Natural Product: NPC257240

Natural Product ID:  NPC257240
Common Name:   Ingenol Mebutate
IUPAC Name:  
Synonyms:   Ingenol Mebutate; PEP-005; Picato
Molecular Formula:   C25H34O6
Standard InCHIKey:  VDJHFHXMUKFKET-WDUFCVPESA-N
Standard InCHI:  InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
Canonical SMILES:  C/C=C(C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C)/C
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
NPO1853 Euphorbia canariensis Species Euphorbiaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT881 Individual Protein Protein kinase C delta Homo sapiens EC50 = 4.1 nM 23993332
NPT165 Cell Line HeLa Homo sapiens LC50 = 230000 nM 23993332
NPT2 Others Unspecified EC50 = 10.3 nM 23993332
NPT2 Others Unspecified EC50 = 11.2 nM 23993332
NPT2 Others Unspecified EC50 = 8.7 nM 23993332
NPT165 Cell Line HeLa Homo sapiens LC50 = 230000 nM 24332494
NPT2 Others Unspecified EC50 = 11.2 nM 24332494
NPT2 Others Unspecified EC50 = 10.3 nM 24332494
NPT2 Others Unspecified EC50 = 8.7 nM 24332494
NPT881 Individual Protein Protein kinase C delta Homo sapiens EC50 = 4.1 nM 24332494
NPT2 Others Unspecified Ratio CC50/EC50 = 7847 25970561
NPT2 Others Unspecified Ratio CC50/EC50 = 2.3 25970561
NPT2 Others Unspecified EC50 = 22900 nM 25970561
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 17 nM 25970561
NPT332 Organism Human immunodeficiency virus type 2 (ISOLATE ROD) Human immunodeficiency virus type 2 (ISOLATE ROD) EC50 = 9 nM 25970561
NPT2 Others Unspecified Ratio CC50/EC50 = 13451 25970561

