((1R,2R,3S,4R)-4-[(6-([(S)-4-fluoro-2,3-dihydro-1H-inden-1-yl]amino)pyrimidin-4-yl]amino)-2,3-dihydroxycyclopentyl)methyl sulfamate

ID: ALA3982725

PubChem CID: 24829702

Max Phase: Preclinical

Molecular Formula: C19H24FN5O5S

Molecular Weight: 453.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1C[C@@H](Nc2cc(N[C@H]3CCc4c(F)cccc43)ncn2)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H24FN5O5S/c20-13-3-1-2-12-11(13)4-5-14(12)24-16-7-17(23-9-22-16)25-15-6-10(18(26)19(15)27)8-30-31(21,28)29/h1-3,7,9-10,14-15,18-19,26-27H,4-6,8H2,(H2,21,28,29)(H2,22,23,24,25)/t10-,14+,15-,18-,19+/m1/s1

Standard InChI Key:  LUCDTZVVNNUGKA-BLHUUYCUSA-N

Molfile:  

     RDKit          2D

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    1.3991   -6.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -6.9420    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203   -6.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -7.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557   -7.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3090   -6.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6471   -6.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -6.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529   -8.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347   -8.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -6.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -7.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081   -7.4920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0909   -6.6466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2633   -5.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -5.5981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2159   -4.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6059   -4.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8233   -4.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561   -5.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109   -3.9555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832   -3.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287   -2.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0379   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362   -1.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284   -1.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089   -1.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -1.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0156   -2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2355   -0.4195    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  4  9  1  6
  5 10  1  6
  8 11  1  1
 11 12  1  0
 12  2  1  0
  2 13  1  0
  6 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 19 21  1  0
 22 21  1  6
 22 23  1  0
 23 24  1  0
 24 26  1  0
 25 22  1  0
 25 26  2  0
 26 27  1  0
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 28 29  1  0
 29 30  2  0
 30 25  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982725

   [(1R,2R,3S,4R)-4-[[6-[[(1S)-4-fluoro-2,3-dihydro-1H-inden-1-yl]amino]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]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: 453.50

Molecular Weight (Monoisotopic): 453.1482

AlogP: 0.46

#Rotatable Bonds: 7

Polar Surface Area: 159.69

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.39

CX Basic pKa: 7.09

CX LogP: 0.25

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.12

References

1.  (2008)  Heteroaryl compounds useful as inhibitors of E1 activating enzymes, 

2.  (2013)  Inhibitors of nedd8-activating enzyme, 

Source

Source(1):

• Patent Bioactivity Data