2'-beta-D-Arabinouridine

ID: ALA1092065

Cas Number: 3083-77-0

PubChem CID: 18323

Product Number: U101145, Order Now?

Max Phase: Preclinical

Molecular Formula: C9H12N2O6

Molecular Weight: 244.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Arauridine | Spongouridine|3083-77-0|Arauridine|1-beta-D-Arabinofuranosyluracil|ARABINOFURANOSYLURACIL|Uracil arabinoside|Ara-U|Uracil-beta-D-arabinofuranoside|1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione|Arabinosyluracil|Spongouridin|ZK0WMW5NQF|CHEBI:68346|MFCD00065998|Uridine arabinoside|Spongouridine (VAN)|1-beta-D-Arabinofuranosylpyrimidine-2,4(1H,3H)-dione (Uracil Arabinoside)|NSC 68928|1beta-D-Arabinofuranosyluracil|1-beta-D-ArabinofurnosShow 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-CCXZUQQUSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    6.7416  -16.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5666  -16.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8234  -15.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1541  -14.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4891  -15.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6092  -15.0661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3196  -15.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0345  -15.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0440  -14.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3323  -13.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6112  -14.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3146  -16.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0508  -16.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7044  -15.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558  -16.7710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915  -15.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7626  -13.8444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  1  2  1  0
  7 12  2  0
  3  6  1  1
  2 13  1  1
  6  7  1  0
  5 14  1  1
  1 15  1  6
  2  3  1  0
 14 16  1  0
  3  4  1  0
  9 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092065

   Uracil 1-β-D-arabinofuranoside

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: 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

1. Mehellou Y, Valente R, Mottram H, Walsby E, Mills KI, Balzarini J, McGuigan C..  (2010)  Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.,  18  (7): [PMID:20299228] [10.1016/j.bmc.2010.02.059]

2. Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ..  (2011)  Bioactive compounds from the fern Lepisorus contortus.,  74  (2): [PMID:21261296] [10.1021/np100373f]

3. Torrence PF, Huang GF, Edwards MW, Bhooshan B, Descamps J, De Clercq E..  (1979)  5-Substituted uracil arabinonucleosides as potential antiviral agents.,  22  (3): [PMID:218014] [10.1021/jm00189a020]

4. Kulikowski T, Zawadzki Z, Shugar D, Descamps J, De Clercq E..  (1979)  Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.,  22  (6): [PMID:222908] [10.1021/jm00192a008]

5. Schinazi RF, Chen MS, Prusoff WH..  (1979)  Antiviral and antineoplastic activities of pyrimidine arabinosyl nucleosides and their 5'-amino derivatives.,  22  (10): [PMID:229223] [10.1021/jm00196a025]

6. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

7. Guinan M, Huang N, Smith M, Miller GJ..  (2022)  Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides.,  61  [PMID:35123007] [10.1016/j.bmcl.2022.128605]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data