Natural Product: NPC215109

Natural Product ID:  NPC215109
Common Name:   (5Z)-5-[(2S,6E,8E)-2,6-Dimethyl-9-[(7S)-7-Methyl-5,6-Dihydro-4H-1-Benzofuran-7-Yl]Nona-6,8-Dienylidene]-4-Hydroxy-3-Methylfuran-2-One
IUPAC Name:   (5Z)-5-[(2S,6E,8E)-2,6-dimethyl-9-[(7S)-7-methyl-5,6-dihydro-4H-1-benzofuran-7-yl]nona-6,8-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:  
Molecular Formula:   C25H32O4
Standard InCHIKey:  PRWPWIZPRXATNU-NYXRGYENSA-N
Standard InCHI:  InChI=1S/C25H32O4/c1-17(8-5-9-18(2)16-21-22(26)19(3)24(27)29-21)10-6-13-25(4)14-7-11-20-12-15-28-23(20)25/h6,10,12-13,15-16,18,26H,5,7-9,11,14H2,1-4H3/b13-6+,17-10+,21-16-/t18-,25+/m0/s1
Canonical SMILES:  C/C(=CC=C[C@]1(C)CCCc2c1occ2)/CCC[C@@H](/C=C/1OC(=O)C(=C1O)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
NPO32608 ircinia sp. Species Irciniidae Eukaryota Okinawan PMID[12608859]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 >= 1 ug/ml 18341287