  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 NPC257240 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
0.9712 High Similarity NPC46269
0.9712 High Similarity NPC106395
0.9706 High Similarity NPC477102
0.9619 High Similarity NPC133677
0.9619 High Similarity NPC67290
0.9619 High Similarity NPC138303
0.9615 High Similarity NPC76550
0.9615 High Similarity NPC138757
0.9615 High Similarity NPC123855
0.9612 High Similarity NPC477103
0.9608 High Similarity NPC308191
0.9604 High Similarity NPC179891
0.9333 High Similarity NPC287311
0.9327 High Similarity NPC47951
0.8857 High Similarity NPC475661
0.8857 High Similarity NPC473488
0.8774 High Similarity NPC473911
0.8713 High Similarity NPC261341
0.8585 High Similarity NPC203659
0.8585 High Similarity NPC100487
0.8505 High Similarity NPC243998
0.8491 Intermediate Similarity NPC110989
0.8426 Intermediate Similarity NPC26617
0.8421 Intermediate Similarity NPC477092
0.8396 Intermediate Similarity NPC86077
0.8396 Intermediate Similarity NPC225353
0.8333 Intermediate Similarity NPC475401
0.8333 Intermediate Similarity NPC223450
0.8319 Intermediate Similarity NPC234858
0.8319 Intermediate Similarity NPC154363
0.8319 Intermediate Similarity NPC471127
0.8318 Intermediate Similarity NPC475871
0.8318 Intermediate Similarity NPC475945
0.8302 Intermediate Similarity NPC150923
0.8291 Intermediate Similarity NPC472399
0.8246 Intermediate Similarity NPC10721
0.8246 Intermediate Similarity NPC475305
0.8241 Intermediate Similarity NPC474741
0.823 Intermediate Similarity NPC472400
0.8224 Intermediate Similarity NPC474747
0.819 Intermediate Similarity NPC477949
0.819 Intermediate Similarity NPC157252
0.819 Intermediate Similarity NPC145182
0.819 Intermediate Similarity NPC471126
0.819 Intermediate Similarity NPC471128
0.819 Intermediate Similarity NPC475885
0.8174 Intermediate Similarity NPC124676
0.8174 Intermediate Similarity NPC146280
0.8173 Intermediate Similarity NPC304886
0.8148 Intermediate Similarity NPC472755
0.8142 Intermediate Similarity NPC472757
0.8142 Intermediate Similarity NPC71889
0.8131 Intermediate Similarity NPC171759
0.8131 Intermediate Similarity NPC474742
0.812 Intermediate Similarity NPC52839
0.812 Intermediate Similarity NPC472401
0.8113 Intermediate Similarity NPC141191
0.8103 Intermediate Similarity NPC236918
0.8103 Intermediate Similarity NPC156745
0.8087 Intermediate Similarity NPC156252
0.8087 Intermediate Similarity NPC475323
0.8077 Intermediate Similarity NPC470013
0.8077 Intermediate Similarity NPC470010
0.8077 Intermediate Similarity NPC477131
0.8077 Intermediate Similarity NPC167219
0.8077 Intermediate Similarity NPC323008
0.8077 Intermediate Similarity NPC198853
0.8077 Intermediate Similarity NPC262133
0.807 Intermediate Similarity NPC474872
0.8058 Intermediate Similarity NPC476705
0.8051 Intermediate Similarity NPC162009
0.8051 Intermediate Similarity NPC257017
0.8051 Intermediate Similarity NPC19464
0.8037 Intermediate Similarity NPC288876
0.8034 Intermediate Similarity NPC329080
0.8034 Intermediate Similarity NPC472759
0.8019 Intermediate Similarity NPC170143
0.8019 Intermediate Similarity NPC311904
0.8019 Intermediate Similarity NPC108475
0.8019 Intermediate Similarity NPC161493
0.8019 Intermediate Similarity NPC169205
0.8019 Intermediate Similarity NPC213947
0.8017 Intermediate Similarity NPC171905
0.8017 Intermediate Similarity NPC472397
0.8017 Intermediate Similarity NPC472758
0.8017 Intermediate Similarity NPC471125
0.8017 Intermediate Similarity NPC236999
0.8017 Intermediate Similarity NPC288679
0.8 Intermediate Similarity NPC14961
0.8 Intermediate Similarity NPC67584
0.8 Intermediate Similarity NPC52044
0.8 Intermediate Similarity NPC270013
0.8 Intermediate Similarity NPC220221
0.8 Intermediate Similarity NPC54737
0.8 Intermediate Similarity NPC469873
0.8 Intermediate Similarity NPC36954
0.7982 Intermediate Similarity NPC124881
0.7981 Intermediate Similarity NPC475912
0.7966 Intermediate Similarity NPC470829
0.7966 Intermediate Similarity NPC473228
0.7965 Intermediate Similarity NPC475937
