tetrahydrouridine

ID: ALA1236475

PubChem CID: 9543506

Max Phase: Phase

Molecular Formula: C9H16N2O6

Molecular Weight: 248.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tetrahydrouridine | NSC-112907 | NSC-112907-D | U-23284 | TETRAHYDROURIDINE|NSC-112907-D|U-23284|SCHEMBL172272|CHEMBL1236475|BDBM50007025|1-(3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-4- HYDROXY-TETRAHYDRO-PYRIMIDIN-2-ONE|TYU|NS00068732|(4R)-4-hydroxy-1-beta-D-ribofuranosyltetrahydropyrimidin-2(1H)-one

Canonical SMILES:  O=C1N[C@H](O)CCN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C9H16N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4-8,12-15H,1-3H2,(H,10,16)/t4-,5-,6-,7-,8-/m1/s1

Standard InChI Key:  UCKYOOZPSJFJIZ-FMDGEEDCSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -1.2995    2.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850    2.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850    1.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824    0.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3124   -0.5147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329   -0.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684    0.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -1.0959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822   -1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -2.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4618   -1.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.5147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371    1.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  3  4  1  0
 16  3  1  0
  5  4  1  0
  5  6  1  1
  5 14  1  0
  7  6  1  0
  8  6  1  0
 13  7  1  0
  8  9  2  0
  8 10  1  0
 11 10  1  0
 11 12  1  6
 11 13  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1236475

   TETRAHYDROURIDINE

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 248.24

Molecular Weight (Monoisotopic): 248.1008

AlogP: -2.84

#Rotatable Bonds: 2

Polar Surface Area: 122.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: ┄

CX LogP: -2.74

CX LogD: -2.74

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.36

Np Likeness Score: 1.79

References

1. Ferraris D, Duvall B, Delahanty G, Mistry B, Alt J, Rojas C, Rowbottom C, Sanders K, Schuck E, Huang KC, Redkar S, Slusher BB, Tsukamoto T..  (2014)  Design, synthesis, and pharmacological evaluation of fluorinated tetrahydrouridine derivatives as inhibitors of cytidine deaminase.,  57  (6): [PMID:24520856] [10.1021/jm401856k]

2. Unpublished dataset, 

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

5. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21