  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 NPC215109 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 NPC170604
0.907 High Similarity NPC75557
0.907 High Similarity NPC71274
0.9008 High Similarity NPC474438
0.9008 High Similarity NPC474279
0.8915 High Similarity NPC476351
0.8881 High Similarity NPC473982
0.8855 High Similarity NPC329694
0.8855 High Similarity NPC474260
0.8855 High Similarity NPC329922
0.8855 High Similarity NPC81912
0.8837 High Similarity NPC289911
0.8837 High Similarity NPC283284
0.8788 High Similarity NPC476016
0.876 High Similarity NPC474136
0.8705 High Similarity NPC202260
0.8626 High Similarity NPC475818
0.8623 High Similarity NPC303217
0.8605 High Similarity NPC473969
0.8571 High Similarity NPC294511
0.8571 High Similarity NPC121615
0.8562 High Similarity NPC228842
0.8561 High Similarity NPC118853
0.8561 High Similarity NPC307401
0.8507 High Similarity NPC474830
0.8483 Intermediate Similarity NPC71821
0.845 Intermediate Similarity NPC131801
0.8444 Intermediate Similarity NPC329707
0.8444 Intermediate Similarity NPC207294
0.8444 Intermediate Similarity NPC112706
0.844 Intermediate Similarity NPC107571
0.8433 Intermediate Similarity NPC138139
0.8433 Intermediate Similarity NPC46536
0.8425 Intermediate Similarity NPC93666
0.8421 Intermediate Similarity NPC243269
0.8421 Intermediate Similarity NPC188377
0.8421 Intermediate Similarity NPC65735
0.8406 Intermediate Similarity NPC293253
0.8403 Intermediate Similarity NPC218712
0.8403 Intermediate Similarity NPC267004
0.8403 Intermediate Similarity NPC307346
0.8403 Intermediate Similarity NPC261733
0.8397 Intermediate Similarity NPC474817
0.8394 Intermediate Similarity NPC89133
0.8385 Intermediate Similarity NPC21831
0.8385 Intermediate Similarity NPC187547
0.8382 Intermediate Similarity NPC59502
0.838 Intermediate Similarity NPC473983
0.838 Intermediate Similarity NPC148374
0.838 Intermediate Similarity NPC201370
0.8358 Intermediate Similarity NPC473885
0.8358 Intermediate Similarity NPC471074
0.8358 Intermediate Similarity NPC179354
0.8358 Intermediate Similarity NPC474829
0.8346 Intermediate Similarity NPC16922
0.8345 Intermediate Similarity NPC56731
0.8344 Intermediate Similarity NPC88007
0.8344 Intermediate Similarity NPC7059
0.8344 Intermediate Similarity NPC194499
0.8333 Intermediate Similarity NPC97566
0.8311 Intermediate Similarity NPC212257
0.8308 Intermediate Similarity NPC144745
0.8308 Intermediate Similarity NPC208906
0.8308 Intermediate Similarity NPC217180
0.8308 Intermediate Similarity NPC312525
0.8298 Intermediate Similarity NPC278832
0.8298 Intermediate Similarity NPC64157
0.8298 Intermediate Similarity NPC473268
0.8289 Intermediate Similarity NPC84349
0.8286 Intermediate Similarity NPC159786
0.8248 Intermediate Similarity NPC208389
0.8244 Intermediate Similarity NPC243704
0.8243 Intermediate Similarity NPC234494
0.8235 Intermediate Similarity NPC8389
0.8235 Intermediate Similarity NPC83178
0.8235 Intermediate Similarity NPC290955
0.8224 Intermediate Similarity NPC195954
0.8222 Intermediate Similarity NPC471559
0.8201 Intermediate Similarity NPC196979
0.8201 Intermediate Similarity NPC15083
0.8201 Intermediate Similarity NPC97740
0.8201 Intermediate Similarity NPC470976
0.8201 Intermediate Similarity NPC470977
0.8201 Intermediate Similarity NPC471817
0.82 Intermediate Similarity NPC33938
0.8182 Intermediate Similarity NPC68848
0.8182 Intermediate Similarity NPC79571
0.8182 Intermediate Similarity NPC90953
0.8175 Intermediate Similarity NPC279877
0.8175 Intermediate Similarity NPC26532
0.8162 Intermediate Similarity NPC23086
0.8162 Intermediate Similarity NPC74612
0.8156 Intermediate Similarity NPC14650
0.8156 Intermediate Similarity NPC476947
0.8154 Intermediate Similarity NPC205523
0.8143 Intermediate Similarity NPC474425
0.8143 Intermediate Similarity NPC218838
0.8143 Intermediate Similarity NPC474407
0.8143 Intermediate Similarity NPC474426
0.8143 Intermediate Similarity NPC470740
0.8138 Intermediate Similarity NPC263337
