(2R,3R,4S)-3-acetamido-2-((1R,2R)-1-(3-(4-(4-(((1R,2R)-1-((2R,3R,4S)-3-acetamido-6-carboxy-4-guanidino-3,4-dihydro-2H-pyran-2-yl)-2,3-dihydroxypropoxy)carbonylamino)butyl)-1H-1,2,3-triazol-1-yl)propylcarbamoyloxy)-2,3-dihydroxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid

ID: ALA3218399

PubChem CID: 90665666

Max Phase: Preclinical

Molecular Formula: C35H55N13O16

Molecular Weight: 913.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](OC(=O)NCCCCc2cn(CCCNC(=O)O[C@@H]([C@@H]3OC(C(=O)O)=C[C@H](NC(=N)N)[C@H]3NC(C)=O)[C@H](O)CO)nn2)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1NC(=N)N

Standard InChI:  InChI=1S/C35H55N13O16/c1-15(51)42-24-18(44-32(36)37)10-22(30(55)56)61-28(24)26(20(53)13-49)63-34(59)40-7-4-3-6-17-12-48(47-46-17)9-5-8-41-35(60)64-27(21(54)14-50)29-25(43-16(2)52)19(45-33(38)39)11-23(62-29)31(57)58/h10-12,18-21,24-29,49-50,53-54H,3-9,13-14H2,1-2H3,(H,40,59)(H,41,60)(H,42,51)(H,43,52)(H,55,56)(H,57,58)(H4,36,37,44)(H4,38,39,45)/t18-,19-,20+,21+,24+,25+,26+,27+,28+,29+/m0/s1

Standard InChI Key:  BUZVBQWEPJJXRM-XUGABSMISA-N

Molfile:  

     RDKit          2D

 66 68  0  0  0  0  0  0  0  0999 V2000
   17.5985   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5985   -3.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3038   -4.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0091   -3.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0091   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3038   -2.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8872   -1.9501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1831   -3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3038   -5.2127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5961   -5.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5961   -6.4385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8884   -5.2127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7162   -4.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7180   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7150   -5.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4221   -5.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0067   -5.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4245   -3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7204   -1.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4293   -1.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0138   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0162   -0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1334   -2.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8399   -3.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1358   -1.9543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8447   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5512   -1.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2601   -1.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9666   -1.9626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0470   -2.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8458   -2.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2565   -2.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7114   -1.6283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1760   -3.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0018   -2.3566    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9885   -3.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3187   -4.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1312   -4.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8064   -8.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6236   -8.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0200   -8.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6076   -7.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7905   -7.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3857   -8.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4079   -9.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5908   -9.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8266  -10.2543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8372   -8.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2537   -8.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0709   -8.8046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8532   -9.5261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0092   -6.7077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3760   -6.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8264   -6.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2280   -5.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2419   -7.4033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7786   -6.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5588   -6.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1443   -6.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1561   -7.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3390   -7.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3641   -5.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7668   -4.5979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5469   -5.3158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9772   -7.5116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  1
 10 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  6
  5 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  1  1
 15 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 30  1  0
 32 35  1  0
  5 36  1  6
 35 37  1  0
 37 38  1  0
 38 39  1  0
 40 41  2  0
 40 45  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 40 46  1  0
 46 47  2  0
 46 48  1  0
 42 49  1  1
 49 50  1  0
 50 51  2  0
 50 52  1  0
 43 53  1  6
 44 54  1  0
 53 55  1  0
 55 56  1  0
 55 57  2  0
 54 58  1  1
 54 59  1  0
 59 60  1  1
 59 61  1  0
 61 62  1  0
 58 63  1  0
 63 64  2  0
 63 65  1  0
 65 39  1  0
 44 66  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3218399

   (2R,3R,4S)-3-acetamido-2-[(1R,2R)-1-[4-[1-[3-[[(1R,2R)-1-[(2R,3R,4S)-3-acetamido-6-carboxy-4-(diaminomethylideneamino)-3,4-dihydro-2H-pyran-2-yl]-2,3-dihydroxypropoxy]carbonylamino]propyl]triazol-4-yl]butylcarbamoyloxy]-2,3-dihydroxypropyl]-4-(diaminometh

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: 913.90

Molecular Weight (Monoisotopic): 913.3890

AlogP: -5.67

#Rotatable Bonds: 23

Polar Surface Area: 463.35

Molecular Species: ZWITTERION

HBA: 19

HBD: 16

#RO5 Violations: 3

HBA (Lipinski): 29

HBD (Lipinski): 18

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.08

CX Basic pKa: 11.82

CX LogP: -10.17

CX LogD: -10.17

Aromatic Rings: 1

Heavy Atoms: 64

QED Weighted: 0.03

Np Likeness Score: -0.01

References

1. Fraser BH, Hamilton S, Krause-Heuer AM, Wright PJ, Greguric I, Tucker SP, Draffan AG, Fokin VV, Sharpless KB.  (2013)  Synthesis of 1,4-triazole linked zanamivir dimers as highly potent inhibitors of influenza A and B,  4  (2): [10.1039/C2MD20300F]

Source

Source(1):

• Scientific Literature