Natural Product: NPC78594

Natural Product ID:  NPC78594
Common Name:   Chloraeudolide
IUPAC Name:   (4aR,5R,8R,8aR,9aS)-5,8,9a-trihydroxy-3,5,8a-trimethyl-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
Synonyms:   Chloraeudolide
Molecular Formula:   C15H22O5
Standard InCHIKey:  BWOFLNFAFOQHRS-BBIZWXPBSA-N
Standard InCHI:  InChI=1S/C15H22O5/c1-8-9-6-10-13(2,7-15(9,19)20-12(8)17)11(16)4-5-14(10,3)18/h10-11,16,18-19H,4-7H2,1-3H3/t10-,11-,13-,14-,15+/m1/s1
Canonical SMILES:  O=C1O[C@@]2(C(=C1C)C[C@@H]1[C@](C2)(C)[C@H](O)CC[C@@]1(C)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
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota Whole plant Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota whole plants Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO28765 Miliusa balansae Species Annonaceae Eukaryota Leaves PMID[26238320]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota TCM_Taiwan*
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota Whole Plants PMID[21142110]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 < 10000 nM 21142110
NPT1997 Cell Line OS-RC-2 Homo sapiens IC50 < 10000 nM 21142110
NPT81 Cell Line A549 Homo sapiens IC50 < 10000 nM 21142110
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 < 10000 nM 21142110
NPT165 Cell Line HeLa Homo sapiens IC50 < 10000 nM 21142110
NPT83 Cell Line MCF7 Homo sapiens IC50 < 10000 nM 21142110
NPT515 Cell Line SGC-7901 Homo sapiens IC50 < 10000 nM 21142110
NPT114 Cell Line LoVo Homo sapiens IC50 < 10000 nM 21142110

