(R)-2-(4-((1-(2-(3,4-dihydroxyphenyl)-2-oxoethyl)-1H-benzo[d]imidazole-6-carboxamido)methyl)-1H-1,2,3-triazol-1-yl)-N1-(3-phenoxyphenyl)pentanediamide

ID: ALA5190490

PubChem CID: 168280113

Max Phase: Preclinical

Molecular Formula: C36H32N8O7

Molecular Weight: 688.70

Names and Identifiers

Canonical SMILES:  NC(=O)CC[C@H](C(=O)Nc1cccc(Oc2ccccc2)c1)n1cc(CNC(=O)c2ccc3ncn(CC(=O)c4ccc(O)c(O)c4)c3c2)nn1

Standard InChI:  InChI=1S/C36H32N8O7/c37-34(48)14-12-29(36(50)40-24-5-4-8-27(17-24)51-26-6-2-1-3-7-26)44-19-25(41-42-44)18-38-35(49)23-9-11-28-30(15-23)43(21-39-28)20-33(47)22-10-13-31(45)32(46)16-22/h1-11,13,15-17,19,21,29,45-46H,12,14,18,20H2,(H2,37,48)(H,38,49)(H,40,50)/t29-/m1/s1

Standard InChI Key:  QUPGQQQDAHDFGU-GDLZYMKVSA-N

Molfile:  

 
     RDKit          2D

 51 56  0  0  0  0  0  0  0  0999 V2000
   10.8048   -1.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8036   -2.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5170   -2.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2319   -2.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2291   -1.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5153   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -1.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5127   -0.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9414   -2.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9427   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6561   -4.0404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6537   -2.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9643   -4.3112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4114   -3.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5519   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7494   -4.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2064   -5.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4605   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2669   -6.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8105   -5.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9115   -6.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1059   -6.6903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1720   -7.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9774   -7.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2338   -8.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7544   -9.2556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2425   -9.9199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0239   -9.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0202   -8.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6925  -10.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6106  -10.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4427   -9.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1072  -10.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5246   -8.9867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2750   -8.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9426   -9.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6884   -8.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7749   -7.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1014   -7.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3542   -7.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1804   -6.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9295   -6.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5985   -6.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3430   -6.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4266   -5.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7514   -5.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0056   -5.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8603  -11.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7785  -12.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0281  -12.4553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4428  -12.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 11 16  1  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 25  2  0
 30 28  1  1
 30 31  1  0
 30 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
 39 41  1  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 42  1  0
 31 48  1  0
 48 49  1  0
 49 50  1  0
 49 51  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5190490

   ---

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: 688.70

Molecular Weight (Monoisotopic): 688.2394

AlogP: 4.09

#Rotatable Bonds: 14

Polar Surface Area: 216.58

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.84

CX Basic pKa: 5.23

CX LogP: 2.86

CX LogD: 2.72

Aromatic Rings: 6

Heavy Atoms: 51

QED Weighted: 0.08

Np Likeness Score: -1.22

References

1. Bassi G, Favalli N, Pellegrino C, Onda Y, Scheuermann J, Cazzamalli S, Manz MG, Neri D..  (2021)  Specific Inhibitor of Placental Alkaline Phosphatase Isolated from a DNA-Encoded Chemical Library Targets Tumor of the Female Reproductive Tract.,  64  (21.0): [PMID:34709820] [10.1021/acs.jmedchem.1c01103]

Source

Source(1):

• Scientific Literature