(S)-3-(benzo[d][1,3]dioxol-5-ylmethylamino)-2-(3-methylbut-2-enamido)-3-oxopropyl dihydrogen phosphate

ID: ALA4240436

PubChem CID: 145984973

Max Phase: Preclinical

Molecular Formula: C16H21N2O8P

Molecular Weight: 400.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CC(=O)N[C@@H](COP(=O)(O)O)C(=O)NCc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C16H21N2O8P/c1-10(2)5-15(19)18-12(8-26-27(21,22)23)16(20)17-7-11-3-4-13-14(6-11)25-9-24-13/h3-6,12H,7-9H2,1-2H3,(H,17,20)(H,18,19)(H2,21,22,23)/t12-/m0/s1

Standard InChI Key:  QXQMKZXCRGZPFP-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    5.3076   -3.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0153   -3.1738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076   -4.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8922   -3.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7230   -3.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7230   -4.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384   -3.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307   -2.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307   -4.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307   -5.6254    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384   -6.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7230   -6.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1348   -5.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8462   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5539   -3.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8922   -4.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5518   -4.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2587   -4.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2573   -3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9647   -3.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9683   -4.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7493   -4.6491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2284   -3.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7434   -3.3224    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  2  0
  2  6  1  0
  6  7  1  0
  6  8  1  6
  7  9  1  0
  7 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 12 15  1  0
  9 16  1  0
 16 17  1  0
  5 18  1  0
  5 19  1  0
 17 20  2  0
 20 21  1  0
 21 24  2  0
 23 22  2  0
 22 17  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4240436

   ---

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: 400.32

Molecular Weight (Monoisotopic): 400.1036

AlogP: 0.59

#Rotatable Bonds: 8

Polar Surface Area: 143.42

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.37

CX Basic pKa: ┄

CX LogP: 0.22

CX LogD: -3.19

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: 0.17

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