4-(13-(((3S,5S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)amino)-13-oxotridec-1-yn-1-yl)-7-methoxy-1-(((S)-5-oxopyrrolidin-2-yl)methoxy)isoquinoline-6-carboxamide

ID: ALA4582179

PubChem CID: 155562155

Max Phase: Preclinical

Molecular Formula: C56H76N8O8

Molecular Weight: 989.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@H](C(=O)N1C[C@@H](NC(=O)CCCCCCCCCCC#Cc2cnc(OC[C@@H]3CCC(=O)N3)c3cc(OC)c(C(N)=O)cc23)C[C@H]1C(=O)N[C@@H]1CCCc2ccccc21)C1CCCCC1

Standard InChI:  InChI=1S/C56H76N8O8/c1-36(58-2)53(68)63-51(38-21-14-12-15-22-38)56(70)64-34-41(30-47(64)54(69)62-46-26-19-24-37-20-17-18-25-42(37)46)61-49(65)27-16-11-9-7-5-4-6-8-10-13-23-39-33-59-55(72-35-40-28-29-50(66)60-40)44-32-48(71-3)45(52(57)67)31-43(39)44/h17-18,20,25,31-33,36,38,40-41,46-47,51,58H,4-12,14-16,19,21-22,24,26-30,34-35H2,1-3H3,(H2,57,67)(H,60,66)(H,61,65)(H,62,69)(H,63,68)/t36-,40-,41-,46+,47-,51-/m0/s1

Standard InChI Key:  CVFKSFVSLDSCBQ-ROZMQCGGSA-N

Molfile:  

 
     RDKit          2D

 72 78  0  0  0  0  0  0  0  0999 V2000
   17.6296   -6.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6285   -7.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3442   -7.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3424   -5.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0589   -6.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0596   -7.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7760   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4920   -7.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4873   -6.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7703   -5.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7777   -8.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7660   -4.9978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4794   -4.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4749   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1395   -3.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8774   -2.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0518   -2.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8023   -3.2765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5654   -1.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9181   -5.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9179   -5.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9167   -7.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2016   -7.0661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9161   -8.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7803   -9.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7828   -9.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4996  -10.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2138   -9.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9306  -10.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6447   -9.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3574  -10.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0716   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7884  -10.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5026   -9.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2194  -10.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9336   -9.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6504  -10.3370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9310   -9.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6530  -11.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9910  -11.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2472  -12.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0728  -12.4343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3241  -11.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5294  -12.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8180  -12.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5214  -13.6651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8019  -14.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0974  -13.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3800  -14.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3677  -14.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7984  -14.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0801  -15.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0654  -16.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7683  -16.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4914  -16.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5026  -15.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7862  -12.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7863  -13.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5016  -12.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2172  -12.8436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5016  -11.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9327  -12.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6482  -12.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9327  -11.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6482  -13.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3596  -12.4328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0750  -12.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2160  -11.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2179  -10.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5043   -9.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7870  -10.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7834  -11.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  7 11  1  0
 10 12  1  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 17 19  2  0
  1 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  1  0
 22 24  2  0
 11 25  3  0
 25 26  1  0
 26 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
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 39 37  1  6
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 39  1  0
 41 44  1  6
 44 45  2  0
 44 46  1  0
 47 46  1  1
 47 48  1  0
 47 51  1  0
 48 49  1  0
 49 50  1  0
 50 52  1  0
 51 52  2  0
 52 53  1  0
 53 54  2  0
 54 55  1  0
 55 56  2  0
 56 51  1  0
 42 57  1  0
 57 58  2  0
 57 59  1  0
 59 60  1  0
 59 61  1  6
 60 62  1  0
 62 63  1  0
 62 64  2  0
 63 65  1  1
 63 66  1  0
 66 67  1  0
 61 68  1  0
 61 72  1  0
 68 69  1  0
 69 70  1  0
 70 71  1  0
 71 72  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582179

   ---

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: 989.27

Molecular Weight (Monoisotopic): 988.5786

AlogP: 6.20

#Rotatable Bonds: 23

Polar Surface Area: 223.18

Molecular Species: BASE

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 12.32

CX Basic pKa: 8.60

CX LogP: 6.02

CX LogD: 4.80

Aromatic Rings: 3

Heavy Atoms: 72

QED Weighted: 0.05

Np Likeness Score: -0.35

References

1. Nunes J, McGonagle GA, Eden J, Kiritharan G, Touzet M, Lewell X, Emery J, Eidam H, Harling JD, Anderson NA..  (2019)  Targeting IRAK4 for Degradation with PROTACs.,  10  (7): [PMID:31312412] [10.1021/acsmedchemlett.9b00219]

Source

Source(1):

• Scientific Literature