[(2R,3S,4R,5R)-5-(4-amino-3-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate

ID: ALA4740719

PubChem CID: 162645016

Max Phase: Preclinical

Molecular Formula: C10H14N6O7S

Molecular Weight: 362.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(O)nn2[C@@H]1O[C@H](COS(N)(=O)=O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H14N6O7S/c11-7-4-8(14-2-13-7)16(15-9(4)19)10-6(18)5(17)3(23-10)1-22-24(12,20)21/h2-3,5-6,10,17-18H,1H2,(H,15,19)(H2,11,13,14)(H2,12,20,21)/t3-,5-,6-,10-/m1/s1

Standard InChI Key:  WHHFECDVBHGXJN-BHBWVORQSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   13.0090   -7.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6046   -6.8595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1956   -7.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1979   -4.5426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9075   -4.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9047   -3.3105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1961   -2.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1937   -2.0881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4898   -4.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4911   -3.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7106   -3.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2269   -3.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7086   -4.3862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4546   -5.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6771   -5.4190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6759   -6.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4527   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9339   -5.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0140   -6.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7511   -5.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7042   -7.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2680   -6.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8601   -6.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4592   -2.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  9  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 10  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 14 13  1  1
 16 19  1  1
 18 20  1  6
 17 21  1  6
 19 22  1  0
 22  2  1  0
  2 23  1  0
 11 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740719

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.32

Molecular Weight (Monoisotopic): 362.0645

AlogP: -3.05

#Rotatable Bonds: 4

Polar Surface Area: 208.93

Molecular Species: ACID

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.48

CX Basic pKa: 3.25

CX LogP: -2.56

CX LogD: -4.11

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: 0.25

References

1. Huang SC,Adhikari S,Brownell JE,Calderwood EF,Chouitar J,D'Amore NR,England DB,Foley K,Harrison SJ,LeRoy PJ,Lok D,Lublinsky A,Ma LT,Menon S,Yang Y,Zhang J,Gould AE.  (2020)  Discovery and optimization of pyrazolopyrimidine sulfamates as ATG7 inhibitors.,  28  (19): [PMID:32912429] [10.1016/j.bmc.2020.115681]

Source

Source(1):

• Scientific Literature