Natural Product: NPC12854

Natural Product ID:  NPC12854
Common Name:   Piperkadsin C
IUPAC Name:   (1R,6S)-6-[(R)-1,3-benzodioxol-5-yl(hydroxy)methyl]-7-methoxy-6-methyl-3-prop-2-enylbicyclo[3.1.1]hepta-3,5(7)-dien-2-one
Synonyms:   Piperkadsin C
Molecular Formula:   C20H20O5
Standard InCHIKey:  NOXNHMNKQIHADP-PWIZWCRZSA-N
Standard InCHI:  InChI=1S/C20H20O5/c1-4-5-11-8-13-18(23-3)16(17(11)21)20(13,2)19(22)12-6-7-14-15(9-12)25-10-24-14/h4,6-9,16,19,22H,1,5,10H2,2-3H3/t16-,19+,20+/m0/s1
Canonical SMILES:  C=CCC1=CC2=C([C@H](C1=O)[C@]2(C)[C@@H](c1ccc2c(c1)OCO2)O)OC
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
NPO4865 Piper kadsura Species Piperaceae Eukaryota PMID[19900811]
NPO2639 Caulis piperis kadsurae NA NA NA TCMSP*
NPO4865 Piper kadsura Species Piperaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT34 Cell Line BV-2 Mus musculus Inhibition = 60.8 % 19900811
NPT34 Cell Line BV-2 Mus musculus IC50 = 14600 nM 19900811

