Natural Product: NPC315036

Natural Product ID:  NPC315036
Common Name:   Apramycin
IUPAC Name:   (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol
Synonyms:   Apramycin
Molecular Formula:   C21H41N5O11
Standard InCHIKey:  XZNUGFQTQHRASN-XQENGBIVSA-N
Standard InCHI:  InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
Canonical SMILES:  CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO9026 Streptoalloteichus tenebrarius Species Pseudonocardiaceae Bacteria StreptomeDB*
NPO9026.5 Streptomyces tenebrarius ud2 Subspecies Pseudonocardiaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Potency 14299.9 nM PubChem BioAssay data set
NPT2 Others Unspecified IC50 = 31.21 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 0.06 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 5 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 128.89 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 58.03 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 26.06 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 49.17 ug/ml 10.1039/C4MD00119B
NPT2 Others Unspecified IC50 = 23.77 ug/ml 10.1039/C4MD00119B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 8 ug/ml 10.1039/C4MD00119B
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 16 ug/ml 10.1039/C4MD00119B
NPT19 Organism Escherichia coli Escherichia coli MIC = 4 ug/ml 10.1039/C4MD00119B
NPT19 Organism Escherichia coli Escherichia coli MIC = 16 ug/ml 10.1039/C4MD00119B
NPT19 Organism Escherichia coli Escherichia coli MIC = 8 ug/ml 10.1039/C4MD00119B
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 0.39 ug/ml 26510047

