(R)-2-({(2S,5S)-5-[(S)-2-(Acetyl-methyl-amino)-3-(S)-methyl-pentanoylamino]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carbonyl}-amino)-3-oxo-propionic acid

ID: ALA304368

PubChem CID: 44309811

Max Phase: Preclinical

Molecular Formula: C25H32N4O7

Molecular Weight: 500.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H](C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)N[C@H](C=O)C(=O)O)C3)N(C)C(C)=O

Standard InChI:  InChI=1S/C25H32N4O7/c1-5-13(2)20(28(4)14(3)31)23(33)26-17-10-9-15-7-6-8-16-11-19(29(21(15)16)24(17)34)22(32)27-18(12-30)25(35)36/h6-8,12-13,17-20H,5,9-11H2,1-4H3,(H,26,33)(H,27,32)(H,35,36)/t13-,17-,18+,19-,20-/m0/s1

Standard InChI Key:  MZDVCOYYTAHLOR-WUTPFUBCSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  1  0  0  0  0  0999 V2000
    6.1292   -2.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -3.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -4.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -3.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -4.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -4.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -3.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -4.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -4.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4792   -4.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -2.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  8  1  0
  2  5  1  1
  6  1  1  0
  7  6  1  0
 12  8  1  1
  9  2  1  0
 10  5  1  0
 11 10  1  0
 12  3  1  0
 14 13  1  6
 14  4  1  0
 11 15  1  1
 16 13  1  0
 17  4  2  0
 18  3  2  0
 19  6  2  0
 20  5  2  0
 21 12  1  0
 22 15  2  0
 23 16  2  0
 24 11  1  0
 25 19  1  0
 26 24  2  0
 27 14  1  0
 28 15  1  0
 29  7  2  0
 30 13  1  0
 31 16  1  0
 32 33  2  0
 33 19  1  0
 34 27  1  0
 27 35  1  1
 36 34  1  0
  7  9  1  0
 25 21  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA304368

   (2R)-2-[[(2S,11S)-11-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carbonyl]amino]-3-oxopropanoic acid

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: 500.55

Molecular Weight (Monoisotopic): 500.2271

AlogP: 0.04

#Rotatable Bonds: 9

Polar Surface Area: 153.19

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.40

CX Basic pKa: ┄

CX LogP: 0.15

CX LogD: -3.26

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: 0.30

References

1. Willoughby CA, Bull HG, Garcia-Calvo M, Jiang J, Chapman KT, Thornberry NA..  (2002)  Discovery of potent, selective human granzyme B inhibitors that inhibit CTL mediated apoptosis.,  12  (16): [PMID:12127536] [10.1016/s0960-894x(02)00363-3]

Source

Source(1):

• Scientific Literature