(2R,3R,4R,5S)-5-((R)-2-amino-1-(((2R,3R,4R)-3,4-dihydroxy-6-(((3S,7R)-7-methyl-2-oxoazepan-3-yl)carbamoyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-oxoethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methoxytetrahydrofuran-3-yl decanoate

ID: ALA5282446

Max Phase: Preclinical

Molecular Formula: C34H51N5O13

Molecular Weight: 737.80

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC(=O)O[C@@H]1[C@H](OC)[C@@H]([C@@H](O[C@@H]2OC(C(=O)N[C@H]3CCC[C@@H](C)NC3=O)=C[C@@H](O)[C@H]2O)C(N)=O)O[C@H]1n1ccc(=O)[nH]c1=O

Standard InChI:  InChI=1S/C34H51N5O13/c1-4-5-6-7-8-9-10-14-23(42)50-28-25(48-3)26(51-32(28)39-16-15-22(41)38-34(39)47)27(29(35)44)52-33-24(43)20(40)17-21(49-33)31(46)37-19-13-11-12-18(2)36-30(19)45/h15-20,24-28,32-33,40,43H,4-14H2,1-3H3,(H2,35,44)(H,36,45)(H,37,46)(H,38,41,47)/t18-,19+,20-,24-,25-,26+,27-,28-,32-,33+/m1/s1

Standard InChI Key:  MTVCVDHANKHRCR-KMCLKLANSA-N

Molfile:  

 
     RDKit          2D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -1.7499    0.8211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1624    0.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873    0.1066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -0.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1624   -1.3222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -1.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3999   -0.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -0.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373    0.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248    0.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4623    0.1066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8748    0.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4586    1.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7622    2.3121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5512    2.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7647    3.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2363    2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2958    1.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -1.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -2.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3998   -2.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -2.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249   -0.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4356   -1.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -0.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4447    0.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0053    0.3024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774    1.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970    1.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249    0.4614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -0.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -1.4918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -2.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6075   -2.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -2.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295   -2.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -2.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516   -3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2030   -2.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737   -3.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -2.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2958   -3.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -2.7253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -2.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -2.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969   -1.3441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  4  2  1  1
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  0
 16 17  1  1
 18 16  1  0
 19 18  1  0
 20 19  1  0
 20 12  1  0
  8 21  2  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24  6  1  0
 24 25  1  6
 26  4  1  0
 26 27  1  0
 28 27  1  0
 29 28  1  0
 30 29  1  0
 30 26  1  0
 29 31  1  1
 32 31  1  0
 33 32  2  0
 34 33  1  0
 34 35  2  0
 36 34  1  0
 37 36  1  0
 31 37  1  0
 37 38  2  0
 28 39  1  6
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 40 50  2  0
 27 51  1  6
 51 52  1  0
 26 53  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5282446

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 737.80

Molecular Weight (Monoisotopic): 737.3483

AlogP: -0.49

#Rotatable Bonds: 17

Polar Surface Area: 259.83

Molecular Species: NEUTRAL

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: 0.44

CX LogD: 0.44

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.09

Np Likeness Score: 0.95

References

1. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature