Natural Product: NPC476939

Natural Product ID:  NPC476939
Common Name:   n.a.
IUPAC Name:  
Synonyms:  
Molecular Formula:   C23H26O8
Standard InCHIKey:  HTVMZRDDOHBSER-WIDHOSKQSA-N
Standard InCHI:  InChI=1S/C23H26O8/c1-12-9-18(29-13(2)24)23-15(19(25)27-3)5-4-6-17(23)22(12)10-16(14-7-8-28-11-14)30-21(22)31-20(23)26/h5,7-8,11,16-18,20-21,26H,1,4,6,9-10H2,2-3H3/t16-,17+,18+,20+,21+,22+,23+/m1/s1
Canonical SMILES:  COC(=O)C1=CCC[C@@H]2[C@]31[C@@H](O)O[C@H]1[C@]2(C(=C)C[C@@H]3OC(=O)C)C[C@@H](O1)c1cocc1
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
NPO33579 Croton laui Species Euphorbiaceae Eukaryota Twigs Hainan Province, China PMID[24735527]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 >= 10000 nM 24735527
NPT168 Cell Line P388 Mus musculus IC50 >= 10000 nM 24735527
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 150000 nM 24735527
NPT1277 Organism Staphylococcus epidermidis ATCC 12228 Staphylococcus epidermidis ATCC 12228 MIC > 150000 nM 24735527
NPT2 Others Unspecified MIC > 150000 nM 24735527
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 150000 nM 24735527
NPT19 Organism Escherichia coli Escherichia coli MIC > 150000 nM 24735527
NPT2909 Organism Shigella flexneri Shigella flexneri MIC > 150000 nM 24735527
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 150000 nM 24735527
NPT20 Organism Candida albicans Candida albicans MIC > 150000 nM 24735527
NPT1533 Organism Saccharomyces Saccharomyces MIC > 150000 nM 24735527
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC > 150000 nM 24735527
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC > 150000 nM 24735527

  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 NPC476939 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
1.0 High Similarity NPC476940
0.9653 High Similarity NPC476938
0.9653 High Similarity NPC476937
0.9586 High Similarity NPC476941
0.9586 High Similarity NPC476942
0.9324 High Similarity NPC476936
0.932 High Similarity NPC7388
0.929 High Similarity NPC100333
0.9281 High Similarity NPC211777
0.9221 High Similarity NPC198047
0.92 High Similarity NPC147168
0.9139 High Similarity NPC57998
0.9122 High Similarity NPC250228
0.9114 High Similarity NPC160818
0.9114 High Similarity NPC169299
0.9073 High Similarity NPC469503
0.9051 High Similarity NPC82602
0.9032 High Similarity NPC207978
0.9026 High Similarity NPC262872
0.9 High Similarity NPC195325
0.8981 High Similarity NPC97574
0.8981 High Similarity NPC93172
0.8961 High Similarity NPC472777
0.8961 High Similarity NPC472778
0.8961 High Similarity NPC472776
0.8954 High Similarity NPC469336
0.8954 High Similarity NPC44675
0.8954 High Similarity NPC214541
0.8954 High Similarity NPC35000
0.8926 High Similarity NPC346
0.8903 High Similarity NPC307383
0.8889 High Similarity NPC178932
0.8889 High Similarity NPC30222
0.8867 High Similarity NPC10088
0.8854 High Similarity NPC419
0.8851 High Similarity NPC223415
0.8839 High Similarity NPC36655
0.8839 High Similarity NPC261597
0.8836 High Similarity NPC90953
0.8828 High Similarity NPC186626
0.88 High Similarity NPC276676
0.8792 High Similarity NPC476944
0.8782 High Similarity NPC475967
0.8766 High Similarity NPC282445
0.875 High Similarity NPC472654
0.8742 High Similarity NPC221809
0.8718 High Similarity NPC187149
0.8718 High Similarity NPC472772
0.8718 High Similarity NPC299038
0.8712 High Similarity NPC262386
0.871 High Similarity NPC264943
0.8701 High Similarity NPC75906
0.8699 High Similarity NPC470742
0.8693 High Similarity NPC159927
0.8693 High Similarity NPC469335
0.8679 High Similarity NPC146991
0.8679 High Similarity NPC470182
0.8671 High Similarity NPC69028
0.8667 High Similarity NPC251865
0.8625 High Similarity NPC472141
0.8625 High Similarity NPC214600
0.8618 High Similarity NPC470941
0.8616 High Similarity NPC472139
0.8616 High Similarity NPC165218
0.8608 High Similarity NPC477402
0.86 High Similarity NPC470741
0.8599 High Similarity NPC249021
0.8599 High Similarity NPC45101
0.8591 High Similarity NPC20500
0.8571 High Similarity NPC476850
0.8571 High Similarity NPC476861
0.8571 High Similarity NPC476122
0.8571 High Similarity NPC472651
0.8571 High Similarity NPC310830
0.8562 High Similarity NPC123088
0.8562 High Similarity NPC92941
0.8562 High Similarity NPC276551
0.8553 High Similarity NPC5079
0.8553 High Similarity NPC472771
0.8553 High Similarity NPC200782
0.8553 High Similarity NPC472767
0.8544 High Similarity NPC477403
0.8544 High Similarity NPC475226
0.8519 High Similarity NPC472652
0.8519 High Similarity NPC271235
0.8516 High Similarity NPC18135
0.8509 High Similarity NPC307781
0.8509 High Similarity NPC472670
0.8509 High Similarity NPC478178
0.8509 High Similarity NPC470875
0.85 High Similarity NPC51568
0.85 High Similarity NPC302369
0.85 High Similarity NPC292389
0.85 High Similarity NPC39986
0.85 High Similarity NPC477405
0.85 High Similarity NPC234660
0.85 High Similarity NPC469338
0.85 High Similarity NPC472773
0.85 High Similarity NPC134254
0.8497 Intermediate Similarity NPC471174
0.8491 Intermediate Similarity NPC335761
0.8491 Intermediate Similarity NPC472653
0.8487 Intermediate Similarity NPC41182
0.8477 Intermediate Similarity NPC267632
0.8471 Intermediate Similarity NPC469850
0.8462 Intermediate Similarity NPC476201
0.8462 Intermediate Similarity NPC472672
0.8452 Intermediate Similarity NPC196864
0.8452 Intermediate Similarity NPC477404
