Natural Product: NPC476661

Natural Product ID:  NPC476661
Common Name:   Kipukasin A
IUPAC Name:   [(2R,3R,4S,5S)-4-acetyloxy-5-[(2,4-dioxopyrimidin-1-yl)methyl]-2-(hydroxymethyl)oxolan-3-yl] 2,4-dimethoxy-6-methylbenzoate
Synonyms:  
Molecular Formula:   C22H26N2O10
Standard InCHIKey:  ZTGGVKXNOBHWBN-ACZWYYKOSA-N
Standard InCHI:  InChI=1S/C22H26N2O10/c1-11-7-13(30-3)8-14(31-4)18(11)21(28)34-20-16(10-25)33-15(19(20)32-12(2)26)9-24-6-5-17(27)23-22(24)29/h5-8,15-16,19-20,25H,9-10H2,1-4H3,(H,23,27,29)/t15-,16+,19-,20+/m0/s1
Canonical SMILES:  OC[C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)c1c(C)cc(cc1OC)OC)OC(=O)C)Cn1ccc(nc1=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
NPO15067 Aspergillus versicolor Species Aspergillaceae Eukaryota isolated from the surface of a basidioma of Gandoderma australe found growing on a living tree in a montane mesic forest Kipuka Pauula (Bird Park), Volcanoes National Park, Hawaii PMID[17608440]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 18 mm 17608440

  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 NPC476661 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
0.9944 High Similarity NPC476662
0.798 Intermediate Similarity NPC286135
0.7895 Intermediate Similarity NPC477816
0.7833 Intermediate Similarity NPC240768
0.7833 Intermediate Similarity NPC200773
0.7789 Intermediate Similarity NPC309692
0.7778 Intermediate Similarity NPC83019
0.7772 Intermediate Similarity NPC18306
0.7735 Intermediate Similarity NPC215921
0.7735 Intermediate Similarity NPC70016
0.7727 Intermediate Similarity NPC204580
0.7672 Intermediate Similarity NPC129578
0.7659 Intermediate Similarity NPC293347
0.764 Intermediate Similarity NPC210425
0.764 Intermediate Similarity NPC280404
0.764 Intermediate Similarity NPC277426
0.764 Intermediate Similarity NPC86373
0.7617 Intermediate Similarity NPC473562
0.7602 Intermediate Similarity NPC469437
0.7598 Intermediate Similarity NPC80472
0.7582 Intermediate Similarity NPC469670
0.7582 Intermediate Similarity NPC469619
0.7562 Intermediate Similarity NPC313453
0.7561 Intermediate Similarity NPC79130
0.7528 Intermediate Similarity NPC474385
0.7527 Intermediate Similarity NPC77679
0.7527 Intermediate Similarity NPC84935
0.7527 Intermediate Similarity NPC190020
0.7514 Intermediate Similarity NPC210320
0.7513 Intermediate Similarity NPC329816
0.7512 Intermediate Similarity NPC314946
0.7512 Intermediate Similarity NPC475768
0.7487 Intermediate Similarity NPC279732
0.7487 Intermediate Similarity NPC94499
0.7486 Intermediate Similarity NPC179178
0.7486 Intermediate Similarity NPC51106
0.7473 Intermediate Similarity NPC73411
0.7473 Intermediate Similarity NPC215711
0.7473 Intermediate Similarity NPC150227
0.7472 Intermediate Similarity NPC158634
0.7433 Intermediate Similarity NPC246466
0.7432 Intermediate Similarity NPC476684
0.7432 Intermediate Similarity NPC237440
0.7432 Intermediate Similarity NPC270160
0.743 Intermediate Similarity NPC469579
0.7427 Intermediate Similarity NPC246303
0.7419 Intermediate Similarity NPC16082
0.7419 Intermediate Similarity NPC99381
0.7419 Intermediate Similarity NPC82592
0.7419 Intermediate Similarity NPC69043
0.7419 Intermediate Similarity NPC5674
0.7419 Intermediate Similarity NPC478230
0.7419 Intermediate Similarity NPC199926
0.7419 Intermediate Similarity NPC79998
0.7418 Intermediate Similarity NPC472036
0.7416 Intermediate Similarity NPC158472
0.7405 Intermediate Similarity NPC478224
0.7391 Intermediate Similarity NPC96501
0.7389 Intermediate Similarity NPC469542
0.7385 Intermediate Similarity NPC470847
0.7377 Intermediate Similarity NPC471641
0.7377 Intermediate Similarity NPC240253