  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 NPC78594 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
0.9438 High Similarity NPC471915
0.9432 High Similarity NPC472641
0.9432 High Similarity NPC472640
0.9425 High Similarity NPC472642
0.9294 High Similarity NPC253604
0.9176 High Similarity NPC32223
0.9032 High Similarity NPC324841
0.9032 High Similarity NPC16601
0.9011 High Similarity NPC111273
0.9 High Similarity NPC110022
0.8913 High Similarity NPC165632
0.8901 High Similarity NPC105490
0.8842 High Similarity NPC471914
0.8791 High Similarity NPC7349
0.875 High Similarity NPC471938
0.866 High Similarity NPC471937
0.8646 High Similarity NPC475038
0.8646 High Similarity NPC109195
0.8557 High Similarity NPC474822
0.8556 High Similarity NPC242448
0.8485 Intermediate Similarity NPC471205
0.8478 Intermediate Similarity NPC472811
0.8404 Intermediate Similarity NPC276110
0.8404 Intermediate Similarity NPC472441
0.84 Intermediate Similarity NPC181994
0.8387 Intermediate Similarity NPC472812
0.8367 Intermediate Similarity NPC471208
0.8351 Intermediate Similarity NPC11974
0.8333 Intermediate Similarity NPC131813
0.8316 Intermediate Similarity NPC134072
0.8316 Intermediate Similarity NPC234993
0.83 Intermediate Similarity NPC122816
0.8298 Intermediate Similarity NPC57117
0.828 Intermediate Similarity NPC329842
0.828 Intermediate Similarity NPC473675
0.8276 Intermediate Similarity NPC10636
0.8265 Intermediate Similarity NPC472815
0.8265 Intermediate Similarity NPC121423
0.8265 Intermediate Similarity NPC162973
0.8247 Intermediate Similarity NPC476767
0.8247 Intermediate Similarity NPC38855
0.8218 Intermediate Similarity NPC325054
0.8218 Intermediate Similarity NPC38948
0.8211 Intermediate Similarity NPC329435
0.82 Intermediate Similarity NPC51719
0.8191 Intermediate Similarity NPC53555
0.8182 Intermediate Similarity NPC281378
0.8182 Intermediate Similarity NPC160583
0.8182 Intermediate Similarity NPC45897
0.8182 Intermediate Similarity NPC120009
0.8172 Intermediate Similarity NPC78973
0.8163 Intermediate Similarity NPC471412
0.8152 Intermediate Similarity NPC472810
0.8152 Intermediate Similarity NPC472809
0.8144 Intermediate Similarity NPC275086
0.8144 Intermediate Similarity NPC278673
0.8144 Intermediate Similarity NPC325229
0.8137 Intermediate Similarity NPC206618
0.8137 Intermediate Similarity NPC31522
0.8137 Intermediate Similarity NPC322912
0.8125 Intermediate Similarity NPC475380
0.8125 Intermediate Similarity NPC209297
0.8119 Intermediate Similarity NPC475074
0.8111 Intermediate Similarity NPC102048
0.8105 Intermediate Similarity NPC140277
0.8105 Intermediate Similarity NPC470255
0.8081 Intermediate Similarity NPC58329
0.8081 Intermediate Similarity NPC476081
0.8081 Intermediate Similarity NPC165250
0.8081 Intermediate Similarity NPC295791
0.8061 Intermediate Similarity NPC251680
0.8061 Intermediate Similarity NPC471413
0.8043 Intermediate Similarity NPC473891
0.8041 Intermediate Similarity NPC311241
0.8041 Intermediate Similarity NPC205143
0.8041 Intermediate Similarity NPC199099
0.8041 Intermediate Similarity NPC51499
0.8041 Intermediate Similarity NPC100912
0.8041 Intermediate Similarity NPC475446
0.8039 Intermediate Similarity NPC300614
0.8039 Intermediate Similarity NPC90946
0.802 Intermediate Similarity NPC218158
0.8 Intermediate Similarity NPC472821
0.8 Intermediate Similarity NPC159533
0.8 Intermediate Similarity NPC152778
0.8 Intermediate Similarity NPC205034
0.8 Intermediate Similarity NPC139692
0.8 Intermediate Similarity NPC165608
0.8 Intermediate Similarity NPC162615
0.8 Intermediate Similarity NPC311070
0.798 Intermediate Similarity NPC247701
0.798 Intermediate Similarity NPC25177
0.798 Intermediate Similarity NPC295110
0.798 Intermediate Similarity NPC268829
0.798 Intermediate Similarity NPC198992
0.798 Intermediate Similarity NPC222875
0.7979 Intermediate Similarity NPC310479
0.7979 Intermediate Similarity NPC182136
0.7979 Intermediate Similarity NPC221111
0.7979 Intermediate Similarity NPC280149
0.7961 Intermediate Similarity NPC299590
