ID: ALA2017005

Max Phase: Preclinical

Molecular Formula: C19H22N6O6S

Molecular Weight: 462.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(N[C@H]4CCc5ccccc54)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H22N6O6S/c20-32(28,29)30-7-13-15(26)16(27)19(31-13)25-9-23-14-17(21-8-22-18(14)25)24-12-6-5-10-3-1-2-4-11(10)12/h1-4,8-9,12-13,15-16,19,26-27H,5-7H2,(H2,20,28,29)(H,21,22,24)/t12-,13+,15+,16+,19+/m0/s1

Standard InChI Key:  PGAMXUGSHMQFKD-BPAMBQHCSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 462.49

Molecular Weight (Monoisotopic): 462.1322

AlogP: -0.23

#Rotatable Bonds: 6

Polar Surface Area: 174.71

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: 3.69

CX LogP: -0.04

CX LogD: -0.04

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: 0.29

References

1. Lukkarila JL, da Silva SR, Ali M, Shahani VM, Xu GW, Berman J, Roughton A, Dhe-Paganon S, Schimmer AD, Gunning PT..  (2011)  Identification of NAE Inhibitors Exhibiting Potent Activity in Leukemia Cells: Exploring the Structural Determinants of NAE Specificity.,  2  (8): [PMID:24900352] [10.1021/ml2000615]

2. da Silva SR, Paiva SL, Lukkarila JL, Gunning PT..  (2013)  Exploring a new frontier in cancer treatment: targeting the ubiquitin and ubiquitin-like activating enzymes.,  56  (6): [PMID:23360215] [10.1021/jm301420b]

3.  (2006)  Inhibitors of E1 activating enzymes, 

4. Xiong C, Zhou L, Tan J, Song S, Bao X, Zhang N, Ding H, Zhao J, He JX, Miao ZH, Zhang A..  (2021)  Development of Potent NEDD8-Activating Enzyme Inhibitors Bearing a Pyrimidotriazole Scaffold.,  64  (9.0): [PMID:33857374] [10.1021/acs.jmedchem.1c00242]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data