Natural Product: NPC241597

Natural Product ID:  NPC241597
Common Name:   Sisomicin
IUPAC Name:   (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Synonyms:   Sisomicin; Sissomicin
Molecular Formula:   C19H37N5O7
Standard InCHIKey:  URWAJWIAIPFPJE-YFMIWBNJSA-N
Standard InCHI:  InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
Canonical SMILES:  NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   BGC0000714 ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32431 Streptomyces jp95 Species Streptomycetaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT317 Uncleic Acid Nucleic Acid MIC > 100000 nM 9457241
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 7 nM 12643896
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 75 % 12643896
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 100 % 12643896
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.125 ug/ml 17088477
NPT1521 Organism Stenotrophomonas maltophilia Stenotrophomonas maltophilia MIC = 8 ug/ml 17088477
NPT19 Organism Escherichia coli Escherichia coli MIC = 8 ug/ml 17470660
NPT19 Organism Escherichia coli Escherichia coli MIC <= 0.25 ug/ml 17470660
NPT19 Organism Escherichia coli Escherichia coli MIC > 256 ug/ml 17875999
NPT19 Organism Escherichia coli Escherichia coli MIC <= 0.06 ug/ml 17875999
NPT19 Organism Escherichia coli Escherichia coli MIC = 256 ug/ml 17875999
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.13 ug/ml 17875999
NPT19 Organism Escherichia coli Escherichia coli MIC = 8 ug/ml 20145089
NPT19 Organism Escherichia coli Escherichia coli MIC = 4 ug/ml 20145089
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.25 ug/ml 20145089
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 32 ug/ml 19349516
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.5 ug/ml 19349516
NPT19 Organism Escherichia coli Escherichia coli MIC = 1 ug/ml 19349516
NPT19 Organism Escherichia coli Escherichia coli MIC = 2 ug/ml 19349516
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.5 ug/ml 20805391
NPT19 Organism Escherichia coli Escherichia coli MIC = 64 ug/ml 20805391
NPT19 Organism Escherichia coli Escherichia coli MIC = 32 ug/ml 20805391
NPT19 Organism Escherichia coli Escherichia coli MIC > 64 ug/ml 20805391
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.25 ug/ml 20805391
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 0.25 ug/ml 20805391
NPT2895 Organism Providencia stuartii Providencia stuartii MIC = 64 ug/ml 20805391
NPT1248 Organism Serratia marcescens Serratia marcescens MIC = 8 ug/ml 20805391
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.5 ug/ml 20805391
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1 ug/ml 20805391
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.25 ug/ml 20805391
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 64 ug/ml 20805391
NPT1207 Organism Acinetobacter Acinetobacter MIC = 0.5 ug/ml 20805391
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC = 0.5 ug/ml 20805391
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC = 8 ug/ml 20805391
NPT3163 Organism Acinetobacter calcoaceticus Acinetobacter calcoaceticus MIC = 32 ug/ml 20805391
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 0.5 ug/ml 20805391
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 1 ug/ml 20805391
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 0.125 ug/ml 20805391
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 32 ug/ml 20805391
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.75 ug/ml 413921
NPT19 Organism Escherichia coli Escherichia coli MIC = 7.5 ug/ml 413921
NPT19 Organism Escherichia coli Escherichia coli MIC = 17.5 ug/ml 413921
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 0.3 ug/ml 413921
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 17.5 ug/ml 413921
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 7.5 ug/ml 413921
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 0.3 ug/ml 413921
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 7.5 ug/ml 413921
NPT5397 Organism Providencia Providencia MIC = 3 ug/ml 413921
NPT172 Organism Proteus mirabilis Proteus mirabilis MIC = 0.3 ug/ml 413921
NPT2894 Organism Providencia rettgeri Providencia rettgeri MIC = 3 ug/ml 413921
NPT2894 Organism Providencia rettgeri Providencia rettgeri MIC > 25 ug/ml 413921
NPT1248 Organism Serratia marcescens Serratia marcescens MIC = 0.3 ug/ml 413921
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 0.3 ug/ml 413921
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC < 0.01 ug/ml 413921
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.03 ug/ml 413921
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC = 17.5 ug/ml 413921
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC = 3 ug/ml 413921
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC = 7.5 ug/ml 413921
NPT32 Organism Mus musculus Mus musculus LD50 = 34 mg/kg 413921
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC <= 0.25 ug/ml 26617967
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 4.7 ug/ml 26617967
NPT564 Organism Listeria monocytogenes Listeria monocytogenes MIC = 2.3 ug/ml 26617967
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 9.4 ug/ml 26617967
NPT2 Others Unspecified MIC <= 0.25 ug/ml 26617967
NPT1122 Organism Haemophilus influenzae Haemophilus influenzae MIC = 4.7 ug/ml 26617967
NPT1548 Organism Pseudomonas aeruginosa PAO1 Pseudomonas aeruginosa PAO1 MIC = 1.2 ug/ml 26617967
NPT1107 Organism Mycobacterium smegmatis str. MC2 155 Mycobacterium smegmatis str. MC2 155 MIC <= 0.25 ug/ml 26617967
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.5 ug/ml 10.1039/C5MD00429B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.5 ug/ml 10.1039/C5MD00429B
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 0.25 ug/ml 10.1039/C5MD00429B
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC = 0.5 ug/ml 10.1039/C5MD00429B
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 0.5 ug/ml 10.1039/C5MD00429B
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MIC > 64 ug/ml 10.1039/C5MD00429B
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.25 ug/ml 10.1039/C5MD00429B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.25 ug/ml 10.1039/C5MD00429B
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC > 64 ug/ml 10.1039/C5MD00429B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1 ug/ml 10.1039/C5MD00429B
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 1 ug/ml 10.1039/C5MD00429B
NPT19 Organism Escherichia coli Escherichia coli MIC = 64 ug/ml 10.1039/C5MD00429B
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 32 ug/ml 10.1039/C5MD00429B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 64 ug/ml 10.1039/C5MD00429B
NPT19 Organism Escherichia coli Escherichia coli MIC = 32 ug/ml 10.1039/C5MD00429B
NPT19 Organism Escherichia coli Escherichia coli MIC > 64 ug/ml 10.1039/C5MD00429B

