(3S,7S,8R)-7-Hydroxy-3-isopropyl-8-(mercaptomethyl)-1,4,9-triazacyclohenicosane-2,5,10-trione

ID: ALA4522728

PubChem CID: 155543610

Max Phase: Preclinical

Molecular Formula: C22H41N3O4S

Molecular Weight: 443.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1NC(=O)C[C@H](O)[C@H](CS)NC(=O)CCCCCCCCCCCNC1=O

Standard InChI:  InChI=1S/C22H41N3O4S/c1-16(2)21-22(29)23-13-11-9-7-5-3-4-6-8-10-12-19(27)24-17(15-30)18(26)14-20(28)25-21/h16-18,21,26,30H,3-15H2,1-2H3,(H,23,29)(H,24,27)(H,25,28)/t17-,18-,21-/m0/s1

Standard InChI Key:  ZOSLVKUEZLHWGS-WFXMLNOXSA-N

Molfile:  

 
     RDKit          2D

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    5.7305  -13.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4217  -13.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088  -13.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7959  -13.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4788  -13.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659  -13.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659  -14.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435  -14.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8489  -14.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8489  -15.5143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564  -14.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693  -15.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435  -15.7990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435  -16.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7305  -16.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4217  -16.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088  -16.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7959  -16.5915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088  -17.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7305  -17.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4788  -16.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3599  -16.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4788  -17.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7959  -18.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659  -18.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396  -16.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9284  -17.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375  -17.8126    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  9  1  0
  8 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  6
 20 23  1  0
 23 24  1  0
 23 25  1  6
 25 26  1  0
 25 27  1  0
 24 11  1  0
 16 28  1  6
 24 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522728

   ---

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: 443.65

Molecular Weight (Monoisotopic): 443.2818

AlogP: 2.32

#Rotatable Bonds: 2

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.02

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 0.90

References

1. Houštecká R, Hadzima M, Fanfrlík J, Brynda J, Pallová L, Hánová I, Mertlíková-Kaiserová H, Lepšík M, Horn M, Smrčina M, Majer P, Mareš M..  (2020)  Biomimetic Macrocyclic Inhibitors of Human Cathepsin D: Structure-Activity Relationship and Binding Mode Analysis.,  63  (4): [PMID:32003991] [10.1021/acs.jmedchem.9b01351]

Source

Source(1):

• Scientific Literature