US9212206, VII

ID: ALA3954917

PubChem CID: 118579584

Max Phase: Preclinical

Molecular Formula: C20H33N3O5S

Molecular Weight: 427.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](S)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N(C)[C@@H](C)C(=O)O

Standard InChI:  InChI=1S/C20H33N3O5S/c1-12(2)11-16(29)19(26)23-10-6-8-15(23)18(25)22-9-5-7-14(22)17(24)21(4)13(3)20(27)28/h12-16,29H,5-11H2,1-4H3,(H,27,28)/t13-,14-,15-,16-/m0/s1

Standard InChI Key:  GODDKMSRPVPPPQ-VGWMRTNUSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  1  0  0  0  0  0999 V2000
    6.2100   -4.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9888   -2.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -3.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -0.9864    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -3.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281   -2.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218   -2.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157   -3.6164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -3.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -5.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -6.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7701   -4.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557   -6.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -3.8262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417   -2.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6299   -3.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1245   -5.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5051   -2.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6993   -2.8725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0105   -1.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 20 21  1  1
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3954917

   US9212206, VII

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: 427.57

Molecular Weight (Monoisotopic): 427.2141

AlogP: 1.24

#Rotatable Bonds: 7

Polar Surface Area: 98.23

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.72

CX Basic pKa: ┄

CX LogP: 0.99

CX LogD: -2.32

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.45

References

1.  (2015)  4-Fluoro-Thio-containing inhibitors of APP2, compositions thereof and method of use, 

2. Maggiora, L L LL, Orawski, A T AT and Simmons, W H WH.  1999-07-01  Apstatin analogue inhibitors of aminopeptidase P, a bradykinin-degrading enzyme.  [PMID:10395480]

Source

Source(1):

• BindingDB Database