Natural Product: NPC471386

Natural Product ID:  NPC471386
Common Name:   (15S,19E,2's,3's,7'r,15's,19'e)-Gardovatine
IUPAC Name:  
Synonyms:  
Molecular Formula:   C38H38N4O
Standard InCHIKey:  OSKKNZHUYWQWKZ-SWNWXBJPSA-N
Standard InCHI:  InChI=1S/C38H38N4O/c1-3-23-19-39-16-14-38-31-10-6-8-12-33(31)42-21-29-28-18-35(43)40(20-24(28)4-2)15-13-26-25-9-5-7-11-32(25)41(36(26)29)22-30(37(38)42)27(23)17-34(38)39/h3-12,21-22,27-28,34,37H,13-20H2,1-2H3/b23-3-,24-4-,29-21-,30-22-/t27-,28-,34-,37-,38+/m0/s1
Canonical SMILES:  C/C=C1/CN2CC[C@@]34[C@@H]2C[C@@H]1C1=Cn2c5C(=CN([C@H]31)c1c4cccc1)[C@H]1CC(=O)N(CCc5c3c2cccc3)C/C/1=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
NPO32800 gardneria oveta Species Loganiaceae Eukaryota PMID[24012119]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens IC50 = 14200 nM 19271717
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 10500 nM 19778087
NPT660 Cell Line SW480 Homo sapiens IC50 = 16100 nM 21741249
NPT83 Cell Line MCF7 Homo sapiens IC50 = 13900 nM 21839640
NPT116 Cell Line HL-60 Homo sapiens IC50 = 9800 nM 21839640

  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 NPC471386 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
0.8171 Intermediate Similarity NPC194881
0.7857 Intermediate Similarity NPC161861
0.7727 Intermediate Similarity NPC200743
0.7637 Intermediate Similarity NPC56233
0.7527 Intermediate Similarity NPC271797
0.7527 Intermediate Similarity NPC21174
0.75 Intermediate Similarity NPC104483
0.75 Intermediate Similarity NPC248462
0.7487 Intermediate Similarity NPC308931
0.7487 Intermediate Similarity NPC99939
0.7475 Intermediate Similarity NPC477065
0.7471 Intermediate Similarity NPC20144
0.7368 Intermediate Similarity NPC477714
0.7363 Intermediate Similarity NPC221786
0.7363 Intermediate Similarity NPC474880
0.7363 Intermediate Similarity NPC475990
0.7358 Intermediate Similarity NPC478077
0.7354 Intermediate Similarity NPC64436
0.7344 Intermediate Similarity NPC472119
0.7322 Intermediate Similarity NPC229173
0.7312 Intermediate Similarity NPC475248
0.7312 Intermediate Similarity NPC63047
0.7292 Intermediate Similarity NPC470205
0.7292 Intermediate Similarity NPC143533
0.7283 Intermediate Similarity NPC469741
0.7277 Intermediate Similarity NPC15840
0.7273 Intermediate Similarity NPC474897
0.7273 Intermediate Similarity NPC470731
0.7268 Intermediate Similarity NPC141612
0.7268 Intermediate Similarity NPC135601
0.7268 Intermediate Similarity NPC17273
0.7268 Intermediate Similarity NPC87755
0.7264 Intermediate Similarity NPC474896
0.7254 Intermediate Similarity NPC258480
0.7238 Intermediate Similarity NPC477715
0.723 Intermediate Similarity NPC253987
0.723 Intermediate Similarity NPC31097
0.722 Intermediate Similarity NPC54420
0.7216 Intermediate Similarity NPC472107
0.7216 Intermediate Similarity NPC133003
0.7216 Intermediate Similarity NPC79062
0.7198 Intermediate Similarity NPC475422
0.7198 Intermediate Similarity NPC126066
0.7188 Intermediate Similarity NPC91179
0.7179 Intermediate Similarity NPC66210
0.7165 Intermediate Similarity NPC472294
0.7163 Intermediate Similarity NPC19170
0.7151 Intermediate Similarity NPC478182
0.715 Intermediate Similarity NPC327095
0.715 Intermediate Similarity NPC162860
0.715 Intermediate Similarity NPC312942
0.7143 Intermediate Similarity NPC297862
0.7136 Intermediate Similarity NPC272174
0.7135 Intermediate Similarity NPC81229
0.7135 Intermediate Similarity NPC255229
0.7127 Intermediate Similarity NPC40070
0.7121 Intermediate Similarity NPC473763
0.7121 Intermediate Similarity NPC117244
0.7116 Intermediate Similarity NPC40455
0.7095 Intermediate Similarity NPC469735
