(S)-N-((2S,3R)-1-((S)-1-(4-(aminomethyl)phenyl)-4-(methylsulfonyl)but-3-en-2-ylamino)-3-hydroxy-1-oxobutan-2-yl)-2-((S)-2-azido-3-phenylpropanamido)-4-methylpentanamide

ID: ALA4590398

PubChem CID: 155567712

Max Phase: Preclinical

Molecular Formula: C31H43N7O6S

Molecular Weight: 641.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)N=[N+]=[N-])C(=O)N[C@H](C(=O)N[C@H](/C=C/S(C)(=O)=O)Cc1ccc(CN)cc1)[C@@H](C)O

Standard InChI:  InChI=1S/C31H43N7O6S/c1-20(2)16-26(35-30(41)27(37-38-33)18-22-8-6-5-7-9-22)29(40)36-28(21(3)39)31(42)34-25(14-15-45(4,43)44)17-23-10-12-24(19-32)13-11-23/h5-15,20-21,25-28,39H,16-19,32H2,1-4H3,(H,34,42)(H,35,41)(H,36,40)/b15-14+/t21-,25-,26+,27+,28+/m1/s1

Standard InChI Key:  OSCQGDIKEUNOAP-XNQSZOFZSA-N

Molfile:  

 
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M  CHG  2  42   1  43  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4590398

   ---

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: 641.80

Molecular Weight (Monoisotopic): 641.2996

AlogP: 2.05

#Rotatable Bonds: 17

Polar Surface Area: 216.45

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -10.27

CX Basic pKa: 9.29

CX LogP: 1.23

CX LogD: -0.75

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.10

Np Likeness Score: 0.35

References

1. Xin BT, Huber EM, de Bruin G, Heinemeyer W, Maurits E, Espinal C, Du Y, Janssens M, Weyburne ES, Kisselev AF, Florea BI, Driessen C, van der Marel GA, Groll M, Overkleeft HS..  (2019)  Structure-Based Design of Inhibitors Selective for Human Proteasome β2c or β2i Subunits.,  62  (3): [PMID:30657666] [10.1021/acs.jmedchem.8b01884]

Source

Source(1):

• Scientific Literature