Natural Product: NPC54066

Natural Product ID:  NPC54066
Common Name:   Peyonine
IUPAC Name:   1-[2-(3,4,5-trimethoxyphenyl)ethyl]pyrrole-2-carboxylic acid
Synonyms:   Peyonine
Molecular Formula:   C16H19NO5
Standard InCHIKey:  DDYNENGLSGKEPO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H19NO5/c1-20-13-9-11(10-14(21-2)15(13)22-3)6-8-17-7-4-5-12(17)16(18)19/h4-5,7,9-10H,6,8H2,1-3H3,(H,18,19)
Canonical SMILES:  COc1cc(CCn2cccc2C(=O)O)cc(c1OC)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
NPO25443 Citrus reticulata Species Rutaceae Eukaryota TM-MC*
NPO10082 Citrus unshiu Species Rutaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT355 Organism Phaseolus vulgaris Phaseolus vulgaris Inhibition = 0 % 10.1021/np50013a017

  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 NPC54066 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
0.8431 Intermediate Similarity NPC210256
0.8408 Intermediate Similarity NPC127085
0.8043 Intermediate Similarity NPC183537
0.8038 Intermediate Similarity NPC472287
0.8038 Intermediate Similarity NPC472286
0.8028 Intermediate Similarity NPC236668
0.8018 Intermediate Similarity NPC15406
0.7991 Intermediate Similarity NPC146976
0.7991 Intermediate Similarity NPC129897
0.7965 Intermediate Similarity NPC77878
0.7946 Intermediate Similarity NPC90875
0.7937 Intermediate Similarity NPC233334
0.7904 Intermediate Similarity NPC124313
0.7895 Intermediate Similarity NPC207283
0.7895 Intermediate Similarity NPC84164
0.7851 Intermediate Similarity NPC210296
0.783 Intermediate Similarity NPC318068
0.7792 Intermediate Similarity NPC107123
0.7788 Intermediate Similarity NPC472284
0.7773 Intermediate Similarity NPC119134
0.7772 Intermediate Similarity NPC295158
0.7768 Intermediate Similarity NPC24019
0.7753 Intermediate Similarity NPC108342
0.7746 Intermediate Similarity NPC193238
0.7719 Intermediate Similarity NPC189903
0.7719 Intermediate Similarity NPC182907
0.7685 Intermediate Similarity NPC241025
0.7664 Intermediate Similarity NPC321428
0.7647 Intermediate Similarity NPC174049
0.7636 Intermediate Similarity NPC473822
0.7617 Intermediate Similarity NPC134637
0.7609 Intermediate Similarity NPC166722
0.7588 Intermediate Similarity NPC22481
0.7588 Intermediate Similarity NPC172222
0.7578 Intermediate Similarity NPC210434
0.7578 Intermediate Similarity NPC122463
0.7548 Intermediate Similarity NPC195268
0.7548 Intermediate Similarity NPC133140
0.7547 Intermediate Similarity NPC477019
0.7533 Intermediate Similarity NPC278525
0.7523 Intermediate Similarity NPC146418
0.7489 Intermediate Similarity NPC476995
0.7488 Intermediate Similarity NPC224928
0.7478 Intermediate Similarity NPC253675
0.7455 Intermediate Similarity NPC266931
0.7444 Intermediate Similarity NPC74360
0.7424 Intermediate Similarity NPC201508
0.7424 Intermediate Similarity NPC476999
0.7419 Intermediate Similarity NPC313189
0.7418 Intermediate Similarity NPC4071
0.7418 Intermediate Similarity NPC476578
0.7418 Intermediate Similarity NPC476582