0.7965 Intermediate Similarity NPC260786
0.7965 Intermediate Similarity NPC96739
0.7965 Intermediate Similarity NPC475495
0.7965 Intermediate Similarity NPC317107
0.7965 Intermediate Similarity NPC174471
0.7965 Intermediate Similarity NPC474871
0.7965 Intermediate Similarity NPC158523
0.7963 Intermediate Similarity NPC474339
0.7963 Intermediate Similarity NPC472753
0.7963 Intermediate Similarity NPC477950
0.7963 Intermediate Similarity NPC164598
0.7961 Intermediate Similarity NPC473448
0.7949 Intermediate Similarity NPC5991
0.7949 Intermediate Similarity NPC255081
0.7949 Intermediate Similarity NPC5989
0.7949 Intermediate Similarity NPC471108
0.7949 Intermediate Similarity NPC22628
0.7949 Intermediate Similarity NPC275696
0.7946 Intermediate Similarity NPC273433
0.7944 Intermediate Similarity NPC221615
0.7931 Intermediate Similarity NPC471145
0.7931 Intermediate Similarity NPC471146
0.7925 Intermediate Similarity NPC230800
0.7925 Intermediate Similarity NPC213078
0.7925 Intermediate Similarity NPC18019
0.7925 Intermediate Similarity NPC24956
0.7925 Intermediate Similarity NPC476315
0.7925 Intermediate Similarity NPC185553
0.7925 Intermediate Similarity NPC279621
0.7917 Intermediate Similarity NPC473709
0.7917 Intermediate Similarity NPC473919
0.7917 Intermediate Similarity NPC144625
0.7917 Intermediate Similarity NPC145238
0.7909 Intermediate Similarity NPC472756
0.7909 Intermediate Similarity NPC220964
0.7909 Intermediate Similarity NPC475676
0.7909 Intermediate Similarity NPC146731
0.7909 Intermediate Similarity NPC309190
0.7909 Intermediate Similarity NPC296950
0.7905 Intermediate Similarity NPC65829
0.7905 Intermediate Similarity NPC474035
0.7905 Intermediate Similarity NPC81386
0.7895 Intermediate Similarity NPC477093
0.7895 Intermediate Similarity NPC215643
0.7895 Intermediate Similarity NPC17138
0.7895 Intermediate Similarity NPC475391
0.7895 Intermediate Similarity NPC317687
0.7895 Intermediate Similarity NPC89227
0.7895 Intermediate Similarity NPC265499
0.7895 Intermediate Similarity NPC473522
0.7895 Intermediate Similarity NPC35069
0.7895 Intermediate Similarity NPC101825
0.7895 Intermediate Similarity NPC170212
0.7895 Intermediate Similarity NPC475277
0.7895 Intermediate Similarity NPC151216
0.7895 Intermediate Similarity NPC258711
0.7895 Intermediate Similarity NPC221511
0.789 Intermediate Similarity NPC472754
0.789 Intermediate Similarity NPC118405
0.7885 Intermediate Similarity NPC30515
0.7885 Intermediate Similarity NPC184463
0.7885 Intermediate Similarity NPC131209
0.7885 Intermediate Similarity NPC133698
0.7881 Intermediate Similarity NPC19336
0.7881 Intermediate Similarity NPC185876
0.7876 Intermediate Similarity NPC153036
0.787 Intermediate Similarity NPC280963
0.787 Intermediate Similarity NPC70865
0.7863 Intermediate Similarity NPC472760
0.7863 Intermediate Similarity NPC475372
0.7857 Intermediate Similarity NPC14862
0.7857 Intermediate Similarity NPC233379
0.7857 Intermediate Similarity NPC474664
0.7851 Intermediate Similarity NPC222307
0.785 Intermediate Similarity NPC474313
0.785 Intermediate Similarity NPC40812
0.7833 Intermediate Similarity NPC129992
0.7833 Intermediate Similarity NPC473802
0.783 Intermediate Similarity NPC213698
0.783 Intermediate Similarity NPC193645
0.783 Intermediate Similarity NPC275960
0.783 Intermediate Similarity NPC90121
0.783 Intermediate Similarity NPC475900
0.783 Intermediate Similarity NPC170120
0.783 Intermediate Similarity NPC48803
0.7826 Intermediate Similarity NPC474937
0.7826 Intermediate Similarity NPC209058
0.7818 Intermediate Similarity NPC4620
0.7818 Intermediate Similarity NPC474165
0.7818 Intermediate Similarity NPC69171
0.7818 Intermediate Similarity NPC475873
0.7815 Intermediate Similarity NPC46570
0.7815 Intermediate Similarity NPC67569
0.781 Intermediate Similarity NPC212486
0.781 Intermediate Similarity NPC469645
0.781 Intermediate Similarity NPC125674
0.781 Intermediate Similarity NPC469692
0.781 Intermediate Similarity NPC475838
0.781 Intermediate Similarity NPC228451

