ID: ALA566812

Max Phase: Preclinical

Molecular Formula: C10H17N2O13P3

Molecular Weight: 466.17

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cn([C@H]2CC[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H17N2O13P3/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(23-8)5-22-27(18,19)25-28(20,21)24-26(15,16)17/h4,7-8H,2-3,5H2,1H3,(H,18,19)(H,20,21)(H,11,13,14)(H2,15,16,17)/t7-,8+/m0/s1

Standard InChI Key:  URGJWIFLBWJRMF-JGVFFNPUSA-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: 466.17

Molecular Weight (Monoisotopic): 465.9943

AlogP: -0.13

#Rotatable Bonds: 8

Polar Surface Area: 223.91

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.90

CX Basic pKa:

CX LogP: -1.38

CX LogD: -8.79

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 1.11

References

1. Mansuri MM, Starrett JE, Ghazzouli I, Hitchcock MJ, Sterzycki RZ, Brankovan V, Lin TS, August EM, Prusoff WH, Sommadossi JP..  (1989)  1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent.,  32  (2): [PMID:2536441] [10.1021/jm00122a029]

2. Boyer PL, Vu BC, Ambrose Z, Julias JG, Warnecke S, Liao C, Meier C, Marquez VE, Hughes SH..  (2009)  The nucleoside analogue D-carba T blocks HIV-1 reverse transcription.,  52  (17): [PMID:19678643] [10.1021/jm801176e]

3. Pryde DC, Webster R, Butler SL, Murray EJ, Whitby K, Pickford C, Westby M, Palmer MJ, Bull DJ, Vuong H, Blakemore DC, Stead D, Ashcroft C, Gardner I, Bru C, Cheung W, Roberts IO, Morton J, Bissell RA.  (2013)  Discovery of an HIV integrase inhibitor with an excellent resistance profile,  4  (4): [10.1039/C3MD00014A]

4. Le DH, Takenaka Y, Hamada N, Mizushina Y, Tanahashi T..  (2014)  Polyketides from the cultured lichen mycobiont of a Vietnamese Pyrenula sp.,  77  (6): [PMID:24926891] [10.1021/np500143k]

5. Le DH, Nishimura K, Takenaka Y, Mizushina Y, Tanahashi T..  (2016)  Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.,  79  (7): [PMID:27409517] [10.1021/acs.jnatprod.6b00255]

6. Zhou S, Mahmoud S, Liu P, Zhou L, Ehteshami M, Bassit L, Tao S, Domaoal RA, Sari O, Schutter C, Amiralaei S, Khalil A, Ollinger Russell O, McBrayer T, Whitaker T, Abou-Taleb N, Amblard F, Coats SJ, Schinazi RF..  (2017)  2'-Chloro,2'-fluoro Ribonucleotide Prodrugs with Potent Pan-genotypic Activity against Hepatitis C Virus Replication in Culture.,  60  (13): [PMID:28595015] [10.1021/acs.jmedchem.7b00067]

Source

Source(1):

• Scientific Literature