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC241597 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8318 Intermediate Similarity NPC471628
0.8318 Intermediate Similarity NPC56298
0.7705 Intermediate Similarity NPC20035
0.7658 Intermediate Similarity NPC315036
0.7453 Intermediate Similarity NPC43850
0.7453 Intermediate Similarity NPC477060
0.7453 Intermediate Similarity NPC314408
0.7453 Intermediate Similarity NPC123746
0.7453 Intermediate Similarity NPC314007
0.7373 Intermediate Similarity NPC121479
0.7373 Intermediate Similarity NPC57436
0.7315 Intermediate Similarity NPC195969
0.7315 Intermediate Similarity NPC176381
0.7308 Intermediate Similarity NPC263058
0.729 Intermediate Similarity NPC214376
0.7212 Intermediate Similarity NPC315969
0.7196 Intermediate Similarity NPC313552
0.7143 Intermediate Similarity NPC330590
0.7117 Intermediate Similarity NPC315334
0.7107 Intermediate Similarity NPC314306
0.7009 Intermediate Similarity NPC221148
0.6864 Remote Similarity NPC55336
0.6833 Remote Similarity NPC315426
0.6744 Remote Similarity NPC94319
0.6557 Remote Similarity NPC319537
0.6557 Remote Similarity NPC313272
0.6542 Remote Similarity NPC318258
0.6525 Remote Similarity NPC315170
0.6475 Remote Similarity NPC475918
0.6429 Remote Similarity NPC306838
0.6403 Remote Similarity NPC297058
0.6389 Remote Similarity NPC70574
0.6372 Remote Similarity NPC470282
0.6296 Remote Similarity NPC98750
0.6293 Remote Similarity NPC61894
0.6293 Remote Similarity NPC475603
0.6279 Remote Similarity NPC313813
0.6273 Remote Similarity NPC36927
0.6273 Remote Similarity NPC271772
0.6269 Remote Similarity NPC296686
0.6241 Remote Similarity NPC471262
0.6239 Remote Similarity NPC100204
0.6239 Remote Similarity NPC83248
0.623 Remote Similarity NPC477198
0.6216 Remote Similarity NPC165119
0.6131 Remote Similarity NPC163783
0.6119 Remote Similarity NPC469943
0.6103 Remote Similarity NPC471263
0.6036 Remote Similarity NPC471420
0.6 Remote Similarity NPC316807
0.6 Remote Similarity NPC25455
0.6 Remote Similarity NPC15249
0.5985 Remote Similarity NPC315058
0.5971 Remote Similarity NPC313962
0.5957 Remote Similarity NPC122819
0.5956 Remote Similarity NPC471255
0.5932 Remote Similarity NPC242503
0.5932 Remote Similarity NPC74672
0.5932 Remote Similarity NPC139782
0.5932 Remote Similarity NPC209047
0.5932 Remote Similarity NPC43074
0.5923 Remote Similarity NPC1111
0.5923 Remote Similarity NPC261750
0.5917 Remote Similarity NPC262312
0.5917 Remote Similarity NPC192066
0.5917 Remote Similarity NPC70323
0.5917 Remote Similarity NPC35269
0.5917 Remote Similarity NPC17290
0.5917 Remote Similarity NPC3568
0.5917 Remote Similarity NPC256570
0.5917 Remote Similarity NPC23454
0.5915 Remote Similarity NPC147753
0.5915 Remote Similarity NPC150057
0.5897 Remote Similarity NPC470284
0.5882 Remote Similarity NPC473604
0.5882 Remote Similarity NPC478138
0.5882 Remote Similarity NPC473581
0.5882 Remote Similarity NPC111567
0.5882 Remote Similarity NPC263545
0.5882 Remote Similarity NPC182632
0.5882 Remote Similarity NPC473950
