(S)-N-((S)-1-cyclohexyl-2-((R)-2-methyloxiran-2-yl)-2-oxoethyl)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanamide

ID: ALA4570830

PubChem CID: 155561390

Max Phase: Preclinical

Molecular Formula: C30H44N4O7

Molecular Weight: 572.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C[C@H](NC(=O)[C@H](C)NC(=O)CN2CCOCC2)C(=O)N[C@H](C(=O)[C@@]2(C)CO2)C2CCCCC2)cc1

Standard InChI:  InChI=1S/C30H44N4O7/c1-20(31-25(35)18-34-13-15-40-16-14-34)28(37)32-24(17-21-9-11-23(39-3)12-10-21)29(38)33-26(22-7-5-4-6-8-22)27(36)30(2)19-41-30/h9-12,20,22,24,26H,4-8,13-19H2,1-3H3,(H,31,35)(H,32,37)(H,33,38)/t20-,24-,26-,30+/m0/s1

Standard InChI Key:  HPDUMJMJUGLHJL-TVYSDHEISA-N

Molfile:  

 
     RDKit          2D

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   19.1955   -4.2882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4878   -3.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9032   -3.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.9032   -3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6109   -5.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.7341   -3.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.8572   -5.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.0724   -3.8796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0767   -3.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3731   -2.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6630   -3.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6610   -3.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3692   -4.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7341   -5.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7300   -6.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4369   -6.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.1430   -5.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4355   -5.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8538   -6.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8549   -7.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1495   -3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8596   -2.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8615   -1.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1556   -1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4461   -1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4425   -2.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  5  7  2  0
  6  8  1  0
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  8 10  1  1
  9 11  2  0
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 12 13  1  0
 13 14  1  0
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  2 21  1  6
  4 22  1  0
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 18 36  1  1
 36 37  1  0
 36 41  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570830

   ---

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: 572.70

Molecular Weight (Monoisotopic): 572.3210

AlogP: 0.98

#Rotatable Bonds: 13

Polar Surface Area: 138.60

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.86

CX Basic pKa: 5.04

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.30

Np Likeness Score: -0.47

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