(S)-1-((S)-2-((2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxamido)-4-methylpentanoyl)pyrrolidine-2-carboxylic acid

ID: ALA4566711

PubChem CID: 10384528

Max Phase: Preclinical

Molecular Formula: C17H26N2O7

Molecular Weight: 370.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)O

Standard InChI:  InChI=1S/C17H26N2O7/c1-4-25-17(24)13-12(26-13)14(20)18-10(8-9(2)3)15(21)19-7-5-6-11(19)16(22)23/h9-13H,4-8H2,1-3H3,(H,18,20)(H,22,23)/t10-,11-,12-,13-/m0/s1

Standard InChI Key:  HPRJAQUIZKLSIG-CYDGBPFRSA-N

Molfile:  

 
     RDKit          2D

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    6.5454  -18.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3626  -18.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7711  -18.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7711  -20.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7711  -19.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4802  -19.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974  -19.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7060  -19.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7060  -20.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5232  -19.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9318  -19.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7490  -19.9082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5232  -20.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9318  -18.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368  -18.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196  -18.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5232  -17.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9318  -17.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7060  -17.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2297  -20.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0069  -20.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0069  -19.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2297  -19.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8163  -21.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991  -21.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2189  -21.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  4  5  1  0
  5  6  1  0
  4  6  1  0
  5  2  1  6
  7  8  1  0
  7  9  2  0
  8 10  1  0
  6  7  1  1
  1  2  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  1  1
  1 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 12 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 12  1  0
 20 24  1  1
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4566711

   (2S)-1-[(2S)-2-[[(2S,3S)-3-ethoxycarbonyloxirane-2-carbonyl]amino]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

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: 370.40

Molecular Weight (Monoisotopic): 370.1740

AlogP: -0.08

#Rotatable Bonds: 8

Polar Surface Area: 125.54

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.81

CX Basic pKa: ┄

CX LogP: 0.29

CX LogD: -2.97

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 0.03

References

1. Schmitz J, Gilberg E, Löser R, Bajorath J, Bartz U, Gütschow M..  (2019)  Cathepsin B: Active site mapping with peptidic substrates and inhibitors.,  27  (1): [PMID:30473362] [10.1016/j.bmc.2018.10.017]

Source

Source(1):

• Scientific Literature