(S)-2-(2-(4-azidobenzamido)acetamido)-3-(4-hydroxyphenethylamino)-3-oxopropyl dihydrogen phosphate

ID: ALA4250552

PubChem CID: 49793813

Max Phase: Preclinical

Molecular Formula: C20H23N6O8P

Molecular Weight: 506.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=Nc1ccc(C(=O)NCC(=O)N[C@@H](COP(=O)(O)O)C(=O)NCCc2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C20H23N6O8P/c21-26-25-15-5-3-14(4-6-15)19(29)23-11-18(28)24-17(12-34-35(31,32)33)20(30)22-10-9-13-1-7-16(27)8-2-13/h1-8,17,27H,9-12H2,(H,22,30)(H,23,29)(H,24,28)(H2,31,32,33)/t17-/m0/s1

Standard InChI Key:  KPRPEUSNRKOIDZ-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    7.6436   -9.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3513   -9.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9359   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6436  -10.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282   -9.6371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5205   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8128   -9.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5205   -8.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1058   -9.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3985   -9.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3981  -10.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108  -10.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151  -10.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0590   -9.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7668   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0590  -10.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4745   -9.6371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7668   -8.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7668  -10.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7668  -11.6801    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.4745  -12.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0590  -12.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4708  -11.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1822   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8899   -9.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5976   -9.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3042   -9.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0114   -9.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0119   -8.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2992   -8.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5949   -8.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7190   -8.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6909  -10.8607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827  -10.4530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712  -10.0415    0.0000 N   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
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
 11 33  1  0
 33 34  2  0
 34 35  2  0
M  CHG  2  34   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4250552

   [(2S)-2-[[2-[(4-azidobenzoyl)amino]acetyl]amino]-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxopropyl] dihydrogen phosphate

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: 506.41

Molecular Weight (Monoisotopic): 506.1315

AlogP: 1.02

#Rotatable Bonds: 12

Polar Surface Area: 223.05

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -10.67

CX Basic pKa: ┄

CX LogP: 0.37

CX LogD: -3.16

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.11

Np Likeness Score: -0.27

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