1-Acetyl-4-hydroxy-pyrrolidine-2-carboxylic acid [1-(benzothiazole-2-carbonyl)-4-guanidino-butyl]-amide hydrochloride

ID: ALA556199

PubChem CID: 45265199

Max Phase: Preclinical

Molecular Formula: C20H27ClN6O4S

Molecular Weight: 446.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)c1nc2ccccc2s1.Cl

Standard InChI:  InChI=1S/C20H26N6O4S.ClH/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19;/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23);1H/t12-,14+,15+;/m1./s1

Standard InChI Key:  RJGFYDAIAYFTCT-WEMUQIOZSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   14.5749    2.4831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4020    3.9202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5560    2.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0553    2.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3216    1.3676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9149    5.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905    5.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4296    1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8337    3.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    5.1513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.9931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417    3.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8508    1.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7020    6.2428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795    3.8805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940    6.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8296    1.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7370    5.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509    2.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802    3.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502    2.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  2  5  1  0
  2  6  1  0
  3  7  1  0
  7  8  1  1
  8  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
 12  9  1  6
  6 14  1  0
 11 14  1  0
  7 15  1  0
  3 16  1  0
 13 17  1  0
  5 18  2  0
  8 19  2  0
 15 20  1  0
 16 20  1  0
 10 21  2  0
 13 22  2  0
 13 23  1  0
 20 24  1  6
 10 25  1  0
 12 26  1  0
 11 27  2  0
 14 28  2  0
 22 29  1  0
 26 30  1  0
 29 30  1  0
 28 31  1  0
 27 32  1  0
 31 32  2  0
M  END

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: 446.53

Molecular Weight (Monoisotopic): 446.1736

AlogP: 0.00

#Rotatable Bonds: 8

Polar Surface Area: 164.00

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.24

CX Basic pKa: 11.05

CX LogP: -1.07

CX LogD: -3.26

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -0.30

References

1. Costanzo MJ, Yabut SC, Almond HR, Andrade-Gordon P, Corcoran TW, De Garavilla L, Kauffman JA, Abraham WM, Recacha R, Chattopadhyay D, Maryanoff BE..  (2003)  Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone.,  46  (18): [PMID:12930148] [10.1021/jm030050p]

Source

Source(1):

• Scientific Literature