(2S,3R)-2-[3-((R)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid tert-butyl ester

ID: ALA325014

PubChem CID: 44341537

Max Phase: Preclinical

Molecular Formula: C40H55N5O12

Molecular Weight: 797.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2c(=O)ccn([C@@H]3OC([C@H](O)[C@H](NCCCNC(=O)[C@@H](CC(C)C)NC(=O)OCc4ccccc4)C(=O)OC(C)(C)C)[C@@H](O)[C@H]3O)c2=O)cc1

Standard InChI:  InChI=1S/C40H55N5O12/c1-24(2)21-28(43-38(52)55-23-26-11-8-7-9-12-26)35(50)42-19-10-18-41-30(37(51)57-40(3,4)5)31(47)34-32(48)33(49)36(56-34)44-20-17-29(46)45(39(44)53)22-25-13-15-27(54-6)16-14-25/h7-9,11-17,20,24,28,30-34,36,41,47-49H,10,18-19,21-23H2,1-6H3,(H,42,50)(H,43,52)/t28-,30+,31-,32+,33-,34?,36-/m1/s1

Standard InChI Key:  OYCITDHDVOEPGB-RIFMTGOTSA-N

Molfile:  

     RDKit          2D

 57 60  0  0  1  0  0  0  0  0999 V2000
    9.6042   -5.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9167   -6.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -6.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -4.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2417   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7542   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -6.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -6.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4042   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7625   -7.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0667   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -6.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -4.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -5.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -5.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -7.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -6.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -5.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0792   -7.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4167   -9.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2542   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5667   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2417   -9.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9292   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5125   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -9.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -7.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5792  -10.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -7.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -8.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -2.3125    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  1
  5  7  1  0
  6  4  1  0
  7  4  1  0
  8  6  1  0
  9  1  1  0
 10 13  1  0
 11  5  1  0
 12 11  1  0
 13  9  2  0
 14 12  1  0
 15 16  1  0
 16 18  1  0
 17 32  1  0
 18 17  1  0
 19  3  1  0
 20 14  1  0
 21  2  2  0
 22 14  2  0
 23 10  2  0
 24 15  2  0
 25 17  2  0
 12 26  1  6
 27 15  1  0
 18 28  1  1
 29 20  1  0
  6 30  1  6
  8 31  1  6
 32 46  1  0
 11 33  1  1
 34 19  1  0
 35 39  1  0
 36 27  1  0
 37 34  2  0
 38 34  1  0
 39 38  2  0
 40 37  1  0
 41 36  1  0
 42 45  1  0
 43 35  1  0
 44 28  1  0
 45 26  1  0
 46 42  1  0
 47 29  1  0
 48 29  1  0
 49 29  1  0
 50 41  1  0
 51 41  2  0
 52 43  1  0
 53 44  1  0
 54 44  1  0
 55 51  1  0
 56 50  2  0
 57 55  2  0
 10  3  1  0
  8  5  1  0
 35 40  2  0
 57 56  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA325014

   tert-butyl (2S,3R)-3-[(3S,4R,5R)-3,4-dihydroxy-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxy-2-[3-[[(2R)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propylamino]propanoate

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: 797.90

Molecular Weight (Monoisotopic): 797.3847

AlogP: 1.19

#Rotatable Bonds: 18

Polar Surface Area: 228.91

Molecular Species: NEUTRAL

HBA: 15

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.42

CX Basic pKa: 5.75

CX LogP: 2.10

CX LogD: 2.09

Aromatic Rings: 3

Heavy Atoms: 57

QED Weighted: 0.08

Np Likeness Score: -0.02

References

1. Yamashita A, Norton E, Petersen PJ, Rasmussen BA, Singh G, Yang Y, Mansour TS, Ho DM..  (2003)  Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues.,  13  (19): [PMID:12951123] [10.1016/s0960-894x(03)00671-1]

Source

Source(1):

• Scientific Literature