((2R,3S,4R,5R)-5-(6-((2R,4S)-bicyclo[2.2.1]heptan-2-ylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

ID: ALA2017025

Chembl Id: CHEMBL2017025

PubChem CID: 70695876

Max Phase: Preclinical

Molecular Formula: C17H24N6O6S

Molecular Weight: 440.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(N[C@@H]4C[C@H]5CCC4C5)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H24N6O6S/c18-30(26,27)28-5-11-13(24)14(25)17(29-11)23-7-21-12-15(19-6-20-16(12)23)22-10-4-8-1-2-9(10)3-8/h6-11,13-14,17,24-25H,1-5H2,(H2,18,26,27)(H,19,20,22)/t8-,9?,10+,11+,13+,14+,17+/m0/s1

Standard InChI Key:  MZJLOMLHSSUWBH-XXTQSAJPSA-N

Alternative Forms

1. Parent:

   

   ALA2017025

   [(2R,3S,4R,5R)-5-[6-[[(2R,4S)-2-bicyclo[2.2.1]heptanyl]amino]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: 440.48

Molecular Weight (Monoisotopic): 440.1478

AlogP: -0.73

#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: 3.73

CX LogP: -0.77

CX LogD: -0.77

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: 0.47

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