NA

ID: ALA4751982

PubChem CID: 153154795

Max Phase: Preclinical

Molecular Formula: C20H21F2N9O9P2S2

Molecular Weight: 695.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(S)O[C@H]3[C@@H](F)[C@H](n4cnc5c(O)ncnc54)O[C@@H]3COP(=O)(S)O[C@H]2[C@H]1F

Standard InChI:  InChI=1S/C20H21F2N9O9P2S2/c21-9-13-7(37-19(9)30-5-28-11-15(23)24-3-25-16(11)30)1-35-42(34,44)40-14-8(2-36-41(33,43)39-13)38-20(10(14)22)31-6-29-12-17(31)26-4-27-18(12)32/h3-10,13-14,19-20H,1-2H2,(H,33,43)(H,34,44)(H2,23,24,25)(H,26,27,32)/t7-,8-,9-,10-,13-,14-,19-,20-,41?,42?/m1/s1

Standard InChI Key:  WBEHEZDHRLNQIK-IRYAPSAPSA-N

Molfile:  

 
     RDKit          2D

 48 54  0  0  0  0  0  0  0  0999 V2000
   10.2149  -12.4601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6235  -11.2013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9647  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7355  -13.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184  -13.1198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6648  -13.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3254  -14.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9870  -13.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2864  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0302  -12.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5721  -13.0645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3702  -12.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6236  -12.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0801  -11.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3244  -15.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8873  -14.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7164  -14.9473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9388  -15.1988    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7679  -15.9979    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322  -14.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0316  -15.6045    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.0306  -16.4217    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7398  -15.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5157  -15.7743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3334  -10.7396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3051  -16.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5430  -16.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868  -17.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3764  -17.8856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8206  -17.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7893  -17.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3206  -16.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9523  -18.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2297  -19.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9922  -19.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146  -18.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590  -17.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908  -17.2607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785  -17.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358  -17.9040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065  -18.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4632  -19.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8568  -16.4153    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7639  -14.1518    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6135  -14.7796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0894  -16.3480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2214  -17.9039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0811  -13.3144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  9  2  1  0
  2  3  2  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  4  1  1  1
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 15 21  1  0
 21 22  1  0
 21 23  2  0
 18 24  1  0
 21 32  1  0
 14 25  1  0
 26 24  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 30 31  1  0
 31 32  1  0
 28 33  1  1
 33 37  1  0
 36 34  1  0
 34 35  2  0
 35 33  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
 41 42  1  0
 27 43  1  6
  8 44  1  6
  7 45  1  1
 26 46  1  1
 30 47  1  6
  6 48  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4751982

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 695.52

Molecular Weight (Monoisotopic): 695.0347

AlogP: 2.32

#Rotatable Bonds: 2

Polar Surface Area: 222.97

Molecular Species: ACID

HBA: 18

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.67

CX Basic pKa: 4.92

CX LogP: -1.90

CX LogD: -1.92

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.17

Np Likeness Score: 0.27

References

1. Lioux T,Mauny MA,Lamoureux A,Bascoul N,Hays M,Vernejoul F,Baudru AS,Boularan C,Lopes-Vicente J,Qushair G,Tiraby G.  (2016)  Design, Synthesis, and Biological Evaluation of Novel Cyclic Adenosine-Inosine Monophosphate (cAIMP) Analogs That Activate Stimulator of Interferon Genes (STING).,  59  (22.0): [PMID:27783523] [10.1021/acs.jmedchem.6b01300]

Source

Source(1):

• Scientific Literature