Natural Product: NPC201191

Natural Product ID:  NPC201191
Common Name:   Fraxinuacidoside
IUPAC Name:   (Z)-2-methyl-3-[(2R,3S)-5-methyl-3-[(5S)-2,6,6-trimethyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexen-1-yl]-3,6-dihydro-2H-pyran-2-yl]prop-2-enoic acid
Synonyms:   fraxinuacidoside
Molecular Formula:   C25H38O9
Standard InCHIKey:  FZWWJIXYNHHIJI-OFULADLDSA-N
Standard InCHI:  InChI=1S/C25H38O9/c1-12-8-15(16(32-11-12)9-14(3)23(30)31)19-13(2)6-7-18(25(19,4)5)34-24-22(29)21(28)20(27)17(10-26)33-24/h8-9,15-18,20-22,24,26-29H,6-7,10-11H2,1-5H3,(H,30,31)/b14-9-/t15-,16-,17-,18+,20-,21+,22-,24+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@H]2CCC(=C(C2(C)C)[C@@H]2C=C(C)CO[C@@H]2/C=C(C(=O)O)/C)C)[C@@H]([C@H]([C@@H]1O)O)O
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
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota Stem barks PMID[17461599]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell Line A2780 Homo sapiens IC50 > 5000 nM 10.6019/CHEMBL1201861
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 5000 nM 10.6019/CHEMBL1201861
NPT81 Cell Line A549 Homo sapiens IC50 > 5000 nM 10.6019/CHEMBL1201861
NPT1084 Subcellular Liver microsomes Rattus norvegicus IC50 > 10000 nM 26222905

