ID: ALA2016758

Max Phase: Preclinical

Molecular Formula: C12H16N4O4

Molecular Weight: 280.28

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@]1(c2ccc3c(N)ncnn23)O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H16N4O4/c1-12(10(19)9(18)7(4-17)20-12)8-3-2-6-11(13)14-5-15-16(6)8/h2-3,5,7,9-10,17-19H,4H2,1H3,(H2,13,14,15)/t7-,9-,10-,12+/m1/s1

Standard InChI Key:  DUADFEIIDXPYEK-LTGWCKQJSA-N

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

Properties

Molecular Weight: 280.28

Molecular Weight (Monoisotopic): 280.1172

AlogP: -1.36

#Rotatable Bonds: 2

Polar Surface Area: 126.13

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.62

CX Basic pKa: 0.76

CX LogP: -1.36

CX LogD: -1.36

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: 0.64

References

1. Cho A, Saunders OL, Butler T, Zhang L, Xu J, Vela JE, Feng JY, Ray AS, Kim CU..  (2012)  Synthesis and antiviral activity of a series of 1'-substituted 4-aza-7,9-dideazaadenosine C-nucleosides.,  22  (8): [PMID:22446091] [10.1016/j.bmcl.2012.02.105]

2. Siegel D, Hui HC, Doerffler E, Clarke MO, Chun K, Zhang L, Neville S, Carra E, Lew W, Ross B, Wang Q, Wolfe L, Jordan R, Soloveva V, Knox J, Perry J, Perron M, Stray KM, Barauskas O, Feng JY, Xu Y, Lee G, Rheingold AL, Ray AS, Bannister R, Strickley R, Swaminathan S, Lee WA, Bavari S, Cihlar T, Lo MK, Warren TK, Mackman RL..  (2017)  Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.,  60  (5): [PMID:28124907] [10.1021/acs.jmedchem.6b01594]

3. 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