(12S,16S,17S)-17-Benzyl-16-hydroxy-12-isopropyl-1,4,7-trioxa-10,13,18-triazacyclohenicosane-11,14,19-trione

ID: ALA4555649

PubChem CID: 155557206

Max Phase: Preclinical

Molecular Formula: C25H39N3O7

Molecular Weight: 493.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1NC(=O)C[C@H](O)[C@H](Cc2ccccc2)NC(=O)CCOCCOCCOCCNC1=O

Standard InChI:  InChI=1S/C25H39N3O7/c1-18(2)24-25(32)26-9-11-34-13-15-35-14-12-33-10-8-22(30)27-20(21(29)17-23(31)28-24)16-19-6-4-3-5-7-19/h3-7,18,20-21,24,29H,8-17H2,1-2H3,(H,26,32)(H,27,30)(H,28,31)/t20-,21-,24-/m0/s1

Standard InChI Key:  XESPVRXMKMJFDF-HFMPRLQTSA-N

Molfile:  

 
     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    6.0959  -26.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8036  -26.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5031  -26.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3923  -26.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3923  -25.7580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5031  -27.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2067  -26.5711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9144  -26.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180  -26.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180  -25.7580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3215  -26.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0959  -27.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888  -26.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9144  -27.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8036  -23.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5031  -22.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2067  -23.3147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9144  -22.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888  -27.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9828  -28.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824  -29.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6865  -29.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3925  -29.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893  -28.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2067  -28.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180  -28.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3215  -25.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3215  -24.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180  -24.1278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180  -23.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8036  -24.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1289  -24.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218  -25.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870  -24.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139  -25.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  5  1  0
  3  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  1 12  1  6
  4 13  1  6
  8 14  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 14 25  1  0
 14 26  1  0
 10 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 18  1  0
 15 31  1  0
 31 32  1  0
  5 33  1  0
 32 34  1  0
 33 34  1  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555649

   ---

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: 493.60

Molecular Weight (Monoisotopic): 493.2788

AlogP: 0.18

#Rotatable Bonds: 3

Polar Surface Area: 135.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: -0.08

CX LogD: -0.08

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.47

Np Likeness Score: 0.64

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