0.8447 Intermediate Similarity NPC469849
0.8447 Intermediate Similarity NPC476856
0.8447 Intermediate Similarity NPC470940
0.8447 Intermediate Similarity NPC271657
0.8447 Intermediate Similarity NPC476857
0.8447 Intermediate Similarity NPC476858
0.8447 Intermediate Similarity NPC472664
0.8443 Intermediate Similarity NPC470938
0.8438 Intermediate Similarity NPC82851
0.8438 Intermediate Similarity NPC117986
0.8438 Intermediate Similarity NPC149896
0.8428 Intermediate Similarity NPC474611
0.8421 Intermediate Similarity NPC137295
0.8414 Intermediate Similarity NPC61788
0.8411 Intermediate Similarity NPC121158
0.8408 Intermediate Similarity NPC237259
0.8408 Intermediate Similarity NPC302054
0.8408 Intermediate Similarity NPC98206
0.8408 Intermediate Similarity NPC253201
0.8408 Intermediate Similarity NPC34421
0.8405 Intermediate Similarity NPC472673
0.8405 Intermediate Similarity NPC471397
0.8395 Intermediate Similarity NPC23387
0.8389 Intermediate Similarity NPC220094
0.8389 Intermediate Similarity NPC476943
0.8385 Intermediate Similarity NPC663
0.8385 Intermediate Similarity NPC224394
0.8377 Intermediate Similarity NPC216755
0.8375 Intermediate Similarity NPC25255
0.8365 Intermediate Similarity NPC304692
0.8365 Intermediate Similarity NPC286722
0.8365 Intermediate Similarity NPC472283
0.8365 Intermediate Similarity NPC470118
0.8365 Intermediate Similarity NPC197137
0.8355 Intermediate Similarity NPC476946
0.8354 Intermediate Similarity NPC476262
0.8354 Intermediate Similarity NPC141538
0.8354 Intermediate Similarity NPC296807
0.8354 Intermediate Similarity NPC92979
0.8354 Intermediate Similarity NPC472660
0.8354 Intermediate Similarity NPC155939
0.8344 Intermediate Similarity NPC472775
0.8344 Intermediate Similarity NPC472282
0.8344 Intermediate Similarity NPC472764
0.8344 Intermediate Similarity NPC173516
0.8344 Intermediate Similarity NPC476853
0.8344 Intermediate Similarity NPC478179
0.8344 Intermediate Similarity NPC268905
0.8344 Intermediate Similarity NPC472774
0.8344 Intermediate Similarity NPC44577
0.8333 Intermediate Similarity NPC476860
0.8333 Intermediate Similarity NPC470997
0.8333 Intermediate Similarity NPC156189
0.8323 Intermediate Similarity NPC193798
0.8323 Intermediate Similarity NPC470792
0.8323 Intermediate Similarity NPC290400
0.8323 Intermediate Similarity NPC18347
0.8323 Intermediate Similarity NPC96443
0.8323 Intermediate Similarity NPC329938
0.8323 Intermediate Similarity NPC263432
0.8313 Intermediate Similarity NPC475295
0.8313 Intermediate Similarity NPC473473
0.8312 Intermediate Similarity NPC262198
0.8303 Intermediate Similarity NPC159232
0.8302 Intermediate Similarity NPC204663
0.8302 Intermediate Similarity NPC469485
0.8302 Intermediate Similarity NPC126723
0.8302 Intermediate Similarity NPC209364
0.8302 Intermediate Similarity NPC104736
0.8293 Intermediate Similarity NPC472766
0.8293 Intermediate Similarity NPC472765
0.8288 Intermediate Similarity NPC298190
0.8288 Intermediate Similarity NPC89133
0.8282 Intermediate Similarity NPC149945
0.828 Intermediate Similarity NPC471000
0.8278 Intermediate Similarity NPC67003
0.8272 Intermediate Similarity NPC469846
0.8269 Intermediate Similarity NPC470790
0.8269 Intermediate Similarity NPC470791
0.8269 Intermediate Similarity NPC125182
0.8269 Intermediate Similarity NPC69647
0.8269 Intermediate Similarity NPC211625
0.8267 Intermediate Similarity NPC236532
0.8264 Intermediate Similarity NPC319140
0.8264 Intermediate Similarity NPC95567
0.8261 Intermediate Similarity NPC470789
0.8261 Intermediate Similarity NPC305016
0.8258 Intermediate Similarity NPC255414
0.8255 Intermediate Similarity NPC146872
0.825 Intermediate Similarity NPC195131
0.825 Intermediate Similarity NPC470119

