4,4',4''-(Benzene-1,3,5-triyltris(oxy))tribenzimidamide

ID: ALA5269464

Max Phase: Preclinical

Molecular Formula: C27H24N6O3

Molecular Weight: 480.53

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(Oc2cc(Oc3ccc(C(=N)N)cc3)cc(Oc3ccc(C(=N)N)cc3)c2)cc1

Standard InChI:  InChI=1S/C27H24N6O3/c28-25(29)16-1-7-19(8-2-16)34-22-13-23(35-20-9-3-17(4-10-20)26(30)31)15-24(14-22)36-21-11-5-18(6-12-21)27(32)33/h1-15H,(H3,28,29)(H3,30,31)(H3,32,33)

Standard InChI Key:  FJZLYGDCIBSPGQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -0.7126    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137    1.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126    1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -0.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331   -0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -1.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745   -1.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598   -2.4757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    2.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    1.2367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4273    2.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    1.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5699    1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    2.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845    0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845    0.0003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846   -0.0010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9992    1.2381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
  3 17  1  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 21 24  1  0
 24 25  1  0
  1 26  1  0
 26 27  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
 31 30  1  0
 32 31  2  0
 27 32  1  0
 30 33  1  0
 33 34  1  0
 24 35  2  0
 33 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269464

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 480.53

Molecular Weight (Monoisotopic): 480.1910

AlogP: 4.92

#Rotatable Bonds: 9

Polar Surface Area: 177.30

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.15

CX LogP: 3.24

CX LogD: -3.99

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: -0.06

References

1. Hammerschmidt SJ, Maus H, Weldert AC, Gütschow M, Kersten C..  (2023)  Improving binding entropy by higher ligand symmetry? - A case study with human matriptase.,  14  (5): [PMID:37252099] [10.1039/d3md00125c]

Source

Source(1):

• Scientific Literature