(6S,9S,12S,15S)-1-amino-1-imino-12,15-diisobutyl-9-methyl-8,11,14,17-tetraoxo-2,7,10,13,16-pentaazaoctadecane-6-carboxylic acid

ID: ALA1093412

PubChem CID: 46883591

Max Phase: Preclinical

Molecular Formula: C23H43N7O6

Molecular Weight: 513.64

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C23H43N7O6/c1-12(2)10-17(28-15(6)31)21(34)30-18(11-13(3)4)20(33)27-14(5)19(32)29-16(22(35)36)8-7-9-26-23(24)25/h12-14,16-18H,7-11H2,1-6H3,(H,27,33)(H,28,31)(H,29,32)(H,30,34)(H,35,36)(H4,24,25,26)/t14-,16-,17-,18-/m0/s1

Standard InChI Key:  WQQNPOJZKMSEDI-DKIMLUQUSA-N

Molfile:  

     RDKit          2D

 36 35  0  0  0  0  0  0  0  0999 V2000
    1.2660  -22.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853  -22.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6857  -23.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951  -22.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946  -21.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139  -20.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234  -19.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238  -21.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4144  -22.0232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1243  -22.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8530  -21.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8435  -22.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1148  -23.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247  -23.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153  -24.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440  -23.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533  -22.4610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2726  -22.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9731  -23.3029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2821  -21.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9825  -22.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8125  -24.9866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8032  -25.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0839  -26.2155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5130  -26.2324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7018  -22.0739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117  -22.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1404  -21.2660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1310  -22.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023  -23.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1121  -23.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1027  -24.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8408  -22.5119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562  -21.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640  -21.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653  -22.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21 26  1  0
 29 33  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
  6  8  1  0
  9 10  1  0
 10 12  1  0
 12 11  2  0
 10 13  1  6
 13 14  1  0
 14 15  1  0
 14 16  1  0
 17 18  1  0
 18 21  1  0
 21 19  2  0
 18 20  1  1
 22 23  1  0
 23 24  1  0
 23 25  2  0
 26 27  1  0
 27 29  1  0
 29 28  2  0
 27 30  1  6
 30 31  1  0
 31 32  1  0
 32 22  1  0
  1 34  1  0
  4  9  1  0
 12 17  1  0
 34 35  2  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093412

   Ac-Leu-Leu-Ala-Arg-OH

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: 513.64

Molecular Weight (Monoisotopic): 513.3275

AlogP: -0.59

#Rotatable Bonds: 16

Polar Surface Area: 215.60

Molecular Species: ZWITTERION

HBA: 6

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.94

CX Basic pKa: 11.84

CX LogP: -2.42

CX LogD: -2.42

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.08

Np Likeness Score: 0.19

References

1. Ruiz-Gómez G, Lim J, Halili MA, Le GT, Madala PK, Abbenante G, Fairlie DP..  (2009)  Structure-activity relationships for substrate-based inhibitors of human complement factor B.,  52  (19): [PMID:19743866] [10.1021/jm900781m]

Source

Source(1):

• Scientific Literature