0.7377 Intermediate Similarity NPC471642
0.7377 Intermediate Similarity NPC240622
0.7374 Intermediate Similarity NPC1704
0.7374 Intermediate Similarity NPC67650
0.7374 Intermediate Similarity NPC90411
0.7374 Intermediate Similarity NPC475730
0.7366 Intermediate Similarity NPC2173
0.7366 Intermediate Similarity NPC281477
0.7366 Intermediate Similarity NPC137301
0.7366 Intermediate Similarity NPC202771
0.7366 Intermediate Similarity NPC119818
0.7366 Intermediate Similarity NPC328700
0.7361 Intermediate Similarity NPC475442
0.736 Intermediate Similarity NPC32360
0.736 Intermediate Similarity NPC247409
0.736 Intermediate Similarity NPC475566
0.7358 Intermediate Similarity NPC329992
0.7354 Intermediate Similarity NPC472055
0.7348 Intermediate Similarity NPC184702
0.7348 Intermediate Similarity NPC470932
0.734 Intermediate Similarity NPC472889
0.7327 Intermediate Similarity NPC475624
0.7326 Intermediate Similarity NPC472890
0.7326 Intermediate Similarity NPC170189
0.7326 Intermediate Similarity NPC208173
0.7317 Intermediate Similarity NPC316164
0.7316 Intermediate Similarity NPC117985
0.7312 Intermediate Similarity NPC184284
0.7312 Intermediate Similarity NPC167903
0.7312 Intermediate Similarity NPC76041
0.7312 Intermediate Similarity NPC115249
0.731 Intermediate Similarity NPC206061
0.7308 Intermediate Similarity NPC472034
0.7308 Intermediate Similarity NPC83272
0.7306 Intermediate Similarity NPC283041
0.7302 Intermediate Similarity NPC470339
0.7297 Intermediate Similarity NPC472891
0.7293 Intermediate Similarity NPC472006
0.7292 Intermediate Similarity NPC191930
0.7287 Intermediate Similarity NPC227062
0.7286 Intermediate Similarity NPC14390
0.7281 Intermediate Similarity NPC252156
0.7281 Intermediate Similarity NPC475292
0.7281 Intermediate Similarity NPC475565
0.7281 Intermediate Similarity NPC475349
0.7273 Intermediate Similarity NPC478231
0.7268 Intermediate Similarity NPC472033
0.7268 Intermediate Similarity NPC107625
0.7268 Intermediate Similarity NPC470357
0.7263 Intermediate Similarity NPC268052
0.7263 Intermediate Similarity NPC470358
0.726 Intermediate Similarity NPC314987
0.7254 Intermediate Similarity NPC20237
0.7253 Intermediate Similarity NPC27106
0.7249 Intermediate Similarity NPC473395
0.7249 Intermediate Similarity NPC26353
0.7249 Intermediate Similarity NPC478225
0.7247 Intermediate Similarity NPC135837
0.7241 Intermediate Similarity NPC308709
0.724 Intermediate Similarity NPC249181
0.7238 Intermediate Similarity NPC82913
0.7238 Intermediate Similarity NPC297985
0.7238 Intermediate Similarity NPC250755
0.7234 Intermediate Similarity NPC478221
0.7234 Intermediate Similarity NPC317585
0.7231 Intermediate Similarity NPC221792
0.7228 Intermediate Similarity NPC166583
0.7228 Intermediate Similarity NPC8817
0.7228 Intermediate Similarity NPC53362
0.7225 Intermediate Similarity NPC35345
0.7219 Intermediate Similarity NPC271681
0.7219 Intermediate Similarity NPC475116
0.7216 Intermediate Similarity NPC254053
0.7213 Intermediate Similarity NPC312789
0.7208 Intermediate Similarity NPC99723
0.7207 Intermediate Similarity NPC94248
0.7207 Intermediate Similarity NPC33144
0.7207 Intermediate Similarity NPC478200
0.7207 Intermediate Similarity NPC212693
0.7204 Intermediate Similarity NPC475460
0.7204 Intermediate Similarity NPC197125
0.7204 Intermediate Similarity NPC56204
0.7202 Intermediate Similarity NPC7752
0.7198 Intermediate Similarity NPC478202
0.7196 Intermediate Similarity NPC54928
0.7196 Intermediate Similarity NPC472050
0.7192 Intermediate Similarity NPC264938
0.7189 Intermediate Similarity NPC153417
0.7189 Intermediate Similarity NPC470359
