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

ID: ALA5270940

Chembl Id: CHEMBL5270940

Max Phase: Preclinical

Molecular Formula: C20H24N8O9S

Molecular Weight: 552.53

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CC[C@H](N)C(=O)O)S(=O)(=O)c2cccc([N+](=O)[O-])c2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H24N8O9S/c21-12(20(31)32)4-5-26(38(35,36)11-3-1-2-10(6-11)28(33)34)7-13-15(29)16(30)19(37-13)27-9-25-14-17(22)23-8-24-18(14)27/h1-3,6,8-9,12-13,15-16,19,29-30H,4-5,7,21H2,(H,31,32)(H2,22,23,24)/t12-,13+,15+,16+,19+/m0/s1

Standard InChI Key:  UIYTWXAQVAGPIB-BPAMBQHCSA-N

Alternative Forms

1. Parent:

   

   ALA5270940

   ---

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: 552.53

Molecular Weight (Monoisotopic): 552.1387

AlogP: -1.57

#Rotatable Bonds: 10

Polar Surface Area: 263.15

Molecular Species: ZWITTERION

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.93

CX Basic pKa: 9.09

CX LogP: -3.92

CX LogD: -3.92

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.14

Np Likeness Score: -0.31

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