((1R,2R,3S,4R)-2,3-dihydroxy-4-(6-(phenylethynyl)pyrimidin-4-ylamino)cyclopentyl)methyl sulfamate

ID: ALA3979808

PubChem CID: 59671408

Max Phase: Preclinical

Molecular Formula: C18H20N4O5S

Molecular Weight: 404.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)OC[C@H]1C[C@@H](Nc2cc(C#Cc3ccccc3)ncn2)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H20N4O5S/c19-28(25,26)27-10-13-8-15(18(24)17(13)23)22-16-9-14(20-11-21-16)7-6-12-4-2-1-3-5-12/h1-5,9,11,13,15,17-18,23-24H,8,10H2,(H2,19,25,26)(H,20,21,22)/t13-,15-,17-,18+/m1/s1

Standard InChI Key:  CXTFXBMNGCICJQ-UWIFEVILSA-N

Molfile:  

     RDKit          2D

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    1.4239  -20.6774    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323  -19.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383  -21.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555  -21.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099  -20.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469  -20.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5881  -20.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571  -22.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108  -20.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038  -20.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194  -21.2252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350  -22.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6874  -20.3839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2939  -20.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1206  -21.7288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7263  -22.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048  -22.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6742  -21.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671  -20.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4508  -20.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2253  -20.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0021  -20.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6086  -21.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3848  -20.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5549  -19.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9426  -19.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1687  -19.6656    0.0000 C   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
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  7  8  1  0
  8  4  1  0
  4  9  1  6
  8 10  1  1
 10 11  1  0
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  2 12  1  0
  5 13  1  6
  6 14  1  1
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 15 16  2  0
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 19 20  2  0
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 22 23  1  0
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 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979808

   [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[6-(2-phenylethynyl)pyrimidin-4-yl]amino]cyclopentyl]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: 404.45

Molecular Weight (Monoisotopic): 404.1154

AlogP: -0.38

#Rotatable Bonds: 5

Polar Surface Area: 147.66

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.39

CX Basic pKa: 3.47

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -0.02

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