Methyl 4-Hydroxy-6-(5-(3-methylguanidino)pentanamido)-2-naphthoate

ID: ALA5209034

PubChem CID: 168297744

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 372.43

Names and Identifiers

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

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

Standard InChI Key:  FOOYPQGIDJDMIO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.2119   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3569    0.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0714    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5019    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0729   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0747    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7894    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    0.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -0.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570   -0.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425    0.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 20 21  1  0
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 24 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5209034

   ---

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: 2.18

#Rotatable Bonds: 7

Polar Surface Area: 123.54

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.68

CX Basic pKa: 12.32

CX LogP: 1.61

CX LogD: 0.38

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.22

Np Likeness Score: -0.06

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