0.8134 Intermediate Similarity NPC477967
0.8129 Intermediate Similarity NPC88841
0.8129 Intermediate Similarity NPC17681
0.8129 Intermediate Similarity NPC136340
0.8129 Intermediate Similarity NPC282230
0.8129 Intermediate Similarity NPC285567
0.8129 Intermediate Similarity NPC288602
0.8129 Intermediate Similarity NPC283209
0.8129 Intermediate Similarity NPC183348
0.8125 Intermediate Similarity NPC56197
0.8117 Intermediate Similarity NPC287559
0.8112 Intermediate Similarity NPC472376
0.8108 Intermediate Similarity NPC224418
0.8102 Intermediate Similarity NPC246392
0.8099 Intermediate Similarity NPC146872
0.8095 Intermediate Similarity NPC34056
0.8085 Intermediate Similarity NPC288209
0.8082 Intermediate Similarity NPC254198
0.8079 Intermediate Similarity NPC246164
0.8077 Intermediate Similarity NPC261184
0.8071 Intermediate Similarity NPC45358
0.8067 Intermediate Similarity NPC470997
0.8065 Intermediate Similarity NPC18986
0.8065 Intermediate Similarity NPC188649
0.8058 Intermediate Similarity NPC66246
0.8058 Intermediate Similarity NPC170546
0.8054 Intermediate Similarity NPC113428
0.8054 Intermediate Similarity NPC61284
0.8043 Intermediate Similarity NPC477966
0.8043 Intermediate Similarity NPC477040
0.8043 Intermediate Similarity NPC477123
0.8041 Intermediate Similarity NPC104924
0.8041 Intermediate Similarity NPC233763
0.8039 Intermediate Similarity NPC104736
0.8039 Intermediate Similarity NPC41880
0.8038 Intermediate Similarity NPC296558
0.803 Intermediate Similarity NPC227660
0.8029 Intermediate Similarity NPC88403
0.8028 Intermediate Similarity NPC265793
0.8025 Intermediate Similarity NPC277618
0.8015 Intermediate Similarity NPC477965
0.8015 Intermediate Similarity NPC178382
0.8015 Intermediate Similarity NPC477038
0.8015 Intermediate Similarity NPC150895
0.8014 Intermediate Similarity NPC121158
0.8 Intermediate Similarity NPC69647
0.8 Intermediate Similarity NPC473379
0.8 Intermediate Similarity NPC298190
0.8 Intermediate Similarity NPC61788
0.8 Intermediate Similarity NPC477645
0.8 Intermediate Similarity NPC317217
0.8 Intermediate Similarity NPC125182
0.8 Intermediate Similarity NPC475092
0.8 Intermediate Similarity NPC471549
0.7987 Intermediate Similarity NPC255414
0.7987 Intermediate Similarity NPC308799
0.7987 Intermediate Similarity NPC216755
0.7987 Intermediate Similarity NPC471174
0.7987 Intermediate Similarity NPC304692
0.7984 Intermediate Similarity NPC105249
0.7975 Intermediate Similarity NPC310572
0.7974 Intermediate Similarity NPC296807
0.7974 Intermediate Similarity NPC155939
0.7974 Intermediate Similarity NPC141538
0.7974 Intermediate Similarity NPC25351
0.7973 Intermediate Similarity NPC469642
0.7973 Intermediate Similarity NPC247221
0.7973 Intermediate Similarity NPC290038
0.7972 Intermediate Similarity NPC204592
0.7971 Intermediate Similarity NPC473355
0.7971 Intermediate Similarity NPC471554
0.7971 Intermediate Similarity NPC471573
0.7971 Intermediate Similarity NPC137570
0.7971 Intermediate Similarity NPC471501
0.797 Intermediate Similarity NPC254958
0.797 Intermediate Similarity NPC291619
0.797 Intermediate Similarity NPC293424
0.7959 Intermediate Similarity NPC80635
0.7959 Intermediate Similarity NPC476946
0.7959 Intermediate Similarity NPC267632
0.7958 Intermediate Similarity NPC106247
0.7955 Intermediate Similarity NPC476031
0.7955 Intermediate Similarity NPC79202
0.7955 Intermediate Similarity NPC476014
0.7955 Intermediate Similarity NPC59035
0.7949 Intermediate Similarity NPC471003
0.7935 Intermediate Similarity NPC474611
0.7929 Intermediate Similarity NPC476925
0.7923 Intermediate Similarity NPC26157
0.7923 Intermediate Similarity NPC1811
0.7919 Intermediate Similarity NPC346
0.7917 Intermediate Similarity NPC186626
0.7917 Intermediate Similarity NPC42400
0.7914 Intermediate Similarity NPC477039
0.7914 Intermediate Similarity NPC327527
0.7914 Intermediate Similarity NPC476917
0.7911 Intermediate Similarity NPC121995
0.7911 Intermediate Similarity NPC475779
0.791 Intermediate Similarity NPC4898

