6-(5-(3,3-Dimethylguanidino)pentanamido)-4-hydroxy-2-naphthoic Acid

ID: ALA5208851

PubChem CID: 168297283

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 372.43

Names and Identifiers

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

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

Standard InChI Key:  MFWHDYHTQSMABU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.5691   -1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9997    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7142    0.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9997    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709    0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    0.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    0.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -1.6475    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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  9 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208851

   ---

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: 2.44

#Rotatable Bonds: 7

Polar Surface Area: 125.75

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: 12.46

CX LogP: 0.16

CX LogD: 0.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -0.24

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