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

ID: ALA5268682

Chembl Id: CHEMBL5268682

Max Phase: Preclinical

Molecular Formula: C21H26N8O7

Molecular Weight: 502.49

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CC[C@H](N)C(=O)O)Cc2ccc([N+](=O)[O-])cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H26N8O7/c22-13(21(32)33)5-6-27(7-11-1-3-12(4-2-11)29(34)35)8-14-16(30)17(31)20(36-14)28-10-26-15-18(23)24-9-25-19(15)28/h1-4,9-10,13-14,16-17,20,30-31H,5-8,22H2,(H,32,33)(H2,23,24,25)/t13-,14+,16+,17+,20+/m0/s1

Standard InChI Key:  AQQLJWZXYWXYOS-SWQDORGXSA-N

Alternative Forms

1. Parent:

   

   ALA5268682

   ---

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: 502.49

Molecular Weight (Monoisotopic): 502.1924

AlogP: -0.76

#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: 2.64

CX Basic pKa: 9.19

CX LogP: -3.06

CX LogD: -3.05

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.17

Np Likeness Score: 0.02

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