(2S,4R)-1-((S)-2-(4-bromobenzamido)-3-methylbutanoyl)-N-((S)-1-fluoro-6-guanidino-2-oxohexan-3-yl)-4-hydroxypyrrolidine-2-carboxamide

ID: ALA4586042

PubChem CID: 126680466

Max Phase: Preclinical

Molecular Formula: C24H34BrFN6O5

Molecular Weight: 585.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)c1ccc(Br)cc1)C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)CF

Standard InChI:  InChI=1S/C24H34BrFN6O5/c1-13(2)20(31-21(35)14-5-7-15(25)8-6-14)23(37)32-12-16(33)10-18(32)22(36)30-17(19(34)11-26)4-3-9-29-24(27)28/h5-8,13,16-18,20,33H,3-4,9-12H2,1-2H3,(H,30,36)(H,31,35)(H4,27,28,29)/t16-,17+,18+,20+/m1/s1

Standard InChI Key:  ZHDIHIZTRHGAAP-LXZJYRNTSA-N

Molfile:  

 
     RDKit          2D

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   21.5186  -27.4110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8086  -27.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8041  -28.6328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2134  -28.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5025  -29.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9179  -29.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1032  -27.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1110  -26.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4063  -26.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6935  -27.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3987  -27.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9894  -26.1666    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.9295  -26.5985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   27.0926  -29.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0850  -29.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3721  -30.2212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0033  -26.1332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7046  -26.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1184  -26.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8294  -26.1575    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.7880  -30.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9283  -27.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6354  -27.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0450  -24.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  2  0
  1  5  1  6
  5  6  1  0
  5  7  1  0
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  8  9  2  0
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 16 21  1  1
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 26 28  1  6
 28 29  1  0
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 30 22  1  0
 27 32  1  0
 32 33  1  0
 23 34  1  0
 15 35  1  0
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 35 36  2  0
 18 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4586042

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 585.48

Molecular Weight (Monoisotopic): 584.1758

AlogP: 0.45

#Rotatable Bonds: 12

Polar Surface Area: 177.71

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.51

CX Basic pKa: 11.88

CX LogP: -0.04

CX LogD: -2.12

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.12

Np Likeness Score: -0.12

References

1. Hatcher JM, Du G, Fontán L, Us I, Qiao Q, Chennamadhavuni S, Shao J, Wu H, Melnick A, Gray NS, Scott DA..  (2019)  Peptide-based covalent inhibitors of MALT1 paracaspase.,  29  (11): [PMID:30954428] [10.1016/j.bmcl.2019.03.046]

Source

Source(1):

• Scientific Literature