0.7188 Intermediate Similarity NPC474858
0.7179 Intermediate Similarity NPC117713
0.7179 Intermediate Similarity NPC292213
0.7175 Intermediate Similarity NPC185031
0.7174 Intermediate Similarity NPC85734
0.7174 Intermediate Similarity NPC473023
0.7174 Intermediate Similarity NPC260946
0.7174 Intermediate Similarity NPC32058
0.7173 Intermediate Similarity NPC200594
0.7172 Intermediate Similarity NPC312630
0.7172 Intermediate Similarity NPC324220
0.7171 Intermediate Similarity NPC46744
0.7171 Intermediate Similarity NPC215098
0.7171 Intermediate Similarity NPC70290
0.7171 Intermediate Similarity NPC124302
0.7171 Intermediate Similarity NPC73020
0.7171 Intermediate Similarity NPC14622
0.717 Intermediate Similarity NPC92235
0.7166 Intermediate Similarity NPC228662
0.7166 Intermediate Similarity NPC473732
0.7158 Intermediate Similarity NPC478226
0.7158 Intermediate Similarity NPC66404
0.7158 Intermediate Similarity NPC95123
0.7156 Intermediate Similarity NPC470846
0.7151 Intermediate Similarity NPC70380
0.7143 Intermediate Similarity NPC257266
0.7143 Intermediate Similarity NPC16286
0.7143 Intermediate Similarity NPC473241
0.7143 Intermediate Similarity NPC279218
0.7143 Intermediate Similarity NPC108937
0.7143 Intermediate Similarity NPC314596
0.7143 Intermediate Similarity NPC471640
0.7143 Intermediate Similarity NPC471644
0.7135 Intermediate Similarity NPC96031
0.7135 Intermediate Similarity NPC182496
0.7135 Intermediate Similarity NPC137296
0.7135 Intermediate Similarity NPC180905
0.7135 Intermediate Similarity NPC202494
0.7135 Intermediate Similarity NPC69868
0.7135 Intermediate Similarity NPC92589
0.7135 Intermediate Similarity NPC317544
0.7129 Intermediate Similarity NPC169605
0.7128 Intermediate Similarity NPC472894
0.7128 Intermediate Similarity NPC256141
0.7128 Intermediate Similarity NPC473094
0.7128 Intermediate Similarity NPC295646
0.7128 Intermediate Similarity NPC471180
0.7128 Intermediate Similarity NPC249977
0.7128 Intermediate Similarity NPC273483

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476661 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
0.7806 Intermediate Similarity NPD3473 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5710 Approved
0.7647 Intermediate Similarity NPD5711 Approved
0.7565 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7565 Approved
0.7525 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD6863 Phase 2
0.7366 Intermediate Similarity NPD5006 Approved
0.7366 Intermediate Similarity NPD5005 Approved
0.7263 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD8469 Approved
0.7234 Intermediate Similarity NPD5353 Approved
0.723 Intermediate Similarity NPD7930 Approved
0.7225 Intermediate Similarity NPD6973 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD4360 Phase 2
0.7192 Intermediate Similarity NPD4363 Phase 3
0.7171 Intermediate Similarity NPD4420 Approved
0.7157 Intermediate Similarity NPD4361 Phase 2
0.7157 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD5242 Approved
0.7143 Intermediate Similarity NPD7583 Approved
0.7136 Intermediate Similarity NPD7811 Phase 3
0.7136 Intermediate Similarity NPD7810 Phase 3
0.7127 Intermediate Similarity NPD2654 Approved
0.712 Intermediate Similarity NPD2534 Approved
0.712 Intermediate Similarity NPD2533 Approved
0.712 Intermediate Similarity NPD2532 Approved
0.7109 Intermediate Similarity NPD7585 Approved
0.7075 Intermediate Similarity NPD8151 Discontinued
0.7062 Intermediate Similarity NPD7584 Approved
0.7053 Intermediate Similarity NPD3817 Phase 2
0.7044 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD7701 Phase 2
0.7027 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD8059 Phase 3