  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 NPC201191 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
0.8947 High Similarity NPC472195
0.8947 High Similarity NPC238090
0.8947 High Similarity NPC472196
0.8854 High Similarity NPC159698
0.8725 High Similarity NPC82251
0.87 High Similarity NPC198992
0.8679 High Similarity NPC264153
0.8614 High Similarity NPC121423
0.8544 High Similarity NPC239961
0.8505 High Similarity NPC473159
0.8485 Intermediate Similarity NPC143446
0.8462 Intermediate Similarity NPC472390
0.8454 Intermediate Similarity NPC477749
0.8447 Intermediate Similarity NPC470768
0.8411 Intermediate Similarity NPC470025
0.8411 Intermediate Similarity NPC328074
0.8411 Intermediate Similarity NPC317460
0.8411 Intermediate Similarity NPC321272
0.8381 Intermediate Similarity NPC177524
0.8381 Intermediate Similarity NPC392
0.8381 Intermediate Similarity NPC219900
0.8378 Intermediate Similarity NPC48692
0.8351 Intermediate Similarity NPC202886
0.8349 Intermediate Similarity NPC207637
0.8333 Intermediate Similarity NPC470027
0.8318 Intermediate Similarity NPC17791
0.8317 Intermediate Similarity NPC477928
0.8304 Intermediate Similarity NPC476204
0.8304 Intermediate Similarity NPC170084
0.8288 Intermediate Similarity NPC470914
0.8283 Intermediate Similarity NPC256368
0.8257 Intermediate Similarity NPC181145
0.8247 Intermediate Similarity NPC477748
0.8224 Intermediate Similarity NPC83005
0.8224 Intermediate Similarity NPC316708
0.8218 Intermediate Similarity NPC155319
0.8218 Intermediate Similarity NPC91197
0.8218 Intermediate Similarity NPC96597
0.8218 Intermediate Similarity NPC239547
0.8218 Intermediate Similarity NPC125551
0.8218 Intermediate Similarity NPC309503
0.8208 Intermediate Similarity NPC48548
0.8208 Intermediate Similarity NPC135015
0.8208 Intermediate Similarity NPC217921
0.8208 Intermediate Similarity NPC470024
0.8208 Intermediate Similarity NPC128795
0.8198 Intermediate Similarity NPC470515
0.8198 Intermediate Similarity NPC234522
0.819 Intermediate Similarity NPC470763
0.819 Intermediate Similarity NPC85670
0.819 Intermediate Similarity NPC470767
0.8173 Intermediate Similarity NPC197736
0.8165 Intermediate Similarity NPC293658
0.8165 Intermediate Similarity NPC474410
0.8165 Intermediate Similarity NPC311592
0.8165 Intermediate Similarity NPC75167
0.8155 Intermediate Similarity NPC57586
0.8155 Intermediate Similarity NPC2313
0.8155 Intermediate Similarity NPC475655
0.8155 Intermediate Similarity NPC280991
0.8155 Intermediate Similarity NPC471637
0.8155 Intermediate Similarity NPC154132
0.8155 Intermediate Similarity NPC475157
0.8148 Intermediate Similarity NPC470026
0.8137 Intermediate Similarity NPC40182
0.8137 Intermediate Similarity NPC198422
0.8131 Intermediate Similarity NPC206618
0.8131 Intermediate Similarity NPC316974
0.8131 Intermediate Similarity NPC257853
0.8131 Intermediate Similarity NPC40728
0.8125 Intermediate Similarity NPC470517
0.8125 Intermediate Similarity NPC470911
0.8125 Intermediate Similarity NPC470915
0.8113 Intermediate Similarity NPC88013
0.8113 Intermediate Similarity NPC109376
0.8113 Intermediate Similarity NPC125423
0.8108 Intermediate Similarity NPC473968
0.8108 Intermediate Similarity NPC474483
0.8108 Intermediate Similarity NPC203862
0.8105 Intermediate Similarity NPC266718
0.81 Intermediate Similarity NPC294293
0.8081 Intermediate Similarity NPC472197
0.8081 Intermediate Similarity NPC472199
0.8073 Intermediate Similarity NPC174836
0.8058 Intermediate Similarity NPC64348
0.8039 Intermediate Similarity NPC240372
0.8037 Intermediate Similarity NPC475263
0.8037 Intermediate Similarity NPC311223
0.8037 Intermediate Similarity NPC224660
0.8037 Intermediate Similarity NPC38948
0.8021 Intermediate Similarity NPC471494
0.8021 Intermediate Similarity NPC470124
0.8021 Intermediate Similarity NPC163606
0.8019 Intermediate Similarity NPC218158
0.8019 Intermediate Similarity NPC315070
0.8019 Intermediate Similarity NPC172867
0.8 Intermediate Similarity NPC7613
0.8 Intermediate Similarity NPC7644
0.8 Intermediate Similarity NPC127933