0.7959 Intermediate Similarity NPC72647
0.7959 Intermediate Similarity NPC473154
0.7959 Intermediate Similarity NPC218107
0.7959 Intermediate Similarity NPC107806
0.7959 Intermediate Similarity NPC474440
0.7957 Intermediate Similarity NPC291665
0.7941 Intermediate Similarity NPC216636
0.7941 Intermediate Similarity NPC67321
0.7941 Intermediate Similarity NPC319438
0.7941 Intermediate Similarity NPC187435
0.7938 Intermediate Similarity NPC319861
0.7938 Intermediate Similarity NPC242848
0.7938 Intermediate Similarity NPC473153
0.7938 Intermediate Similarity NPC194132
0.7935 Intermediate Similarity NPC471219
0.7931 Intermediate Similarity NPC189206
0.7921 Intermediate Similarity NPC161775
0.7917 Intermediate Similarity NPC474554
0.7917 Intermediate Similarity NPC161998
0.7917 Intermediate Similarity NPC474555
0.7905 Intermediate Similarity NPC42658
0.79 Intermediate Similarity NPC472552
0.7895 Intermediate Similarity NPC72845
0.7895 Intermediate Similarity NPC41239
0.7895 Intermediate Similarity NPC124374
0.7885 Intermediate Similarity NPC177047
0.7879 Intermediate Similarity NPC20113
0.7879 Intermediate Similarity NPC228251
0.7879 Intermediate Similarity NPC477716
0.7879 Intermediate Similarity NPC161527
0.7879 Intermediate Similarity NPC477972
0.7879 Intermediate Similarity NPC219285
0.7879 Intermediate Similarity NPC472644
0.7879 Intermediate Similarity NPC477968
0.7879 Intermediate Similarity NPC477721
0.7879 Intermediate Similarity NPC477971
0.7872 Intermediate Similarity NPC474396
0.7872 Intermediate Similarity NPC470734
0.7872 Intermediate Similarity NPC170633
0.7872 Intermediate Similarity NPC50488
0.7857 Intermediate Similarity NPC121402
0.7857 Intermediate Similarity NPC132753
0.7857 Intermediate Similarity NPC477719
0.7857 Intermediate Similarity NPC224356
0.7857 Intermediate Similarity NPC175351
0.7857 Intermediate Similarity NPC477718
0.7857 Intermediate Similarity NPC151681
0.7857 Intermediate Similarity NPC287668
0.785 Intermediate Similarity NPC471816
0.7849 Intermediate Similarity NPC471796
0.7849 Intermediate Similarity NPC166857
0.7849 Intermediate Similarity NPC471779
0.7843 Intermediate Similarity NPC239961
0.7843 Intermediate Similarity NPC81630
0.7843 Intermediate Similarity NPC477090
0.7843 Intermediate Similarity NPC119855
0.7843 Intermediate Similarity NPC34768
0.7843 Intermediate Similarity NPC220217
0.7843 Intermediate Similarity NPC471206
0.7843 Intermediate Similarity NPC472818
0.7822 Intermediate Similarity NPC97487
0.7822 Intermediate Similarity NPC120321
0.7822 Intermediate Similarity NPC196471
0.7822 Intermediate Similarity NPC187302
0.7822 Intermediate Similarity NPC189588
0.7822 Intermediate Similarity NPC10232
0.7812 Intermediate Similarity NPC99653
0.7812 Intermediate Similarity NPC472303
0.7802 Intermediate Similarity NPC321385
0.7802 Intermediate Similarity NPC476927
0.78 Intermediate Similarity NPC477717
0.78 Intermediate Similarity NPC472554
0.7789 Intermediate Similarity NPC209816
0.7789 Intermediate Similarity NPC220216
0.7789 Intermediate Similarity NPC477782
0.7788 Intermediate Similarity NPC475030
0.7778 Intermediate Similarity NPC170303
0.7767 Intermediate Similarity NPC472820
0.7766 Intermediate Similarity NPC106332
0.7766 Intermediate Similarity NPC93411
0.7755 Intermediate Similarity NPC154526
0.7755 Intermediate Similarity NPC472363
0.7755 Intermediate Similarity NPC202833
0.7755 Intermediate Similarity NPC16967
0.7755 Intermediate Similarity NPC93245
0.7755 Intermediate Similarity NPC29952
0.7755 Intermediate Similarity NPC240673
0.7755 Intermediate Similarity NPC472362
0.7755 Intermediate Similarity NPC17578
0.7753 Intermediate Similarity NPC110373
0.7753 Intermediate Similarity NPC5908
0.7753 Intermediate Similarity NPC80471
0.7745 Intermediate Similarity NPC472819
0.7742 Intermediate Similarity NPC474062
0.7742 Intermediate Similarity NPC329692
0.7732 Intermediate Similarity NPC119562
0.7732 Intermediate Similarity NPC279410
0.7732 Intermediate Similarity NPC472416
0.7732 Intermediate Similarity NPC191521