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC215109 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
0.8182 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD4628 Phase 3
0.7708 Intermediate Similarity NPD6355 Discontinued
0.7671 Intermediate Similarity NPD2799 Discontinued
0.7606 Intermediate Similarity NPD6832 Phase 2
0.7597 Intermediate Similarity NPD7458 Discontinued
0.7584 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD8434 Phase 2
0.7554 Intermediate Similarity NPD9717 Approved
0.75 Intermediate Similarity NPD2313 Discontinued
0.747 Intermediate Similarity NPD6764 Approved
0.747 Intermediate Similarity NPD6765 Approved
0.7465 Intermediate Similarity NPD5647 Approved
0.7436 Intermediate Similarity NPD6599 Discontinued
0.741 Intermediate Similarity NPD3496 Discontinued
0.7407 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6273 Approved
0.7394 Intermediate Similarity NPD2797 Approved
0.7386 Intermediate Similarity NPD6799 Approved
0.7379 Intermediate Similarity NPD3268 Approved
0.7379 Intermediate Similarity NPD6798 Discontinued
0.7375 Intermediate Similarity NPD7075 Discontinued
0.7355 Intermediate Similarity NPD920 Approved
0.7353 Intermediate Similarity NPD7157 Approved
0.7347 Intermediate Similarity NPD447 Suspended
0.7343 Intermediate Similarity NPD2798 Approved
0.7333 Intermediate Similarity NPD6005 Phase 3
0.7333 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2344 Approved
0.7333 Intermediate Similarity NPD6004 Phase 3
0.7333 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6002 Phase 3
0.7333 Intermediate Similarity NPD1241 Discontinued
0.732 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD4308 Phase 3
0.731 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7003 Approved
0.7303 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6653 Approved
0.7296 Intermediate Similarity NPD5760 Phase 2
0.7296 Intermediate Similarity NPD5761 Phase 2
0.7294 Intermediate Similarity NPD6785 Approved
0.7294 Intermediate Similarity NPD6784 Approved
0.7273 Intermediate Similarity NPD1203 Approved
0.7267 Intermediate Similarity NPD1551 Phase 2
0.7267 Intermediate Similarity NPD2935 Discontinued
0.7262 Intermediate Similarity NPD6559 Discontinued
0.7244 Intermediate Similarity NPD5403 Approved
0.7234 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6801 Discontinued
0.7226 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD919 Approved
0.7222 Intermediate Similarity NPD1019 Discontinued
0.7219 Intermediate Similarity NPD2346 Discontinued
0.7214 Intermediate Similarity NPD1778 Approved
0.7211 Intermediate Similarity NPD8032 Phase 2
0.7192 Intermediate Similarity NPD7095 Approved
0.719 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD4110 Phase 3
0.7183 Intermediate Similarity NPD3972 Approved
0.7179 Intermediate Similarity NPD5049 Phase 3
0.7172 Intermediate Similarity NPD9494 Approved
0.7162 Intermediate Similarity NPD4060 Phase 1
0.7162 Intermediate Similarity NPD4307 Phase 2
0.7161 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD3267 Approved
0.7153 Intermediate Similarity NPD3266 Approved
0.7153 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1358 Approved
0.7143 Intermediate Similarity NPD2354 Approved
0.7143 Intermediate Similarity NPD2309 Approved
0.7143 Intermediate Similarity NPD5585 Approved
0.7143 Intermediate Similarity NPD411 Approved
0.7143 Intermediate Similarity NPD3887 Approved
0.7132 Intermediate Similarity NPD7843 Approved
0.7124 Intermediate Similarity NPD1243 Approved
0.7115 Intermediate Similarity NPD5401 Approved
0.7114 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1933 Approved
0.7111 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1471 Phase 3
0.7095 Intermediate Similarity NPD4062 Phase 3
0.7095 Intermediate Similarity NPD6233 Phase 2
0.709 Intermediate Similarity NPD2684 Approved
0.7083 Intermediate Similarity NPD1876 Approved
0.7081 Intermediate Similarity NPD7819 Suspended
0.7078 Intermediate Similarity NPD3750 Approved
0.7078 Intermediate Similarity NPD8166 Discontinued
0.7071 Intermediate Similarity NPD9545 Approved
0.7068 Intermediate Similarity NPD3134 Approved
0.7063 Intermediate Similarity NPD1608 Approved
0.7063 Intermediate Similarity NPD7411 Suspended
0.7063 Intermediate Similarity NPD6677 Suspended
0.7059 Intermediate Similarity NPD4534 Discontinued
0.705 Intermediate Similarity NPD9493 Approved
0.7037 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5402 Approved
0.703 Intermediate Similarity NPD8127 Discontinued
0.7029 Intermediate Similarity NPD2629 Approved
0.7027 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7097 Phase 1