0.7095 Intermediate Similarity NPC470440
0.7083 Intermediate Similarity NPC234987
0.7079 Intermediate Similarity NPC171317
0.7064 Intermediate Similarity NPC56109
0.7064 Intermediate Similarity NPC191382
0.7062 Intermediate Similarity NPC2949
0.7056 Intermediate Similarity NPC472323
0.705 Intermediate Similarity NPC304203
0.7037 Intermediate Similarity NPC476817
0.7035 Intermediate Similarity NPC472097
0.7033 Intermediate Similarity NPC33421
0.7033 Intermediate Similarity NPC206592
0.7031 Intermediate Similarity NPC280852
0.7028 Intermediate Similarity NPC470732
0.702 Intermediate Similarity NPC473666
0.701 Intermediate Similarity NPC286994
0.7005 Intermediate Similarity NPC94752
0.6995 Remote Similarity NPC34837
0.699 Remote Similarity NPC228835
0.699 Remote Similarity NPC317701
0.699 Remote Similarity NPC21429
0.6989 Remote Similarity NPC293487
0.6989 Remote Similarity NPC65408
0.6974 Remote Similarity NPC113626
0.697 Remote Similarity NPC17059
0.6968 Remote Similarity NPC478184
0.6966 Remote Similarity NPC238499
0.6961 Remote Similarity NPC153123
0.6961 Remote Similarity NPC469740
0.6961 Remote Similarity NPC201266
0.6961 Remote Similarity NPC475914
0.6961 Remote Similarity NPC220797
0.6961 Remote Similarity NPC478186
0.6961 Remote Similarity NPC474318
0.6961 Remote Similarity NPC268744
0.6959 Remote Similarity NPC11126
0.6957 Remote Similarity NPC281094
0.695 Remote Similarity NPC476460
0.6939 Remote Similarity NPC159125
0.6935 Remote Similarity NPC216643
0.6931 Remote Similarity NPC57994
0.6931 Remote Similarity NPC289299
0.6927 Remote Similarity NPC77241
0.6927 Remote Similarity NPC242269
0.6927 Remote Similarity NPC13456
0.6927 Remote Similarity NPC269203
0.6927 Remote Similarity NPC166209
0.6923 Remote Similarity NPC21605
0.6907 Remote Similarity NPC14325
0.6907 Remote Similarity NPC28848
0.6907 Remote Similarity NPC237188
0.6904 Remote Similarity NPC467063
0.69 Remote Similarity NPC324091
0.69 Remote Similarity NPC329858
0.69 Remote Similarity NPC472112
0.6897 Remote Similarity NPC472116
0.6897 Remote Similarity NPC245916
0.6895 Remote Similarity NPC114637
0.6895 Remote Similarity NPC475338
0.6895 Remote Similarity NPC478183
0.6895 Remote Similarity NPC909
0.6893 Remote Similarity NPC314102
0.6893 Remote Similarity NPC251722
0.6891 Remote Similarity NPC469938
0.6884 Remote Similarity NPC473310
0.6882 Remote Similarity NPC51054
0.6878 Remote Similarity NPC470730
0.6878 Remote Similarity NPC477175
0.6875 Remote Similarity NPC471123
0.6875 Remote Similarity NPC126492
0.6875 Remote Similarity NPC201634
0.6872 Remote Similarity NPC59084
0.6864 Remote Similarity NPC476491
0.6864 Remote Similarity NPC475258
0.686 Remote Similarity NPC162730
0.6854 Remote Similarity NPC473757
0.685 Remote Similarity NPC196251
0.685 Remote Similarity NPC175474
0.685 Remote Similarity NPC111602
0.685 Remote Similarity NPC63199
0.685 Remote Similarity NPC102338
0.685 Remote Similarity NPC213629
0.6847 Remote Similarity NPC475859
0.6847 Remote Similarity NPC475969
0.6845 Remote Similarity NPC104345
0.6845 Remote Similarity NPC129721
0.6842 Remote Similarity NPC2165
0.6842 Remote Similarity NPC195507
0.6835 Remote Similarity NPC155444
0.6833 Remote Similarity NPC473868
0.6833 Remote Similarity NPC63157
0.6832 Remote Similarity NPC472113
0.6829 Remote Similarity NPC52557
0.6828 Remote Similarity NPC476219
0.6825 Remote Similarity NPC478158
0.6825 Remote Similarity NPC478185
0.6823 Remote Similarity NPC91895
0.6822 Remote Similarity NPC478157
0.6821 Remote Similarity NPC157583
0.6818 Remote Similarity NPC477003
0.6816 Remote Similarity NPC88097
0.6816 Remote Similarity NPC165743
