(S)-5-amino-5-oxo-4-(4-(4-phenylthiophen-2-yl)benzamido)pentanoic acid

ID: ALA4761188

PubChem CID: 57336496

Max Phase: Preclinical

Molecular Formula: C22H20N2O4S

Molecular Weight: 408.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H](CCC(=O)O)NC(=O)c1ccc(-c2cc(-c3ccccc3)cs2)cc1

Standard InChI:  InChI=1S/C22H20N2O4S/c23-21(27)18(10-11-20(25)26)24-22(28)16-8-6-15(7-9-16)19-12-17(13-29-19)14-4-2-1-3-5-14/h1-9,12-13,18H,10-11H2,(H2,23,27)(H,24,28)(H,25,26)/t18-/m0/s1

Standard InChI Key:  ADDJDJQFPKUMAF-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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    6.3680  -10.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0827  -11.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7992  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7962   -9.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0809   -9.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6517  -11.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983  -10.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458  -11.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578  -12.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648  -12.0563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278  -11.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937  -10.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8878  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269  -12.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455  -12.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5091   -9.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2252   -9.9864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5060   -8.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9380   -9.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6540   -9.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9349   -8.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6478   -8.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6447   -7.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3576   -7.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9287   -7.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6571  -10.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3669   -9.5658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
  2  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 22 28  2  0
 22 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761188

   N~2~-[4-(4-Phenylthiophen-2-Yl)benzoyl]-L-Alpha-Glutamine

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: 408.48

Molecular Weight (Monoisotopic): 408.1144

AlogP: 3.53

#Rotatable Bonds: 8

Polar Surface Area: 109.49

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.49

References

1. Zipfel P,Rochais C,Baranger K,Rivera S,Dallemagne P.  (2020)  Matrix Metalloproteinases as New Targets in Alzheimer's Disease: Opportunities and Challenges.,  63  (19.0): [PMID:32459966] [10.1021/acs.jmedchem.0c00352]

Source

Source(1):

• Scientific Literature