  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 NPC12854 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
0.8986 High Similarity NPC476336
0.8966 High Similarity NPC51681
0.8912 High Similarity NPC15743
0.8824 High Similarity NPC476364
0.8667 High Similarity NPC472560
0.8552 High Similarity NPC37065
0.8544 High Similarity NPC476337
0.8543 High Similarity NPC30890
0.8523 High Similarity NPC104956
0.8514 High Similarity NPC470855
0.8514 High Similarity NPC322021
0.8503 High Similarity NPC166184
0.85 High Similarity NPC100420
0.8487 Intermediate Similarity NPC476338
0.8487 Intermediate Similarity NPC153620
0.8487 Intermediate Similarity NPC25496
0.8487 Intermediate Similarity NPC24257
0.8487 Intermediate Similarity NPC476359
0.8481 Intermediate Similarity NPC68619
0.8481 Intermediate Similarity NPC475095
0.8452 Intermediate Similarity NPC56184
0.8447 Intermediate Similarity NPC474301
0.8428 Intermediate Similarity NPC239818
0.8428 Intermediate Similarity NPC218471
0.8421 Intermediate Similarity NPC189054
0.8421 Intermediate Similarity NPC3982
0.8403 Intermediate Similarity NPC477694
0.8403 Intermediate Similarity NPC477705
0.8395 Intermediate Similarity NPC476277
0.8389 Intermediate Similarity NPC278076
0.8365 Intermediate Similarity NPC76211
0.8356 Intermediate Similarity NPC327410
0.8355 Intermediate Similarity NPC327052
0.8345 Intermediate Similarity NPC477706
0.8333 Intermediate Similarity NPC28398
0.8333 Intermediate Similarity NPC151425
0.8323 Intermediate Similarity NPC177830
0.8323 Intermediate Similarity NPC475170
0.8322 Intermediate Similarity NPC64948
0.8289 Intermediate Similarity NPC46880
0.8289 Intermediate Similarity NPC239608
0.8289 Intermediate Similarity NPC46161
0.8288 Intermediate Similarity NPC104077
0.8288 Intermediate Similarity NPC219671
0.8288 Intermediate Similarity NPC147616
0.8288 Intermediate Similarity NPC259742
0.828 Intermediate Similarity NPC308555
0.828 Intermediate Similarity NPC245948
0.8278 Intermediate Similarity NPC476842
0.8278 Intermediate Similarity NPC52664
0.8278 Intermediate Similarity NPC476840
0.8278 Intermediate Similarity NPC46180
0.8276 Intermediate Similarity NPC280399
0.8276 Intermediate Similarity NPC233961
0.8276 Intermediate Similarity NPC195292
0.8276 Intermediate Similarity NPC142985
0.8276 Intermediate Similarity NPC339621
0.8269 Intermediate Similarity NPC62354
0.8267 Intermediate Similarity NPC474784
0.8258 Intermediate Similarity NPC477698
0.8243 Intermediate Similarity NPC174191
0.8243 Intermediate Similarity NPC470990
0.8239 Intermediate Similarity NPC478055
0.8235 Intermediate Similarity NPC223185
0.8228 Intermediate Similarity NPC136757
0.8228 Intermediate Similarity NPC25127
0.8221 Intermediate Similarity NPC475738
0.8219 Intermediate Similarity NPC469480
0.8217 Intermediate Similarity NPC476335
0.8212 Intermediate Similarity NPC100675
0.821 Intermediate Similarity NPC476244
0.8205 Intermediate Similarity NPC229882
0.8205 Intermediate Similarity NPC158635
0.8204 Intermediate Similarity NPC469438
0.8194 Intermediate Similarity NPC304821
0.8187 Intermediate Similarity NPC475663
0.8187 Intermediate Similarity NPC286919
0.8176 Intermediate Similarity NPC186316
0.8176 Intermediate Similarity NPC254163
0.8176 Intermediate Similarity NPC267242
0.817 Intermediate Similarity NPC50696
0.8169 Intermediate Similarity NPC244876
0.8165 Intermediate Similarity NPC327225
0.8165 Intermediate Similarity NPC245615
0.8165 Intermediate Similarity NPC180388
0.8165 Intermediate Similarity NPC61604
0.8165 Intermediate Similarity NPC299706
0.8165 Intermediate Similarity NPC115466
0.8163 Intermediate Similarity NPC471505
0.8163 Intermediate Similarity NPC106739
0.816 Intermediate Similarity NPC469518
0.816 Intermediate Similarity NPC469475
0.816 Intermediate Similarity NPC100425
0.8153 Intermediate Similarity NPC178048
0.8153 Intermediate Similarity NPC164082
0.8148 Intermediate Similarity NPC477627
0.8141 Intermediate Similarity NPC472567
0.8141 Intermediate Similarity NPC478242
0.8137 Intermediate Similarity NPC469384
