(4S,7S,10S,13S)-4-sec-butyl-15,15-difluoro-7-((R)-1-hydroxyethyl)-10,13-dimethyl-2,5,8,11,14,16-hexaoxo-3,6,9,12,17-pentaazanonadecan-19-oic acid

ID: ALA3310822

PubChem CID: 118706813

Max Phase: Preclinical

Molecular Formula: C22H35F2N5O9

Molecular Weight: 551.54

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)N[C@@H](C)C(=O)N[C@@H](C)C(=O)C(F)(F)C(=O)NCC(=O)O)[C@@H](C)O

Standard InChI:  InChI=1S/C22H35F2N5O9/c1-7-9(2)15(28-13(6)31)19(36)29-16(12(5)30)20(37)27-11(4)18(35)26-10(3)17(34)22(23,24)21(38)25-8-14(32)33/h9-12,15-16,30H,7-8H2,1-6H3,(H,25,38)(H,26,35)(H,27,37)(H,28,31)(H,29,36)(H,32,33)/t9-,10-,11-,12+,15-,16-/m0/s1

Standard InChI Key:  AQGOQBYAZBTQQB-CVYVPXSGSA-N

Molfile:  

     RDKit          2D

 38 37  0  0  0  0  0  0  0  0999 V2000
    1.4559  -15.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671  -16.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741  -15.1882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902  -14.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790  -16.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902  -16.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741  -16.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741  -17.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9951  -15.5948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7022  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134  -16.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7022  -14.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134  -13.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204  -15.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5364  -14.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253  -16.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5364  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2435  -15.5948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9485  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6597  -16.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9485  -14.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6597  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3666  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0715  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0715  -16.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7827  -15.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4898  -15.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1948  -15.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1948  -14.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9058  -15.5948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976  -13.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9541  -14.4738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7713  -14.4738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  7 12  1  0
 15 18  1  0
 22 23  1  0
 27 28  1  0
 31 32  1  0
  1  3  1  0
  3  2  2  0
  4  5  1  0
  5  7  1  6
  7  6  2  0
  5  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 12 13  1  0
 13 15  1  1
 15 14  2  0
 13 16  1  0
 16 17  1  0
 18 19  1  0
 19 22  1  0
 22 20  2  0
 19 21  1  6
 23 24  1  0
 24 27  1  0
 27 25  2  0
 24 26  1  1
 28 29  1  0
 29 31  1  0
 29 30  2  0
 32 33  1  0
 33 35  1  0
 33 34  2  0
 16 36  1  6
 28 37  1  0
 28 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3310822

   ---

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: 551.54

Molecular Weight (Monoisotopic): 551.2403

AlogP: -2.18

#Rotatable Bonds: 15

Polar Surface Area: 220.10

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.56

CX Basic pKa: ┄

CX LogP: -1.78

CX LogD: -5.14

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.11

Np Likeness Score: -0.01

References

1. Giovani S, Penzo M, Brogi S, Brindisi M, Gemma S, Novellino E, Savini L, Blackman MJ, Campiani G, Butini S..  (2014)  Rational design of the first difluorostatone-based PfSUB1 inhibitors.,  24  (15): [PMID:24909083] [10.1016/j.bmcl.2014.05.044]

2. Lidumniece E, Withers-Martinez C, Hackett F, Blackman MJ, Jirgensons A..  (2022)  Subtilisin-like Serine Protease 1 (SUB1) as an Emerging Antimalarial Drug Target: Current Achievements in Inhibitor Discovery.,  65  (19.0): [PMID:36137276] [10.1021/acs.jmedchem.2c01093]

Source

Source(1):

• Scientific Literature