[[(2R,3S,4R,5R)-5-[5-(5-formyl-2-thienyl)-2,4-dioxo-pyrimidin-1-yl]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl][(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]hydrogen phosphate

ID: ALA1229737

Chembl Id: CHEMBL1229737

PubChem CID: 44829124

Max Phase: Preclinical

Molecular Formula: C20H26N2O18P2S

Molecular Weight: 676.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=Cc1ccc(-c2cn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)c(=O)[nH]c2=O)s1

Standard InChI:  InChI=1S/C20H26N2O18P2S/c23-4-7-1-2-11(43-7)8-3-22(20(31)21-17(8)30)18-15(28)13(26)10(37-18)6-36-41(32,33)40-42(34,35)39-19-16(29)14(27)12(25)9(5-24)38-19/h1-4,9-10,12-16,18-19,24-29H,5-6H2,(H,32,33)(H,34,35)(H,21,30,31)/t9-,10-,12+,13-,14+,15-,16-,18-,19-/m1/s1

Standard InChI Key:  KKHANSZRQMPJKN-PCGMDOMSSA-N

Alternative Forms

1. Parent:

   

   ALA1229737

   5-(2-Formylthien-5-Yl)-Uridine-5'-Diphosphate-Alpha-D-Galactose

2. Alternative Forms:

   

   ALA1229737

   disodium;[[(2R,3S,4R,5R)-5-[5-(5-formylthiophen-2-yl)-2,4-dioxopyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 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: 676.44

Molecular Weight (Monoisotopic): 676.0377

AlogP: -3.25

#Rotatable Bonds: 11

Polar Surface Area: 314.06

Molecular Species: ACID

HBA: 18

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.73

CX Basic pKa: ┄

CX LogP: -3.57

CX LogD: -8.32

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.08

Np Likeness Score: 0.93

References

1. Descroix K, Pesnot T, Yoshimura Y, Gehrke SS, Wakarchuk W, Palcic MM, Wagner GK..  (2012)  Inhibition of galactosyltransferases by a novel class of donor analogues.,  55  (5): [PMID:22356319] [10.1021/jm201154p]

2. Tedaldi L, Evitt A, Goos N, Jiang J, Wagner GK.  (2014)  A practical glycosyltransferase assay for the identification of new inhibitor chemotypes,  5  (8): [10.1039/C4MD00077C]

3. Tedaldi L, Wagner GK.  (2014)  Beyond substrate analogues: new inhibitor chemotypes for glycosyltransferases,  5  (8): [10.1039/C4MD00086B]

Source

Source(1):

• Scientific Literature