{(1S,2S,4R)-2-hydroxy-4-[(6-{[(1R,2S)-2-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]amino}pyrimidin-4-yl)oxy]cyclopentyl}methyl sulfamate

ID: ALA4532893

PubChem CID: 155547060

Max Phase: Preclinical

Molecular Formula: C21H28N4O6S

Molecular Weight: 464.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@H]1CCc2ccccc2[C@@H]1Nc1cc(O[C@@H]2C[C@@H](COS(N)(=O)=O)[C@H](O)C2)ncn1

Standard InChI:  InChI=1S/C21H28N4O6S/c1-29-18-7-6-13-4-2-3-5-16(13)21(18)25-19-10-20(24-12-23-19)31-15-8-14(17(26)9-15)11-30-32(22,27)28/h2-5,10,12,14-15,17-18,21,26H,6-9,11H2,1H3,(H2,22,27,28)(H,23,24,25)/t14-,15+,17+,18-,21-/m0/s1

Standard InChI Key:  QPHSWYSKBXDWBT-WNXQOTDXSA-N

Molfile:  

 
     RDKit          2D

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   19.3041  -16.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1271  -16.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6080  -17.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3560  -17.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0227  -18.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6894  -17.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4333  -17.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4738  -18.1365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5274  -16.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9176  -16.7769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0878  -17.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8721  -17.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4862  -17.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3118  -16.4813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2704  -17.5412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4407  -18.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8267  -18.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9969  -19.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7812  -19.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3952  -19.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1796  -19.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7936  -19.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6233  -18.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8391  -18.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2249  -18.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0423  -18.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4283  -19.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5717  -18.1365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8206  -15.8486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0018  -15.9339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8139  -15.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6123  -15.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  3  7  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 16 25  1  0
 20 25  2  0
 26 27  1  0
 17 26  1  6
 16 15  1  1
 13 15  1  0
  8 11  1  0
  6  8  1  1
  4 28  1  1
  3  2  1  6
  1  2  1  0
  1 29  1  0
 29 30  1  0
 29 31  2  0
 29 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532893

   ---

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: 464.54

Molecular Weight (Monoisotopic): 464.1730

AlogP: 1.33

#Rotatable Bonds: 8

Polar Surface Area: 145.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.40

CX Basic pKa: 5.55

CX LogP: 1.18

CX LogD: 1.17

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: 0.29

References

1.  (2013)  Inhibitors of nedd8-activating enzyme, 

Source

Source(1):

• Patent Bioactivity Data