phase: Preclinical

Molecular Formula: C18H19FN4

Molecular Weight: 310.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(F)cc1[C@@H]1C/C(=N\N=C(N)N)c2ccccc2C1

Standard InChI:  InChI=1S/C18H19FN4/c1-11-6-7-14(19)10-16(11)13-8-12-4-2-3-5-15(12)17(9-13)22-23-18(20)21/h2-7,10,13H,8-9H2,1H3,(H4,20,21,23)/b22-17+/t13-/m0/s1

Standard InChI Key:  UELISXYRBFANME-OLDCTRRGSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   22.7237   -7.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7237   -8.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4362   -8.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4362   -7.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1487   -7.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1471   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8585   -8.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5720   -8.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5696   -7.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8576   -7.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0102   -8.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2944   -8.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5806   -8.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5814   -9.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3019   -9.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0128   -9.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8652   -8.3158    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.7295   -9.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4362   -6.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7212   -5.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0063   -6.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2913   -5.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0063   -7.0715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  2 11  1  6
 13 17  1  0
 16 18  1  0
  4 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980085

   ---

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: 310.38

Molecular Weight (Monoisotopic): 310.1594

AlogP: 2.84

#Rotatable Bonds: 2

Polar Surface Area: 76.76

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.98

CX LogP: 3.18

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: -0.55

References

1.  (2014)  NHE3-binding compounds and methods for inhibiting phosphate transport, 

2. Lee, Sunkyung S and 5 more authors.  2005-04-21  (5-Arylfuran-2-ylcarbonyl)guanidines as cardioprotectives through the inhibition of Na+/H+ exchanger isoform-1.  [PMID:15828827]

3. Lee, Sunkyung S and 6 more authors.  2005-06-15  4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na+/H+ exchanger isoform-1 (NHE-1) inhibitors.  [PMID:15914000]

4. Huber, John D JD and 19 more authors.  2012-08-23  Identification of a potent sodium hydrogen exchanger isoform 1 (NHE1) inhibitor with a suitable profile for chronic dosing and demonstrated cardioprotective effects in a preclinical model of myocardial infarction in the rat.  [PMID:22803959]

Source

Source(1):

• Patent Bioactivity Data