(2R,4R)-4-((S)-2,5-diaminopentanamido)-N-hydroxy-1-(4-methoxyphenylsulfonyl)pyrrolidine-2-carboxamide

ID: ALA4765192

PubChem CID: 162661718

Max Phase: Preclinical

Molecular Formula: C17H27N5O6S

Molecular Weight: 429.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2C[C@H](NC(=O)[C@@H](N)CCCN)C[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C17H27N5O6S/c1-28-12-4-6-13(7-5-12)29(26,27)22-10-11(9-15(22)17(24)21-25)20-16(23)14(19)3-2-8-18/h4-7,11,14-15,25H,2-3,8-10,18-19H2,1H3,(H,20,23)(H,21,24)/t11-,14+,15-/m1/s1

Standard InChI Key:  VNHNLDUXLRLXAA-BYCMXARLSA-N

Molfile:  

 
     RDKit          2D

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    8.2875  -26.7197    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9978  -27.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -24.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101  -24.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864  -24.5735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219  -24.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296  -24.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415  -24.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3533  -24.5735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0651  -24.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1502  -25.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9536  -25.9692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3664  -25.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8154  -24.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296  -23.7522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415  -25.8076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1832  -25.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6636  -25.8370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4804  -25.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5155  -24.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8057  -27.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9903  -27.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5086  -27.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8466  -28.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667  -28.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1406  -28.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3648  -29.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5476  -29.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  8 16  1  6
  9 17  2  0
 14 18  1  6
 18 19  1  0
 19 20  1  0
 18 21  2  0
 13  2  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4765192

   ---

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: 429.50

Molecular Weight (Monoisotopic): 429.1682

AlogP: -1.49

#Rotatable Bonds: 9

Polar Surface Area: 177.08

Molecular Species: BASE

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.68

CX Basic pKa: 9.93

CX LogP: -3.33

CX LogD: -5.35

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: -0.65

References

1. Lenci E,Contini A,Trabocchi A.  (2020)  Discovery of a d-pro-lys peptidomimetic inhibitor of MMP9: Addressing the gelatinase selectivity beyond S1' subsite.,  30  (20.0): [PMID:32768649] [10.1016/j.bmcl.2020.127467]

Source

Source(1):

• Scientific Literature