General Information of the Compound
Compound ID
CP0036726
Compound Name
(2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
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Synonyms
GANA
(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
139110-80-8
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid
4-Guanidino-Neu5Ac2en
4-Guanidino-NeueAc2en
4-guanidino-Neu5Ac2en
5-(acetylamino)-4-{[amino(imino)methyl]amino}-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid
AK163166
BAC-zanamivir
C12H20N4O7
CHEBI:50663
CHEMBL222813
DSSTox_CID_3749
DSSTox_GSID_23749
DSSTox_RID_77184
GANA
GANA (inhibitor)
GG 167
GG-167
GG167
GNA
GR 121167X
GR-121167X
GR121167X
HSDB 7437
L6O3XI777I
MODIFIED SIALIC ACID
Relenza
Relenza (TN)
UNII-L6O3XI777I
ZMR
ZNV
Zanamavir
Zanamivir
Zanamivir (Relenza)
Zanamivir (USAN/INN)
Zanamivir [USAN:INN:BAN]
Zanamivir hydrate
zanamivir
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Structure
Formula
C12H20N4O7
Molecular Weight
332.313
Canonical SMILES
CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O)N=C(N)N
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InChI
InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1
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InChIKey
ARAIBEBZBOPLMB-UFGQHTETSA-N
CAS
139110-80-8
Physicochemical Property
logP
-3.7855
Rotatable Bonds
6
Heavy Atom Count
23
Polar Areas
200.72
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
7
Complexity
23

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 60855
SID: 14801980
ChEMBL ID
CHEMBL222813
DrugBank ID
DB00558
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00018, Neuraminidase
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  8
1
IC50 = 0.6 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
IC50 = 0.7 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
IC50 = 1.7 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
IC50 = 1.9 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
IC50 = 4.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
6
IC50 = 6 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
7
IC50 = 45 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
8
IC50 > 83000 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 0.03 nM
2 IC50 = 0.04 nM
3 IC50 = 0.05 nM
4 IC50 = 0.2 nM
5 IC50 = 0.29 nM
6 IC50 = 0.45 nM
7 IC50 = 0.47 nM
8 IC50 = 0.49 nM
9 IC50 = 0.58 nM
10 IC50 = 0.66 nM
11 IC50 = 0.7 nM
12 IC50 = 0.751 nM
13 IC50 = 0.8 nM
14 IC50 = 0.88 nM
15 IC50 = 1 nM
16 IC50 = 1.1 nM
17 IC50 = 1.14 nM
18 IC50 = 1.17 nM
19 IC50 = 1.19 nM
20 IC50 = 1.38 nM
21 IC50 = 1.4 nM
22 IC50 = 1.5 nM
23 IC50 = 1.6 nM
24 IC50 = 1.63 nM
25 IC50 = 1.66 nM
26 IC50 = 1.68 nM
27 IC50 = 1.8 nM
28 IC50 = 1.83 nM
29 IC50 = 1.9 nM
30 IC50 = 2 nM
31 IC50 = 2.05 nM
32 IC50 = 2.17 nM
33 IC50 = 2.2 nM
34 IC50 = 2.33 nM
35 IC50 = 2.4 nM
36 IC50 = 2.42 nM
37 IC50 = 2.5 nM
38 IC50 = 2.55 nM
39 IC50 = 2.7 nM
40 IC50 = 2.99 nM
41 IC50 = 3.05 nM
42 IC50 = 3.31 nM
43 IC50 = 3.4 nM
44 IC50 = 3.42 nM
45 IC50 = 3.51 nM
46 IC50 = 3.62 nM
47 IC50 = 3.65 nM
48 IC50 = 3.66 nM
49 IC50 = 3.97 nM
50 IC50 = 4 nM
51 IC50 = 4.32 nM
52 IC50 = 4.82 nM
53 IC50 = 4.84 nM
54 IC50 = 5 nM
55 IC50 = 5.11 nM
56 IC50 = 5.44 nM
57 IC50 = 5.53 nM
58 IC50 = 5.58 nM
59 IC50 = 5.8 nM
60 IC50 = 5.86 nM
61 IC50 = 6 nM
62 IC50 = 6.04 nM
63 IC50 = 6.45 nM
64 IC50 = 6.82 nM
65 IC50 = 7.16 nM
66 IC50 = 7.33 nM
67 IC50 = 7.35 nM
68 IC50 = 7.39 nM
69 IC50 = 7.58 nM
70 IC50 = 7.71 nM
71 IC50 = 7.8 nM
72 IC50 = 7.82 nM
73 IC50 = 8.21 nM
74 IC50 = 8.29 nM
75 IC50 = 8.57 nM
76 IC50 = 8.74 nM
77 IC50 = 9.08 nM
78 IC50 = 9.15 nM
79 IC50 = 9.3 nM
80 IC50 = 9.81 nM
81 IC50 = 10 nM
82 IC50 = 10.7 nM
83 IC50 = 11 nM
84 IC50 = 11.2 nM
85 IC50 = 11.5 nM
86 IC50 = 11.51 nM
87 IC50 = 12 nM
88 IC50 = 13.01 nM
89 IC50 = 13.5 nM
90 IC50 = 13.8 nM
91 IC50 = 14.2 nM
92 IC50 = 17.61 nM
93 IC50 = 22.8 nM
94 IC50 = 33.55 nM
95 IC50 = 500 nM
96 IC50 = 678.4 nM
97 IC50 = 815.9 nM
98 IC50 = 1659 nM
99 Ki = 0.06 nM
100 Ki = 0.16 nM
101 Ki = 0.2 nM
102 Ki = 0.3 nM
Protein ID: PT02681, Neuraminidase
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000031 MDCK
 Cell Line Info 
Canis lupus familiaris (Dog)  1
1
IC50 = 0.8 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 1 nM
2 IC50 = 1.6 nM
3 IC50 = 2.4 nM
4 IC50 = 2.9 nM
Clinical Information about the Compound
Drug 1 ( Zanamivir )
Drug Name Zanamivir
Company GlaxoSmithKline
Indication
Influenza virus infection
Approved
Target(s)
Influenza Neuraminidase (Influ NA)
 Target Info 
Inhibitor
Drug 2 ( Zanamivir )
Drug Name Zanamivir
Indication
Influenza virus infection
Approved
Severe acute respiratory syndrome (SARS)
Investigative