0.8137 Intermediate Similarity NPC472565
0.8133 Intermediate Similarity NPC14022
0.8125 Intermediate Similarity NPC237946
0.8125 Intermediate Similarity NPC32373
0.8117 Intermediate Similarity NPC469683
0.8113 Intermediate Similarity NPC60084
0.8113 Intermediate Similarity NPC287504
0.811 Intermediate Similarity NPC180586
0.8105 Intermediate Similarity NPC86455
0.8105 Intermediate Similarity NPC125134
0.8105 Intermediate Similarity NPC472564
0.8105 Intermediate Similarity NPC474966
0.8105 Intermediate Similarity NPC137920
0.8101 Intermediate Similarity NPC477699
0.8098 Intermediate Similarity NPC125991
0.8092 Intermediate Similarity NPC166137
0.8092 Intermediate Similarity NPC82336
0.8092 Intermediate Similarity NPC78987
0.8092 Intermediate Similarity NPC323601
0.8092 Intermediate Similarity NPC282291
0.8089 Intermediate Similarity NPC205054
0.8086 Intermediate Similarity NPC472961
0.8086 Intermediate Similarity NPC472962
0.8079 Intermediate Similarity NPC178290
0.8077 Intermediate Similarity NPC1580
0.8075 Intermediate Similarity NPC474990
0.8075 Intermediate Similarity NPC207584
0.8075 Intermediate Similarity NPC19947
0.8075 Intermediate Similarity NPC40920
0.8075 Intermediate Similarity NPC476340
0.8075 Intermediate Similarity NPC223335
0.8069 Intermediate Similarity NPC12022
0.8069 Intermediate Similarity NPC293641
0.8069 Intermediate Similarity NPC20287
0.8069 Intermediate Similarity NPC20404
0.8067 Intermediate Similarity NPC90431
0.8063 Intermediate Similarity NPC38699
0.8063 Intermediate Similarity NPC131532
0.8054 Intermediate Similarity NPC45404
0.8054 Intermediate Similarity NPC145769
0.8052 Intermediate Similarity NPC474036
0.8052 Intermediate Similarity NPC469615
0.805 Intermediate Similarity NPC44730
0.8049 Intermediate Similarity NPC475865
0.8047 Intermediate Similarity NPC469397
0.8041 Intermediate Similarity NPC239302
0.8038 Intermediate Similarity NPC475311
0.8038 Intermediate Similarity NPC477700
0.8038 Intermediate Similarity NPC473680
0.8038 Intermediate Similarity NPC234152
0.8038 Intermediate Similarity NPC32079
0.8038 Intermediate Similarity NPC473579
0.8038 Intermediate Similarity NPC475454
0.8038 Intermediate Similarity NPC31132
0.8038 Intermediate Similarity NPC163002
0.8037 Intermediate Similarity NPC288149
0.8036 Intermediate Similarity NPC473467
0.8036 Intermediate Similarity NPC475197
0.8036 Intermediate Similarity NPC105137
0.8027 Intermediate Similarity NPC215941
0.8027 Intermediate Similarity NPC137427
0.8027 Intermediate Similarity NPC311419
0.8027 Intermediate Similarity NPC244246
0.8027 Intermediate Similarity NPC65935
0.8027 Intermediate Similarity NPC319282
0.8027 Intermediate Similarity NPC275724
0.8027 Intermediate Similarity NPC123196
0.8026 Intermediate Similarity NPC147379
0.8025 Intermediate Similarity NPC179914
0.8025 Intermediate Similarity NPC62518
0.8025 Intermediate Similarity NPC215375
0.8025 Intermediate Similarity NPC145569
0.8025 Intermediate Similarity NPC216223
0.8025 Intermediate Similarity NPC469654
0.8025 Intermediate Similarity NPC474903
0.8014 Intermediate Similarity NPC278308
0.8013 Intermediate Similarity NPC52968
0.8013 Intermediate Similarity NPC231719
0.8013 Intermediate Similarity NPC88345
0.8012 Intermediate Similarity NPC163635
0.8012 Intermediate Similarity NPC228357
0.8012 Intermediate Similarity NPC471180
0.8012 Intermediate Similarity NPC109765
0.8012 Intermediate Similarity NPC188217
0.8012 Intermediate Similarity NPC261090
0.8 Intermediate Similarity NPC101624
0.8 Intermediate Similarity NPC476841
0.8 Intermediate Similarity NPC142547
0.8 Intermediate Similarity NPC18576
0.8 Intermediate Similarity NPC184938
0.8 Intermediate Similarity NPC135777
0.8 Intermediate Similarity NPC476843
0.8 Intermediate Similarity NPC474158
0.8 Intermediate Similarity NPC62051
0.7988 Intermediate Similarity NPC475244
0.7988 Intermediate Similarity NPC56735
0.7988 Intermediate Similarity NPC76687
0.7988 Intermediate Similarity NPC61594
0.7987 Intermediate Similarity NPC28724
0.7987 Intermediate Similarity NPC476434
0.7987 Intermediate Similarity NPC203664