0.7414 Intermediate Similarity NPC15801
0.7412 Intermediate Similarity NPC246381
0.7412 Intermediate Similarity NPC476997
0.7409 Intermediate Similarity NPC112206
0.7409 Intermediate Similarity NPC202605
0.7406 Intermediate Similarity NPC473814
0.7406 Intermediate Similarity NPC78767
0.7393 Intermediate Similarity NPC93390
0.7387 Intermediate Similarity NPC41717
0.738 Intermediate Similarity NPC476996
0.738 Intermediate Similarity NPC476998
0.7379 Intermediate Similarity NPC207851
0.7361 Intermediate Similarity NPC475774
0.7359 Intermediate Similarity NPC255800
0.7359 Intermediate Similarity NPC96584
0.7339 Intermediate Similarity NPC473639
0.7336 Intermediate Similarity NPC215837
0.7336 Intermediate Similarity NPC476994
0.7331 Intermediate Similarity NPC316224
0.733 Intermediate Similarity NPC296482
0.733 Intermediate Similarity NPC202768
0.733 Intermediate Similarity NPC53069
0.7327 Intermediate Similarity NPC36229
0.7327 Intermediate Similarity NPC476581
0.7327 Intermediate Similarity NPC16452
0.73 Intermediate Similarity NPC471013
0.73 Intermediate Similarity NPC148896
0.73 Intermediate Similarity NPC180668
0.7273 Intermediate Similarity NPC48042
0.7273 Intermediate Similarity NPC304179
0.7273 Intermediate Similarity NPC475301
0.7273 Intermediate Similarity NPC85879
0.7273 Intermediate Similarity NPC260434
0.7273 Intermediate Similarity NPC326930
0.7273 Intermediate Similarity NPC472550
0.7273 Intermediate Similarity NPC53255
0.7264 Intermediate Similarity NPC230403
0.726 Intermediate Similarity NPC135549
0.7252 Intermediate Similarity NPC316981
0.7249 Intermediate Similarity NPC473506
0.7246 Intermediate Similarity NPC49672
0.7246 Intermediate Similarity NPC148889
0.7243 Intermediate Similarity NPC13603
0.724 Intermediate Similarity NPC470020
0.7237 Intermediate Similarity NPC76565
0.7237 Intermediate Similarity NPC250807
0.7237 Intermediate Similarity NPC57797
0.7235 Intermediate Similarity NPC66815
0.7235 Intermediate Similarity NPC57398
0.723 Intermediate Similarity NPC146724
0.7227 Intermediate Similarity NPC63041
0.7224 Intermediate Similarity NPC191489
0.7222 Intermediate Similarity NPC234197
0.7217 Intermediate Similarity NPC87152
0.7217 Intermediate Similarity NPC475600
0.7217 Intermediate Similarity NPC228377
0.7217 Intermediate Similarity NPC477787
0.7217 Intermediate Similarity NPC328186
0.7217 Intermediate Similarity NPC122968
0.7217 Intermediate Similarity NPC475631
0.7217 Intermediate Similarity NPC476110
0.7212 Intermediate Similarity NPC168209
0.7205 Intermediate Similarity NPC473850
0.7205 Intermediate Similarity NPC475137
0.7205 Intermediate Similarity NPC475498
0.72 Intermediate Similarity NPC6981
0.72 Intermediate Similarity NPC246658
0.7197 Intermediate Similarity NPC475533
0.7195 Intermediate Similarity NPC325297
0.7189 Intermediate Similarity NPC31930
0.7186 Intermediate Similarity NPC470486
0.7186 Intermediate Similarity NPC471977
0.7186 Intermediate Similarity NPC475644
0.7186 Intermediate Similarity NPC471190
0.7178 Intermediate Similarity NPC10904