0.8 Intermediate Similarity NPC475889
0.8 Intermediate Similarity NPC281378
0.7982 Intermediate Similarity NPC233500
0.7982 Intermediate Similarity NPC202051
0.7981 Intermediate Similarity NPC477717
0.798 Intermediate Similarity NPC3952
0.798 Intermediate Similarity NPC177668
0.7965 Intermediate Similarity NPC219656
0.7965 Intermediate Similarity NPC122971
0.7961 Intermediate Similarity NPC475653
0.7961 Intermediate Similarity NPC70733
0.7961 Intermediate Similarity NPC56071
0.7944 Intermediate Similarity NPC293512
0.7944 Intermediate Similarity NPC473586
0.7941 Intermediate Similarity NPC472995
0.7941 Intermediate Similarity NPC255410
0.7941 Intermediate Similarity NPC165632
0.7941 Intermediate Similarity NPC90583
0.7938 Intermediate Similarity NPC208473
0.7938 Intermediate Similarity NPC311163
0.7931 Intermediate Similarity NPC318135
0.7925 Intermediate Similarity NPC470321
0.7925 Intermediate Similarity NPC201880
0.7925 Intermediate Similarity NPC81567
0.7925 Intermediate Similarity NPC473207
0.7925 Intermediate Similarity NPC264867
0.7921 Intermediate Similarity NPC25701
0.7921 Intermediate Similarity NPC2003
0.7921 Intermediate Similarity NPC211238
0.7921 Intermediate Similarity NPC104925
0.7921 Intermediate Similarity NPC72817
0.7921 Intermediate Similarity NPC472198
0.7921 Intermediate Similarity NPC178949
0.7921 Intermediate Similarity NPC477927
0.7921 Intermediate Similarity NPC298973
0.7921 Intermediate Similarity NPC96736
0.7917 Intermediate Similarity NPC126518
0.7917 Intermediate Similarity NPC475035
0.7913 Intermediate Similarity NPC196130
0.7905 Intermediate Similarity NPC472552
0.7905 Intermediate Similarity NPC214277
0.7905 Intermediate Similarity NPC470571
0.7905 Intermediate Similarity NPC223834
0.7905 Intermediate Similarity NPC150463
0.7905 Intermediate Similarity NPC238397
0.7905 Intermediate Similarity NPC471363
0.79 Intermediate Similarity NPC302584
0.7895 Intermediate Similarity NPC476150
0.7895 Intermediate Similarity NPC470312
0.7895 Intermediate Similarity NPC476127
0.789 Intermediate Similarity NPC177047
0.789 Intermediate Similarity NPC119550
0.7885 Intermediate Similarity NPC477716
0.7885 Intermediate Similarity NPC477721
0.7881 Intermediate Similarity NPC245094
0.7879 Intermediate Similarity NPC133450
0.7876 Intermediate Similarity NPC218093
0.7876 Intermediate Similarity NPC473617
0.7876 Intermediate Similarity NPC291564
0.7876 Intermediate Similarity NPC473828
0.787 Intermediate Similarity NPC181994
0.7864 Intermediate Similarity NPC120299
0.7864 Intermediate Similarity NPC278506
0.7864 Intermediate Similarity NPC205143
0.7864 Intermediate Similarity NPC475332
0.7863 Intermediate Similarity NPC297950
0.7857 Intermediate Similarity NPC5311
0.7857 Intermediate Similarity NPC193382
0.7857 Intermediate Similarity NPC199428
0.7857 Intermediate Similarity NPC99620
0.7857 Intermediate Similarity NPC313658
0.7857 Intermediate Similarity NPC316138
0.7857 Intermediate Similarity NPC310341
0.7857 Intermediate Similarity NPC475037
0.785 Intermediate Similarity NPC476740
0.785 Intermediate Similarity NPC476738
0.785 Intermediate Similarity NPC88349
0.7843 Intermediate Similarity NPC108141
0.7843 Intermediate Similarity NPC469543
0.7843 Intermediate Similarity NPC300710
0.7833 Intermediate Similarity NPC231240
0.783 Intermediate Similarity NPC134270
0.783 Intermediate Similarity NPC284929
0.783 Intermediate Similarity NPC309398
0.783 Intermediate Similarity NPC118761
0.783 Intermediate Similarity NPC151516
0.783 Intermediate Similarity NPC197541
0.783 Intermediate Similarity NPC473123
0.783 Intermediate Similarity NPC267869
0.783 Intermediate Similarity NPC234304
0.783 Intermediate Similarity NPC473124
0.7826 Intermediate Similarity NPC129434
0.7822 Intermediate Similarity NPC61201
0.7822 Intermediate Similarity NPC474835
0.7822 Intermediate Similarity NPC91654
0.7822 Intermediate Similarity NPC320089
0.7822 Intermediate Similarity NPC67398
0.7822 Intermediate Similarity NPC474792
0.7815 Intermediate Similarity NPC476966
0.781 Intermediate Similarity NPC11974
0.781 Intermediate Similarity NPC472554

