(S)-3-{[(S)-(5S,7S)-6-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-5-oxo-octahydro-indolizine-3-carbonyl]-amino}-4-oxo-butyric acid

ID: ALA71937

PubChem CID: 44309904

Max Phase: Preclinical

Molecular Formula: C21H32N4O7

Molecular Weight: 452.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)N[C@H]1CC[C@H]2CC[C@@H](C(=O)N[C@H](C=O)CC(=O)O)N2C1=O

Standard InChI:  InChI=1S/C21H32N4O7/c1-4-11(2)18(22-12(3)27)20(31)24-15-7-5-14-6-8-16(25(14)21(15)32)19(30)23-13(10-26)9-17(28)29/h10-11,13-16,18H,4-9H2,1-3H3,(H,22,27)(H,23,30)(H,24,31)(H,28,29)/t11-,13-,14-,15-,16-,18-/m0/s1

Standard InChI Key:  AGTSGMXJICZTML-QSUVNEBKSA-N

Molfile:  

     RDKit          2D

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    5.2417   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6042   -3.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -3.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0417   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0500   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7542   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7500   -3.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0292   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.7792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  3  5  1  1
  7  6  1  1
  7  2  1  0
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  9  5  1  0
  8 10  1  6
 11  1  1  0
 19 12  1  1
 13  3  1  0
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 16  2  2  0
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 22 14  2  0
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 24 11  1  0
 25 27  2  0
 26  8  1  0
 27 19  1  0
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 29 15  1  0
 30 26  1  0
 26 31  1  1
 32 30  1  0
 11 33  1  6
 13 21  1  0
  7 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA71937

   (S)-3-{[(S)-(5S,7S)-6-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-5-oxo-octahydro-indolizine-3-carbonyl]-amino}-4-oxo-butyric 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: 452.51

Molecular Weight (Monoisotopic): 452.2271

AlogP: -0.67

#Rotatable Bonds: 10

Polar Surface Area: 161.98

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: -1.46

CX LogD: -4.63

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.29

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