(S)-6-amino-2-(4-methylphenylsulfonamido)-N-(4-nitrophenyl)hexanamide

ID: ALA4521828

PubChem CID: 14082458

Max Phase: Preclinical

Molecular Formula: C19H24N4O5S

Molecular Weight: 420.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)N[C@@H](CCCCN)C(=O)Nc2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C19H24N4O5S/c1-14-5-11-17(12-6-14)29(27,28)22-18(4-2-3-13-20)19(24)21-15-7-9-16(10-8-15)23(25)26/h5-12,18,22H,2-4,13,20H2,1H3,(H,21,24)/t18-/m0/s1

Standard InChI Key:  UDLIYHCVMFPMTL-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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    9.8599   -7.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4555   -6.8595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0465   -7.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3327   -5.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3315   -6.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0396   -6.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7492   -6.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464   -5.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0378   -5.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6249   -5.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1646   -6.4505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8730   -6.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5801   -6.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2884   -6.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5788   -5.6311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8743   -7.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1672   -8.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1685   -8.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614   -9.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4627  -10.1289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9955   -6.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7010   -6.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4076   -6.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4067   -5.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6934   -5.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9897   -5.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1168   -5.2121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1145   -4.3949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8257   -5.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
  7  2  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  2  0
 27 29  1  0
 24 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4521828

   (2S)-6-amino-2-[(4-methylphenyl)sulfonylamino]-N-(4-nitrophenyl)hexanamide

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: 420.49

Molecular Weight (Monoisotopic): 420.1467

AlogP: 2.32

#Rotatable Bonds: 10

Polar Surface Area: 144.43

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.59

CX Basic pKa: 9.98

CX LogP: 2.09

CX LogD: 0.03

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -1.30

References

1. Steinmetzer T, Pilgram O, Wenzel BM, Wiedemeyer SJA..  (2020)  Fibrinolysis Inhibitors: Potential Drugs for the Treatment and Prevention of Bleeding.,  63  (4): [PMID:31658420] [10.1021/acs.jmedchem.9b01060]

Source

Source(1):

• Scientific Literature