0.7021 Intermediate Similarity NPD4380 Phase 2
0.7 Intermediate Similarity NPD7819 Suspended
0.6976 Remote Similarity NPD4466 Phase 1
0.6971 Remote Similarity NPD8285 Discontinued
0.6967 Remote Similarity NPD8319 Approved
0.6967 Remote Similarity NPD8320 Phase 1
0.6963 Remote Similarity NPD7874 Approved
0.6963 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6955 Remote Similarity NPD8366 Approved
0.6954 Remote Similarity NPD3818 Discontinued
0.6954 Remote Similarity NPD7177 Discontinued
0.6947 Remote Similarity NPD6801 Discontinued
0.6944 Remote Similarity NPD4377 Discontinued
0.6934 Remote Similarity NPD7999 Approved
0.6931 Remote Similarity NPD5036 Approved
0.693 Remote Similarity NPD7782 Clinical (unspecified phase)
0.693 Remote Similarity NPD7783 Phase 2
0.693 Remote Similarity NPD7801 Approved
0.6923 Remote Similarity NPD6232 Discontinued
0.6912 Remote Similarity NPD6836 Approved
0.6906 Remote Similarity NPD8491 Approved
0.6897 Remote Similarity NPD5037 Approved
0.6897 Remote Similarity NPD5038 Approved
0.6895 Remote Similarity NPD6385 Approved
0.6895 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6895 Remote Similarity NPD6386 Approved
0.6891 Remote Similarity NPD7075 Discontinued
0.6891 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6799 Approved
0.6881 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6878 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5402 Approved
0.6875 Remote Similarity NPD7318 Phase 3
0.6872 Remote Similarity NPD8162 Phase 2
0.6872 Remote Similarity NPD6823 Phase 2
0.6872 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6859 Remote Similarity NPD1934 Approved
0.6858 Remote Similarity NPD8067 Phase 3
0.6839 Remote Similarity NPD3882 Suspended
0.6834 Remote Similarity NPD7054 Approved
0.6823 Remote Similarity NPD2801 Approved
0.6823 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6823 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6746 Phase 2
0.682 Remote Similarity NPD8461 Discontinued
0.6818 Remote Similarity NPD7473 Discontinued
0.6816 Remote Similarity NPD7038 Approved
0.6816 Remote Similarity NPD7039 Approved
0.6816 Remote Similarity NPD5030 Phase 2
0.6804 Remote Similarity NPD5219 Approved
0.6804 Remote Similarity NPD5218 Approved
0.68 Remote Similarity NPD7472 Approved
0.6794 Remote Similarity NPD7282 Approved
0.6793 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6782 Remote Similarity NPD36 Approved
0.6782 Remote Similarity NPD5026 Approved
0.6782 Remote Similarity NPD5028 Approved
0.6782 Remote Similarity NPD4954 Approved
0.6782 Remote Similarity NPD5034 Approved
0.6782 Remote Similarity NPD4955 Approved
0.6782 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6782 Approved
0.6777 Remote Similarity NPD6777 Approved
0.6777 Remote Similarity NPD6779 Approved
0.6777 Remote Similarity NPD6780 Approved
0.6777 Remote Similarity NPD6776 Approved
0.6777 Remote Similarity NPD6778 Approved
0.6777 Remote Similarity NPD6781 Approved
0.6772 Remote Similarity NPD5403 Approved
0.6771 Remote Similarity NPD6844 Discontinued
0.6771 Remote Similarity NPD7317 Phase 3
0.6768 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6166 Phase 2
0.6768 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6797 Phase 2
0.6755 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3157 Approved
0.6755 Remote Similarity NPD3158 Phase 1
0.6755 Remote Similarity NPD3146 Approved
0.6754 Remote Similarity NPD4678 Approved
0.6754 Remote Similarity NPD4675 Approved
0.6754 Remote Similarity NPD6599 Discontinued
0.6753 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6751 Remote Similarity NPD7315 Approved