  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 NPC315036 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
0.9167 High Similarity NPC471628
0.9167 High Similarity NPC56298
0.8804 High Similarity NPC477060
0.8804 High Similarity NPC314007
0.8804 High Similarity NPC314408
0.8804 High Similarity NPC43850
0.8804 High Similarity NPC123746
0.8737 High Similarity NPC315334
0.8617 High Similarity NPC176381
0.8617 High Similarity NPC195969
0.8404 Intermediate Similarity NPC214376
0.8367 Intermediate Similarity NPC330590
0.8298 Intermediate Similarity NPC313552
0.8261 Intermediate Similarity NPC263058
0.8152 Intermediate Similarity NPC315969
0.7981 Intermediate Similarity NPC221148
0.7935 Intermediate Similarity NPC318258
0.7917 Intermediate Similarity NPC306838
0.787 Intermediate Similarity NPC121479
0.787 Intermediate Similarity NPC57436
0.7766 Intermediate Similarity NPC271772
0.7766 Intermediate Similarity NPC36927
0.7658 Intermediate Similarity NPC241597
0.7553 Intermediate Similarity NPC70574
0.75 Intermediate Similarity NPC165119
0.7475 Intermediate Similarity NPC470282
0.7474 Intermediate Similarity NPC471420
0.7447 Intermediate Similarity NPC98750
0.7263 Intermediate Similarity NPC150557
0.7188 Intermediate Similarity NPC83248
0.7188 Intermediate Similarity NPC100204
0.7143 Intermediate Similarity NPC94319
0.7083 Intermediate Similarity NPC316807
0.6893 Remote Similarity NPC470284
0.6832 Remote Similarity NPC125253
0.6832 Remote Similarity NPC253975
0.6832 Remote Similarity NPC192025
0.681 Remote Similarity NPC314306
0.678 Remote Similarity NPC313813
0.6765 Remote Similarity NPC83839
0.6748 Remote Similarity NPC68327
0.6721 Remote Similarity NPC139857
0.6721 Remote Similarity NPC20035
0.6702 Remote Similarity NPC476694
0.6702 Remote Similarity NPC476695
0.6702 Remote Similarity NPC476696
0.6698 Remote Similarity NPC328646
0.6667 Remote Similarity NPC317534
0.663 Remote Similarity NPC291650
0.663 Remote Similarity NPC322801
0.663 Remote Similarity NPC129100
0.6613 Remote Similarity NPC75839
0.6574 Remote Similarity NPC470283
0.6542 Remote Similarity NPC208537
0.6542 Remote Similarity NPC270005
0.6518 Remote Similarity NPC188453
0.6518 Remote Similarity NPC42320
0.6489 Remote Similarity NPC268922
0.6458 Remote Similarity NPC474468
0.6383 Remote Similarity NPC471418
0.6346 Remote Similarity NPC476523
0.626 Remote Similarity NPC262050
0.625 Remote Similarity NPC327486
0.625 Remote Similarity NPC223174
0.625 Remote Similarity NPC473710
0.625 Remote Similarity NPC475694
0.625 Remote Similarity NPC327753
0.6207 Remote Similarity NPC62845
0.6207 Remote Similarity NPC92874
0.6207 Remote Similarity NPC322449
0.6207 Remote Similarity NPC166242
0.6207 Remote Similarity NPC189854
0.617 Remote Similarity NPC286851
0.617 Remote Similarity NPC303798
0.6154 Remote Similarity NPC325900
0.6154 Remote Similarity NPC10897
0.6139 Remote Similarity NPC314968
0.6139 Remote Similarity NPC314772
0.6121 Remote Similarity NPC314413
0.6121 Remote Similarity NPC314398
0.6121 Remote Similarity NPC239705
0.6064 Remote Similarity NPC471892
0.6064 Remote Similarity NPC223386
0.6064 Remote Similarity NPC471780
0.6064 Remote Similarity NPC75435
0.6064 Remote Similarity NPC142290
0.6064 Remote Similarity NPC198341
0.602 Remote Similarity NPC285014
0.602 Remote Similarity NPC137554
0.602 Remote Similarity NPC28959
0.602 Remote Similarity NPC299603
0.602 Remote Similarity NPC255535
0.6 Remote Similarity NPC315980
0.5966 Remote Similarity NPC59589
0.5946 Remote Similarity NPC61894
0.5946 Remote Similarity NPC475603
0.5914 Remote Similarity NPC477753
0.5914 Remote Similarity NPC477762
0.5914 Remote Similarity NPC477763
0.5914 Remote Similarity NPC477757
0.5914 Remote Similarity NPC477755
0.5914 Remote Similarity NPC477750
0.5897 Remote Similarity NPC227622
0.5882 Remote Similarity NPC475918
0.5862 Remote Similarity NPC206711
0.5862 Remote Similarity NPC255175
0.5862 Remote Similarity NPC271207
0.5862 Remote Similarity NPC225978
0.5859 Remote Similarity NPC52268
0.5859 Remote Similarity NPC53760
0.5851 Remote Similarity NPC218150
0.5851 Remote Similarity NPC69669
0.5851 Remote Similarity NPC2432
0.5851 Remote Similarity NPC306462
0.5851 Remote Similarity NPC17455
0.5851 Remote Similarity NPC150680
0.5851 Remote Similarity NPC22774
0.5833 Remote Similarity NPC77191
0.5833 Remote Similarity NPC69798
0.5833 Remote Similarity NPC116377
0.5833 Remote Similarity NPC101746
0.5833 Remote Similarity NPC473952
0.5816 Remote Similarity NPC67099
0.5789 Remote Similarity NPC476967
0.5789 Remote Similarity NPC163134
0.5789 Remote Similarity NPC471419
0.5784 Remote Similarity NPC244539
0.5776 Remote Similarity NPC315170
0.5766 Remote Similarity NPC297058
0.5761 Remote Similarity NPC472025
0.5729 Remote Similarity NPC474928
0.5728 Remote Similarity NPC313762
0.5725 Remote Similarity NPC296686
0.5704 Remote Similarity NPC15249
0.5704 Remote Similarity NPC25455
0.5702 Remote Similarity NPC137453
0.5699 Remote Similarity NPC317023
0.5676 Remote Similarity NPC292345
0.567 Remote Similarity NPC190418
0.567 Remote Similarity NPC471761
0.567 Remote Similarity NPC471760
0.5662 Remote Similarity NPC122819
0.5652 Remote Similarity NPC148424
0.5652 Remote Similarity NPC8979
0.5635 Remote Similarity NPC259586
0.562 Remote Similarity NPC150057
0.562 Remote Similarity NPC147753
0.5612 Remote Similarity NPC477752
0.5612 Remote Similarity NPC477764
0.5612 Remote Similarity NPC477756
0.5612 Remote Similarity NPC477751
0.5607 Remote Similarity NPC81006
0.5603 Remote Similarity NPC313821
0.5603 Remote Similarity NPC189629

