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

ID: ALA3957275

PubChem CID: 134155427

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-/m1/s1

Standard InChI Key:  UELISXYRBFANME-OVEYAIEOSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   22.8487   -2.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8487   -3.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5613   -3.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5613   -2.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2738   -2.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2722   -3.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9836   -3.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6971   -3.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6947   -2.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9827   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1353   -3.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4196   -3.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7056   -3.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7064   -4.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4269   -5.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1379   -4.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9903   -3.5001    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8546   -5.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5613   -1.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8463   -1.0173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1314   -1.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4164   -1.0173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1314   -2.2557    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  1
 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:

   

   ALA3957275

   ---

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