Methyl 6-(6-Guanidinohexanamido)-4-hydroxy-2-naphthoate

ID: ALA5202463

PubChem CID: 168292593

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 372.43

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H24N4O4/c1-27-18(26)13-9-12-6-7-14(11-15(12)16(24)10-13)23-17(25)5-3-2-4-8-22-19(20)21/h6-7,9-11,24H,2-5,8H2,1H3,(H,23,25)(H4,20,21,22)

Standard InChI Key:  BRWPQBVHUNXYSR-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
   -3.9281   -0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570    0.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6425    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7844   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.8226    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
    2.4991   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -0.4101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714   -0.4101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569   -1.6475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0
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 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202463

   ---

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: 2.31

#Rotatable Bonds: 8

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: 8.68

CX Basic pKa: 12.15

CX LogP: 1.77

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.21

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