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC12854 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
0.828 Intermediate Similarity NPD37 Approved
0.8153 Intermediate Similarity NPD7028 Phase 2
0.8125 Intermediate Similarity NPD4967 Phase 2
0.8125 Intermediate Similarity NPD4965 Approved
0.8125 Intermediate Similarity NPD4966 Approved
0.8 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6234 Discontinued
0.7904 Intermediate Similarity NPD3818 Discontinued
0.7817 Intermediate Similarity NPD1357 Approved
0.7711 Intermediate Similarity NPD8127 Discontinued
0.7692 Intermediate Similarity NPD4110 Phase 3
0.7692 Intermediate Similarity NPD7228 Approved
0.7692 Intermediate Similarity NPD4628 Phase 3
0.7692 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD3705 Approved
0.7644 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD5494 Approved
0.7531 Intermediate Similarity NPD7458 Discontinued
0.7514 Intermediate Similarity NPD6559 Discontinued
0.7514 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7074 Phase 3
0.747 Intermediate Similarity NPD3882 Suspended
0.7468 Intermediate Similarity NPD8166 Discontinued
0.7442 Intermediate Similarity NPD7054 Approved
0.7432 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7473 Discontinued
0.7414 Intermediate Similarity NPD7240 Approved
0.7414 Intermediate Similarity NPD7685 Pre-registration
0.7401 Intermediate Similarity NPD8434 Phase 2
0.7399 Intermediate Similarity NPD7472 Approved
0.7396 Intermediate Similarity NPD7199 Phase 2
0.7394 Intermediate Similarity NPD1934 Approved
0.7368 Intermediate Similarity NPD3027 Phase 3
0.7353 Intermediate Similarity NPD6232 Discontinued
0.7349 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD3620 Phase 2
0.7321 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD5536 Phase 2
0.7278 Intermediate Similarity NPD7266 Discontinued
0.7273 Intermediate Similarity NPD7808 Phase 3
0.7273 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD6797 Phase 2
0.725 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD2801 Approved
0.7241 Intermediate Similarity NPD5844 Phase 1
0.7239 Intermediate Similarity NPD6273 Approved
0.7237 Intermediate Similarity NPD9494 Approved
0.7232 Intermediate Similarity NPD8313 Approved
0.7232 Intermediate Similarity NPD8312 Approved
0.7216 Intermediate Similarity NPD7251 Discontinued
0.7215 Intermediate Similarity NPD2935 Discontinued
0.7209 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6674 Discontinued
0.7184 Intermediate Similarity NPD3751 Discontinued
0.7179 Intermediate Similarity NPD447 Suspended
0.7178 Intermediate Similarity NPD2534 Approved
0.7178 Intermediate Similarity NPD2533 Approved
0.7178 Intermediate Similarity NPD2532 Approved
0.7171 Intermediate Similarity NPD5647 Approved
0.7171 Intermediate Similarity NPD2798 Approved
0.7169 Intermediate Similarity NPD4380 Phase 2
0.7168 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6166 Phase 2
0.7153 Intermediate Similarity NPD5283 Phase 1
0.7152 Intermediate Similarity NPD2799 Discontinued
0.7152 Intermediate Similarity NPD1653 Approved
0.7101 Intermediate Similarity NPD3817 Phase 2
0.7099 Intermediate Similarity NPD6190 Approved
0.7095 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2800 Approved
0.7073 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6355 Discontinued
0.7066 Intermediate Similarity NPD6599 Discontinued
0.7063 Intermediate Similarity NPD6004 Phase 3
0.7063 Intermediate Similarity NPD6005 Phase 3
0.7063 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6002 Phase 3
0.7059 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD2932 Approved
0.7045 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD1283 Approved
0.702 Intermediate Similarity NPD3972 Approved
0.7006 Intermediate Similarity NPD4140 Approved
0.7006 Intermediate Similarity NPD3226 Approved
0.6994 Remote Similarity NPD1247 Approved
0.698 Remote Similarity NPD1651 Approved
0.6977 Remote Similarity NPD919 Approved
0.6975 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6962 Remote Similarity NPD230 Phase 1
0.6957 Remote Similarity NPD2346 Discontinued
0.6954 Remote Similarity NPD3787 Discontinued
0.6943 Remote Similarity NPD8032 Phase 2
0.6941 Remote Similarity NPD5761 Phase 2
0.6941 Remote Similarity NPD7819 Suspended
0.6941 Remote Similarity NPD5760 Phase 2
0.6941 Remote Similarity NPD8455 Phase 2
0.6941 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6937 Remote Similarity NPD1510 Phase 2
