ID: ALA480707

Max Phase: Preclinical

Molecular Formula: C10H16N5O13P3

Molecular Weight: 507.18

Molecule Type: Small molecule

Representations

Synonyms (1): 3'-dGTP
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C10H16N5O13P3/c11-10-13-7-6(8(17)14-10)12-3-15(7)9-5(16)1-4(26-9)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-5,9,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,9+/m0/s1

Standard InChI Key:  QGYIFQKZZSSUCR-OBXARNEKSA-N

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

Properties

Molecular Weight: 507.18

Molecular Weight (Monoisotopic): 506.9957

AlogP: -1.31

#Rotatable Bonds: 8

Polar Surface Area: 278.87

Molecular Species: ACID

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: 0.31

CX LogP: -3.44

CX LogD: -10.39

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.20

Np Likeness Score: 1.31

References

1. Deval J, Powdrill MH, D'Abramo CM, Cellai L, Götte M..  (2007)  Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase.,  51  (8): [PMID:17502402] [10.1128/aac.00186-07]

2. Allard PM, Dau ET, Eydoux C, Guillemot JC, Dumontet V, Poullain C, Canard B, Guéritte F, Litaudon M..  (2011)  Alkylated flavanones from the bark of Cryptocarya chartacea as dengue virus NS5 polymerase inhibitors.,  74  (11): [PMID:22050318] [10.1021/np200715v]

3. Bourjot M, Leyssen P, Eydoux C, Guillemot JC, Canard B, Rasoanaivo P, Guéritte F, Litaudon M..  (2012)  Flacourtosides A-F, phenolic glycosides isolated from Flacourtia ramontchi.,  75  (4): [PMID:22439591] [10.1021/np300059n]

4. Huchting J, Vanderlinden E, Winkler M, Nasser H, Naesens L, Meier C..  (2018)  Prodrugs of the Phosphoribosylated Forms of Hydroxypyrazinecarboxamide Pseudobase T-705 and Its De-Fluoro Analogue T-1105 as Potent Influenza Virus Inhibitors.,  61  (14): [PMID:29906392] [10.1021/acs.jmedchem.8b00617]

5. Novotná B, Vaneková L, Zavřel M, Buděšínský M, Dejmek M, Smola M, Gutten O, Tehrani ZA, Pimková Polidarová M, Brázdová A, Liboska R, Štěpánek I, Vavřina Z, Jandušík T, Nencka R, Rulíšek L, Bouřa E, Brynda J, Páv O, Birkuš G..  (2019)  Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.,  62  (23): [PMID:31715099] [10.1021/acs.jmedchem.9b01062]

Source

Source(1):

• Scientific Literature