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC201191 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
0.8381 Intermediate Similarity NPD6686 Approved
0.7961 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD7503 Approved
0.78 Intermediate Similarity NPD46 Approved
0.78 Intermediate Similarity NPD6698 Approved
0.7719 Intermediate Similarity NPD7327 Approved
0.7719 Intermediate Similarity NPD7328 Approved
0.7672 Intermediate Similarity NPD8033 Approved
0.7652 Intermediate Similarity NPD7516 Approved
0.7624 Intermediate Similarity NPD7838 Discovery
0.7586 Intermediate Similarity NPD8377 Approved
0.7586 Intermediate Similarity NPD8294 Approved
0.7521 Intermediate Similarity NPD8378 Approved
0.7521 Intermediate Similarity NPD8513 Phase 3
0.7521 Intermediate Similarity NPD8296 Approved
0.7521 Intermediate Similarity NPD8380 Approved
0.7521 Intermediate Similarity NPD8335 Approved
0.7521 Intermediate Similarity NPD8379 Approved
0.7477 Intermediate Similarity NPD5344 Discontinued
0.7453 Intermediate Similarity NPD4225 Approved
0.7417 Intermediate Similarity NPD7507 Approved
0.7373 Intermediate Similarity NPD8515 Approved
0.7373 Intermediate Similarity NPD8516 Approved
0.7373 Intermediate Similarity NPD8517 Approved
0.7345 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6412 Phase 2
0.7236 Intermediate Similarity NPD7319 Approved
0.7222 Intermediate Similarity NPD7640 Approved
0.7222 Intermediate Similarity NPD7639 Approved
0.7168 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD7638 Approved
0.7107 Intermediate Similarity NPD8328 Phase 3
0.7069 Intermediate Similarity NPD8133 Approved
0.7064 Intermediate Similarity NPD6648 Approved
0.7034 Intermediate Similarity NPD7115 Discovery
0.6891 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7983 Approved
0.687 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7830 Approved
0.6829 Remote Similarity NPD7829 Approved
0.681 Remote Similarity NPD6371 Approved
0.68 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6637 Remote Similarity NPD7632 Discontinued
0.6614 Remote Similarity NPD7736 Approved
0.6613 Remote Similarity NPD6370 Approved
0.6574 Remote Similarity NPD6411 Approved
0.6574 Remote Similarity NPD7637 Suspended
0.656 Remote Similarity NPD7642 Approved
0.6557 Remote Similarity NPD7641 Discontinued
0.6555 Remote Similarity NPD6053 Discontinued
0.6555 Remote Similarity NPD6882 Approved
0.6552 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6535 Remote Similarity NPD8293 Discontinued
0.6508 Remote Similarity NPD7492 Approved
0.6486 Remote Similarity NPD7839 Suspended
0.6475 Remote Similarity NPD6009 Approved
0.6457 Remote Similarity NPD6616 Approved
0.6452 Remote Similarity NPD6054 Approved
0.6452 Remote Similarity NPD6319 Approved
0.6417 Remote Similarity NPD8297 Approved
0.641 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6406 Remote Similarity NPD7078 Approved
0.64 Remote Similarity NPD8444 Approved
0.6389 Remote Similarity NPD6101 Approved
0.6389 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4632 Approved
0.6356 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6355 Remote Similarity NPD7524 Approved
0.633 Remote Similarity NPD5785 Approved
0.6328 Remote Similarity NPD8451 Approved
0.632 Remote Similarity NPD6059 Approved
0.6306 Remote Similarity NPD7748 Approved
0.6299 Remote Similarity NPD6067 Discontinued
0.6283 Remote Similarity NPD7902 Approved
0.6279 Remote Similarity NPD8448 Approved
0.6273 Remote Similarity NPD7515 Phase 2
0.627 Remote Similarity NPD6016 Approved
0.627 Remote Similarity NPD6015 Approved
0.626 Remote Similarity NPD8390 Approved
0.626 Remote Similarity NPD8392 Approved
0.626 Remote Similarity NPD8391 Approved
0.625 Remote Similarity NPD8299 Approved
0.625 Remote Similarity NPD8342 Approved
0.625 Remote Similarity NPD8341 Approved
0.625 Remote Similarity NPD8340 Approved
0.6226 Remote Similarity NPD7338 Clinical (unspecified phase)
0.622 Remote Similarity NPD5988 Approved
0.6218 Remote Similarity NPD6881 Approved
0.6218 Remote Similarity NPD6899 Approved
0.6216 Remote Similarity NPD6399 Phase 3
0.6212 Remote Similarity NPD7260 Phase 2
0.6204 Remote Similarity NPD4251 Approved
0.6204 Remote Similarity NPD4250 Approved
0.6198 Remote Similarity NPD6649 Approved
0.6198 Remote Similarity NPD6650 Approved
0.619 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6187 Remote Similarity NPD7266 Discontinued
0.6186 Remote Similarity NPD6675 Approved
0.6186 Remote Similarity NPD6402 Approved