0.7176 Intermediate Similarity NPC123395
0.7175 Intermediate Similarity NPC171409
0.7175 Intermediate Similarity NPC472553
0.7175 Intermediate Similarity NPC96405
0.7173 Intermediate Similarity NPC217554
0.7168 Intermediate Similarity NPC294579
0.7168 Intermediate Similarity NPC314270
0.7168 Intermediate Similarity NPC144779
0.7167 Intermediate Similarity NPC324619
0.7167 Intermediate Similarity NPC161801
0.7167 Intermediate Similarity NPC475315
0.7166 Intermediate Similarity NPC471978
0.7163 Intermediate Similarity NPC74153
0.7162 Intermediate Similarity NPC290689
0.7156 Intermediate Similarity NPC470306
0.7156 Intermediate Similarity NPC42678
0.7156 Intermediate Similarity NPC477907
0.7156 Intermediate Similarity NPC477909
0.7156 Intermediate Similarity NPC477910
0.7155 Intermediate Similarity NPC469792
0.7155 Intermediate Similarity NPC284141
0.7154 Intermediate Similarity NPC473833
0.7149 Intermediate Similarity NPC67401
0.7149 Intermediate Similarity NPC470042
0.7143 Intermediate Similarity NPC146824
0.7137 Intermediate Similarity NPC301368
0.7137 Intermediate Similarity NPC216428
0.7137 Intermediate Similarity NPC84815
0.7137 Intermediate Similarity NPC308906
0.7137 Intermediate Similarity NPC315804
0.7137 Intermediate Similarity NPC313804
0.7126 Intermediate Similarity NPC282346
0.7124 Intermediate Similarity NPC292416
0.7124 Intermediate Similarity NPC316841
0.7124 Intermediate Similarity NPC473689
0.7124 Intermediate Similarity NPC475303
0.7124 Intermediate Similarity NPC475596
0.7124 Intermediate Similarity NPC206343
0.7124 Intermediate Similarity NPC477908
0.7124 Intermediate Similarity NPC471014
0.7124 Intermediate Similarity NPC471016
0.7124 Intermediate Similarity NPC475408
0.7123 Intermediate Similarity NPC317572
0.7118 Intermediate Similarity NPC243633
0.7118 Intermediate Similarity NPC175150
0.7118 Intermediate Similarity NPC477788
0.7112 Intermediate Similarity NPC475362
0.7112 Intermediate Similarity NPC194740
0.7112 Intermediate Similarity NPC274640
0.7111 Intermediate Similarity NPC228331
0.7111 Intermediate Similarity NPC319128
0.7108 Intermediate Similarity NPC88923
0.7108 Intermediate Similarity NPC100734
0.7108 Intermediate Similarity NPC315634
0.7106 Intermediate Similarity NPC182222
0.7103 Intermediate Similarity NPC307963
0.7103 Intermediate Similarity NPC473821
0.7098 Intermediate Similarity NPC251160
0.7097 Intermediate Similarity NPC328928
0.7094 Intermediate Similarity NPC244839
0.7094 Intermediate Similarity NPC320324
0.7094 Intermediate Similarity NPC30456
0.7094 Intermediate Similarity NPC319880
0.7093 Intermediate Similarity NPC62367
0.7093 Intermediate Similarity NPC184408
0.7093 Intermediate Similarity NPC173080
0.7091 Intermediate Similarity NPC329708
0.7091 Intermediate Similarity NPC118832
0.7091 Intermediate Similarity NPC47059
0.7091 Intermediate Similarity NPC165349
0.7091 Intermediate Similarity NPC274291
0.7091 Intermediate Similarity NPC264166
0.709 Intermediate Similarity NPC471015

