2-Acetoxymethyl-4-[2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-6H-pyrimidin-1-yl)-acetylamino]-pent-2-enoic acid methyl ester

ID: ALA117221

PubChem CID: 10257276

Max Phase: Preclinical

Molecular Formula: C29H30N4O8

Molecular Weight: 562.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C(=C/[C@H](C)NC(=O)Cn1c(-c2ccccc2)ncc(NC(=O)OCc2ccccc2)c1=O)COC(C)=O

Standard InChI:  InChI=1S/C29H30N4O8/c1-19(14-23(28(37)39-3)18-40-20(2)34)31-25(35)16-33-26(22-12-8-5-9-13-22)30-15-24(27(33)36)32-29(38)41-17-21-10-6-4-7-11-21/h4-15,19H,16-18H2,1-3H3,(H,31,35)(H,32,38)/b23-14+/t19-/m0/s1

Standard InChI Key:  DGGOUXDLXNNULW-WQZUMXOESA-N

Molfile:  

     RDKit          2D

 41 43  0  0  1  0  0  0  0  0999 V2000
    4.3875   -2.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -1.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -2.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3875   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -2.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -3.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3917   -3.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167   -2.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000   -2.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8167   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6 11  2  0
  7  5  1  0
  8  3  1  0
  9  8  1  0
 10  6  1  0
 11 24  1  0
 12  1  1  0
 13 12  1  0
 14 13  1  0
 15  2  2  0
 16  6  1  0
 17  4  1  0
 18 23  1  0
 19  9  2  0
 20 10  2  0
 21 13  2  0
 22  9  1  0
 23 16  1  0
 24 14  1  0
 25 18  2  0
 26 10  1  0
 27 22  1  0
 28 27  1  0
 29 18  1  0
 30 17  2  0
 31 17  1  0
 24 32  1  1
 33 26  1  0
 34 28  2  0
 35 28  1  0
 36 31  2  0
 37 30  1  0
 38 35  2  0
 39 34  1  0
 40 38  1  0
 41 36  1  0
  3  7  2  0
 37 41  2  0
 39 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117221

   methyl (E,4S)-2-(acetyloxymethyl)-4-[[2-[6-oxo-2-phenyl-5-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]pent-2-enoate

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: 562.58

Molecular Weight (Monoisotopic): 562.2064

AlogP: 2.83

#Rotatable Bonds: 11

Polar Surface Area: 154.92

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.19

CX Basic pKa: 0.41

CX LogP: 2.25

CX LogD: 2.25

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: -0.37

References

1. Zhu S, Hudson TH, Kyle DE, Lin AJ..  (2002)  Synthesis and in vitro studies of novel pyrimidinyl peptidomimetics as potential antimalarial therapeutic agents.,  45  (16): [PMID:12139460] [10.1021/jm020104f]

Source

Source(1):

• Scientific Literature