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC257240 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 NPD6371 Approved
0.8426 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD5785 Approved
0.7619 Intermediate Similarity NPD6698 Approved
0.7619 Intermediate Similarity NPD46 Approved
0.7524 Intermediate Similarity NPD1695 Approved
0.7479 Intermediate Similarity NPD7115 Discovery
0.7308 Intermediate Similarity NPD5363 Approved
0.7297 Intermediate Similarity NPD4225 Approved
0.729 Intermediate Similarity NPD7838 Discovery
0.7241 Intermediate Similarity NPD6686 Approved
0.7222 Intermediate Similarity NPD7983 Approved
0.7091 Intermediate Similarity NPD5282 Discontinued
0.7019 Intermediate Similarity NPD4269 Approved
0.7019 Intermediate Similarity NPD5209 Approved
0.7019 Intermediate Similarity NPD4270 Approved
0.7018 Intermediate Similarity NPD5344 Discontinued
0.7 Intermediate Similarity NPD6053 Discontinued
0.6952 Remote Similarity NPD5362 Discontinued
0.6923 Remote Similarity NPD5369 Approved
0.6916 Remote Similarity NPD5786 Approved
0.688 Remote Similarity NPD6319 Approved
0.6846 Remote Similarity NPD7319 Approved
0.6842 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6827 Remote Similarity NPD4252 Approved
0.6822 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6792 Remote Similarity NPD7154 Phase 3
0.6783 Remote Similarity NPD7639 Approved
0.6783 Remote Similarity NPD7640 Approved
0.6777 Remote Similarity NPD8413 Clinical (unspecified phase)
0.675 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6744 Remote Similarity NPD7507 Approved
0.6723 Remote Similarity NPD6412 Phase 2
0.6697 Remote Similarity NPD4251 Approved
0.6697 Remote Similarity NPD4250 Approved
0.6696 Remote Similarity NPD5779 Approved
0.6696 Remote Similarity NPD7638 Approved
0.6696 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD4821 Approved
0.6667 Remote Similarity NPD4819 Approved
0.6667 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD4820 Approved
0.6667 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4822 Approved
0.6638 Remote Similarity NPD6648 Approved
0.6635 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6615 Remote Similarity NPD6616 Approved
0.6614 Remote Similarity NPD6054 Approved
0.6609 Remote Similarity NPD6084 Phase 2
0.6609 Remote Similarity NPD6083 Phase 2
0.6607 Remote Similarity NPD7637 Suspended
0.6606 Remote Similarity NPD4249 Approved
0.6589 Remote Similarity NPD7604 Phase 2
0.6585 Remote Similarity NPD8297 Approved
0.6565 Remote Similarity NPD7078 Approved
0.6562 Remote Similarity NPD8513 Phase 3
0.6562 Remote Similarity NPD8516 Approved
0.6562 Remote Similarity NPD8517 Approved
0.6562 Remote Similarity NPD8515 Approved
0.6557 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6542 Remote Similarity NPD6435 Approved
0.6529 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6529 Remote Similarity NPD6899 Approved
0.6529 Remote Similarity NPD6881 Approved
0.6515 Remote Similarity NPD7736 Approved
0.6512 Remote Similarity NPD6370 Approved
0.6504 Remote Similarity NPD6649 Approved
0.6504 Remote Similarity NPD6650 Approved
0.65 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD6008 Approved
0.65 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD6675 Approved
0.65 Remote Similarity NPD6402 Approved
0.6489 Remote Similarity NPD8273 Phase 1
0.6484 Remote Similarity NPD6059 Approved
0.6476 Remote Similarity NPD4271 Approved
0.6476 Remote Similarity NPD4268 Approved
0.6475 Remote Similarity NPD6372 Approved
0.6475 Remote Similarity NPD6373 Approved
0.6462 Remote Similarity NPD7642 Approved
0.6457 Remote Similarity NPD7327 Approved
0.6457 Remote Similarity NPD7328 Approved
0.6446 Remote Similarity NPD5697 Approved
0.6439 Remote Similarity NPD8293 Discontinued
0.6435 Remote Similarity NPD5695 Phase 3
0.6434 Remote Similarity NPD7503 Approved
0.6434 Remote Similarity NPD6015 Approved
0.6434 Remote Similarity NPD6016 Approved
0.6434 Remote Similarity NPD8033 Approved
0.6423 Remote Similarity NPD6883 Approved
0.6423 Remote Similarity NPD7290 Approved
0.6423 Remote Similarity NPD7102 Approved
0.6423 Remote Similarity NPD4634 Approved
0.641 Remote Similarity NPD5696 Approved
0.6406 Remote Similarity NPD7516 Approved
0.6404 Remote Similarity NPD6399 Phase 3
0.6393 Remote Similarity NPD7320 Approved
0.6389 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5988 Approved
0.6378 Remote Similarity NPD6009 Approved
0.6371 Remote Similarity NPD6869 Approved
