((2R,3S,4R,5R)-5-(6-((3-(1H-imidazol-1-yl)propyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

ID: ALA2017004

Chembl Id: CHEMBL2017004

PubChem CID: 70687497

Max Phase: Preclinical

Molecular Formula: C16H22N8O6S

Molecular Weight: 454.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(NCCCn4ccnc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H22N8O6S/c17-31(27,28)29-6-10-12(25)13(26)16(30-10)24-9-22-11-14(20-7-21-15(11)24)19-2-1-4-23-5-3-18-8-23/h3,5,7-10,12-13,16,25-26H,1-2,4,6H2,(H2,17,27,28)(H,19,20,21)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  VICUUFDPYRTNGN-XNIJJKJLSA-N

Alternative Forms

1. Parent:

   

   ALA2017004

   [(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(3-imidazol-1-ylpropylamino)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: 454.47

Molecular Weight (Monoisotopic): 454.1383

AlogP: -1.64

#Rotatable Bonds: 9

Polar Surface Area: 192.53

Molecular Species: NEUTRAL

HBA: 13

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: 6.53

CX LogP: -2.34

CX LogD: -2.38

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.15

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