2-Hydroxy-N-{4-[hydroxy-(3-phenyl-acryloyl)-amino]-butyl}-2-({4-[hydroxy-(3-phenyl-acryloyl)-amino]-butylcarbamoyl}-methyl)-succinamic acid

ID: ALA63221

PubChem CID: 11135904

Max Phase: Preclinical

Molecular Formula: C32H40N4O9

Molecular Weight: 624.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC(O)(CC(=O)NCCCCN(O)C(=O)/C=C/c1ccccc1)C(=O)O)NCCCCN(O)C(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C32H40N4O9/c37-27(33-19-7-9-21-35(44)29(39)17-15-25-11-3-1-4-12-25)23-32(43,31(41)42)24-28(38)34-20-8-10-22-36(45)30(40)18-16-26-13-5-2-6-14-26/h1-6,11-18,43-45H,7-10,19-24H2,(H,33,37)(H,34,38)(H,41,42)/b17-15+,18-16+

Standard InChI Key:  XHYPIYRXLIHWDF-YTEMWHBBSA-N

Molfile:  

     RDKit          2D

 45 46  0  0  0  0  0  0  0  0999 V2000
    5.8125   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2375   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9542   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6667   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5250   -2.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -3.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2375   -1.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -1.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -2.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -3.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -0.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3792   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5292   -3.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -4.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8125   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0875   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3792   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0917   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8042   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8125   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4 13  1  0
  5 14  1  0
  6  1  1  0
  7  5  1  0
  8  4  1  0
  9  3  1  0
 10  2  1  0
 11  8  2  0
 12  7  2  0
 13 29  1  0
 14 28  1  0
 15  4  2  0
 16  5  2  0
 17  6  2  0
 18  9  2  0
 19 10  2  0
 20 10  1  0
 21  9  1  0
 22  1  1  0
 23  6  1  0
 24 12  1  0
 25 11  1  0
 26 13  1  0
 27 14  1  0
 28 37  1  0
 29 36  1  0
 30 20  1  0
 31 21  1  0
 32 24  1  0
 33 25  1  0
 34 24  2  0
 35 25  2  0
 36 38  1  0
 37 39  1  0
 38 31  1  0
 39 30  1  0
 40 34  1  0
 41 32  2  0
 42 35  1  0
 43 33  2  0
 44 40  2  0
 45 42  2  0
 43 45  1  0
 44 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA63221

   2-hydroxy-4-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-[2-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-oxoethyl]-4-oxobutanoic acid

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: 624.69

Molecular Weight (Monoisotopic): 624.2795

AlogP: 2.24

#Rotatable Bonds: 19

Polar Surface Area: 196.81

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.86

CX Basic pKa: ┄

CX LogP: 1.42

CX LogD: -1.85

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.06

Np Likeness Score: 0.08

References

1. Guo H, Naser SA, Ghobrial G, Phanstiel O..  (2002)  Synthesis and biological evaluation of new citrate-based siderophores as potential probes for the mechanism of iron uptake in mycobacteria.,  45  (10): [PMID:11985473] [10.1021/jm0104522]

Source

Source(1):

• Scientific Literature