0.6371 Remote Similarity NPD6847 Approved
0.6371 Remote Similarity NPD6617 Approved
0.6371 Remote Similarity NPD8130 Phase 1
0.6364 Remote Similarity NPD1694 Approved
0.6357 Remote Similarity NPD8377 Approved
0.6357 Remote Similarity NPD8294 Approved
0.6355 Remote Similarity NPD5368 Approved
0.6341 Remote Similarity NPD6013 Approved
0.6341 Remote Similarity NPD6014 Approved
0.6341 Remote Similarity NPD6012 Approved
0.633 Remote Similarity NPD5331 Approved
0.633 Remote Similarity NPD5332 Approved
0.632 Remote Similarity NPD6882 Approved
0.6316 Remote Similarity NPD6411 Approved
0.6316 Remote Similarity NPD8074 Phase 3
0.6311 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5701 Approved
0.6308 Remote Similarity NPD8296 Approved
0.6308 Remote Similarity NPD8380 Approved
0.6308 Remote Similarity NPD5983 Phase 2
0.6308 Remote Similarity NPD8335 Approved
0.6308 Remote Similarity NPD8379 Approved
0.6308 Remote Similarity NPD8378 Approved
0.6296 Remote Similarity NPD4790 Discontinued
0.6293 Remote Similarity NPD6356 Clinical (unspecified phase)
0.627 Remote Similarity NPD8133 Approved
0.626 Remote Similarity NPD6011 Approved
0.625 Remote Similarity NPD7632 Discontinued
0.625 Remote Similarity NPD7524 Approved
0.625 Remote Similarity NPD5211 Phase 2
0.6241 Remote Similarity NPD6336 Discontinued
0.6239 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7839 Suspended
0.6212 Remote Similarity NPD7829 Approved
0.6212 Remote Similarity NPD8328 Phase 3
0.6212 Remote Similarity NPD7830 Approved
0.6182 Remote Similarity NPD6110 Phase 1
0.6174 Remote Similarity NPD5693 Phase 1
0.6174 Remote Similarity NPD5284 Approved
0.6174 Remote Similarity NPD5281 Approved
0.6161 Remote Similarity NPD7334 Approved
0.6161 Remote Similarity NPD6684 Approved
0.6161 Remote Similarity NPD5330 Approved
0.6161 Remote Similarity NPD7146 Approved
0.6161 Remote Similarity NPD7521 Approved
0.6161 Remote Similarity NPD6409 Approved
0.6154 Remote Similarity NPD5210 Approved
0.6154 Remote Similarity NPD4629 Approved
0.6148 Remote Similarity NPD5141 Approved
0.6143 Remote Similarity NPD7966 Clinical (unspecified phase)
0.614 Remote Similarity NPD5764 Clinical (unspecified phase)
0.614 Remote Similarity NPD4753 Phase 2
0.614 Remote Similarity NPD6101 Approved
0.614 Remote Similarity NPD5370 Suspended
0.6131 Remote Similarity NPD7260 Phase 2
0.6126 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6126 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6083 Remote Similarity NPD4696 Approved
0.6083 Remote Similarity NPD5285 Approved
0.6083 Remote Similarity NPD5286 Approved
0.6058 Remote Similarity NPD5956 Approved
0.6053 Remote Similarity NPD6903 Approved
0.6053 Remote Similarity NPD7513 Clinical (unspecified phase)
0.605 Remote Similarity NPD4755 Approved
0.605 Remote Similarity NPD7902 Approved
0.6047 Remote Similarity NPD6274 Approved
0.6036 Remote Similarity NPD6695 Phase 3
0.6034 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6031 Remote Similarity NPD4522 Approved
0.6031 Remote Similarity NPD7100 Approved
0.6031 Remote Similarity NPD7101 Approved
0.6029 Remote Similarity NPD6033 Approved
0.6 Remote Similarity NPD6904 Approved
0.6 Remote Similarity NPD6673 Approved
0.6 Remote Similarity NPD6080 Approved
0.6 Remote Similarity NPD8451 Approved
0.6 Remote Similarity NPD7500 Approved
0.5984 Remote Similarity NPD4633 Approved
0.5984 Remote Similarity NPD5224 Approved
0.5984 Remote Similarity NPD5225 Approved
0.5984 Remote Similarity NPD5226 Approved
0.5983 Remote Similarity NPD4202 Approved
0.5982 Remote Similarity NPD3665 Phase 1
0.5982 Remote Similarity NPD3133 Approved
0.5982 Remote Similarity NPD3666 Approved
0.5956 Remote Similarity NPD8448 Approved
0.5954 Remote Similarity NPD7641 Discontinued
0.5954 Remote Similarity NPD6335 Approved
0.5952 Remote Similarity NPD8132 Clinical (unspecified phase)
0.595 Remote Similarity NPD4700 Approved
0.594 Remote Similarity NPD8444 Approved
0.594 Remote Similarity NPD6921 Approved
0.5935 Remote Similarity NPD5174 Approved
0.5935 Remote Similarity NPD5175 Approved
0.5932 Remote Similarity NPD7748 Approved

Structure

External Identifiers

PubChem CID   6918670
ChEMBL   CHEMBL1863513
ZINC  

Physicochemical Properties

Molecular Weight:  430.24
ALogP:  0.8605
MLogP:  3.55
XLogP:  3.215
# Rotatable Bonds:  13
Polar Surface Area:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  31

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs