((2R,3S,4R,5R)-3,4-dihydroxy-5-(6-(octahydroisoquinolin-2(1H)-yl)-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl sulfamate

ID: ALA2017019

Chembl Id: CHEMBL2017019

PubChem CID: 70695875

Max Phase: Preclinical

Molecular Formula: C19H28N6O6S

Molecular Weight: 468.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(N4CCC5CCCCC5C4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H28N6O6S/c20-32(28,29)30-8-13-15(26)16(27)19(31-13)25-10-23-14-17(21-9-22-18(14)25)24-6-5-11-3-1-2-4-12(11)7-24/h9-13,15-16,19,26-27H,1-8H2,(H2,20,28,29)/t11?,12?,13-,15-,16-,19-/m1/s1

Standard InChI Key:  GKCLRLPMQAYRLM-UIKOTCIDSA-N

Alternative Forms

1. Parent:

   

   ALA2017019

   [(2R,3S,4R,5R)-5-[6-(3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl)purin-9-yl]-3,4-dihydroxyoxolan-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: 468.54

Molecular Weight (Monoisotopic): 468.1791

AlogP: -0.32

#Rotatable Bonds: 5

Polar Surface Area: 165.92

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: 3.58

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: 0.25

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