N-((S)-1-{(R)-2-[(R)-2-((R)-3-Chloro-1-isopropyl-2-oxo-propylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethylcarbamoyl}-ethyl)-succinamic acid methyl ester

ID: ALA2311166

Cas Number: 65144-34-5

PubChem CID: 5486692

Product Number: S274813, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H35ClN4O7

Molecular Weight: 503.00

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)N1CCC[C@H]1C(=O)N[C@H](C(=O)CCl)C(C)C

Standard InChI:  InChI=1S/C22H35ClN4O7/c1-12(2)19(16(28)11-23)26-21(32)15-7-6-10-27(15)22(33)14(4)25-20(31)13(3)24-17(29)8-9-18(30)34-5/h12-15,19H,6-11H2,1-5H3,(H,24,29)(H,25,31)(H,26,32)/t13-,14-,15-,19-/m0/s1

Standard InChI Key:  PJGDFLJMBAYGGC-XLPNERPQSA-N

Molfile:  

     RDKit          2D

 34 34  0  0  1  0  0  0  0  0999 V2000
    1.3254  -14.9434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129  -14.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504  -13.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379  -13.5351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879  -14.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246  -14.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246  -14.5309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129  -13.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996  -14.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379  -13.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621  -14.9434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871  -14.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496  -14.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0746  -16.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129  -13.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379  -13.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246  -15.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379  -12.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7121  -13.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7996  -15.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129  -15.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254  -14.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871  -14.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621  -15.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496  -17.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004  -15.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9629  -13.3601    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2504  -13.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254  -15.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996  -15.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496  -13.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129  -15.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379  -15.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496  -17.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5  3  1  6
  4  3  1  0
  5  1  1  0
  6  7  1  0
  7  9  1  0
  8  4  1  6
  9  2  1  0
 10  8  1  0
 11 13  1  0
 12 11  1  0
 13  6  1  0
 14 24  1  0
 15  2  2  0
 16  3  2  0
 17  6  2  0
 18 10  2  0
 19 12  2  0
 20 14  2  0
 21  1  1  0
  8 22  1  0
 23 12  1  0
 24 23  1  0
 25 14  1  0
  5 26  1  0
 27 28  1  0
 28 10  1  0
 29 21  1  0
  9 30  1  6
 13 31  1  1
 32 22  1  0
 33 22  1  0
 34 25  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2311166

   MeOSuc-AAPV-CMK

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: 503.00

Molecular Weight (Monoisotopic): 502.2194

AlogP: -0.11

#Rotatable Bonds: 12

Polar Surface Area: 150.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.96

CX Basic pKa: ┄

CX LogP: -0.37

CX LogD: -0.37

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.25

Np Likeness Score: -0.43

References

1. Buynak JD, Rao AS, Ford GP, Carver C, Adam G, Geng B, Bachmann B, Shobassy S, Lackey S..  (1997)  7-alkylidenecephalosporin esters as inhibitors of human leukocyte elastase.,  40  (21): [PMID:9341917] [10.1021/jm970351x]

2. Khalfin B,Lichtenstein A,Albeck A,Nathan I.  (2021)  Targeting Necrosis: Elastase-like Protease Inhibitors Curtail Necrotic Cell Death Both In Vitro and in Three In Vivo Disease Models.,  64  (3.0): [PMID:33522230] [10.1021/acs.jmedchem.0c01683]

3. Cui Y, Zhang M, Xu H, Zhang T, Zhang S, Zhao X, Jiang P, Li J, Ye B, Sun Y, Wang M, Deng Y, Meng Q, Liu Y, Fu Q, Lin J, Wang L, Chen Y..  (2022)  Elastase Inhibitor Cyclotheonellazole A: Total Synthesis and In Vivo Biological Evaluation for Acute Lung Injury.,  65  (4.0): [PMID:35005973] [10.1021/acs.jmedchem.1c01583]

Source

Source(1):

• Scientific Literature