(2R,3R,4S,5R)-2-(2-chloro-6-(3-iodobenzylamino)-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diol

ID: ALA4081182

PubChem CID: 137648795

Max Phase: Preclinical

Molecular Formula: C19H19ClIN9O3

Molecular Weight: 583.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1nnc([C@H]2O[C@@H](n3cnc4c(NCc5cccc(I)c5)nc(Cl)nc43)[C@H](O)[C@@H]2O)n1

Standard InChI:  InChI=1S/C19H19ClIN9O3/c1-2-30-27-16(26-28-30)14-12(31)13(32)18(33-14)29-8-23-11-15(24-19(20)25-17(11)29)22-7-9-4-3-5-10(21)6-9/h3-6,8,12-14,18,31-32H,2,7H2,1H3,(H,22,24,25)/t12-,13+,14-,18+/m0/s1

Standard InChI Key:  YCFJBJJRZOIEFY-MOROJQBDSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   32.2939  -17.2580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2928  -18.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0075  -18.4982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0057  -16.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7212  -17.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7214  -18.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5118  -18.3420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0002  -17.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5114  -16.9974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7670  -19.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2845  -19.7946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7696  -20.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5542  -20.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5538  -19.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5149  -21.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7337  -21.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7339  -22.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5186  -22.5815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0032  -21.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7738  -23.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2220  -23.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2217  -20.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2210  -18.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0033  -16.0203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7165  -15.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7141  -14.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4292  -14.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4270  -13.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7108  -13.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9952  -13.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0009  -14.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2781  -13.1464    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   31.5780  -18.4973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10  7  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 12 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
 18 20  1  0
 20 21  1  0
 13 22  1  6
 14 23  1  6
  4 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 30 32  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081182

   ---

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: 583.78

Molecular Weight (Monoisotopic): 583.0344

AlogP: 1.69

#Rotatable Bonds: 6

Polar Surface Area: 148.92

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.30

CX Basic pKa: 1.96

CX LogP: 2.86

CX LogD: 2.86

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.81

References

1. Petrelli R, Scortichini M, Kachler S, Boccella S, Cerchia C, Torquati I, Del Bello F, Salvemini D, Novellino E, Luongo L, Maione S, Jacobson KA, Lavecchia A, Klotz KN, Cappellacci L..  (2017)  Exploring the Role of N6-Substituents in Potent Dual Acting 5'-C-Ethyltetrazolyladenosine Derivatives: Synthesis, Binding, Functional Assays, and Antinociceptive Effects in Mice ∇.,  60  (10): [PMID:28447789] [10.1021/acs.jmedchem.7b00291]

Source

Source(1):

• Scientific Literature