3-(3-{2-[(2S,3R)-2-((2S,3S)-2-Acetylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-acetylamino}-4-hydroxy-2-oxo-butyrylamino)-propionic acid

ID: ALA3326344

PubChem CID: 118711579

Max Phase: Preclinical

Molecular Formula: C21H37N5O9

Molecular Weight: 503.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H37N5O9/c1-5-11(2)16(24-13(4)30)20(34)26-17(12(3)29)19(33)23-9-15(31)25-14(10-28)18(32)21(35)22-7-6-8-27/h11-12,14,16-17,27-29H,5-10H2,1-4H3,(H,22,35)(H,23,33)(H,24,30)(H,25,31)(H,26,34)/t11-,12+,14?,16-,17-/m0/s1

Standard InChI Key:  BJGAULNLGODBJV-XETWEVHHSA-N

Molfile:  

     RDKit          2D

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    2.8056  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5220  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636  -12.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6659  -12.5621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794  -10.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3786  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5220  -13.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0940  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6664  -12.1484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519  -11.3222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0909  -12.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776  -12.5621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519  -12.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9543  -13.3849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2402  -12.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636  -11.3222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0940  -13.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238  -12.1473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2402  -11.3222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519  -13.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794  -10.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079  -12.1473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9543  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038  -10.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379  -13.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056  -13.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916  -11.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238  -13.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0
  2 20  1  0
 35 24  1  6
 17  7  1  0
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  2  7  1  0
  3 22  2  0
  9 28  1  0
  6 12  1  0
 33 30  1  6
  1 32  2  0
 20 29  1  0
 35 31  1  0
 19 33  1  0
  4 16  1  0
 12 18  1  0
  9 23  2  0
  3 13  1  0
 33  5  1  0
 35 14  1  0
 18  8  1  0
 31 26  1  6
 21  3  1  0
 16  9  1  0
 10  6  1  0
 14 11  2  0
  1 24  1  0
 14  4  1  0
 31 34  1  0
 28  2  1  0
 19 13  1  1
 29 15  2  0
 20 25  2  0
  5 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326344

   ---

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: 503.55

Molecular Weight (Monoisotopic): 503.2591

AlogP: -3.94

#Rotatable Bonds: 16

Polar Surface Area: 223.26

Molecular Species: NEUTRAL

HBA: 9

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.46

CX Basic pKa: ┄

CX LogP: -4.21

CX LogD: -4.21

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.08

Np Likeness Score: -0.02

References

1. Kher SS, Penzo M, Fulle S, Finn PW, Blackman MJ, Jirgensons A..  (2014)  Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1.,  24  (18): [PMID:25129616] [10.1016/j.bmcl.2014.07.086]

Source

Source(1):

• Scientific Literature