ID: ALA1160556

Max Phase: Preclinical

Molecular Formula: C11H17N4O13P3

Molecular Weight: 506.19

Molecule Type: Small molecule

Representations

Synonyms (1): Tubercidin Triphosphate
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1ncnc2c1ccn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H17N4O13P3/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(17)7(16)6(26-11)3-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,4,6-8,11,16-17H,3H2,(H,21,22)(H,23,24)(H2,12,13,14)(H2,18,19,20)/t6-,7-,8-,11-/m1/s1

Standard InChI Key:  GVVRDIINMFAFEO-KCGFPETGSA-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: 506.19

Molecular Weight (Monoisotopic): 506.0005

AlogP: -1.02

#Rotatable Bonds: 8

Polar Surface Area: 266.24

Molecular Species: ACID

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: 7.66

CX LogP: -4.61

CX LogD: -9.93

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: 1.21

References

1. Hoffmann C, Genieser H, Veron M, Jastorff B.  (1996)  Novel synthesis of nucleoside 5-polyphosphates,  6  (21): [10.1016/0960-894X(96)00461-1]

2. Bourderioux A, Naus P, Perlíková P, Pohl R, Pichová I, Votruba I, Dzubák P, Konecný P, Hajdúch M, Stray KM, Wang T, Ray AS, Feng JY, Birkus G, Cihlar T, Hocek M..  (2011)  Synthesis and significant cytostatic activity of 7-hetaryl-7-deazaadenosines.,  54  (15): [PMID:21711054] [10.1021/jm2005173]

3. 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