(S)-N5-tert-butyl-N1-((S)-1-((4-fluoronaphthalen-1-yl)methylamino)-3-methoxy-1-oxopropan-2-yl)-2-(4-methylphenylsulfonamido)pentanediamide

ID: ALA4741140

PubChem CID: 162646492

Max Phase: Preclinical

Molecular Formula: C31H39FN4O6S

Molecular Weight: 614.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC[C@H](NC(=O)[C@H](CCC(=O)NC(C)(C)C)NS(=O)(=O)c1ccc(C)cc1)C(=O)NCc1ccc(F)c2ccccc12

Standard InChI:  InChI=1S/C31H39FN4O6S/c1-20-10-13-22(14-11-20)43(40,41)36-26(16-17-28(37)35-31(2,3)4)30(39)34-27(19-42-5)29(38)33-18-21-12-15-25(32)24-9-7-6-8-23(21)24/h6-15,26-27,36H,16-19H2,1-5H3,(H,33,38)(H,34,39)(H,35,37)/t26-,27-/m0/s1

Standard InChI Key:  ACKUOPORWYFMTA-SVBPBHIXSA-N

Molfile:  

 
     RDKit          2D

 43 45  0  0  0  0  0  0  0  0999 V2000
   15.0007  -29.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5924  -28.4638    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1795  -29.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0383  -32.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4550  -31.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6296  -31.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3090  -28.0513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0216  -28.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7342  -28.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4466  -28.4554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1592  -28.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8717  -28.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5843  -28.0388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2967  -28.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0093  -28.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0234  -29.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7323  -27.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8735  -29.2764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1574  -27.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4339  -27.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7153  -26.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0062  -27.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4405  -28.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7235  -28.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7228  -29.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4385  -29.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1564  -29.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1535  -28.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7388  -29.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7406  -30.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4560  -30.9316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0270  -30.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1732  -32.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8800  -28.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8804  -27.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1654  -26.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4512  -27.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4566  -28.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1721  -28.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7349  -26.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1457  -26.7954    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.8710  -26.8038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8692  -25.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  6
  9 17  2  0
 12 18  2  0
 11 19  1  1
 15 24  2  0
 23 20  2  0
 20 21  1  0
 21 22  2  0
 22 15  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 16 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 31  5  1  0
  5 33  1  0
  7  2  1  0
  2 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 34  1  0
 37 40  1  0
 20 41  1  0
 19 42  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741140

   ---

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: 614.74

Molecular Weight (Monoisotopic): 614.2574

AlogP: 3.08

#Rotatable Bonds: 13

Polar Surface Area: 142.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.35

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.23

Np Likeness Score: -1.08

References

1. Zhan W,Singh PK,Ban Y,Qing X,Ah Kioon MD,Fan H,Zhao Q,Wang R,Sukenick G,Salmon J,Warren JD,Ma X,Barrat FJ,Nathan CF,Lin G.  (2020)  Structure-Activity Relationships of Noncovalent Immunoproteasome β5i-Selective Dipeptides.,  63  (21): [PMID:33095579] [10.1021/acs.jmedchem.0c01520]

Source

Source(1):

• Scientific Literature