0.6816 Remote Similarity NPC314333
0.6814 Remote Similarity NPC128244
0.6812 Remote Similarity NPC300183
0.681 Remote Similarity NPC166492
0.681 Remote Similarity NPC473362
0.6809 Remote Similarity NPC6436
0.6809 Remote Similarity NPC41257
0.6809 Remote Similarity NPC56765
0.6808 Remote Similarity NPC75634
0.6804 Remote Similarity NPC469529
0.6791 Remote Similarity NPC472027
0.6779 Remote Similarity NPC474116
0.6768 Remote Similarity NPC117027
0.6768 Remote Similarity NPC472104
0.6766 Remote Similarity NPC321708
0.6763 Remote Similarity NPC252338
0.6757 Remote Similarity NPC53947
0.6757 Remote Similarity NPC66936
0.6755 Remote Similarity NPC222029
0.6753 Remote Similarity NPC473743
0.6749 Remote Similarity NPC47190
0.6749 Remote Similarity NPC272458
0.6736 Remote Similarity NPC32534
0.6736 Remote Similarity NPC471943
0.6735 Remote Similarity NPC326575
0.6735 Remote Similarity NPC284775
0.6721 Remote Similarity NPC469525
0.672 Remote Similarity NPC276085
0.672 Remote Similarity NPC470233
0.6716 Remote Similarity NPC473178
0.6714 Remote Similarity NPC473376
0.671 Remote Similarity NPC469734
0.6704 Remote Similarity NPC150259
0.6701 Remote Similarity NPC213468
0.6701 Remote Similarity NPC6982
0.6701 Remote Similarity NPC133261
0.6699 Remote Similarity NPC232130
0.6699 Remote Similarity NPC162440

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471386 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
0.7709 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7564 Discontinued
0.7462 Intermediate Similarity NPD6664 Approved
0.7449 Intermediate Similarity NPD7619 Phase 3
0.7449 Intermediate Similarity NPD7618 Phase 3
0.7438 Intermediate Similarity NPD7666 Phase 3
0.7438 Intermediate Similarity NPD7665 Phase 2
0.7412 Intermediate Similarity NPD3385 Approved
0.732 Intermediate Similarity NPD6507 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD6999 Discontinued
0.7273 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD5809 Phase 3
0.7188 Intermediate Similarity NPD5473 Discontinued
0.7186 Intermediate Similarity NPD7944 Discontinued
0.7179 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7789 Approved
0.7169 Intermediate Similarity NPD7790 Approved
0.7169 Intermediate Similarity NPD7953 Approved
0.7169 Intermediate Similarity NPD7951 Approved
0.7169 Intermediate Similarity NPD7952 Approved
0.7169 Intermediate Similarity NPD7791 Approved
0.7169 Intermediate Similarity NPD7950 Approved
0.715 Intermediate Similarity NPD7023 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7394 Phase 2
0.7136 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4075 Phase 2
0.7111 Intermediate Similarity NPD4547 Phase 3
0.7076 Intermediate Similarity NPD3654 Approved
0.7064 Intermediate Similarity NPD7781 Approved
0.7064 Intermediate Similarity NPD7780 Approved
0.7059 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7454 Approved
0.7048 Intermediate Similarity NPD7455 Approved
0.7035 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD7824 Approved
0.7031 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD4326 Phase 2
0.7026 Intermediate Similarity NPD3318 Approved
0.7026 Intermediate Similarity NPD3319 Phase 1
0.7026 Intermediate Similarity NPD3320 Approved
0.7021 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD6771 Discontinued
0.6995 Remote Similarity NPD8401 Approved
0.6995 Remote Similarity NPD8402 Approved
0.6995 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6995 Remote Similarity NPD8400 Approved
0.6989 Remote Similarity NPD200 Phase 2
0.6989 Remote Similarity NPD45 Approved
0.6989 Remote Similarity NPD6554 Approved
