6-(3-(3-(1H-Imidazol-1-yl)propyl)ureido)-4-hydroxy-2-naphthoic Acid

ID: ALA5205933

PubChem CID: 168295156

Max Phase: Preclinical

Molecular Formula: C18H18N4O4

Molecular Weight: 354.37

Names and Identifiers

Canonical SMILES:  O=C(NCCCn1ccnc1)Nc1ccc2cc(C(=O)O)cc(O)c2c1

Standard InChI:  InChI=1S/C18H18N4O4/c23-16-9-13(17(24)25)8-12-2-3-14(10-15(12)16)21-18(26)20-4-1-6-22-7-5-19-11-22/h2-3,5,7-11,23H,1,4,6H2,(H,24,25)(H2,20,21,26)

Standard InChI Key:  QJXVNVOUCCZPEA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.1524   -0.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -0.7424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -0.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -0.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479   -0.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5633   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2768   -0.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922   -0.7330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451   -0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985   -1.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8876   -1.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803   -1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189    0.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7271    0.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    0.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560    0.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8696    0.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    1.7230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2985    0.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8696   -0.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5205933

   ---

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: 354.37

Molecular Weight (Monoisotopic): 354.1328

AlogP: 2.65

#Rotatable Bonds: 6

Polar Surface Area: 116.48

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: 6.79

CX LogP: 0.60

CX LogD: -0.12

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.25

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