methyl 4-((S)-1-((R)-1-((S)-1-((S)-2-((R)-1-chloro-4-methyl-2-oxopentan-3-ylcarbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-4-oxobutanoate

ID: ALA1290140

PubChem CID: 52947317

Max Phase: Preclinical

Molecular Formula: C25H40ClN5O8

Molecular Weight: 574.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)CCl)C(C)C

Standard InChI:  InChI=1S/C25H40ClN5O8/c1-13(2)21(18(32)12-26)30-24(37)17-8-7-11-31(17)25(38)16(5)29-23(36)15(4)28-22(35)14(3)27-19(33)9-10-20(34)39-6/h13-17,21H,7-12H2,1-6H3,(H,27,33)(H,28,35)(H,29,36)(H,30,37)/t14-,15+,16-,17-,21+/m0/s1

Standard InChI Key:  WPRNYPXVPOXZMZ-JXVINKLPSA-N

Molfile:  

     RDKit          2D

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    3.1730   -6.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598   -7.6597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8903   -7.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3164   -6.8379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033   -5.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8860   -5.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6829   -7.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4907   -7.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9018   -7.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3562   -6.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5297   -5.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3097   -5.4281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9079   -5.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4682   -4.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2483   -4.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8464   -4.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0090   -3.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0663   -4.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4067   -3.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8701   -4.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1869   -3.2774    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  1  3  1  0
 20 21  1  0
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  4  6  1  0
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 10 12  1  6
 21 24  2  0
 23 25  1  0
  1  2  1  0
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  2  7  1  0
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  7  8  1  0
 29 31  2  0
 15 16  1  0
 32 30  1  6
 32 33  1  0
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 32 34  1  0
  7  9  2  0
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  3  5  2  0
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  8 10  1  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1290140

   MeOSuc-Ala-D-Ala-Ala-Pro-D-Val-CH2Cl

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: 574.08

Molecular Weight (Monoisotopic): 573.2565

AlogP: -0.61

#Rotatable Bonds: 14

Polar Surface Area: 180.08

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.80

CX Basic pKa: ┄

CX LogP: -0.91

CX LogD: -0.91

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: -0.38

References

1. Kore AR, Shanmugasundaram M..  (2010)  Design, synthesis and inhibitory effect of pentapeptidyl chloromethyl ketones on proteinase K.,  18  (23): [PMID:20937562] [10.1016/j.bmc.2010.09.048]

Source

Source(1):

• Scientific Literature