6-(3-(4-Guanidinobutyl)ureido)-4-hydroxy-2-naphthoic Acid

ID: ALA5206099

PubChem CID: 168294563

Max Phase: Preclinical

Molecular Formula: C17H21N5O4

Molecular Weight: 359.39

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21N5O4/c18-16(19)20-5-1-2-6-21-17(26)22-12-4-3-10-7-11(15(24)25)8-14(23)13(10)9-12/h3-4,7-9,23H,1-2,5-6H2,(H,24,25)(H4,18,19,20)(H2,21,22,26)

Standard InChI Key:  KBCNQNCMUHBBEH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.5705   -1.6484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705   -0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.8170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0009   -0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.8139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298   -0.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -0.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5741   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -0.3935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031   -0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031   -1.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7166   -0.3903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0009    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452    0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    0.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741    0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0030    0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0030    1.6484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7166    0.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877   -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  1  0
 14 15  2  0
 14 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
 22 26  1  0
 26  2  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206099

   ---

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: 359.39

Molecular Weight (Monoisotopic): 359.1594

AlogP: 1.63

#Rotatable Bonds: 7

Polar Surface Area: 160.56

Molecular Species: ZWITTERION

HBA: 4

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.76

CX Basic pKa: 12.13

CX LogP: -0.76

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.23

Np Likeness Score: -0.39

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