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476939 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
0.8354 Intermediate Similarity NPD5760 Phase 2
0.8354 Intermediate Similarity NPD5761 Phase 2
0.7836 Intermediate Similarity NPD6559 Discontinued
0.7714 Intermediate Similarity NPD8434 Phase 2
0.7711 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD4966 Approved
0.7381 Intermediate Similarity NPD4965 Approved
0.7381 Intermediate Similarity NPD4967 Phase 2
0.7365 Intermediate Similarity NPD7819 Suspended
0.7345 Intermediate Similarity NPD8313 Approved
0.7345 Intermediate Similarity NPD8312 Approved
0.7337 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD6765 Approved
0.733 Intermediate Similarity NPD6764 Approved
0.7299 Intermediate Similarity NPD3818 Discontinued
0.7296 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD920 Approved
0.7202 Intermediate Similarity NPD37 Approved
0.72 Intermediate Similarity NPD7228 Approved
0.7193 Intermediate Similarity NPD6234 Discontinued
0.7167 Intermediate Similarity NPD6785 Approved
0.7167 Intermediate Similarity NPD6784 Approved
0.716 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4628 Phase 3
0.7152 Intermediate Similarity NPD6273 Approved
0.7091 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2346 Discontinued
0.7065 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2799 Discontinued
0.7062 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD8455 Phase 2
0.7055 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7411 Suspended
0.7039 Intermediate Similarity NPD7240 Approved
0.7035 Intermediate Similarity NPD3749 Approved
0.7035 Intermediate Similarity NPD7075 Discontinued
0.7024 Intermediate Similarity NPD3226 Approved
0.7024 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7074 Phase 3
0.7011 Intermediate Similarity NPD7199 Phase 2
0.7006 Intermediate Similarity NPD7799 Discontinued
0.7 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2532 Approved
0.6988 Remote Similarity NPD2533 Approved
0.6988 Remote Similarity NPD2534 Approved
0.6975 Remote Similarity NPD6004 Phase 3
0.6975 Remote Similarity NPD6002 Phase 3
0.6975 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6005 Phase 3
0.697 Remote Similarity NPD643 Clinical (unspecified phase)
0.6966 Remote Similarity NPD7054 Approved
0.6954 Remote Similarity NPD5494 Approved
0.6951 Remote Similarity NPD3750 Approved
0.6927 Remote Similarity NPD7472 Approved
0.6919 Remote Similarity NPD5402 Approved
0.6919 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1551 Phase 2
0.6914 Remote Similarity NPD8127 Discontinued
0.6914 Remote Similarity NPD2935 Discontinued
0.6901 Remote Similarity NPD6801 Discontinued
0.6899 Remote Similarity NPD2313 Discontinued
0.689 Remote Similarity NPD7421 Clinical (unspecified phase)
0.689 Remote Similarity NPD2800 Approved
0.6889 Remote Similarity NPD6797 Phase 2
0.6885 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6884 Remote Similarity NPD8404 Phase 2
0.6882 Remote Similarity NPD4380 Phase 2
0.6882 Remote Similarity NPD6599 Discontinued
0.6879 Remote Similarity NPD6832 Phase 2
0.6879 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7768 Phase 2
0.6872 Remote Similarity NPD5844 Phase 1
0.686 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6852 Remote Similarity NPD3748 Approved
0.6851 Remote Similarity NPD7251 Discontinued
0.6851 Remote Similarity NPD7685 Pre-registration
0.6836 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6829 Remote Similarity NPD970 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1549 Phase 2
0.6826 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7458 Discontinued
0.6813 Remote Similarity NPD7808 Phase 3
0.681 Remote Similarity NPD2796 Approved
0.6805 Remote Similarity NPD5403 Approved
0.6805 Remote Similarity NPD6980 Clinical (unspecified phase)
0.68 Remote Similarity NPD919 Approved
0.6798 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6795 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6788 Remote Similarity NPD1243 Approved
0.6786 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6786 Remote Similarity NPD5401 Approved
0.677 Remote Similarity NPD1933 Approved
0.6768 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6752 Remote Similarity NPD2798 Approved
0.6748 Remote Similarity NPD7033 Discontinued
0.6726 Remote Similarity NPD6799 Approved
0.6724 Remote Similarity NPD3817 Phase 2
0.6723 Remote Similarity NPD6959 Discontinued
0.6722 Remote Similarity NPD3751 Discontinued
0.671 Remote Similarity NPD9717 Approved