0.6989 Remote Similarity NPD201 Phase 2
0.6971 Remote Similarity NPD8493 Clinical (unspecified phase)
0.697 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6968 Remote Similarity NPD3323 Discontinued
0.6957 Remote Similarity NPD8115 Approved
0.6957 Remote Similarity NPD5426 Phase 3
0.6957 Remote Similarity NPD8114 Approved
0.6951 Remote Similarity NPD6986 Phase 1
0.695 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4779 Clinical (unspecified phase)
0.6946 Remote Similarity NPD2880 Discontinued
0.6941 Remote Similarity NPD7730 Approved
0.6941 Remote Similarity NPD7731 Approved
0.6931 Remote Similarity NPD5904 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4602 Approved
0.6927 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6217 Discontinued
0.6919 Remote Similarity NPD6285 Phase 2
0.6915 Remote Similarity NPD5315 Discontinued
0.6915 Remote Similarity NPD5400 Approved
0.6912 Remote Similarity NPD7204 Clinical (unspecified phase)
0.6904 Remote Similarity NPD7482 Phase 2
0.6904 Remote Similarity NPD7483 Phase 2
0.6897 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4348 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7661 Clinical (unspecified phase)
0.6878 Remote Similarity NPD7308 Discontinued
0.6878 Remote Similarity NPD3583 Phase 2
0.6875 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6872 Remote Similarity NPD2590 Clinical (unspecified phase)
0.6872 Remote Similarity NPD3077 Approved
0.6872 Remote Similarity NPD3079 Approved
0.6872 Remote Similarity NPD3076 Approved
0.6872 Remote Similarity NPD3078 Approved
0.6868 Remote Similarity NPD7469 Discontinued
0.6868 Remote Similarity NPD1683 Approved
0.686 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6859 Remote Similarity NPD2390 Clinical (unspecified phase)
0.6856 Remote Similarity NPD6044 Discontinued
0.6856 Remote Similarity NPD4385 Clinical (unspecified phase)
0.6856 Remote Similarity NPD5104 Approved
0.6854 Remote Similarity NPD8094 Discontinued
0.6849 Remote Similarity NPD7271 Approved
0.6847 Remote Similarity NPD7406 Phase 2
0.6842 Remote Similarity NPD4550 Clinical (unspecified phase)
0.684 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6837 Remote Similarity NPD6277 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5505 Discontinued
0.6818 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6816 Remote Similarity NPD4499 Approved
0.6808 Remote Similarity NPD8093 Discontinued
0.6792 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6784 Remote Similarity NPD8016 Phase 3
0.6784 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7434 Approved
0.6777 Remote Similarity NPD2442 Approved
0.6777 Remote Similarity NPD2443 Approved
0.6774 Remote Similarity NPD2837 Discontinued
0.6771 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7401 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6762 Remote Similarity NPD7001 Phase 3
0.6751 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6749 Remote Similarity NPD4922 Phase 2
0.6742 Remote Similarity NPD1254 Approved
0.6742 Remote Similarity NPD1253 Approved
0.6742 Remote Similarity NPD1255 Approved
0.6742 Remote Similarity NPD1256 Approved
0.6733 Remote Similarity NPD6281 Approved
0.6731 Remote Similarity NPD5017 Discontinued
0.673 Remote Similarity NPD3905 Phase 3
0.6729 Remote Similarity NPD4852 Phase 2
0.6719 Remote Similarity NPD4643 Clinical (unspecified phase)
0.6719 Remote Similarity NPD6446 Discontinued
0.6717 Remote Similarity NPD4383 Clinical (unspecified phase)
0.6716 Remote Similarity NPD3961 Discontinued
0.6706 Remote Similarity NPD4775 Clinical (unspecified phase)