0.675 Remote Similarity NPD5844 Phase 1
0.675 Remote Similarity NPD6020 Phase 2
0.6748 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6559 Discontinued
0.6733 Remote Similarity NPD7251 Discontinued
0.673 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6726 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7907 Approved
0.6718 Remote Similarity NPD1307 Phase 2
0.6718 Remote Similarity NPD1309 Phase 2
0.6718 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6716 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7074 Phase 3
0.6712 Remote Similarity NPD4111 Phase 1
0.6712 Remote Similarity NPD4665 Approved
0.6702 Remote Similarity NPD2649 Approved
0.6702 Remote Similarity NPD2651 Approved
0.6702 Remote Similarity NPD1511 Approved
0.67 Remote Similarity NPD7808 Phase 3
0.67 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6699 Remote Similarity NPD1898 Discontinued
0.6699 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6685 Remote Similarity NPD2238 Phase 2
0.6685 Remote Similarity NPD6032 Approved
0.6684 Remote Similarity NPD3692 Discontinued
0.6684 Remote Similarity NPD1670 Discontinued
0.6683 Remote Similarity NPD7296 Approved
0.6682 Remote Similarity NPD7696 Phase 3
0.6682 Remote Similarity NPD7497 Discontinued
0.6682 Remote Similarity NPD7435 Discontinued
0.6682 Remote Similarity NPD7697 Approved
0.6682 Remote Similarity NPD7698 Approved
0.6667 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5401 Approved
0.6667 Remote Similarity NPD7827 Phase 1
0.6667 Remote Similarity NPD7608 Discontinued
0.6667 Remote Similarity NPD2494 Approved
0.6667 Remote Similarity NPD2493 Approved
0.6667 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6808 Phase 2
0.6652 Remote Similarity NPD7047 Phase 3
0.6651 Remote Similarity NPD7870 Phase 2
0.6651 Remote Similarity NPD6874 Approved
0.6651 Remote Similarity NPD7871 Phase 2
0.665 Remote Similarity NPD5029 Approved
0.665 Remote Similarity NPD8150 Discontinued
0.665 Remote Similarity NPD5027 Approved
0.665 Remote Similarity NPD5031 Approved
0.6649 Remote Similarity NPD3686 Approved
0.6649 Remote Similarity NPD5773 Approved
0.6649 Remote Similarity NPD3687 Approved
0.6649 Remote Similarity NPD4210 Discontinued
0.6649 Remote Similarity NPD5772 Approved
0.6638 Remote Similarity NPD7048 Phase 3
0.6635 Remote Similarity NPD2974 Approved
0.6635 Remote Similarity NPD2973 Approved
0.6635 Remote Similarity NPD2975 Approved
0.6632 Remote Similarity NPD5889 Approved
0.6632 Remote Similarity NPD7411 Suspended
0.6632 Remote Similarity NPD2186 Approved
0.6632 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5890 Approved
0.6632 Remote Similarity NPD1512 Approved
0.6631 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6631 Remote Similarity NPD4628 Phase 3
0.663 Remote Similarity NPD1510 Phase 2
0.6622 Remote Similarity NPD6997 Phase 2
0.6622 Remote Similarity NPD8404 Phase 2
0.6621 Remote Similarity NPD5676 Approved
0.6618 Remote Similarity NPD7549 Discontinued
0.6616 Remote Similarity NPD7199 Phase 2
0.6616 Remote Similarity NPD6959 Discontinued
0.6615 Remote Similarity NPD4005 Discontinued
0.6615 Remote Similarity NPD824 Approved
0.6605 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6602 Remote Similarity NPD3153 Approved
0.6602 Remote Similarity NPD3154 Approved

Structure

External Identifiers

PubChem CID   44445674
ChEMBL   CHEMBL251437
ZINC  

Physicochemical Properties

Molecular Weight:  478.16
ALogP:  -1.4308
MLogP:  2.56
XLogP:  0.805
# Rotatable Bonds:  16
Polar Surface Area:  153.42
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# 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