0.6705 Remote Similarity NPD1934 Approved
0.6701 Remote Similarity NPD7435 Discontinued
0.6688 Remote Similarity NPD2797 Approved
0.6687 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6687 Remote Similarity NPD7097 Phase 1
0.6687 Remote Similarity NPD3764 Approved
0.6685 Remote Similarity NPD6232 Discontinued
0.6684 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1471 Phase 3
0.6667 Remote Similarity NPD7473 Discontinued
0.6667 Remote Similarity NPD2344 Approved
0.6667 Remote Similarity NPD1653 Approved
0.6667 Remote Similarity NPD447 Suspended
0.6647 Remote Similarity NPD7003 Approved
0.6646 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6777 Approved
0.6632 Remote Similarity NPD6780 Approved
0.6632 Remote Similarity NPD6779 Approved
0.6632 Remote Similarity NPD6778 Approved
0.6632 Remote Similarity NPD6776 Approved
0.6632 Remote Similarity NPD6782 Approved
0.6632 Remote Similarity NPD6781 Approved
0.6629 Remote Similarity NPD1247 Approved
0.6625 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6611 Remote Similarity NPD6166 Phase 2
0.6611 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6611 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6605 Remote Similarity NPD4140 Approved
0.6603 Remote Similarity NPD1608 Approved
0.6593 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6592 Remote Similarity NPD5710 Approved
0.6592 Remote Similarity NPD3787 Discontinued
0.6592 Remote Similarity NPD5711 Approved
0.6592 Remote Similarity NPD7229 Phase 3
0.6591 Remote Similarity NPD3882 Suspended
0.659 Remote Similarity NPD7028 Phase 2
0.6588 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6584 Remote Similarity NPD3268 Approved
0.6584 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6582 Remote Similarity NPD1203 Approved
0.6568 Remote Similarity NPD7236 Approved
0.6564 Remote Similarity NPD5124 Phase 1
0.6564 Remote Similarity NPD6355 Discontinued
0.6564 Remote Similarity NPD6823 Phase 2
0.6564 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6559 Remote Similarity NPD8407 Phase 2
0.6552 Remote Similarity NPD7615 Clinical (unspecified phase)
0.655 Remote Similarity NPD7783 Phase 2
0.655 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6545 Remote Similarity NPD4308 Phase 3
0.6545 Remote Similarity NPD1510 Phase 2
0.6541 Remote Similarity NPD1019 Discontinued
0.6538 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1091 Approved
0.6535 Remote Similarity NPD7930 Approved
0.6531 Remote Similarity NPD7696 Phase 3
0.6531 Remote Similarity NPD7698 Approved
0.6531 Remote Similarity NPD7697 Approved
0.6531 Remote Similarity NPD7680 Approved
0.6528 Remote Similarity NPD4420 Approved
0.6522 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6509 Remote Similarity NPD2309 Approved
0.6506 Remote Similarity NPD6100 Approved
0.6506 Remote Similarity NPD6099 Approved
0.6503 Remote Similarity NPD7966 Clinical (unspecified phase)
0.65 Remote Similarity NPD7874 Approved
0.65 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6497 Remote Similarity NPD7870 Phase 2
0.6497 Remote Similarity NPD7871 Phase 2
0.6495 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6489 Remote Similarity NPD8150 Discontinued
0.6486 Remote Similarity NPD8368 Discontinued
0.6481 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6481 Remote Similarity NPD411 Approved
0.6477 Remote Similarity NPD1465 Phase 2
0.6477 Remote Similarity NPD2801 Approved
0.6474 Remote Similarity NPD7239 Suspended
0.6467 Remote Similarity NPD7266 Discontinued
0.6464 Remote Similarity NPD3926 Phase 2
0.645 Remote Similarity NPD8151 Discontinued
0.645 Remote Similarity NPD4110 Phase 3
0.645 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6442 Remote Similarity NPD8032 Phase 2
0.6438 Remote Similarity NPD5647 Approved
0.6432 Remote Similarity NPD5953 Discontinued
0.6429 Remote Similarity NPD2424 Discontinued
0.6424 Remote Similarity NPD6651 Approved
0.642 Remote Similarity NPD6844 Discontinued
0.6414 Remote Similarity NPD8320 Phase 1
0.6414 Remote Similarity NPD8319 Approved
0.641 Remote Similarity NPD1778 Approved
0.641 Remote Similarity NPD17 Approved
0.6409 Remote Similarity NPD6808 Phase 2

Structure

External Identifiers

PubChem CID   90676777
ChEMBL   CHEMBL3263393
ZINC  

Physicochemical Properties

Molecular Weight:  430.16
ALogP:  -0.2794
MLogP:  3.11
XLogP:  1.039
# Rotatable Bonds:  8
Polar Surface Area:  104.43
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  31

Download Data

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Biological Activities  
Similar NPs/Drugs