2-((S)-((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy)((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-1,4-dimethyl-3-oxo-N-tridecyl-2,3,4,7-tetrahydro-1H-1,4-diazepine-5-carboxamide

ID: ALA4589728

PubChem CID: 71653801

Max Phase: Preclinical

Molecular Formula: C35H58N6O11

Molecular Weight: 738.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCNC(=O)C1=CCN(C)[C@@H]([C@H](O[C@@H]2O[C@H](CN)[C@@H](O)[C@H]2O)[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)C(=O)N1C

Standard InChI:  InChI=1S/C35H58N6O11/c1-4-5-6-7-8-9-10-11-12-13-14-17-37-31(47)21-15-18-39(2)24(32(48)40(21)3)29(52-34-28(46)25(43)22(20-36)50-34)30-26(44)27(45)33(51-30)41-19-16-23(42)38-35(41)49/h15-16,19,22,24-30,33-34,43-46H,4-14,17-18,20,36H2,1-3H3,(H,37,47)(H,38,42,49)/t22-,24+,25-,26+,27-,28-,29+,30+,33-,34+/m1/s1

Standard InChI Key:  SIACOEUIZYWWIL-BMBCOVQSSA-N

Molfile:  

 
     RDKit          2D

 55 58  0  0  0  0  0  0  0  0999 V2000
   10.7262  -27.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9617  -26.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4764  -29.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5286  -28.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0027  -25.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8130  -28.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0794  -27.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9533  -30.0267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5549  -29.8940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6866  -30.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9808  -30.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5562  -28.2227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9965  -27.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5259  -27.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2743  -27.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1278  -30.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8738  -29.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3028  -30.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5802  -28.9989    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1664  -26.1578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3183  -28.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4886  -27.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8607  -27.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3650  -29.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9133  -28.1654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4108  -30.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3666  -29.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0456  -29.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6183  -29.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7025  -30.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2954  -28.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8037  -28.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4670  -24.5835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2659  -27.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4725  -27.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1441  -26.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2694  -26.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2123  -29.0241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3559  -26.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1193  -28.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4019  -31.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0170  -28.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9811  -26.5548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2716  -29.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5520  -30.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8428  -29.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1232  -30.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4140  -29.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944  -30.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9852  -29.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656  -30.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564  -29.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5669  -29.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2865  -28.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970  -27.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 23  7  2  0
 42 31  1  0
 39  2  1  0
  3 10  2  0
 39  5  1  1
 14  1  1  6
  7 25  1  0
 31  3  1  0
  4 27  2  0
 13 37  1  0
 37 20  1  0
  6 12  1  0
 12 31  1  0
  5 33  1  0
 26 41  2  0
 20 39  1  0
 42 13  1  6
 28 17  1  0
 40 25  1  1
 32 35  1  0
  8 18  1  0
 40 35  1  0
 22 23  1  0
  2 36  1  6
 17 24  1  6
 32 38  1  6
 28 32  1  0
 14 37  1  0
 16  8  1  0
 28  9  1  6
 37 43  1  6
 29 16  2  0
 30 11  1  0
 32 42  1  0
  4 21  1  0
 12 34  1  0
  3  8  1  0
  6 29  1  0
 22 15  2  0
 16 26  1  0
 25  4  1  0
  2 14  1  0
 21 22  1  0
 26 30  1  0
 17 40  1  0
 31 19  1  6
 11 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4589728

   (2S)-2-[(S)-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxy-tetrahydrofuran-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl]-1,4-dimethyl-3-oxo-N-tridecyl-2,7-dihydro-1,4-diazepine-5-carboxamide

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: 738.88

Molecular Weight (Monoisotopic): 738.4164

AlogP: -0.97

#Rotatable Bonds: 19

Polar Surface Area: 242.14

Molecular Species: BASE

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -0.17

CX LogD: -1.35

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.08

Np Likeness Score: 0.73

References

1. Patel B, Ryan P, Makwana V, Zunk M, Rudrawar S, Grant G..  (2019)  Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY.,  171  [PMID:30933853] [10.1016/j.ejmech.2019.01.071]

2. Arbour CA,Imperiali B.  (2020)  Uridine natural products: Challenging targets and inspiration for novel small molecule inhibitors.,  28  (18): [PMID:32828427] [10.1016/j.bmc.2020.115661]

Source

Source(1):

• Scientific Literature