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC315036 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
0.9167 High Similarity NPD4838 Approved
0.9167 High Similarity NPD4837 Approved
0.9167 High Similarity NPD4835 Approved
0.9167 High Similarity NPD4836 Approved
0.8958 High Similarity NPD4282 Approved
0.8804 High Similarity NPD3201 Approved
0.8804 High Similarity NPD3208 Approved
0.8804 High Similarity NPD3207 Approved
0.8804 High Similarity NPD3209 Approved
0.8804 High Similarity NPD3203 Approved
0.8804 High Similarity NPD3202 Approved
0.8696 High Similarity NPD3200 Clinical (unspecified phase)
0.8617 High Similarity NPD5797 Approved
0.8617 High Similarity NPD5796 Clinical (unspecified phase)
0.8617 High Similarity NPD5798 Approved
0.8617 High Similarity NPD5794 Approved
0.8617 High Similarity NPD5795 Approved
0.8529 High Similarity NPD5376 Approved
0.8404 Intermediate Similarity NPD2698 Approved
0.8367 Intermediate Similarity NPD5381 Approved
0.8367 Intermediate Similarity NPD5378 Approved
0.8367 Intermediate Similarity NPD5377 Approved
0.8131 Intermediate Similarity NPD2690 Discontinued
0.7981 Intermediate Similarity NPD1449 Approved
0.7981 Intermediate Similarity NPD1450 Approved
0.787 Intermediate Similarity NPD35 Approved
0.787 Intermediate Similarity NPD4833 Approved
0.7736 Intermediate Similarity NPD2700 Approved
0.7658 Intermediate Similarity NPD3731 Phase 3
0.7522 Intermediate Similarity NPD4832 Approved
0.7522 Intermediate Similarity NPD4830 Approved
0.7522 Intermediate Similarity NPD4831 Approved
0.7288 Intermediate Similarity NPD6436 Phase 3
0.7281 Intermediate Similarity NPD3204 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD8045 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4826 Approved
0.7143 Intermediate Similarity NPD4827 Approved
0.7143 Intermediate Similarity NPD4828 Approved
0.6916 Remote Similarity NPD6428 Approved
0.6833 Remote Similarity NPD8345 Approved
0.6833 Remote Similarity NPD8346 Approved
0.6833 Remote Similarity NPD8347 Approved
0.681 Remote Similarity NPD6429 Approved
0.681 Remote Similarity NPD6430 Approved
0.6783 Remote Similarity NPD8087 Discontinued
0.6696 Remote Similarity NPD6941 Approved
0.663 Remote Similarity NPD9032 Approved
0.663 Remote Similarity NPD9033 Approved
0.663 Remote Similarity NPD9030 Approved
0.663 Remote Similarity NPD9031 Approved
0.6613 Remote Similarity NPD577 Phase 3
0.6613 Remote Similarity NPD591 Approved
0.6392 Remote Similarity NPD9034 Approved
0.6392 Remote Similarity NPD67 Phase 2
0.6379 Remote Similarity NPD8307 Discontinued
0.6355 Remote Similarity NPD3716 Discontinued
0.6316 Remote Similarity NPD7141 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7140 Approved
0.6316 Remote Similarity NPD7139 Approved
0.6286 Remote Similarity NPD394 Phase 3
0.625 Remote Similarity NPD9445 Approved
0.6239 Remote Similarity NPD8140 Approved
0.6139 Remote Similarity NPD9434 Approved
0.6139 Remote Similarity NPD9435 Approved
0.605 Remote Similarity NPD8174 Phase 2
0.6 Remote Similarity NPD882 Phase 2
0.6 Remote Similarity NPD883 Phase 2
0.5983 Remote Similarity NPD8275 Approved
0.5983 Remote Similarity NPD8276 Approved
0.5965 Remote Similarity NPD881 Approved
0.5897 Remote Similarity NPD8084 Approved
0.5897 Remote Similarity NPD8139 Approved
0.5897 Remote Similarity NPD8086 Approved
0.5897 Remote Similarity NPD8085 Approved
0.5897 Remote Similarity NPD8083 Approved
0.5897 Remote Similarity NPD8138 Approved
0.5897 Remote Similarity NPD8082 Approved
0.5893 Remote Similarity NPD1447 Phase 3
0.5893 Remote Similarity NPD1446 Phase 3
0.5882 Remote Similarity NPD372 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8393 Approved
0.5872 Remote Similarity NPD4759 Clinical (unspecified phase)
0.5851 Remote Similarity NPD9029 Phase 3
0.5851 Remote Similarity NPD9028 Phase 2
0.5851 Remote Similarity NPD9027 Phase 3
0.5851 Remote Similarity NPD9026 Phase 2
0.5806 Remote Similarity NPD9240 Approved
0.5806 Remote Similarity NPD9239 Approved
0.5798 Remote Similarity NPD8081 Approved
0.5776 Remote Similarity NPD2255 Approved
0.5745 Remote Similarity NPD6123 Approved
0.5738 Remote Similarity NPD8305 Approved
0.5738 Remote Similarity NPD8306 Approved
0.5676 Remote Similarity NPD618 Clinical (unspecified phase)
0.5662 Remote Similarity NPD8449 Approved
0.5644 Remote Similarity NPD6704 Discontinued
0.562 Remote Similarity NPD8450 Suspended
0.5603 Remote Similarity NPD3190 Approved
0.5603 Remote Similarity NPD3191 Approved
0.5603 Remote Similarity NPD3189 Approved

Structure

External Identifiers

PubChem CID   3081545
ChEMBL   CHEMBL1230961
ZINC  

Physicochemical Properties

Molecular Weight:  539.28
ALogP:  -7.7234
MLogP:  2.01
XLogP:  -4.994
# Rotatable Bonds:  17
Polar Surface Area:  283.64
# H-Bond Aceptor:  16
# H-Bond Donor:  11
# Rings:  4
# Heavy Atoms:  37

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Similar NPs/Drugs