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC54066 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
0.8066 Intermediate Similarity NPD5866 Approved
0.8044 Intermediate Similarity NPD7885 Phase 2
0.8044 Intermediate Similarity NPD7886 Phase 2
0.7662 Intermediate Similarity NPD1483 Discontinued
0.7548 Intermediate Similarity NPD3924 Approved
0.7548 Intermediate Similarity NPD3922 Approved
0.7548 Intermediate Similarity NPD3921 Approved
0.7548 Intermediate Similarity NPD3923 Approved
0.7543 Intermediate Similarity NPD7417 Discontinued
0.7468 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD6974 Phase 3
0.7426 Intermediate Similarity NPD8350 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD5640 Discontinued
0.7368 Intermediate Similarity NPD3259 Approved
0.7366 Intermediate Similarity NPD3386 Phase 2
0.7354 Intermediate Similarity NPD3326 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD3816 Phase 1
0.733 Intermediate Similarity NPD3815 Phase 1
0.7321 Intermediate Similarity NPD3354 Phase 2
0.7311 Intermediate Similarity NPD3328 Phase 2
0.7282 Intermediate Similarity NPD3178 Discontinued
0.7265 Intermediate Similarity NPD5805 Approved
0.726 Intermediate Similarity NPD4889 Approved
0.7257 Intermediate Similarity NPD7180 Phase 3
0.7257 Intermediate Similarity NPD6856 Discontinued
0.7257 Intermediate Similarity NPD8479 Phase 2
0.7252 Intermediate Similarity NPD7069 Discontinued
0.723 Intermediate Similarity NPD4418 Discontinued
0.7227 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7224 Intermediate Similarity NPD7708 Approved
0.722 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD1923 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD4551 Phase 2
0.7183 Intermediate Similarity NPD6361 Phase 2
0.7181 Intermediate Similarity NPD6242 Discontinued
0.7178 Intermediate Similarity NPD5482 Discontinued
0.7178 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD3263 Phase 3
0.7162 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5612 Discontinued
0.7156 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD3006 Discontinued
0.7143 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD3514 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD3258 Approved
0.7131 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD4131 Phase 3
0.7124 Intermediate Similarity NPD4989 Phase 2
0.7111 Intermediate Similarity NPD4667 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7803 Approved
0.7103 Intermediate Similarity NPD1038 Approved
0.7101 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7395 Discontinued
0.7091 Intermediate Similarity NPD4035 Approved
0.7091 Intermediate Similarity NPD4037 Approved
0.7091 Intermediate Similarity NPD4034 Approved
0.7091 Intermediate Similarity NPD4038 Approved
0.7091 Intermediate Similarity NPD32 Approved
0.7091 Intermediate Similarity NPD4036 Approved
0.7091 Intermediate Similarity NPD31 Approved
0.7091 Intermediate Similarity NPD4039 Approved
0.7091 Intermediate Similarity NPD4033 Approved
0.7091 Intermediate Similarity NPD4122 Approved
0.7071 Intermediate Similarity NPD6716 Phase 1
0.7064 Intermediate Similarity NPD484 Approved
0.7062 Intermediate Similarity NPD4375 Approved
0.7056 Intermediate Similarity NPD6569 Phase 2
0.7045 Intermediate Similarity NPD7956 Approved
0.7045 Intermediate Similarity NPD7955 Approved
0.7043 Intermediate Similarity NPD8356 Approved
0.7029 Intermediate Similarity NPD6790 Phase 1
0.7019 Intermediate Similarity NPD3920 Phase 2
0.7019 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4429 Discontinued
0.7014 Intermediate Similarity NPD2831 Approved
0.7014 Intermediate Similarity NPD3947 Discontinued
0.7009 Intermediate Similarity NPD5022 Discontinued
0.7004 Intermediate Similarity NPD8091 Phase 3
0.7 Intermediate Similarity NPD6517 Phase 3
0.6996 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6996 Remote Similarity NPD4328 Approved
0.6996 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6992 Remote Similarity NPD6494 Phase 2
0.6992 Remote Similarity NPD4080 Discontinued
0.6978 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6978 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5513 Phase 2
0.696 Remote Similarity NPD3257 Approved
0.696 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5512 Phase 3
0.6952 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6951 Remote Similarity NPD7452 Approved
0.6951 Remote Similarity NPD7222 Phase 2
0.6951 Remote Similarity NPD7453 Approved
0.6951 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6727 Phase 2
0.6946 Remote Similarity NPD6825 Phase 1
0.6946 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6943 Remote Similarity NPD6568 Discontinued
0.6943 Remote Similarity NPD5632 Approved
0.6933 Remote Similarity NPD7853 Phase 2
0.6926 Remote Similarity NPD4923 Phase 1
