Phosphoric acid mono-[5-(3-carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA1235764

Cas Number: 40925-28-8

PubChem CID: 100252

Max Phase: Preclinical

Molecular Formula: C8H13N4O8P

Molecular Weight: 324.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-274937 | Ribavirin monophosphate|Ribavirin-5'-phosphate|Virazole 5'-phosphate|40925-28-8|Ribavirin 5'-monophosphate|ICN 3847|Ribavirin 5'-phosphate|O9FVV27P11|1-(5-O-Phosphono-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide|NSC-274937|1beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-phosphate|1H-1,2,4-Triazole-3-carboxamide, 1-(5-O-phosphono-.beta.-D-ribofuranosyl)-|RVP|UNII-O9FVV27P11|Ribavirin-5'-monophosphate|ribavirin-MP|NSC274937|Ribavirin 5'-P|NSC 274937|1me7|1me8|RBV-MP|CHEShow More⌵

Canonical SMILES:  NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)n1

Standard InChI:  InChI=1S/C8H13N4O8P/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(20-8)1-19-21(16,17)18/h2-5,8,13-14H,1H2,(H2,9,15)(H2,16,17,18)/t3-,4-,5-,8-/m1/s1

Standard InChI Key:  SDWIOXKHTFOULX-AFCXAGJDSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    8.4540  -11.9091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8087  -12.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6966  -11.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368  -12.1349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1836  -10.8065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5487  -13.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525  -11.9277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4218  -11.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315  -13.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839  -12.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5114  -11.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8918  -10.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0275  -13.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9494  -12.1115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2486  -13.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7811  -11.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8048  -11.1617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091  -10.7329    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1327   -9.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3130  -10.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1013  -11.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  4  2  0
  4  1  1  0
  5  8  2  0
  6  2  1  0
  7  2  1  0
  8  1  1  0
  9  6  1  0
 10  7  1  0
 11  3  1  0
 12 11  2  0
  6 13  1  6
 14 11  1  0
  9 15  1  6
 10 16  1  1
 17 16  1  0
  3  5  1  0
 10  9  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1235764

   RIBAVIRIN MONOPHOSPHATE

2. Alternative Forms:

   

   ALA1235764

   dilithium;[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
3. 

   ALA1235764

   lithium;[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl 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: 324.19

Molecular Weight (Monoisotopic): 324.0471

AlogP: -2.89

#Rotatable Bonds: 5

Polar Surface Area: 190.25

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: ┄

CX LogP: -2.92

CX LogD: -6.37

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.35

Np Likeness Score: 0.79

References

1. Gebeyehu G, Marquez VE, Van Cott A, Cooney DA, Kelley JA, Jayaram HN, Ahluwalia GS, Dion RL, Wilson YA, Johns DG..  (1985)  Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogues. Synthesis, structure, and interactions with IMP dehydrogenase.,  28  (1): [PMID:2856943] [10.1021/jm00379a018]

2. El-Hachem N, Nemer G..  (2011)  Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.,  19  (5): [PMID:21310620] [10.1016/j.bmc.2011.01.022]

3. Drabikowska AK, Dudycz L, Shugar D..  (1979)  Studies on the mechanism of antiviral action of 1-(beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (ribavirin).,  22  (6): [PMID:222909] [10.1021/jm00192a009]

4. Cook PD, Allen LB, Streeter DG, Huffman JH, Sidwell RW, Robins RK..  (1978)  Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.,  21  (12): [PMID:722730] [10.1021/jm00210a008]

Source

Source(1):

• Scientific Literature