5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl-2-((S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanamido)acetate hydrochloride

ID: ALA4163796

PubChem CID: 145957783

Max Phase: Preclinical

Molecular Formula: C23H31ClFN5O7

Molecular Weight: 507.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(=O)NCC(=O)OCn1cc(F)c(=O)[nH]c1=O.Cl

Standard InChI:  InChI=1S/C23H30FN5O7.ClH/c1-13(2)8-17(27-22(34)19(31)16(25)9-14-6-4-3-5-7-14)21(33)26-10-18(30)36-12-29-11-15(24)20(32)28-23(29)35;/h3-7,11,13,16-17,19,31H,8-10,12,25H2,1-2H3,(H,26,33)(H,27,34)(H,28,32,35);1H/t16-,17+,19+;/m1./s1

Standard InChI Key:  QVBSNIDCWLTTJC-UVXJWDRCSA-N

Molfile:  

     RDKit          2D

 37 37  0  0  0  0  0  0  0  0999 V2000
   10.6228   -0.9590    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -3.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3413   -3.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550   -2.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395   -2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -3.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4867   -3.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -3.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4854   -2.4705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9156   -3.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308   -3.7045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143   -2.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3445   -3.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0597   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433   -2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0571   -2.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0558   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7722   -2.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0610   -4.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -3.2887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4886   -3.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2024   -3.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9175   -3.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2011   -2.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6314   -3.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3464   -3.6955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3449   -4.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0559   -4.9285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7722   -4.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7729   -3.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0573   -3.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6299   -4.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4857   -4.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4881   -3.2812    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
 10 12  1  1
 10 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 17 22  2  0
 17 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 30 35  2  0
 32 36  2  0
 33 37  1  0
M  END

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: 507.52

Molecular Weight (Monoisotopic): 507.2129

AlogP: -1.25

#Rotatable Bonds: 12

Polar Surface Area: 185.61

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.90

CX Basic pKa: 8.54

CX LogP: -1.04

CX LogD: -1.35

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: -0.33

References

1. Jiang Y, Li X, Hou J, Huang Y, Wang X, Jia Y, Wang Q, Xu W, Zhang J, Zhang Y..  (2018)  Synthesis and biological characterization of ubenimex-fluorouracil conjugates for anti-cancer therapy.,  143  [PMID:29202398] [10.1016/j.ejmech.2017.11.074]

Source

Source(1):

• Scientific Literature