0.6926 Remote Similarity NPD6298 Discontinued
0.6923 Remote Similarity NPD7994 Phase 2
0.6923 Remote Similarity NPD8430 Approved
0.6923 Remote Similarity NPD6477 Clinical (unspecified phase)
0.692 Remote Similarity NPD4373 Phase 2
0.6912 Remote Similarity NPD3395 Approved
0.6912 Remote Similarity NPD3396 Approved
0.6911 Remote Similarity NPD7859 Phase 2
0.6907 Remote Similarity NPD1867 Approved
0.6907 Remote Similarity NPD6962 Phase 2
0.6906 Remote Similarity NPD5601 Phase 2
0.6894 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6963 Approved
0.6891 Remote Similarity NPD6964 Approved
0.6885 Remote Similarity NPD6276 Discontinued
0.6878 Remote Similarity NPD7031 Phase 1
0.6878 Remote Similarity NPD4885 Approved
0.687 Remote Similarity NPD2011 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6864 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4952 Phase 3
0.6864 Remote Similarity NPD4898 Clinical (unspecified phase)
0.6863 Remote Similarity NPD1631 Approved
0.6861 Remote Similarity NPD3946 Clinical (unspecified phase)
0.686 Remote Similarity NPD7022 Phase 2
0.686 Remote Similarity NPD4083 Discontinued
0.6853 Remote Similarity NPD5147 Discontinued
0.6847 Remote Similarity NPD2779 Approved
0.6846 Remote Similarity NPD5908 Clinical (unspecified phase)
0.6846 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6845 Remote Similarity NPD2821 Approved
0.684 Remote Similarity NPD3763 Approved
0.6838 Remote Similarity NPD5450 Discontinued
0.6836 Remote Similarity NPD5922 Phase 3
0.6835 Remote Similarity NPD1505 Phase 2
0.6833 Remote Similarity NPD6219 Discontinued
0.6829 Remote Similarity NPD8101 Phase 3
0.6829 Remote Similarity NPD7588 Discontinued
0.6824 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6209 Approved
0.6815 Remote Similarity NPD5532 Phase 2
0.6815 Remote Similarity NPD8463 Approved
0.6813 Remote Similarity NPD6228 Discontinued
0.6812 Remote Similarity NPD1638 Discovery
0.6812 Remote Similarity NPD5417 Clinical (unspecified phase)
0.681 Remote Similarity NPD3590 Clinical (unspecified phase)
0.6804 Remote Similarity NPD6550 Discontinued
0.6803 Remote Similarity NPD7967 Discontinued
0.68 Remote Similarity NPD1392 Approved
0.68 Remote Similarity NPD5429 Discontinued
0.6789 Remote Similarity NPD4558 Phase 2
0.6786 Remote Similarity NPD3397 Phase 2
0.678 Remote Similarity NPD7826 Clinical (unspecified phase)
0.6778 Remote Similarity NPD6223 Clinical (unspecified phase)
0.677 Remote Similarity NPD5658 Approved
0.677 Remote Similarity NPD7467 Discontinued
0.6766 Remote Similarity NPD4132 Clinical (unspecified phase)
0.6759 Remote Similarity NPD4021 Phase 2
0.6754 Remote Similarity NPD7470 Discontinued
0.6754 Remote Similarity NPD5416 Discontinued
0.6749 Remote Similarity NPD820 Phase 3
0.6748 Remote Similarity NPD6205 Discontinued
0.6745 Remote Similarity NPD7673 Phase 3
0.6731 Remote Similarity NPD1573 Approved
0.6731 Remote Similarity NPD1575 Approved
0.673 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6729 Remote Similarity NPD1096 Discontinued
0.6726 Remote Similarity NPD7263 Phase 2
0.6724 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6723 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6722 Remote Similarity NPD4454 Phase 2
0.6716 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6716 Remote Similarity NPD1630 Approved
0.6714 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6713 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6713 Remote Similarity NPD1034 Phase 3
0.6712 Remote Similarity NPD6874 Approved
0.6712 Remote Similarity NPD2778 Approved
0.6711 Remote Similarity NPD5901 Discontinued
0.6711 Remote Similarity NPD3392 Approved
0.6711 Remote Similarity NPD7396 Approved
0.6709 Remote Similarity NPD4086 Phase 1
0.6709 Remote Similarity NPD4845 Discontinued
0.6708 Remote Similarity NPD2929 Clinical (unspecified phase)
0.6708 Remote Similarity NPD7558 Phase 2
0.6708 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6707 Remote Similarity NPD8468 Phase 2
0.6707 Remote Similarity NPD8100 Phase 3
0.6705 Remote Similarity NPD7689 Approved
0.6699 Remote Similarity NPD5088 Discontinued
0.6699 Remote Similarity NPD5242 Approved
0.6698 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6696 Remote Similarity NPD3945 Discontinued
0.6695 Remote Similarity NPD1467 Approved
0.6695 Remote Similarity NPD1466 Phase 3

Structure

External Identifiers

PubChem CID   602258
ChEMBL   CHEMBL455359
ZINC  

Physicochemical Properties

Molecular Weight:  305.13
ALogP:  -0.1148
MLogP:  2.56
XLogP:  1.987
# Rotatable Bonds:  11
Polar Surface Area:  69.92
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  22

Download Data

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Biological Activities  
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