(2R,3R,4R,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-2-cyano-5-(isobutyryloxymethyl)tetrahydrofuran-3,4-diyl bis(2-methylpropanoate)

ID: ALA4876167

Cas Number: 2647442-13-3

PubChem CID: 162625114

Product Number: G650399, Order Now?

Max Phase: Phase

Molecular Formula: C24H31N5O7

Molecular Weight: 501.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(3): Mindeudesivir | Vv-116 | Vv116

Canonical SMILES:  CC(C)C(=O)OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@H](OC(=O)C(C)C)[C@@H]1OC(=O)C(C)C

Standard InChI:  InChI=1S/C24H31N5O7/c1-12(2)21(30)33-9-16-18(34-22(31)13(3)4)19(35-23(32)14(5)6)24(10-25,36-16)17-8-7-15-20(26)27-11-28-29(15)17/h7-8,11-14,16,18-19H,9H2,1-6H3,(H2,26,27,28)/t16-,18-,19-,24+/m1/s1

Standard InChI Key:  RVSSLHFYCSUAHY-JQGROFRJSA-N

Molfile:  

 
     RDKit          2D

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   14.0741  -12.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7365  -12.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8157  -12.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0296  -13.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9948  -12.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4073  -11.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7423  -12.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9576  -11.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7857  -11.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9790  -11.5294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6911  -11.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6911  -10.2961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9790   -9.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2671  -11.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2671  -10.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9790   -9.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3964  -12.6821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0009  -10.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6886  -13.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8267  -13.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0409  -14.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4096  -13.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3541  -12.7056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2028  -14.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8290   -9.9730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3881  -11.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5375  -14.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4581  -15.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6033  -11.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3824  -14.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8380  -14.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
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  8  9  1  1
  9 10  1  0
  6 11  1  6
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 12 13  2  0
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 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  1  2  0
  1 16  1  0
 15 20  1  0
  3 21  3  0
 10 22  1  0
 11 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 23 27  2  0
 23 28  1  0
 22 29  2  0
 22 30  1  0
 30 31  1  0
 28 32  1  0
 25 33  1  0
 30 34  1  0
 28 35  1  0
 25 36  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA4876167

   ---

2. Parent:

   

   ALA4876167

   GS-621763
3. 

   ALA4876167

   MINDEUDESIVIR
4. 

   ALA4876167

   VV-116

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: 501.54

Molecular Weight (Monoisotopic): 501.2223

AlogP: 1.76

#Rotatable Bonds: 8

Polar Surface Area: 168.13

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.65

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.41

Np Likeness Score: 0.32

References

1. Mackman RL, Hui HC, Perron M, Murakami E, Palmiotti C, Lee G, Stray K, Zhang L, Goyal B, Chun K, Byun D, Siegel D, Simonovich S, Du Pont V, Pitts J, Babusis D, Vijjapurapu A, Lu X, Kim C, Zhao X, Chan J, Ma B, Lye D, Vandersteen A, Wortman S, Barrett KT, Toteva M, Jordan R, Subramanian R, Bilello JP, Cihlar T..  (2021)  Prodrugs of a 1'-CN-4-Aza-7,9-dideazaadenosine C-Nucleoside Leading to the Discovery of Remdesivir (GS-5734) as a Potent Inhibitor of Respiratory Syncytial Virus with Efficacy in the African Green Monkey Model of RSV.,  64  (8.0): [PMID:33835812] [10.1021/acs.jmedchem.1c00071]

Source

Source(1):

• Scientific Literature