0.7006 Intermediate Similarity NPD4661 Approved
0.7006 Intermediate Similarity NPD4662 Approved
0.7006 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD9092 Discovery
0.6994 Remote Similarity NPD3882 Suspended
0.6994 Remote Similarity NPD7768 Phase 2
0.6993 Remote Similarity NPD5763 Approved
0.6993 Remote Similarity NPD2353 Approved
0.6993 Remote Similarity NPD5762 Approved
0.6993 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6987 Remote Similarity NPD7440 Discontinued
0.6974 Remote Similarity NPD3748 Approved
0.6972 Remote Similarity NPD17 Approved
0.6972 Remote Similarity NPD4626 Approved
0.6972 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6963 Remote Similarity NPD6831 Clinical (unspecified phase)
0.695 Remote Similarity NPD1894 Discontinued
0.6948 Remote Similarity NPD2424 Discontinued
0.6948 Remote Similarity NPD5958 Discontinued
0.6937 Remote Similarity NPD3226 Approved
0.6933 Remote Similarity NPD3817 Phase 2
0.6928 Remote Similarity NPD4476 Approved
0.6928 Remote Similarity NPD2796 Approved
0.6928 Remote Similarity NPD4477 Approved
0.6918 Remote Similarity NPD6362 Approved
0.6913 Remote Similarity NPD3764 Approved
0.6912 Remote Similarity NPD2067 Discontinued
0.6905 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5691 Approved
0.6899 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6897 Remote Similarity NPD4359 Approved
0.6894 Remote Similarity NPD4380 Phase 2
0.689 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6871 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6871 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6863 Remote Similarity NPD7033 Discontinued
0.6852 Remote Similarity NPD6873 Phase 2
0.6849 Remote Similarity NPD1283 Approved
0.6849 Remote Similarity NPD8651 Approved
0.6848 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3749 Approved
0.6839 Remote Similarity NPD1549 Phase 2
0.6838 Remote Similarity NPD2182 Approved
0.6832 Remote Similarity NPD2651 Approved
0.6832 Remote Similarity NPD2649 Approved
0.6829 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6828 Remote Similarity NPD1481 Phase 2
0.6826 Remote Similarity NPD1247 Approved
0.6824 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2979 Phase 3
0.6821 Remote Similarity NPD3140 Approved
0.6821 Remote Similarity NPD4140 Approved
0.6821 Remote Similarity NPD3142 Approved
0.6818 Remote Similarity NPD2240 Approved
0.6818 Remote Similarity NPD2438 Suspended
0.6818 Remote Similarity NPD2239 Approved
0.6813 Remote Similarity NPD6980 Clinical (unspecified phase)
0.681 Remote Similarity NPD1934 Approved
0.6795 Remote Similarity NPD2800 Approved
0.6792 Remote Similarity NPD2534 Approved
0.6792 Remote Similarity NPD2532 Approved
0.6792 Remote Similarity NPD2533 Approved
0.679 Remote Similarity NPD7028 Phase 2
0.6786 Remote Similarity NPD6808 Phase 2
0.6782 Remote Similarity NPD8313 Approved
0.6782 Remote Similarity NPD8312 Approved
0.6781 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6779 Remote Similarity NPD2614 Approved
0.6776 Remote Similarity NPD4622 Approved
0.6776 Remote Similarity NPD4618 Approved
0.6774 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6766 Remote Similarity NPD5494 Approved
0.6765 Remote Similarity NPD290 Approved
0.6763 Remote Similarity NPD5535 Approved
0.6759 Remote Similarity NPD6287 Discontinued
0.6759 Remote Similarity NPD1535 Discovery
0.6759 Remote Similarity NPD1281 Approved
0.6755 Remote Similarity NPD6663 Approved
0.6753 Remote Similarity NPD1510 Phase 2
0.6748 Remote Similarity NPD958 Approved
0.6747 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6741 Remote Similarity NPD9697 Approved
0.6735 Remote Similarity NPD3225 Approved
0.6731 Remote Similarity NPD2897 Discontinued
0.6731 Remote Similarity NPD970 Clinical (unspecified phase)
0.6725 Remote Similarity NPD2163 Approved
0.6725 Remote Similarity NPD3818 Discontinued
0.6711 Remote Similarity NPD1240 Approved
0.671 Remote Similarity NPD6099 Approved
0.671 Remote Similarity NPD6032 Approved
0.671 Remote Similarity NPD6100 Approved
0.6708 Remote Similarity NPD3873 Phase 3
0.6708 Remote Similarity NPD3869 Phase 3

Structure

External Identifiers

PubChem CID   54690807
ChEMBL   CHEMBL458466
ZINC  

Physicochemical Properties

Molecular Weight:  396.23
ALogP:  1.7813
MLogP:  3.77
XLogP:  6.37
# Rotatable Bonds:  12
Polar Surface Area:  59.67
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  29

Download Data

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Structure MOL file  
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Biological Activities  
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