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

ID: ALA3218398

PubChem CID: 90665665

Max Phase: Preclinical

Molecular Formula: C33H51N13O16

Molecular Weight: 885.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](OC(=O)NCCCn2cc(CCNC(=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/C33H51N13O16/c1-13(49)40-22-16(42-30(34)35)8-20(28(53)54)59-26(22)24(18(51)11-47)61-32(57)38-5-3-7-46-10-15(44-45-46)4-6-39-33(58)62-25(19(52)12-48)27-23(41-14(2)50)17(43-31(36)37)9-21(60-27)29(55)56/h8-10,16-19,22-27,47-48,51-52H,3-7,11-12H2,1-2H3,(H,38,57)(H,39,58)(H,40,49)(H,41,50)(H,53,54)(H,55,56)(H4,34,35,42)(H4,36,37,43)/t16-,17-,18+,19+,22+,23+,24+,25+,26+,27+/m0/s1

Standard InChI Key:  DSZSOGZNDVLACH-ROHOTOPKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3218398

   (2R,3R,4S)-3-acetamido-2-[(1R,2R)-1-[3-[4-[2-[[(1R,2R)-1-[(2R,3R,4S)-3-acetamido-6-carboxy-4-(diaminomethylideneamino)-3,4-dihydro-2H-pyran-2-yl]-2,3-dihydroxypropoxy]carbonylamino]ethyl]triazol-1-yl]propylcarbamoyloxy]-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: 885.85

Molecular Weight (Monoisotopic): 885.3577

AlogP: -6.45

#Rotatable Bonds: 21

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: -10.91

CX LogD: -10.91

Aromatic Rings: 1

Heavy Atoms: 62

QED Weighted: 0.03

Np Likeness Score: -0.05

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