ethyl N5-(2-(2-(4-((6-amino-2-butoxy-8-hydroxy-9H-purin-9-yl)methyl)benzamido)ethoxy)ethyl)-N2-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)glycyl-L-valyl-D-glutaminate

ID: ALA5185123

PubChem CID: 168282589

Max Phase: Preclinical

Molecular Formula: C45H60N10O12

Molecular Weight: 933.03

Names and Identifiers

Canonical SMILES:  CCCCOc1nc(N)c2nc(O)n(Cc3ccc(C(=O)NCCOCCNC(=O)CC[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)/C=C/c4ccc(O)c(OC)c4)C(C)C)C(=O)OCC)cc3)c2n1

Standard InChI:  InChI=1S/C45H60N10O12/c1-6-8-21-67-44-53-39(46)38-40(54-44)55(45(63)52-38)26-29-9-13-30(14-10-29)41(60)48-20-23-65-22-19-47-34(57)18-15-31(43(62)66-7-2)50-42(61)37(27(3)4)51-36(59)25-49-35(58)17-12-28-11-16-32(56)33(24-28)64-5/h9-14,16-17,24,27,31,37,56H,6-8,15,18-23,25-26H2,1-5H3,(H,47,57)(H,48,60)(H,49,58)(H,50,61)(H,51,59)(H,52,63)(H2,46,53,54)/b17-12+/t31-,37+/m1/s1

Standard InChI Key:  YREZZSNAITUJPZ-UQIXBXJYSA-N

Molfile:  

 
     RDKit          2D

 67 70  0  0  0  0  0  0  0  0999 V2000
  -10.5201    0.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8055    0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0935    0.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0935   -0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8036   -0.9267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5201   -0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2346   -0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2346   -1.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9492   -2.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9492   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6640   -3.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3106   -0.7608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8186   -0.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2893    0.5604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9934   -0.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0971   -1.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3000   -1.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7163   -1.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9218   -1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7081   -2.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2876   -2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0855   -2.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9111   -2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -1.8291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6975   -3.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8055    1.5471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5305   -2.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470   -1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -1.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663   -1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694   -1.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859   -0.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -0.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8247   -1.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3722   -0.1931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645    1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315    2.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150    2.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557    0.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7528    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    1.1873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362    0.7602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334    0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3469   -0.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664   -0.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829   -1.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7169    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5140    0.9166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0975    1.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945    1.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8839    2.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4780    1.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2751    1.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8588    2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6533    2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8669    1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875    0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4896    0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2368    2.6097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0231    3.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6640    1.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
 14 13  2  0
  3 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
  2 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  6
 39 40  2  0
 39 41  1  0
 41 42  1  0
 42 43  1  0
 38 44  1  0
 44 45  1  0
 44 46  2  0
 45 47  1  0
 47 48  1  0
 48 49  2  0
 45 50  1  1
 50 51  1  0
 50 52  1  0
 48 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  1  0
 55 57  2  0
 56 58  2  0
 58 59  1  0
 60 59  2  0
 61 60  1  0
 62 61  2  0
 63 62  1  0
 64 63  2  0
 59 64  1  0
 61 65  1  0
 65 66  1  0
 62 67  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5185123

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 933.03

Molecular Weight (Monoisotopic): 932.4392

AlogP: 1.72

#Rotatable Bonds: 27

Polar Surface Area: 309.57

Molecular Species: NEUTRAL

HBA: 17

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.87

CX Basic pKa: 3.39

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: 4

Heavy Atoms: 67

QED Weighted: 0.02

Np Likeness Score: -0.56

References

1. Guzelj S, Weiss M, Slütter B, Frkanec R, Jakopin Ž..  (2022)  Covalently Conjugated NOD2/TLR7 Agonists Are Potent and Versatile Immune Potentiators.,  65  (22.0): [PMID:36335509] [10.1021/acs.jmedchem.2c00808]

Source

Source(1):

• Scientific Literature