Methyl 6-(5-(3,3-Dimethylguanidino)pentanamido)-4-hydroxy-2-naphthoate

ID: ALA5208323

PubChem CID: 168295752

Max Phase: Preclinical

Molecular Formula: C20H26N4O4

Molecular Weight: 386.45

Names and Identifiers

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

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

Standard InChI Key:  KFPSRZVIPTYVIV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.9284    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574    0.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3585   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0704   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429    0.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0719   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574   -1.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208323

   ---

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: 2.53

#Rotatable Bonds: 7

Polar Surface Area: 114.75

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.68

CX Basic pKa: 12.46

CX LogP: 1.88

CX LogD: 0.64

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.25

Np Likeness Score: -0.32

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