(S)-6-amino-2-((S)-2-((S)-2-((S)-2-azido-3-phenylpropanamido)-4-methylpentanamido)-4-methylpentanamido)hexane-1-sulfonylfluoride

ID: ALA4130258

PubChem CID: 145963518

Max Phase: Preclinical

Molecular Formula: C27H44FN7O5S

Molecular Weight: 597.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)N=[N+]=[N-])C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)CS(=O)(=O)F

Standard InChI:  InChI=1S/C27H44FN7O5S/c1-18(2)14-22(25(36)31-21(12-8-9-13-29)17-41(28,39)40)32-26(37)23(15-19(3)4)33-27(38)24(34-35-30)16-20-10-6-5-7-11-20/h5-7,10-11,18-19,21-24H,8-9,12-17,29H2,1-4H3,(H,31,36)(H,32,37)(H,33,38)/t21-,22-,23-,24-/m0/s1

Standard InChI Key:  MGAGNLOPCIZNFW-ZJZGAYNASA-N

Molfile:  

     RDKit          2D

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   38.3710  -21.8085    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.7835  -22.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5127  -22.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2272  -21.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7982  -21.8126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2272  -20.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9416  -22.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6561  -21.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3706  -22.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6561  -20.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3706  -20.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.2285  -23.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2285  -22.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5141  -20.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   37.6575  -22.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9430  -20.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3669  -20.9834    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.6575  -20.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5127  -23.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6575  -19.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3719  -19.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3719  -18.5126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2272  -23.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2224  -24.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9361  -24.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6516  -24.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6488  -23.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9347  -23.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0838  -22.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3693  -22.6376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  6  1  0
  5  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
 12 13  1  0
 12 14  1  0
 10 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  6
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 20 21  1  0
 20 22  1  0
 18 23  1  0
 18 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  1
 26  2  1  0
  2 28  1  0
 27 29  1  0
  4 30  1  6
 29 31  1  0
 31 32  1  0
 32 33  1  0
 30 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
  6 40  2  0
 40 41  2  0
M  CHG  2  40   1  41  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4130258

   ---

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: 597.76

Molecular Weight (Monoisotopic): 597.3109

AlogP: 2.88

#Rotatable Bonds: 19

Polar Surface Area: 196.22

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -10.27

CX Basic pKa: 9.80

CX LogP: 2.64

CX LogD: 0.21

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.06

Np Likeness Score: 0.16

References

1. Artschwager R, Ward DJ, Gannon S, Brouwer AJ, van de Langemheen H, Kowalski H, Liskamp RMJ..  (2018)  Potent and Highly Selective Inhibitors of the Proteasome Trypsin-like Site by Incorporation of Basic Side Chain Containing Amino Acid Derived Sulfonyl Fluorides.,  61  (12): [PMID:29782167] [10.1021/acs.jmedchem.8b00685]

Source

Source(1):

• Scientific Literature