Uridine-5'-diphosphogalactose derivative

ID: ALA2368683

PubChem CID: 73354410

Max Phase: Preclinical

Molecular Formula: C32H45N3O17P2

Molecular Weight: 805.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@@H](CNCCCCCCOCc4ccc5ccccc5c4)[C@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C32H45N3O17P2/c36-24-11-13-35(32(42)34-24)30-28(40)26(38)23(49-30)18-48-53(43,44)52-54(45,46)51-31-29(41)27(39)25(37)22(50-31)16-33-12-5-1-2-6-14-47-17-19-9-10-20-7-3-4-8-21(20)15-19/h3-4,7-11,13,15,22-23,25-31,33,37-41H,1-2,5-6,12,14,16-18H2,(H,43,44)(H,45,46)(H,34,36,42)/t22-,23+,25-,26+,27-,28+,29-,30+,31+/m0/s1

Standard InChI Key:  QWTPJEFEXQBUIZ-OXAWKINHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2368683

   [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[6-(naphthalen-2-ylmethoxy)hexylamino]methyl]oxan-2-yl] hydrogen phosphate

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: 805.66

Molecular Weight (Monoisotopic): 805.2224

AlogP: -0.27

#Rotatable Bonds: 19

Polar Surface Area: 298.02

Molecular Species: ZWITTERION

HBA: 17

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.73

CX Basic pKa: 9.17

CX LogP: -1.96

CX LogD: -4.13

Aromatic Rings: 3

Heavy Atoms: 54

QED Weighted: 0.06

Np Likeness Score: 0.72

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