4-(2-{2-[3-Carboxy-1-(carboxymethyl-carbamoyl)-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-4-[(9,10-dioxo-9,10-dihydro-phenanthrene-2-carbonyl)-amino]-butyric acid

ID: ALA2372894

PubChem CID: 10556825

Max Phase: Preclinical

Molecular Formula: C34H35N5O13

Molecular Weight: 721.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NC(=O)c1ccc2c(c1)C(=O)C(=O)c1ccccc1-2)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)O

Standard InChI:  InChI=1S/C34H35N5O13/c40-25(39-13-3-6-24(39)34(52)38-23(10-12-27(43)44)33(51)36-16-28(45)46)15-35-32(50)22(9-11-26(41)42)37-31(49)17-7-8-19-18-4-1-2-5-20(18)29(47)30(48)21(19)14-17/h1-2,4-5,7-8,14,22-24H,3,6,9-13,15-16H2,(H,35,50)(H,36,51)(H,37,49)(H,38,52)(H,41,42)(H,43,44)(H,45,46)/t22-,23-,24-/m0/s1

Standard InChI Key:  SHTBBHOELGMGDS-HJOGWXRNSA-N

Molfile:  

     RDKit          2D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -6.4013   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1134   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8339   -3.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -3.5026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -4.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8506   -4.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1509   -4.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813   -3.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -3.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6932   -3.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -3.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907   -1.8658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -3.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9935   -3.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -3.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6150   -1.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7307   -4.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -3.1153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9404   -2.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445   -3.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522   -2.1157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7765   -2.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8274   -4.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0948   -1.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760   -2.1657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5378   -2.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -3.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7663   -1.8159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -2.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0185   -4.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490   -4.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5901   -0.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070   -0.6164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265   -2.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -4.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320   -2.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -3.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -1.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -1.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525   -3.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -4.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4637   -1.5785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5729   -4.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744   -0.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5878   -4.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1759   -5.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -3.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617   -4.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9006   -5.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6003   -5.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 12  1  0
  5  1  2  0
 10  6  1  6
  7  8  2  0
  8  5  1  0
  9 15  1  0
 10  4  1  0
 11  1  1  0
 12 28  1  0
 13  6  1  0
 14  9  1  0
 15 11  2  0
 16 21  1  0
 17 20  1  0
 18  5  1  0
 19 16  1  0
 20 13  1  0
 21 14  1  0
 22 17  1  0
 23 40  1  0
 24 42  1  0
 25 41  1  0
 26  2  2  0
 27  3  2  0
 28 19  1  0
 29  6  2  0
 30  9  2  0
 31 15  1  0
 32 12  2  0
 33 16  2  0
 34 17  2  0
 35 25  2  0
 36 23  2  0
 37 24  2  0
 21 38  1  1
 20 39  1  6
 40 22  1  0
 41 38  1  0
 42 39  1  0
 43  4  1  0
 44 23  1  0
 45 24  1  0
 46 25  1  0
 47  7  1  0
 48  8  1  0
 49 10  1  0
 50 43  1  0
 51 48  2  0
 52 51  1  0
 31 18  2  0
  3  7  1  0
 47 52  2  0
 50 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2372894

   (4S)-4-[[(2S)-1-[2-[[(2S)-4-carboxy-2-[(9,10-dioxophenanthrene-2-carbonyl)amino]butanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-5-(carboxymethylamino)-5-oxopentanoic 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: 721.68

Molecular Weight (Monoisotopic): 721.2231

AlogP: -0.65

#Rotatable Bonds: 16

Polar Surface Area: 282.75

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: -1.68

CX LogD: -11.48

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.11

Np Likeness Score: -0.32

References

1. Urbanek RA, Suchard SJ, Steelman GB, Knappenberger KS, Sygowski LA, Veale CA, Chapdelaine MJ..  (2001)  Potent reversible inhibitors of the protein tyrosine phosphatase CD45.,  44  (11): [PMID:11356112] [10.1021/jm000447i]

Source

Source(1):

• Scientific Literature