(S)-3-(benzo[d][1,3]dioxol-5-ylmethylamino)-2-(2-(4-(chloromethyl)benzamido)acetamido)-3-oxopropyl dihydrogen phosphate

ID: ALA4237531

PubChem CID: 145983450

Max Phase: Preclinical

Molecular Formula: C21H23ClN3O9P

Molecular Weight: 527.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CNC(=O)c1ccc(CCl)cc1)N[C@@H](COP(=O)(O)O)C(=O)NCc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C21H23ClN3O9P/c22-8-13-1-4-15(5-2-13)20(27)24-10-19(26)25-16(11-34-35(29,30)31)21(28)23-9-14-3-6-17-18(7-14)33-12-32-17/h1-7,16H,8-12H2,(H,23,28)(H,24,27)(H,25,26)(H2,29,30,31)/t16-/m0/s1

Standard InChI Key:  LRDBMUOWCPZQDD-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   31.4123   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1200   -8.9602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7046   -8.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4123  -10.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9969   -9.3688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2892   -8.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5815   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2892   -8.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8745   -8.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1672   -9.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1668  -10.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8795  -10.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5838  -10.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8278   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5355   -8.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8278  -10.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2432   -9.3688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5355   -8.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5355  -10.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5355  -11.4118    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.2432  -11.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8278  -11.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2395  -10.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9509   -8.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6586   -9.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4596  -10.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7514  -10.1848    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.6565  -10.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3634  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3620   -8.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0694   -9.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0730  -10.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8540  -10.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3331   -9.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8481   -9.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  7  1  0
  2 14  1  0
 14 15  1  0
 14 16  1  6
 15 17  1  0
 15 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  1  0
 17 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 32  2  0
 31 30  2  0
 30 25  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4237531

   ---

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: 527.85

Molecular Weight (Monoisotopic): 527.0860

AlogP: 0.79

#Rotatable Bonds: 11

Polar Surface Area: 172.52

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.36

CX Basic pKa: ┄

CX LogP: 0.17

CX LogD: -3.24

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: -0.46

References

1. Stevers LM, Sijbesma E, Botta M, MacKintosh C, Obsil T, Landrieu I, Cau Y, Wilson AJ, Karawajczyk A, Eickhoff J, Davis J, Hann M, O'Mahony G, Doveston RG, Brunsveld L, Ottmann C..  (2018)  Modulators of 14-3-3 Protein-Protein Interactions.,  61  (9): [PMID:28968506] [10.1021/acs.jmedchem.7b00574]

Source

Source(1):

• Scientific Literature