Methyl 6-(7-Guanidinoheptanamido)-4-hydroxy-2-naphthoate

ID: ALA5204851

PubChem CID: 168297124

Max Phase: Preclinical

Molecular Formula: C20H26N4O4

Molecular Weight: 386.45

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(O)c2cc(NC(=O)CCCCCCNC(=N)N)ccc2c1

Standard InChI:  InChI=1S/C20H26N4O4/c1-28-19(27)14-10-13-7-8-15(12-16(13)17(25)11-14)24-18(26)6-4-2-3-5-9-23-20(21)22/h7-8,10-12,25H,2-6,9H2,1H3,(H,24,26)(H4,21,22,23)

Standard InChI Key:  OYMMXDRXZNDYBB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -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   -0.4164    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    0.8243    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
   -6.4286    0.8243    0.0000 C   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 C   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
    4.9998   -0.8226    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
    6.4286   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    0.4148    0.0000 N   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
  6  7  1  0
  5  8  2  0
  9  4  2  0
 10  9  1  0
 11 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5204851

   ---

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: 386.45

Molecular Weight (Monoisotopic): 386.1954

AlogP: 2.70

#Rotatable Bonds: 9

Polar Surface Area: 137.53

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.69

CX Basic pKa: 12.19

CX LogP: 2.22

CX LogD: 0.99

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.19

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