4-Hydroxy-6-(6-(3-methylguanidino)hexanamido)-2-naphthoic Acid

ID: ALA5200731

PubChem CID: 168291536

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 372.43

Names and Identifiers

Canonical SMILES:  CNC(=N)NCCCCCC(=O)Nc1ccc2cc(C(=O)O)cc(O)c2c1

Standard InChI:  InChI=1S/C19H24N4O4/c1-21-19(20)22-8-4-2-3-5-17(25)23-14-7-6-12-9-13(18(26)27)10-16(24)15(12)11-14/h6-7,9-11,24H,2-5,8H2,1H3,(H,23,25)(H,26,27)(H3,20,21,22)

Standard InChI Key:  ARMSFYDVDRKERM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.9267   -0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    0.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574    1.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2167    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2167   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5041    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585    0.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574   -0.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -1.6478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0719   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  8  4  2  0
  9  8  1  0
 10  9  2  0
  2 10  1  0
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 11 12  2  0
 12 13  1  0
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  9 14  1  0
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 16 18  1  0
 18 19  1  0
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 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5200731

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.43

Molecular Weight (Monoisotopic): 372.1798

AlogP: 2.49

#Rotatable Bonds: 8

Polar Surface Area: 134.54

Molecular Species: ZWITTERION

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.76

CX Basic pKa: 12.35

CX LogP: 0.34

CX LogD: 0.34

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.24

Np Likeness Score: 0.07

References

1. Iannelli G, Milite C, Marechal N, Cura V, Bonnefond L, Troffer-Charlier N, Feoli A, Rescigno D, Wang Y, Cipriano A, Viviano M, Bedford MT, Cavarelli J, Castellano S, Sbardella G..  (2022)  Turning Nonselective Inhibitors of Type I Protein Arginine Methyltransferases into Potent and Selective Inhibitors of Protein Arginine Methyltransferase 4 through a Deconstruction-Reconstruction and Fragment-Growing Approach.,  65  (17.0): [PMID:35482954] [10.1021/acs.jmedchem.2c00252]

Source

Source(1):

• Scientific Literature