Netivudine

ID: ALA1097615

Cas Number: 84558-93-0

PubChem CID: 55281

Max Phase: Phase

Molecular Formula: C12H14N2O6

Molecular Weight: 282.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Netivudine | 882C-87 | 882C87 | NETIVUDINE|84558-93-0|882C87|F7K51T0Q1W|2,4(1H,3H)-Pyrimidinedione, 1-beta-D-arabinofuranosyl-5-(1-propynyl)-|882C-87|1-.beta.-D-Arabinofuranosyl-5-(1-propynyl)uracil|Netivudine [INN:BAN]|UNII-F7K51T0Q1W|5-Propynylarabinofuranosyluracil|PYaraU|BW882C87|DRG-0179|NETIVUDINE [INN]|NETIVUDINE [MART.]|NETIVUDINE [WHO-DD]|1-(beta-D-Arabinofuranosyl)-5-(1-propynyl)uracil|1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione|SCHEMBShow More⌵

Canonical SMILES:  CC#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C12H14N2O6/c1-2-3-6-4-14(12(19)13-10(6)18)11-9(17)8(16)7(5-15)20-11/h4,7-9,11,15-17H,5H2,1H3,(H,13,18,19)/t7-,8-,9+,11-/m1/s1

Standard InChI Key:  QLOCVMVCRJOTTM-SDNRWEOFSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
   -1.0125    0.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125    2.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042    3.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -1.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -3.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9708   -3.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  1  0
  5  6  2  0
  6  1  1  0
  7  2  1  0
  8  2  1  0
  9  5  1  0
 10  7  1  0
 11  8  1  0
 12  5  1  0
 13 12  3  0
 14  3  2  0
 15  9  2  0
  7 16  1  1
 10 17  1  6
 11 18  1  1
 19 18  1  0
 20 13  1  0
  4  9  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097615

   NETIVUDINE

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: 282.25

Molecular Weight (Monoisotopic): 282.0852

AlogP: -2.48

#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: 9.44

CX Basic pKa: ┄

CX LogP: -1.55

CX LogD: -1.55

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 1.26

References

1. Guerra A, Campillo NE, Páez JA..  (2010)  Neural computational prediction of oral drug absorption based on CODES 2D descriptors.,  45  (3): [PMID:20022146] [10.1016/j.ejmech.2009.11.034]

2. Gozalbes R, Jacewicz M, Annand R, Tsaioun K, Pineda-Lucena A..  (2011)  QSAR-based permeability model for drug-like compounds.,  19  (8): [PMID:21458999] [10.1016/j.bmc.2011.03.011]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Unpublished dataset, 

5. Ramesh D, Vijayakumar BG, Kannan T..  (2020)  Therapeutic potential of uracil and its derivatives in countering pathogenic and physiological disorders.,  207  [PMID:32927231] [10.1016/j.ejmech.2020.112801]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names