((2R,3S,4R,5R)-5-(6-((1,4,7,10,13-pentaoxacyclopentadecan-2-yl)methylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

ID: ALA2017020

Chembl Id: CHEMBL2017020

PubChem CID: 70683258

Max Phase: Preclinical

Molecular Formula: C21H34N6O11S

Molecular Weight: 578.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(NCC4COCCOCCOCCOCCO4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H34N6O11S/c22-39(30,31)37-11-15-17(28)18(29)21(38-15)27-13-26-16-19(24-12-25-20(16)27)23-9-14-10-35-6-5-33-2-1-32-3-4-34-7-8-36-14/h12-15,17-18,21,28-29H,1-11H2,(H2,22,30,31)(H,23,24,25)/t14?,15-,17-,18-,21-/m1/s1

Standard InChI Key:  PAKOUDNFCOLNAK-BWZSZYTASA-N

Alternative Forms

1. Parent:

   

   ALA2017020

   [(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(1,4,7,10,13-pentaoxacyclopentadec-2-ylmethylamino)purin-9-yl]oxolan-2-yl]methyl sulfamate

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

Calculated Properties

Molecular Weight: 578.60

Molecular Weight (Monoisotopic): 578.2006

AlogP: -2.46

#Rotatable Bonds: 7

Polar Surface Area: 220.86

Molecular Species: NEUTRAL

HBA: 16

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.30

CX Basic pKa: 4.71

CX LogP: -2.66

CX LogD: -2.66

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.27

Np Likeness Score: 0.10

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]

Source

Source(1):

• Scientific Literature