(S)-2-Amino-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)-methyl)(4-nitro-3-(trifluoromethyl)benzyl)amino)butanoic acid

ID: ALA5278294

Max Phase: Preclinical

Molecular Formula: C22H25F3N8O7

Molecular Weight: 570.49

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CC[C@H](N)C(=O)O)Cc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H25F3N8O7/c23-22(24,25)11-5-10(1-2-13(11)33(38)39)6-31(4-3-12(26)21(36)37)7-14-16(34)17(35)20(40-14)32-9-30-15-18(27)28-8-29-19(15)32/h1-2,5,8-9,12,14,16-17,20,34-35H,3-4,6-7,26H2,(H,36,37)(H2,27,28,29)/t12-,14+,16+,17+,20+/m0/s1

Standard InChI Key:  JPECMMZHGMEUBF-SQIXAUHQSA-N

Molfile:  

 
     RDKit          2D

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M  CHG  2  34   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5278294

   ---

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: 570.49

Molecular Weight (Monoisotopic): 570.1798

AlogP: 0.26

#Rotatable Bonds: 10

Polar Surface Area: 229.01

Molecular Species: ZWITTERION

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.46

CX Basic pKa: 9.19

CX LogP: -2.17

CX LogD: -2.17

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: -0.16

References

1. Schwickert M, Zimmermann RA, Habeck T, Hoba SN, Nidoieva Z, Fischer TR, Stark MM, Kersten C, Lermyte F, Helm M, Schirmeister T..  (2023)  Covalent S-Adenosylhomocysteine-Based DNA Methyltransferase 2 Inhibitors with a New Type of Aryl Warhead.,  14  (6): [PMID:37312859] [10.1021/acsmedchemlett.3c00062]

Source

Source(1):

• Scientific Literature