(uridine) 1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA100259

Cas Number: 58-96-8

PubChem CID: 6029

Product Number: OEM103, Order Now?

Max Phase: Phase

Molecular Formula: C9H12N2O6

Molecular Weight: 244.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1-.beta.-d-ribofuranosyluracil | Uracil riboside | Uridine | NSC-20256 | uridine|58-96-8|Uridin|Uracil riboside|1-beta-D-Ribofuranosyluracil|beta-Uridine|Uracil, 1-beta-D-ribofuranosyl-|d-uridine|b-Uridine|NSC 20256|CHEBI:16704|1-.beta.-D-Ribofuranosyluracil|AI3-52690|UNII-WHI7HQ7H85|EINECS 200-407-5|Urd|WHI7HQ7H85|MFCD00006526|1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione|NSC-20256|MLS000069625|DTXSID40891555|NSC20256|1-beta-D-ribofuranosylpyriShow More⌵

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1

Standard InChI Key:  DRTQHJPVMGBUCF-XVFCMESISA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -0.1397    0.6175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    1.8550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397    2.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    1.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892    0.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397    3.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277   -0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728   -1.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -1.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3124   -0.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577   -2.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071   -0.6925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0371   -2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7016   -2.8982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  6  1  1  0
  9  1  1  1
  2  3  1  0
  2  7  2  0
  4  3  1  0
  4  5  1  0
  4  8  2  0
  5  6  2  0
  9 10  1  0
  9 15  1  0
 10 11  1  0
 10 13  1  6
 11 12  1  0
 11 14  1  6
 12 15  1  0
 12 16  1  1
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA100259

   URIDINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 244.20

Molecular Weight (Monoisotopic): 244.0695

AlogP: -2.85

#Rotatable Bonds: 2

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: -2.42

CX LogD: -2.42

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.44

Np Likeness Score: 1.49

References

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22. Parmenopoulou V, Chatzileontiadou DS, Manta S, Bougiatioti S, Maragozidis P, Gkaragkouni DN, Kaffesaki E, Kantsadi AL, Skamnaki VT, Zographos SE, Zounpoulakis P, Balatsos NA, Komiotis D, Leonidas DD..  (2012)  Triazole pyrimidine nucleosides as inhibitors of Ribonuclease A. Synthesis, biochemical, and structural evaluation.,  20  (24): [PMID:23122937] [10.1016/j.bmc.2012.09.067]

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28. Unpublished dataset, 

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36. Unpublished dataset, 

37. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

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Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21
• Active Ingredient of a Prodrug
• Fraunhofer HDAC6