0.5882 Remote Similarity NPC309898
0.5882 Remote Similarity NPC282705
0.5882 Remote Similarity NPC186840
0.5882 Remote Similarity NPC328646
0.5882 Remote Similarity NPC15851
0.5882 Remote Similarity NPC475125
0.5868 Remote Similarity NPC119225
0.5868 Remote Similarity NPC476261
0.5868 Remote Similarity NPC471635
0.5868 Remote Similarity NPC470382
0.5868 Remote Similarity NPC25033
0.5865 Remote Similarity NPC129100
0.5865 Remote Similarity NPC322801
0.5865 Remote Similarity NPC291650
0.5856 Remote Similarity NPC150557
0.582 Remote Similarity NPC8098
0.582 Remote Similarity NPC183449
0.582 Remote Similarity NPC45313
0.582 Remote Similarity NPC197294
0.5806 Remote Similarity NPC206711
0.5806 Remote Similarity NPC225978
0.5806 Remote Similarity NPC255175
0.5806 Remote Similarity NPC271207
0.5802 Remote Similarity NPC60432
0.5797 Remote Similarity NPC313333
0.5797 Remote Similarity NPC314451
0.5797 Remote Similarity NPC313342
0.5797 Remote Similarity NPC314512
0.5797 Remote Similarity NPC75839
0.5797 Remote Similarity NPC68327
0.5789 Remote Similarity NPC20072
0.5789 Remote Similarity NPC30196
0.5785 Remote Similarity NPC54961
0.5785 Remote Similarity NPC156782
0.5785 Remote Similarity NPC157353
0.5785 Remote Similarity NPC158445
0.5785 Remote Similarity NPC282088
0.5781 Remote Similarity NPC317534
0.5778 Remote Similarity NPC477515
0.5778 Remote Similarity NPC314268
0.5778 Remote Similarity NPC67917
0.5778 Remote Similarity NPC313802
0.5776 Remote Similarity NPC73166
0.5775 Remote Similarity NPC139585
0.5775 Remote Similarity NPC475472
0.5766 Remote Similarity NPC139857
0.5764 Remote Similarity NPC471256
0.5753 Remote Similarity NPC287885
0.5752 Remote Similarity NPC100697
0.5746 Remote Similarity NPC6531
0.5745 Remote Similarity NPC315387
0.5745 Remote Similarity NPC316205
0.5734 Remote Similarity NPC73829
0.5734 Remote Similarity NPC119794
0.5727 Remote Similarity NPC3094
0.5714 Remote Similarity NPC314282
0.5694 Remote Similarity NPC76999
0.5691 Remote Similarity NPC189629
0.5676 Remote Similarity NPC229655
0.5667 Remote Similarity NPC284625
0.5667 Remote Similarity NPC69176
0.5667 Remote Similarity NPC141669
0.5656 Remote Similarity NPC470283
0.5655 Remote Similarity NPC280941
0.5655 Remote Similarity NPC75318
0.5655 Remote Similarity NPC235772
0.5645 Remote Similarity NPC475646
0.5625 Remote Similarity NPC322449
0.5625 Remote Similarity NPC477001
0.5625 Remote Similarity NPC477000
0.5625 Remote Similarity NPC92874
0.5625 Remote Similarity NPC189854
0.5625 Remote Similarity NPC166242
0.5625 Remote Similarity NPC62845
0.562 Remote Similarity NPC208537
0.562 Remote Similarity NPC270005
0.5616 Remote Similarity NPC145899
0.5614 Remote Similarity NPC207657
0.5612 Remote Similarity NPC314629
0.5612 Remote Similarity NPC315783
0.5608 Remote Similarity NPC180770
0.5606 Remote Similarity NPC29501
0.5605 Remote Similarity NPC476742
0.56 Remote Similarity NPC475266
0.56 Remote Similarity NPC475278
0.56 Remote Similarity NPC304299
0.56 Remote Similarity NPC247776
0.56 Remote Similarity NPC309450

