(S)-3-({1-[(S)-2-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-acetyl]-2,3-dihydro-1H-indole-2-carbonyl}-amino)-4-oxo-butyric acid

ID: ALA305293

PubChem CID: 44309905

Max Phase: Preclinical

Molecular Formula: C23H30N4O7

Molecular Weight: 474.51

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)NCC(=O)N1c2ccccc2C[C@H]1C(=O)N[C@H](C=O)CC(=O)O

Standard InChI:  InChI=1S/C23H30N4O7/c1-4-13(2)21(25-14(3)29)23(34)24-11-19(30)27-17-8-6-5-7-15(17)9-18(27)22(33)26-16(12-28)10-20(31)32/h5-8,12-13,16,18,21H,4,9-11H2,1-3H3,(H,24,34)(H,25,29)(H,26,33)(H,31,32)/t13-,16-,18-,21-/m0/s1

Standard InChI Key:  PQDSZTPUEFNPLL-CZBBOPSRSA-N

Molfile:  

     RDKit          2D

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    1.7000   -3.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -3.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8250   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -1.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -4.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
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  8 12  1  0
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  9 11  1  6
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 22 15  2  0
 23 25  2  0
 24  9  1  0
 25 18  1  0
 26 14  1  0
 27  4  1  0
 28  7  1  0
 29 15  1  0
 30 24  1  0
 24 31  1  1
 32 27  2  0
 33 32  1  0
 34 30  1  0
  7  6  1  0
 28 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA305293

   (S)-3-({1-[(S)-2-((3S,4S)-2-Acetylamino-3-methyl-pentanoylamino)-acetyl]-2,3-dihydro-1H-indole-2-carbonyl}-amino)-4-oxo-butyric acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 474.51

Molecular Weight (Monoisotopic): 474.2114

AlogP: -0.23

#Rotatable Bonds: 11

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: 3.86

CX Basic pKa: ┄

CX LogP: -0.84

CX LogD: -4.08

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -0.28

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