0.6933 Remote Similarity NPD4626 Approved
0.6933 Remote Similarity NPD3019 Approved
0.6933 Remote Similarity NPD7003 Approved
0.6923 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6386 Approved
0.6923 Remote Similarity NPD6385 Approved
0.6923 Remote Similarity NPD6873 Phase 2
0.6919 Remote Similarity NPD7075 Discontinued
0.6918 Remote Similarity NPD1241 Discontinued
0.6918 Remote Similarity NPD1607 Approved
0.6918 Remote Similarity NPD6653 Approved
0.6915 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6914 Remote Similarity NPD970 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2424 Discontinued
0.6914 Remote Similarity NPD3926 Phase 2
0.6909 Remote Similarity NPD4357 Discontinued
0.6909 Remote Similarity NPD1511 Approved
0.6908 Remote Similarity NPD1608 Approved
0.6901 Remote Similarity NPD5402 Approved
0.6899 Remote Similarity NPD2979 Phase 3
0.6899 Remote Similarity NPD1240 Approved
0.6897 Remote Similarity NPD228 Approved
0.6894 Remote Similarity NPD2438 Suspended
0.6882 Remote Similarity NPD6801 Discontinued
0.6879 Remote Similarity NPD3764 Approved
0.6879 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7097 Phase 1
0.6867 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6865 Remote Similarity NPD7296 Approved
0.6859 Remote Similarity NPD7680 Approved
0.6855 Remote Similarity NPD5735 Approved
0.6855 Remote Similarity NPD1933 Approved
0.6855 Remote Similarity NPD3657 Discovery
0.6852 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5762 Approved
0.6852 Remote Similarity NPD2344 Approved
0.6852 Remote Similarity NPD5763 Approved
0.6852 Remote Similarity NPD1375 Discontinued
0.6845 Remote Similarity NPD3687 Approved
0.6845 Remote Similarity NPD3686 Approved
0.6842 Remote Similarity NPD2978 Approved
0.6842 Remote Similarity NPD1091 Approved
0.6842 Remote Similarity NPD2977 Approved
0.6842 Remote Similarity NPD1281 Approved
0.6835 Remote Similarity NPD6663 Approved
0.6833 Remote Similarity NPD7038 Approved
0.6833 Remote Similarity NPD7039 Approved
0.6832 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7033 Discontinued
0.6826 Remote Similarity NPD1512 Approved
0.6824 Remote Similarity NPD7157 Approved
0.6821 Remote Similarity NPD1778 Approved
0.6818 Remote Similarity NPD1876 Approved
0.6818 Remote Similarity NPD8651 Approved
0.6815 Remote Similarity NPD7095 Approved
0.6813 Remote Similarity NPD6651 Approved
0.681 Remote Similarity NPD1549 Phase 2
0.6807 Remote Similarity NPD6799 Approved
0.6802 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6802 Remote Similarity NPD5353 Approved
0.6798 Remote Similarity NPD7799 Discontinued
0.6795 Remote Similarity NPD5736 Approved
0.6795 Remote Similarity NPD2861 Phase 2
0.6792 Remote Similarity NPD4060 Phase 1
0.6792 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1613 Approved
0.679 Remote Similarity NPD2796 Approved
0.679 Remote Similarity NPD6099 Approved
0.679 Remote Similarity NPD6100 Approved
0.6789 Remote Similarity NPD6779 Approved
0.6789 Remote Similarity NPD6780 Approved
0.6789 Remote Similarity NPD6778 Approved
0.6789 Remote Similarity NPD6777 Approved
0.6789 Remote Similarity NPD6781 Approved
0.6789 Remote Similarity NPD6782 Approved
0.6789 Remote Similarity NPD6776 Approved
0.6778 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6772 Remote Similarity NPD2313 Discontinued
0.6772 Remote Similarity NPD6798 Discontinued
0.6768 Remote Similarity NPD4236 Phase 3
0.6768 Remote Similarity NPD4237 Approved
0.6766 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6758 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6755 Remote Similarity NPD5691 Approved
0.6755 Remote Similarity NPD5585 Approved
0.6748 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6748 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6747 Remote Similarity NPD5058 Phase 3
0.6744 Remote Similarity NPD5563 Clinical (unspecified phase)
0.674 Remote Similarity NPD6764 Approved
0.674 Remote Similarity NPD6765 Approved
0.673 Remote Similarity NPD6233 Phase 2
0.6727 Remote Similarity NPD3750 Approved

Structure

External Identifiers

PubChem CID   46228396
ChEMBL   CHEMBL604682
ZINC  

Physicochemical Properties

Molecular Weight:  340.13
ALogP:  0.1248
MLogP:  3.11
XLogP:  1.589
# Rotatable Bonds:  8
Polar Surface Area:  64.99
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  25

Download Data

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Biological Activities  
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