2-{3-Hydroxy-6-methyl-4-[3-methyl-2-(3-methyl-butyrylamino)-butyrylamino]-heptanoylamino}-propionic acid methyl ester

ID: ALA3392103

PubChem CID: 118725178

Max Phase: Preclinical

Molecular Formula: C22H41N3O6

Molecular Weight: 443.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)CC(C)C)C(C)C

Standard InChI:  InChI=1S/C22H41N3O6/c1-12(2)9-16(17(26)11-19(28)23-15(7)22(30)31-8)24-21(29)20(14(5)6)25-18(27)10-13(3)4/h12-17,20,26H,9-11H2,1-8H3,(H,23,28)(H,24,29)(H,25,27)/t15-,16-,17-,20-/m0/s1

Standard InChI Key:  IXBBSGVZUPOAKN-BOSXTWCSSA-N

Molfile:  

     RDKit          2D

 32 31  0  0  1  0  0  0  0  0999 V2000
    2.5570   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426   -2.2298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3008   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -1.8173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -1.8173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570   -0.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -3.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -3.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -0.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -0.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -3.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8732   -2.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -3.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -0.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1294   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -3.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -3.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570   -3.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5877   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3008   -0.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136    0.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8439   -1.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1294   -3.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -2.6423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  1  1  0
 11  5  1  0
  6  4  1  0
  7  6  1  0
  8  2  1  6
  9  3  1  0
 12 10  1  0
  8 11  1  0
 12  9  1  0
 13  1  2  0
 14  3  2  0
 15  7  2  0
 16 10  2  0
  8 17  1  0
 18  7  1  0
  4 19  1  1
 20 10  1  0
 11 21  1  1
 22 17  1  0
 23 18  1  0
 12 24  1  1
 25 19  1  0
 26 19  1  0
 27 20  1  0
 28 22  1  0
 29 22  1  0
 30 23  1  0
 31 23  1  0
 11 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3392103

   ---

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: 443.59

Molecular Weight (Monoisotopic): 443.2995

AlogP: 1.13

#Rotatable Bonds: 13

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.35

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: 0.30

References

1. Agarwal NS, Rich DH..  (1986)  Inhibition of cathepsin D by substrate analogues containing statine and by analogues of pepstatin.,  29  (12): [PMID:3783611] [10.1021/jm00162a015]

Source

Source(1):

• Scientific Literature