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC241597 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD3731 Phase 3
0.9811 High Similarity NPD4832 Approved
0.9811 High Similarity NPD4830 Approved
0.9811 High Similarity NPD4831 Approved
0.9286 High Similarity NPD6436 Phase 3
0.8476 Intermediate Similarity NPD4282 Approved
0.8318 Intermediate Similarity NPD4838 Approved
0.8318 Intermediate Similarity NPD4837 Approved
0.8318 Intermediate Similarity NPD4836 Approved
0.8318 Intermediate Similarity NPD4835 Approved
0.7946 Intermediate Similarity NPD5376 Approved
0.7453 Intermediate Similarity NPD3209 Approved
0.7453 Intermediate Similarity NPD3201 Approved
0.7453 Intermediate Similarity NPD3203 Approved
0.7453 Intermediate Similarity NPD3202 Approved
0.7453 Intermediate Similarity NPD3207 Approved
0.7453 Intermediate Similarity NPD3208 Approved
0.7373 Intermediate Similarity NPD4833 Approved
0.7373 Intermediate Similarity NPD35 Approved
0.7358 Intermediate Similarity NPD3200 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5796 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5797 Approved
0.7315 Intermediate Similarity NPD5798 Approved
0.7315 Intermediate Similarity NPD5795 Approved
0.7315 Intermediate Similarity NPD5794 Approved
0.729 Intermediate Similarity NPD2698 Approved
0.7143 Intermediate Similarity NPD5377 Approved
0.7143 Intermediate Similarity NPD5381 Approved
0.7143 Intermediate Similarity NPD5378 Approved
0.7107 Intermediate Similarity NPD6430 Approved
0.7107 Intermediate Similarity NPD6429 Approved
0.7009 Intermediate Similarity NPD1449 Approved
0.7009 Intermediate Similarity NPD1450 Approved
0.6748 Remote Similarity NPD2690 Discontinued
0.6744 Remote Similarity NPD4827 Approved
0.6744 Remote Similarity NPD4828 Approved
0.6744 Remote Similarity NPD4826 Approved
0.6667 Remote Similarity NPD2700 Approved
0.6328 Remote Similarity NPD3204 Clinical (unspecified phase)
0.6179 Remote Similarity NPD8045 Clinical (unspecified phase)
0.6179 Remote Similarity NPD1407 Approved
0.6016 Remote Similarity NPD8087 Discontinued
0.597 Remote Similarity NPD8346 Approved
0.597 Remote Similarity NPD8347 Approved
0.597 Remote Similarity NPD8345 Approved
0.5957 Remote Similarity NPD8449 Approved
0.595 Remote Similarity NPD6428 Approved
0.5932 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5929 Remote Similarity NPD8391 Approved
0.5929 Remote Similarity NPD8392 Approved
0.5929 Remote Similarity NPD8390 Approved
0.5915 Remote Similarity NPD8450 Suspended
0.5913 Remote Similarity NPD394 Phase 3
0.5865 Remote Similarity NPD9032 Approved
0.5865 Remote Similarity NPD9033 Approved
0.5865 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5865 Remote Similarity NPD9031 Approved
0.5865 Remote Similarity NPD9030 Approved
0.5797 Remote Similarity NPD8299 Approved
0.5797 Remote Similarity NPD8342 Approved
0.5797 Remote Similarity NPD8340 Approved
0.5797 Remote Similarity NPD8341 Approved
0.5789 Remote Similarity NPD869 Approved
0.5755 Remote Similarity NPD8451 Approved
0.5714 Remote Similarity NPD8448 Approved
0.5704 Remote Similarity NPD7641 Discontinued
0.5703 Remote Similarity NPD5357 Phase 1
0.5693 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5683 Remote Similarity NPD577 Phase 3
0.5683 Remote Similarity NPD591 Approved
0.5659 Remote Similarity NPD8307 Discontinued
0.5652 Remote Similarity NPD8080 Discontinued
0.5643 Remote Similarity NPD4816 Clinical (unspecified phase)
0.5612 Remote Similarity NPD7829 Approved
0.5612 Remote Similarity NPD7830 Approved

Structure

External Identifiers

PubChem CID   36119
ChEMBL   CHEMBL221886
ZINC  

Physicochemical Properties

Molecular Weight:  447.27
ALogP:  -5.2874
MLogP:  2.23
XLogP:  -3.628
# Rotatable Bonds:  15
Polar Surface Area:  213.72
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  3
# Heavy Atoms:  31

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Similar NPs/Drugs