N-((2S,3S)-3-(ethoxycarbonyl)oxirane-2-carbonyl)-isoleucyl-proline

ID: ALA4533469

Cas Number: 134447-97-5

PubChem CID: 131790

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](C(=O)N1CCC[C@H]1C(=O)O)[C@@H](C)CC

Standard InChI:  InChI=1S/C17H26N2O7/c1-4-9(3)11(15(21)19-8-6-7-10(19)16(22)23)18-14(20)12-13(26-12)17(24)25-5-2/h9-13H,4-8H2,1-3H3,(H,18,20)(H,22,23)/t9-,10-,11-,12-,13-/m0/s1

Standard InChI Key:  RFNNDNGXWCBNGK-VLJOUNFMSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   25.2289  -17.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5872  -18.2389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7726  -18.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6019  -19.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3110  -19.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9216  -18.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4264  -17.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4795  -16.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9958  -17.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2216  -18.2389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8130  -17.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2216  -16.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8130  -16.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9958  -16.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0388  -16.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5872  -16.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0388  -18.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4474  -17.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4474  -19.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4474  -18.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1564  -19.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9736  -19.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3822  -20.0615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3822  -18.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1994  -18.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6080  -17.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  6  1  0
  1  7  2  0
  1  8  1  0
 11 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  6
  9 16  2  0
  2  9  1  0
 17 18  2  0
 19 20  1  0
 20 21  1  0
 19 21  1  0
 20 17  1  6
 22 23  2  0
 25 26  1  0
 24 25  1  0
 22 24  1  0
 21 22  1  1
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533469

   N-(3-Ethoxycarbonyloxirane-2-carbonyl)-isoleucyl-proline

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: 0.37

CX LogD: -2.89

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 0.06

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