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC78594 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
0.8061 Intermediate Similarity NPD7639 Approved
0.8061 Intermediate Similarity NPD7640 Approved
0.7961 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD7638 Approved
0.79 Intermediate Similarity NPD7632 Discontinued
0.7714 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4225 Approved
0.7545 Intermediate Similarity NPD7327 Approved
0.7545 Intermediate Similarity NPD7328 Approved
0.7524 Intermediate Similarity NPD6686 Approved
0.7477 Intermediate Similarity NPD7516 Approved
0.7429 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5344 Discontinued
0.7257 Intermediate Similarity NPD8294 Approved
0.7257 Intermediate Similarity NPD8377 Approved
0.7193 Intermediate Similarity NPD8033 Approved
0.7193 Intermediate Similarity NPD8378 Approved
0.7193 Intermediate Similarity NPD8296 Approved
0.7193 Intermediate Similarity NPD8380 Approved
0.7193 Intermediate Similarity NPD8379 Approved
0.7193 Intermediate Similarity NPD8335 Approved
0.7128 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD7507 Approved
0.7019 Intermediate Similarity NPD6648 Approved
0.6979 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6917 Remote Similarity NPD7319 Approved
0.6897 Remote Similarity NPD7503 Approved
0.6762 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6735 Remote Similarity NPD1694 Approved
0.6699 Remote Similarity NPD7748 Approved
0.6697 Remote Similarity NPD6675 Approved
0.6697 Remote Similarity NPD7128 Approved
0.6697 Remote Similarity NPD6402 Approved
0.6697 Remote Similarity NPD5739 Approved
0.6696 Remote Similarity NPD7115 Discovery
0.6696 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD7637 Suspended
0.6667 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7515 Phase 2
0.6637 Remote Similarity NPD6882 Approved
0.6636 Remote Similarity NPD5701 Approved
0.6636 Remote Similarity NPD5697 Approved
0.6633 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4632 Approved
0.6579 Remote Similarity NPD8133 Approved
0.6577 Remote Similarity NPD6899 Approved
0.6577 Remote Similarity NPD6011 Approved
0.6577 Remote Similarity NPD6881 Approved
0.6577 Remote Similarity NPD7320 Approved
0.6577 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7525 Registered
0.6545 Remote Similarity NPD6008 Approved
0.6531 Remote Similarity NPD6695 Phase 3
0.6518 Remote Similarity NPD6373 Approved
0.6518 Remote Similarity NPD6014 Approved
0.6518 Remote Similarity NPD6013 Approved
0.6518 Remote Similarity NPD6372 Approved
0.6518 Remote Similarity NPD6012 Approved
0.65 Remote Similarity NPD3618 Phase 1
0.6486 Remote Similarity NPD6412 Phase 2
0.6471 Remote Similarity NPD6051 Approved
0.646 Remote Similarity NPD7290 Approved
0.646 Remote Similarity NPD7102 Approved
0.646 Remote Similarity NPD6883 Approved
0.6446 Remote Similarity NPD7492 Approved
0.6442 Remote Similarity NPD6399 Phase 3
0.6442 Remote Similarity NPD4202 Approved
0.6422 Remote Similarity NPD5211 Phase 2
0.6408 Remote Similarity NPD46 Approved
0.6408 Remote Similarity NPD7838 Discovery
0.6408 Remote Similarity NPD6698 Approved
0.6404 Remote Similarity NPD8130 Phase 1
0.6404 Remote Similarity NPD6869 Approved
0.6404 Remote Similarity NPD6847 Approved
0.6404 Remote Similarity NPD6649 Approved
0.6404 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6404 Remote Similarity NPD6650 Approved
0.6404 Remote Similarity NPD6617 Approved
0.6393 Remote Similarity NPD6616 Approved
0.6387 Remote Similarity NPD6054 Approved
0.6387 Remote Similarity NPD6059 Approved
0.6387 Remote Similarity NPD6319 Approved
0.6381 Remote Similarity NPD7900 Approved
0.6381 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6084 Phase 2
0.6355 Remote Similarity NPD4755 Approved
0.6355 Remote Similarity NPD6083 Phase 2
0.6348 Remote Similarity NPD8297 Approved
0.6348 Remote Similarity NPD6053 Discontinued
0.6346 Remote Similarity NPD8034 Phase 2
0.6346 Remote Similarity NPD8035 Phase 2
0.6341 Remote Similarity NPD7078 Approved
0.6341 Remote Similarity NPD8293 Discontinued
0.6333 Remote Similarity NPD6015 Approved
0.6333 Remote Similarity NPD5983 Phase 2
0.6333 Remote Similarity NPD6016 Approved
0.6316 Remote Similarity NPD6371 Approved
0.6311 Remote Similarity NPD5328 Approved
0.6306 Remote Similarity NPD5141 Approved
0.629 Remote Similarity NPD7736 Approved
0.6286 Remote Similarity NPD5778 Approved
0.6286 Remote Similarity NPD5779 Approved
0.6281 Remote Similarity NPD6370 Approved
