Methyl 4-Hydroxy-6-(3-(3-(3-methylguanidino)propyl)ureido)-2-naphthoate

ID: ALA5203516

PubChem CID: 168293137

Max Phase: Preclinical

Molecular Formula: C18H23N5O4

Molecular Weight: 373.41

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H23N5O4/c1-20-17(19)21-6-3-7-22-18(26)23-13-5-4-11-8-12(16(25)27-2)9-15(24)14(11)10-13/h4-5,8-10,24H,3,6-7H2,1-2H3,(H3,19,20,21)(H2,22,23,26)

Standard InChI Key:  BXCVJKNZRMRWIF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.2128   -0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993   -0.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7839   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -0.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -0.8171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740   -0.8139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2164   -0.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.8076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454   -0.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454    0.4314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607   -0.8044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0743   -0.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2164    0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6454    0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6454    1.6484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3589    0.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  7 17  2  0
  5 18  1  0
 18 19  2  0
 20 19  1  0
  3 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 22 27  1  0
 27  2  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203516

   ---

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: 373.41

Molecular Weight (Monoisotopic): 373.1750

AlogP: 1.59

#Rotatable Bonds: 6

Polar Surface Area: 135.57

Molecular Species: BASE

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.68

CX Basic pKa: 12.27

CX LogP: 0.72

CX LogD: -0.51

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: -0.25

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