(S)-3-Acetylamino-N-[(S)-1-((S)-1-carbamoyl-pentylcarbamoyl)-2-(4-sulfooxy-phenyl)-ethyl]-succinamic acid

ID: ALA175257

PubChem CID: 23646469

Max Phase: Preclinical

Molecular Formula: C21H30N4O10S

Molecular Weight: 530.56

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CCCC[C@H](NC(=O)[C@H](Cc1ccc(OS(=O)(=O)O)cc1)NC(=O)[C@H](CC(=O)O)NC(C)=O)C(N)=O

Standard InChI:  InChI=1S/C21H30N4O10S/c1-3-4-5-15(19(22)29)24-20(30)16(25-21(31)17(11-18(27)28)23-12(2)26)10-13-6-8-14(9-7-13)35-36(32,33)34/h6-9,15-17H,3-5,10-11H2,1-2H3,(H2,22,29)(H,23,26)(H,24,30)(H,25,31)(H,27,28)(H,32,33,34)/t15-,16-,17-/m0/s1

Standard InChI Key:  VYEUAVNMANWCSE-ULQDDVLXSA-N

Molfile:  

     RDKit          2D

 36 36  0  0  1  0  0  0  0  0999 V2000
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    1.5542   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1167   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -5.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -6.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5958   -1.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -2.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  8  1  0
  4  8  1  0
  5  3  1  0
  6  2  1  0
  6  7  1  1
  8 19  1  6
  9  6  1  0
 10 14  1  0
 11  7  1  0
 12  1  1  0
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 16  1  2  0
 17  3  2  0
 18  2  2  0
 19 26  1  0
 20 10  2  0
 21  1  1  0
 22 11  2  0
 23 13  2  0
 24 10  1  0
 25 12  1  0
 26 28  1  0
 27 11  1  0
 28 31  2  0
 29 30  1  0
 30 25  2  0
 31 25  1  0
 32 13  1  0
 14 33  1  1
 34 33  1  0
 35 34  1  0
 36 35  1  0
 29 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA175257

   (3S)-3-{[(1S)-1-{[(1S)-1-carbamoylpentyl]carbamoyl}-2-[4-(sulfooxy)phenyl]ethyl]carbamoyl}-3-acetamidopropanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 530.56

Molecular Weight (Monoisotopic): 530.1683

AlogP: -0.96

#Rotatable Bonds: 15

Polar Surface Area: 231.29

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -2.30

CX Basic pKa: ┄

CX LogP: -2.87

CX LogD: -6.56

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: 0.28

References

1. Larsen SD, Stevens FC, Lindberg TJ, Bodnar PM, O'Sullivan TJ, Schostarez HJ, Palazuk BJ, Bleasdale JE..  (2003)  Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: identification of analogues with cellular activity.,  13  (5): [PMID:12617932] [10.1016/s0960-894x(02)01065-x]

2. Kousaxidis A, Petrou A, Lavrentaki V, Fesatidou M, Nicolaou I, Geronikaki A..  (2020)  Aldose reductase and protein tyrosine phosphatase 1B inhibitors as a promising therapeutic approach for diabetes mellitus.,  207  [PMID:32871344] [10.1016/j.ejmech.2020.112742]

Source

Source(1):

• Scientific Literature