(3S,6S,9S)-14-amino-3,6-bis(4-aminobutyl)-1-cyclopropyl-14-imino-1,4,7-trioxo-2,5,8,13-tetraazatetradecane-9-carboxylic acid

ID: ALA3344314

PubChem CID: 118717695

Max Phase: Preclinical

Molecular Formula: C22H42N8O5

Molecular Weight: 498.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)C1CC1)C(=O)O

Standard InChI:  InChI=1S/C22H42N8O5/c23-11-3-1-6-15(28-18(31)14-9-10-14)19(32)29-16(7-2-4-12-24)20(33)30-17(21(34)35)8-5-13-27-22(25)26/h14-17H,1-13,23-24H2,(H,28,31)(H,29,32)(H,30,33)(H,34,35)(H4,25,26,27)/t15-,16-,17-/m0/s1

Standard InChI Key:  FIDADBZEDASXON-ULQDDVLXSA-N

Molfile:  

     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
    5.6987   -8.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4064   -7.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -8.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -8.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4064   -6.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -6.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -5.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8218   -4.4203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8218   -7.6890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5295   -8.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2372   -6.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2372   -7.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5295   -8.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2372   -9.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2372  -10.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449  -10.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449  -11.3664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -5.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -4.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603   -4.0117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7757   -4.0117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449   -8.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6526   -7.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603   -8.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603   -8.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6526   -6.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603   -6.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3603   -5.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -7.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -8.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800   -7.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -6.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4383   -8.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584   -8.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 10  1  0
 13 23  1  0
 26 30  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10 11  1  0
 11 13  1  0
 13 12  2  0
 11 14  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 23 24  1  0
 24 26  1  0
 26 25  2  0
 24 27  1  1
 27 28  1  0
 28 29  1  0
 29 19  1  0
 31 32  1  0
 32  1  1  0
 32 33  2  0
 34 31  1  0
 35 34  1  0
 31 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3344314

   ---

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: 498.63

Molecular Weight (Monoisotopic): 498.3278

AlogP: -1.54

#Rotatable Bonds: 19

Polar Surface Area: 238.54

Molecular Species: ZWITTERION

HBA: 7

HBD: 9

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.74

CX Basic pKa: 11.90

CX LogP: -4.05

CX LogD: -9.08

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.06

Np Likeness Score: 0.11

References

1. Bhakat S, Karubiu W, Jayaprakash V, Soliman ME..  (2014)  A perspective on targeting non-structural proteins to combat neglected tropical diseases: Dengue, West Nile and Chikungunya viruses.,  87  [PMID:25305334] [10.1016/j.ejmech.2014.10.010]

Source

Source(1):

• Scientific Literature