0.6281 Remote Similarity NPD5988 Approved
0.6275 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6275 Remote Similarity NPD7750 Discontinued
0.6275 Remote Similarity NPD7524 Approved
0.6271 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4696 Approved
0.6239 Remote Similarity NPD5285 Approved
0.6239 Remote Similarity NPD5286 Approved
0.6239 Remote Similarity NPD4700 Approved
0.6238 Remote Similarity NPD7520 Clinical (unspecified phase)
0.623 Remote Similarity NPD7604 Phase 2
0.623 Remote Similarity NPD8328 Phase 3
0.6224 Remote Similarity NPD6931 Approved
0.6224 Remote Similarity NPD6930 Phase 2
0.619 Remote Similarity NPD5693 Phase 1
0.619 Remote Similarity NPD6079 Approved
0.6186 Remote Similarity NPD6114 Approved
0.6186 Remote Similarity NPD6274 Approved
0.6186 Remote Similarity NPD6697 Approved
0.6186 Remote Similarity NPD6115 Approved
0.6186 Remote Similarity NPD6118 Approved
0.6182 Remote Similarity NPD5223 Approved
0.6176 Remote Similarity NPD7146 Approved
0.6176 Remote Similarity NPD7521 Approved
0.6176 Remote Similarity NPD5330 Approved
0.6176 Remote Similarity NPD6684 Approved
0.6176 Remote Similarity NPD7334 Approved
0.6176 Remote Similarity NPD6409 Approved
0.6168 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5695 Phase 3
0.6147 Remote Similarity NPD5696 Approved
0.6139 Remote Similarity NPD3133 Approved
0.6139 Remote Similarity NPD3666 Approved
0.6139 Remote Similarity NPD3665 Phase 1
0.6134 Remote Similarity NPD6317 Approved
0.6129 Remote Similarity NPD6336 Discontinued
0.6126 Remote Similarity NPD5224 Approved
0.6126 Remote Similarity NPD4633 Approved
0.6126 Remote Similarity NPD5226 Approved
0.6126 Remote Similarity NPD5225 Approved
0.6122 Remote Similarity NPD7645 Phase 2
0.6122 Remote Similarity NPD6929 Approved
0.6121 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6117 Remote Similarity NPD3573 Approved
0.6111 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4697 Phase 3
0.6111 Remote Similarity NPD5222 Approved
0.6111 Remote Similarity NPD5221 Approved
0.61 Remote Similarity NPD3667 Approved
0.6098 Remote Similarity NPD6067 Discontinued
0.6095 Remote Similarity NPD5785 Approved
0.6095 Remote Similarity NPD3168 Discontinued
0.6083 Remote Similarity NPD6313 Approved
0.6083 Remote Similarity NPD6335 Approved
0.6083 Remote Similarity NPD6314 Approved
0.6082 Remote Similarity NPD6116 Phase 1
0.6078 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6078 Remote Similarity NPD1696 Phase 3
0.6071 Remote Similarity NPD5175 Approved
0.6071 Remote Similarity NPD4754 Approved
0.6071 Remote Similarity NPD5174 Approved
0.6066 Remote Similarity NPD8513 Phase 3
0.6066 Remote Similarity NPD8517 Approved
0.6066 Remote Similarity NPD8515 Approved
0.6066 Remote Similarity NPD8516 Approved
0.6061 Remote Similarity NPD7332 Phase 2
0.6061 Remote Similarity NPD7514 Phase 3
0.6058 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6058 Remote Similarity NPD6672 Approved
0.6058 Remote Similarity NPD6903 Approved
0.6058 Remote Similarity NPD5737 Approved
0.6055 Remote Similarity NPD5173 Approved
0.6038 Remote Similarity NPD7087 Discontinued
0.6036 Remote Similarity NPD4159 Approved
0.6034 Remote Similarity NPD4634 Approved
0.6033 Remote Similarity NPD7100 Approved
0.6033 Remote Similarity NPD7101 Approved
0.6032 Remote Similarity NPD6033 Approved
0.6019 Remote Similarity NPD4519 Discontinued
0.6019 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4623 Approved
0.6019 Remote Similarity NPD4249 Approved
0.6019 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6 Remote Similarity NPD4753 Phase 2
0.5985 Remote Similarity NPD7625 Phase 1
0.598 Remote Similarity NPD4786 Approved
0.5979 Remote Similarity NPD6117 Approved
0.5979 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5965 Remote Similarity NPD4768 Approved
0.5965 Remote Similarity NPD4767 Approved
0.5962 Remote Similarity NPD4251 Approved
0.5962 Remote Similarity NPD4250 Approved
0.5938 Remote Similarity NPD6924 Approved
0.5938 Remote Similarity NPD6926 Approved
0.5935 Remote Similarity NPD6909 Approved
0.5935 Remote Similarity NPD6908 Approved

Structure

External Identifiers

PubChem CID   50993975
ChEMBL   CHEMBL1669185
ZINC  

Physicochemical Properties

Molecular Weight:  282.15
ALogP:  -0.0401
MLogP:  2.56
XLogP:  -0.026
# Rotatable Bonds:  6
Polar Surface Area:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  20

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Biological Activities  
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