0.67 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6698 Remote Similarity NPD2916 Discontinued
0.6698 Remote Similarity NPD6787 Phase 2
0.6684 Remote Similarity NPD4640 Approved
0.6684 Remote Similarity NPD4639 Approved
0.6684 Remote Similarity NPD6471 Clinical (unspecified phase)
0.6684 Remote Similarity NPD4638 Approved
0.6683 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6683 Remote Similarity NPD5464 Approved
0.6683 Remote Similarity NPD7175 Phase 1
0.6683 Remote Similarity NPD7233 Approved
0.6683 Remote Similarity NPD7234 Approved
0.6683 Remote Similarity NPD4345 Clinical (unspecified phase)
0.6683 Remote Similarity NPD4600 Approved
0.6683 Remote Similarity NPD4601 Approved
0.6682 Remote Similarity NPD7470 Discontinued
0.6682 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4397 Phase 1
0.6667 Remote Similarity NPD8630 Approved
0.6667 Remote Similarity NPD3431 Approved
0.6667 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6667 Remote Similarity NPD750 Phase 2
0.6667 Remote Similarity NPD3430 Approved
0.6667 Remote Similarity NPD4112 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2915 Discontinued
0.6667 Remote Similarity NPD5254 Discontinued
0.6667 Remote Similarity NPD7026 Phase 2
0.6652 Remote Similarity NPD7716 Approved
0.6652 Remote Similarity NPD7717 Approved
0.6651 Remote Similarity NPD8322 Phase 2
0.6651 Remote Similarity NPD6470 Phase 3
0.6651 Remote Similarity NPD7195 Clinical (unspecified phase)
0.665 Remote Similarity NPD6178 Phase 3
0.665 Remote Similarity NPD4181 Approved
0.665 Remote Similarity NPD4398 Clinical (unspecified phase)
0.665 Remote Similarity NPD4848 Phase 1
0.665 Remote Similarity NPD1851 Clinical (unspecified phase)
0.665 Remote Similarity NPD6203 Clinical (unspecified phase)
0.665 Remote Similarity NPD7111 Discontinued
0.6648 Remote Similarity NPD3476 Approved
0.6648 Remote Similarity NPD3475 Approved
0.6637 Remote Similarity NPD8047 Clinical (unspecified phase)
0.6636 Remote Similarity NPD6204 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7209 Approved
0.6635 Remote Similarity NPD7208 Approved
0.6635 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7207 Approved
0.6631 Remote Similarity NPD6476 Clinical (unspecified phase)
0.6631 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6631 Remote Similarity NPD6158 Phase 2
0.662 Remote Similarity NPD6521 Phase 3
0.662 Remote Similarity NPD6520 Phase 3
0.6619 Remote Similarity NPD2881 Approved
0.6619 Remote Similarity NPD2879 Approved
0.6617 Remote Similarity NPD5075 Discontinued
0.6617 Remote Similarity NPD5555 Phase 1
0.6615 Remote Similarity NPD5472 Clinical (unspecified phase)
0.6614 Remote Similarity NPD2150 Discontinued
0.6613 Remote Similarity NPD2430 Phase 2
0.6612 Remote Similarity NPD2006 Phase 2
0.6612 Remote Similarity NPD4047 Discontinued
0.6606 Remote Similarity NPD6995 Phase 1
0.6604 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6603 Remote Similarity NPD4500 Approved
0.6603 Remote Similarity NPD4501 Approved
0.6598 Remote Similarity NPD5021 Discontinued
0.6593 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6589 Remote Similarity NPD2408 Discontinued
0.6585 Remote Similarity NPD7098 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   72192891
ChEMBL   CHEMBL2430444
ZINC  

Physicochemical Properties

Molecular Weight:  566.30
ALogP:  0.4462
MLogP:  5.09
XLogP:  6.545
# Rotatable Bonds:  2
Polar Surface Area:  31.72
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  9
# Heavy Atoms:  43

Download Data

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Biological Activities  
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