(2S,4R)-4-{[(S)-2-Carboxy-2-(2,2-dimethyl-butyrylamino)-ethylcarbamoyl]-methoxy}-2-(pyridin-2-ylaminomethyl)-pyrrolidine-1-carboxylic acid benzyl ester

ID: ALA4524794

PubChem CID: 58916207

Max Phase: Preclinical

Molecular Formula: C29H39N5O7

Molecular Weight: 569.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(C)(C)C(=O)N[C@@H](CNC(=O)CO[C@@H]1C[C@@H](CNc2ccccn2)N(C(=O)OCc2ccccc2)C1)C(=O)O

Standard InChI:  InChI=1S/C29H39N5O7/c1-4-29(2,3)27(38)33-23(26(36)37)16-32-25(35)19-40-22-14-21(15-31-24-12-8-9-13-30-24)34(17-22)28(39)41-18-20-10-6-5-7-11-20/h5-13,21-23H,4,14-19H2,1-3H3,(H,30,31)(H,32,35)(H,33,38)(H,36,37)/t21-,22+,23-/m0/s1

Standard InChI Key:  FDEATVNEVKUYSK-ZRBLBEILSA-N

Molfile:  

 
     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
   11.4955   -5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -7.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0224   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7334   -7.2406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2578   -7.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9639   -8.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1453   -8.7916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6229   -8.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8045   -8.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2781   -7.6453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4853   -7.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2150   -8.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3940   -8.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1590   -7.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8405   -7.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060   -6.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4256   -6.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8304   -9.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0383   -9.0793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4746   -9.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -9.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090  -10.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605  -10.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500  -11.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7174  -10.4600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9151   -7.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0763   -7.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6007   -8.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3671   -6.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7510   -8.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2671   -5.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -4.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9516   -4.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -4.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895   -5.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8362   -6.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7859   -5.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816   -5.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9080   -5.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1215   -4.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  5  4  1  6
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  6
 12 11  1  0
 13 12  1  0
 14 13  1  0
 14 15  1  0
 11 15  1  0
 14  2  1  0
  2 16  1  0
 16 17  1  0
 13 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
  8 26  2  0
  5 27  1  0
 27 28  2  0
 27 29  1  0
  3  1  1  0
  2 30  2  0
 17 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
  3 37  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 40 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524794

   (2S)-2-(2,2-dimethylbutanoylamino)-3-[[2-[(3R,5S)-1-phenylmethoxycarbonyl-5-[(pyridin-2-ylamino)methyl]pyrrolidin-3-yl]oxyacetyl]amino]propanoic acid

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: 569.66

Molecular Weight (Monoisotopic): 569.2849

AlogP: 2.41

#Rotatable Bonds: 14

Polar Surface Area: 159.19

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.87

CX Basic pKa: 6.63

CX LogP: 0.55

CX LogD: -0.26

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.27

Np Likeness Score: -0.63

References

1.  (2013)  Compounds for the inhibition of angiogenesis and use thereof, 

Source

Source(1):

• Patent Bioactivity Data