(9S,14S)-1-(4-Iodophenyl)-1,7,12-trioxo-2,8,11,13-tetraazahexadecane-9,14,16-tricarboxylic Acid

ID: ALA4466904

PubChem CID: 150793150

Max Phase: Preclinical

Molecular Formula: C21H27IN4O9

Molecular Weight: 606.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NC(=O)NC[C@H](NC(=O)CCCCNC(=O)c1ccc(I)cc1)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C21H27IN4O9/c22-13-6-4-12(5-7-13)18(30)23-10-2-1-3-16(27)25-15(20(33)34)11-24-21(35)26-14(19(31)32)8-9-17(28)29/h4-7,14-15H,1-3,8-11H2,(H,23,30)(H,25,27)(H,28,29)(H,31,32)(H,33,34)(H2,24,26,35)/t14-,15-/m0/s1

Standard InChI Key:  KEGUTRPRRRFREJ-GJZGRUSLSA-N

Molfile:  

 
     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   16.8993  -16.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4378  -13.0420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1455  -12.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8532  -13.0420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5609  -12.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2686  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9764  -12.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2686  -13.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1455  -11.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5609  -11.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2686  -11.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2686  -10.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9764  -10.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5609  -10.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7301  -12.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0224  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3147  -12.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3147  -11.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6070  -13.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0224  -13.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3147  -14.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3147  -15.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6070  -13.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6070  -15.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6070  -16.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1916  -16.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4839  -16.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7761  -16.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4839  -17.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7725  -17.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7722  -18.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4804  -19.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1905  -18.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1873  -17.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4815  -19.9841    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  3  9  2  0
  5 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  6
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25  1  1  0
  1 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4466904

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 606.37

Molecular Weight (Monoisotopic): 606.0823

AlogP: 0.38

#Rotatable Bonds: 15

Polar Surface Area: 211.23

Molecular Species: ACID

HBA: 6

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.10

CX Basic pKa: ┄

CX LogP: 0.14

CX LogD: -9.64

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.11

Np Likeness Score: -0.64

References

1. Kim K, Kwon H, Barinka C, Motlova L, Nam S, Choi D, Ha H, Nam H, Son SH, Minn I, Pomper MG, Yang X, Kutil Z, Byun Y..  (2020)  Novel β- and γ-Amino Acid-Derived Inhibitors of Prostate-Specific Membrane Antigen.,  63  (6): [PMID:32097010] [10.1021/acs.jmedchem.9b02022]

Source

Source(1):

• Scientific Literature