(2R,4S,5R,6R)-5-acetamido-2-(7,47-dioxo-10,13,16,19,22,25,28,31,34,37,40,43-dodecaoxa-6,46-diazahenheptaconta-56,58-diynyloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid

ID: ALA1916373

PubChem CID: 54757099

Max Phase: Preclinical

Molecular Formula: C68H123N3O23

Molecular Weight: 1350.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCC#CC#CCCCCCCCCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)NCCCCCO[C@]1(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O1

Standard InChI:  InChI=1S/C68H123N3O23/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-25-28-62(76)70-31-34-82-36-38-84-40-42-86-44-46-88-48-50-90-52-54-92-56-55-91-53-51-89-49-47-87-45-43-85-41-39-83-37-35-81-33-29-63(77)69-30-26-24-27-32-93-68(67(79)80)57-60(74)64(71-59(2)73)66(94-68)65(78)61(75)58-72/h60-61,64-66,72,74-75,78H,3-13,18-58H2,1-2H3,(H,69,77)(H,70,76)(H,71,73)(H,79,80)/t60-,61+,64+,65+,66+,68+/m0/s1

Standard InChI Key:  GBLKJPNUUGCCJP-FFJZRORYSA-N

Molfile:  

     RDKit          2D

 95 95  0  0  0  0  0  0  0  0999 V2000
   44.4083  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1208  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8333  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5458  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2583  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9708  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.6833  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.3958  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.1083  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.8208  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.5333  -22.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.2458  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8459  -24.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5584  -24.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2709  -24.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9834  -24.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6959  -24.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4084  -24.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1209  -24.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8334  -24.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4171  -24.2280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1358  -24.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1445  -25.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5484  -24.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2634  -23.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9783  -23.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6933  -22.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9829  -24.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7016  -24.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4117  -24.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1305  -24.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8406  -24.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5594  -24.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2695  -24.6181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9882  -24.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6983  -24.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4097  -24.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1284  -24.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8386  -24.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5573  -24.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2674  -24.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9862  -24.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6963  -24.5282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4150  -24.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1251  -24.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8439  -24.1382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5540  -24.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2728  -24.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875  -24.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875  -25.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245  -25.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365  -25.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365  -24.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245  -23.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458  -23.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414  -23.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4590  -22.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532  -23.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633  -24.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821  -23.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922  -24.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109  -23.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1211  -24.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398  -23.9286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5499  -24.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2687  -23.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413  -25.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9788  -24.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6975  -23.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076  -24.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1264  -23.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8365  -24.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5553  -23.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2654  -24.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9841  -24.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6942  -24.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4130  -24.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1231  -24.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8419  -24.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5520  -24.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2707  -24.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9808  -24.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6996  -24.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245  -26.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014  -25.5260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3032  -23.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002  -26.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140  -26.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851  -26.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3056  -23.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213  -22.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0237  -21.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164  -24.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923  -22.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917  -23.4625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 49 50  1  0
 24 25  3  0
  6  7  1  0
 25 26  1  0
 13 14  1  0
 26 27  3  0
 27  1  1  0
 49 54  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
  3  4  1  0
 53 55  1  1
 14 15  1  0
 55 56  1  0
 28 29  1  0
 55 57  2  0
  7  8  1  0
 53 58  1  0
 29 30  1  0
 58 59  1  0
 15 16  1  0
 59 60  1  0
 30 31  1  0
 60 61  1  0
 61 62  1  0
 31 32  1  0
 62 63  1  0
 16 17  1  0
 63 64  1  0
 32 33  1  0
 64 65  1  0
  8  9  1  0
 65 66  1  0
 33 34  1  0
 65 67  2  0
 17 18  1  0
 66 68  1  0
 34 35  1  0
 68 69  1  0
  4  5  1  0
 69 70  1  0
 35 36  1  0
 70 71  1  0
 18 19  1  0
 71 72  1  0
  9 10  1  0
 72 73  1  0
 37 38  1  0
 73 74  1  0
 19 20  1  0
 74 75  1  0
 38 39  1  0
 75 76  1  0
  2  3  1  0
 76 77  1  0
 39 40  1  0
 77 78  1  0
 10 11  1  0
 78 79  1  0
 40 41  1  0
 79 80  1  0
 21 22  1  0
 80 81  1  0
 41 42  1  0
 81 82  1  0
 22 13  1  0
 82 83  1  0
 83 37  1  0
 42 43  1  0
 51 84  1  6
  5  6  1  0
 50 85  1  1
 43 44  1  0
 49 86  1  0
 22 23  2  0
 85 87  1  0
 44 45  1  0
 87 88  1  0
 11 12  1  0
 87 89  2  0
 45 46  1  0
 86 90  1  0
 20 24  1  0
 90 91  1  0
 46 47  1  0
 91 92  1  0
  1  2  1  0
 86 93  1  6
 47 48  1  0
 90 94  1  1
 36 21  1  0
 48 28  1  0
 49 95  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1916373

   (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[5-[3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(pentacosa-10,12-diynoylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]pentoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxa

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: 1350.73

Molecular Weight (Monoisotopic): 1349.8547

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Aplander K, Marttila M, Manner S, Arnberg N, Sterner O, Ellervik U..  (2011)  Molecular wipes: application to epidemic keratoconjuctivitis.,  54  (19): [PMID:21838327] [10.1021/jm200545m]

Source

Source(1):

• Scientific Literature