0.6186 Remote Similarity NPD7128 Approved
0.6186 Remote Similarity NPD5739 Approved
0.617 Remote Similarity NPD7625 Phase 1
0.6167 Remote Similarity NPD6373 Approved
0.6167 Remote Similarity NPD6372 Approved
0.6154 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6139 Remote Similarity NPD8264 Approved
0.6134 Remote Similarity NPD5697 Approved
0.6132 Remote Similarity NPD6695 Phase 3
0.6132 Remote Similarity NPD6110 Phase 1
0.6132 Remote Similarity NPD7154 Phase 3
0.6116 Remote Similarity NPD7290 Approved
0.6116 Remote Similarity NPD7102 Approved
0.6116 Remote Similarity NPD6883 Approved
0.6111 Remote Similarity NPD4249 Approved
0.6106 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7320 Approved
0.608 Remote Similarity NPD7500 Approved
0.6066 Remote Similarity NPD6617 Approved
0.6066 Remote Similarity NPD6869 Approved
0.6066 Remote Similarity NPD8130 Phase 1
0.6066 Remote Similarity NPD6847 Approved
0.6066 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6047 Remote Similarity NPD7604 Phase 2
0.6036 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6033 Remote Similarity NPD6012 Approved
0.6033 Remote Similarity NPD6014 Approved
0.6033 Remote Similarity NPD6013 Approved
0.6029 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6019 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6019 Remote Similarity NPD1694 Approved
0.6018 Remote Similarity NPD7900 Approved
0.6018 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6016 Remote Similarity NPD5983 Phase 2
0.6016 Remote Similarity NPD6429 Approved
0.6016 Remote Similarity NPD6430 Approved
0.6 Remote Similarity NPD4821 Approved
0.6 Remote Similarity NPD6083 Phase 2
0.6 Remote Similarity NPD6084 Phase 2
0.6 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD4822 Approved
0.6 Remote Similarity NPD4819 Approved
0.6 Remote Similarity NPD4820 Approved
0.6 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5985 Remote Similarity NPD7966 Clinical (unspecified phase)
0.598 Remote Similarity NPD8039 Approved
0.5969 Remote Similarity NPD8080 Discontinued
0.5962 Remote Similarity NPD4268 Approved
0.5962 Remote Similarity NPD4271 Approved
0.5954 Remote Similarity NPD6336 Discontinued
0.5952 Remote Similarity NPD7505 Discontinued
0.5952 Remote Similarity NPD8137 Clinical (unspecified phase)
0.595 Remote Similarity NPD6011 Approved
0.5946 Remote Similarity NPD6051 Approved
0.5932 Remote Similarity NPD5211 Phase 2
0.5926 Remote Similarity NPD6845 Suspended
0.5917 Remote Similarity NPD6640 Phase 3
0.5917 Remote Similarity NPD6008 Approved
0.5913 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7750 Discontinued
0.5905 Remote Similarity NPD6929 Approved
0.5905 Remote Similarity NPD7645 Phase 2
0.59 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5893 Remote Similarity NPD3168 Discontinued
0.5891 Remote Similarity NPD6921 Approved
0.5882 Remote Similarity NPD1407 Approved
0.5877 Remote Similarity NPD5282 Discontinued
0.5876 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5872 Remote Similarity NPD5363 Approved
0.5865 Remote Similarity NPD5776 Phase 2
0.5865 Remote Similarity NPD8336 Approved
0.5865 Remote Similarity NPD6925 Approved
0.5865 Remote Similarity NPD8337 Approved
0.5865 Remote Similarity NPD6033 Approved
0.5854 Remote Similarity NPD6421 Discontinued
0.5854 Remote Similarity NPD4634 Approved
0.5849 Remote Similarity NPD6931 Approved
0.5849 Remote Similarity NPD6930 Phase 2
0.5849 Remote Similarity NPD7332 Phase 2
0.5849 Remote Similarity NPD7514 Phase 3
0.5841 Remote Similarity NPD6079 Approved
0.5839 Remote Similarity NPD8415 Approved
0.5833 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5362 Discontinued
0.5833 Remote Similarity NPD5141 Approved
0.5833 Remote Similarity NPD3669 Approved
0.5833 Remote Similarity NPD8273 Phase 1
0.5826 Remote Similarity NPD5695 Phase 3
0.5818 Remote Similarity NPD6684 Approved
0.5818 Remote Similarity NPD7521 Approved
0.5818 Remote Similarity NPD7334 Approved
0.5818 Remote Similarity NPD7146 Approved
0.5818 Remote Similarity NPD5330 Approved
0.5818 Remote Similarity NPD3618 Phase 1
0.5818 Remote Similarity NPD6409 Approved
0.581 Remote Similarity NPD7145 Approved

Structure

External Identifiers

PubChem CID   16681233
ChEMBL   CHEMBL224070
ZINC  

Physicochemical Properties

Molecular Weight:  482.25
ALogP:  0.511
MLogP:  3.22
XLogP:  0.044
# Rotatable Bonds:  16
Polar Surface Area:  145.91
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  34

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs