Uridine-5'-diphosphogalactose derivative

ID: ALA2368470

PubChem CID: 73346845

Max Phase: Preclinical

Molecular Formula: C23H33N3O8S

Molecular Weight: 511.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1[C@H](OCCCNS(=O)(=O)c2cccc3c(N(C)C)cccc23)O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C23H33N3O8S/c1-14(28)25-20-22(30)21(29)18(13-27)34-23(20)33-12-6-11-24-35(31,32)19-10-5-7-15-16(19)8-4-9-17(15)26(2)3/h4-5,7-10,18,20-24,27,29-30H,6,11-13H2,1-3H3,(H,25,28)/t18-,20-,21-,22+,23+/m0/s1

Standard InChI Key:  VBYQWWMCAKMOQN-YRFMLNNJSA-N

Molfile:  

     RDKit          2D

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    4.4935    2.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8119   -1.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619   -1.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2079    4.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6369   -4.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -2.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7803   -3.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224    0.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    0.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -3.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7803   -2.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -0.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    4.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7803   -5.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3513   -5.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0
  3  2  1  0
  4 21  1  6
  5  4  1  0
  6  8  1  0
  7  1  1  0
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  9  7  1  0
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  3 19  1  6
  6 20  1  6
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  8 22  1  1
 23  9  1  0
 24 29  2  0
 25  7  2  0
 26 30  1  0
 27 31  1  0
 28 22  1  0
 29 25  1  0
 30 23  2  0
 31 16  1  0
 32 15  1  0
 33 17  1  0
 34 17  1  0
 35 27  1  0
 24 10  1  0
 26 12  2  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368470

   N-[(2R,3S,4R,5R,6S)-2-[3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]propoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

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: 511.60

Molecular Weight (Monoisotopic): 511.1988

AlogP: -0.47

#Rotatable Bonds: 10

Polar Surface Area: 157.66

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.91

CX Basic pKa: 4.63

CX LogP: -0.79

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -0.06

References

1. Takaya K, Nagahori N, Kurogochi M, Furuike T, Miura N, Monde K, Lee YC, Nishimura S..  (2005)  Rational design, synthesis, and characterization of novel inhibitors for human beta1,4-galactosyltransferase.,  48  (19): [PMID:16162007] [10.1021/jm0504297]

Source

Source(1):

• Scientific Literature