((2R,3S,4R,5R)-5-(6-(sec-butylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

ID: ALA2017011

Chembl Id: CHEMBL2017011

PubChem CID: 70689547

Max Phase: Preclinical

Molecular Formula: C14H22N6O6S

Molecular Weight: 402.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(N)(=O)=O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H22N6O6S/c1-3-7(2)19-12-9-13(17-5-16-12)20(6-18-9)14-11(22)10(21)8(26-14)4-25-27(15,23)24/h5-8,10-11,14,21-22H,3-4H2,1-2H3,(H2,15,23,24)(H,16,17,19)/t7?,8-,10-,11-,14-/m1/s1

Standard InChI Key:  SUDWCMCLJCFGFM-HVMNINKTSA-N

Alternative Forms

1. Parent:

   

   ALA2017011

   [(2R,3S,4R,5R)-5-[6-(butan-2-ylamino)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: 402.43

Molecular Weight (Monoisotopic): 402.1322

AlogP: -1.12

#Rotatable Bonds: 7

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: -1.01

CX LogD: -1.01

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: 0.28

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