Natural Product: NPC473592

Natural Product ID:  NPC473592
Common Name:   3-[[(1R,4Ar,7R,10As)-7-Ethenyl-1,4A,7-Trimethyl-3,4,6,8,8A,9,10,10A-Octahydro-2H-Phenanthren-1-Yl]Oxy]-3-Oxopropanoic Acid
IUPAC Name:   3-[[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthren-1-yl]oxy]-3-oxopropanoic acid
Synonyms:  
Molecular Formula:   C22H32O4
Standard InCHIKey:  BTAAEEJRNAVSQS-XJCCISBASA-N
Standard InCHI:  InChI=1S/C22H32O4/c1-5-20(2)12-9-16-15(14-20)7-8-17-21(16,3)10-6-11-22(17,4)26-19(25)13-18(23)24/h5,9,15,17H,1,6-8,10-14H2,2-4H3,(H,23,24)/t15?,17-,20+,21-,22+/m0/s1
Canonical SMILES:  C=C[C@]1(C)CC=C2C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)OC(=O)CC(=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
NPO33152 calceolaria pinifolia Species Calceolariaceae Eukaryota Aerial parts 46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (30°21'S; 69°40'W) 1997-JAN PMID[12608857]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 16 ug/ml 15620264
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 8 ug/ml Open TG-GATES in vivo data: Biochemistry
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 32 ug/ml 10.6019/CHEMBL3392926
NPT19 Organism Escherichia coli Escherichia coli MIC > 128 ug/ml 10.6019/CHEMBL1201861

  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 NPC473592 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
0.9615 High Similarity NPC474979
0.9487 High Similarity NPC476101
0.9114 High Similarity NPC474978
0.8353 Intermediate Similarity NPC76333
0.8313 Intermediate Similarity NPC142163
0.8293 Intermediate Similarity NPC100906
0.8256 Intermediate Similarity NPC73038
0.8235 Intermediate Similarity NPC156981
0.8222 Intermediate Similarity NPC184006
0.8222 Intermediate Similarity NPC78580
0.8222 Intermediate Similarity NPC23621
0.8193 Intermediate Similarity NPC37038
0.8171 Intermediate Similarity NPC321514
0.8161 Intermediate Similarity NPC171722
0.8132 Intermediate Similarity NPC23241
0.8132 Intermediate Similarity NPC195715
0.8118 Intermediate Similarity NPC52108
0.8118 Intermediate Similarity NPC476927
0.8118 Intermediate Similarity NPC474789
0.8095 Intermediate Similarity NPC327002
0.8072 Intermediate Similarity NPC231431
0.8049 Intermediate Similarity NPC132542
0.8046 Intermediate Similarity NPC474970
0.8046 Intermediate Similarity NPC325594
0.8046 Intermediate Similarity NPC262085
0.8025 Intermediate Similarity NPC279666
0.8025 Intermediate Similarity NPC192540
0.8 Intermediate Similarity NPC324341
0.8 Intermediate Similarity NPC471588
0.8 Intermediate Similarity NPC966
0.8 Intermediate Similarity NPC288833
0.8 Intermediate Similarity NPC228784
0.8 Intermediate Similarity NPC155120
0.8 Intermediate Similarity NPC282616
0.8 Intermediate Similarity NPC6255
0.7978 Intermediate Similarity NPC474570
0.7978 Intermediate Similarity NPC471342
0.7978 Intermediate Similarity NPC59682
0.7978 Intermediate Similarity NPC474700
0.7978 Intermediate Similarity NPC469866
0.7976 Intermediate Similarity NPC269791
0.7976 Intermediate Similarity NPC104545
0.7957 Intermediate Similarity NPC26413
0.7952 Intermediate Similarity NPC260385
0.7952 Intermediate Similarity NPC179028
0.7952 Intermediate Similarity NPC280654
0.7952 Intermediate Similarity NPC110094
0.7931 Intermediate Similarity NPC191965
0.7931 Intermediate Similarity NPC476602
0.7927 Intermediate Similarity NPC69143
0.7912 Intermediate Similarity NPC86368
0.7907 Intermediate Similarity NPC477373
0.7901 Intermediate Similarity NPC241854
0.7901 Intermediate Similarity NPC103958
0.7901 Intermediate Similarity NPC161923
0.7901 Intermediate Similarity NPC283908
0.7901 Intermediate Similarity NPC251970
0.7901 Intermediate Similarity NPC183503
0.7901 Intermediate Similarity NPC71152
0.7901 Intermediate Similarity NPC476046
0.7889 Intermediate Similarity NPC86372
0.7889 Intermediate Similarity NPC474728
0.7889 Intermediate Similarity NPC120840
0.7889 Intermediate Similarity NPC113989
0.7889 Intermediate Similarity NPC172361
0.7889 Intermediate Similarity NPC471896
0.7882 Intermediate Similarity NPC142244
0.7882 Intermediate Similarity NPC278459
0.7872 Intermediate Similarity NPC164349
0.7857 Intermediate Similarity NPC199595
0.7857 Intermediate Similarity NPC327674
0.7849 Intermediate Similarity NPC98874
0.7849 Intermediate Similarity NPC120708
0.7849 Intermediate Similarity NPC132824
0.7849 Intermediate Similarity NPC269492
0.7849 Intermediate Similarity NPC327788
0.7841 Intermediate Similarity NPC84121
0.7841 Intermediate Similarity NPC137306
0.7841 Intermediate Similarity NPC324063
0.7831 Intermediate Similarity NPC107039
0.7831 Intermediate Similarity NPC283619
0.7831 Intermediate Similarity NPC471897
0.7831 Intermediate Similarity NPC471899
0.7826 Intermediate Similarity NPC148964
0.7826 Intermediate Similarity NPC222047
0.7802 Intermediate Similarity NPC77099
0.7802 Intermediate Similarity NPC476417
0.7802 Intermediate Similarity NPC60755
0.7802 Intermediate Similarity NPC285184
0.7802 Intermediate Similarity NPC470590
0.7792 Intermediate Similarity NPC474768
0.7791 Intermediate Similarity NPC2524
0.7791 Intermediate Similarity NPC256112
0.7791 Intermediate Similarity NPC15910
0.7791 Intermediate Similarity NPC286786
0.7789 Intermediate Similarity NPC473576
0.7789 Intermediate Similarity NPC475156
0.7778 Intermediate Similarity NPC30522
0.7778 Intermediate Similarity NPC270768
0.7778 Intermediate Similarity NPC263393
0.7778 Intermediate Similarity NPC61543
0.7778 Intermediate Similarity NPC16265
0.7778 Intermediate Similarity NPC130520
0.7778 Intermediate Similarity NPC475921
0.7778 Intermediate Similarity NPC121798
0.7778 Intermediate Similarity NPC127689
0.7778 Intermediate Similarity NPC225585
0.7778 Intermediate Similarity NPC474704
0.7778 Intermediate Similarity NPC234346
0.7778 Intermediate Similarity NPC293048
0.7778 Intermediate Similarity NPC59263
0.7766 Intermediate Similarity NPC473456
0.7766 Intermediate Similarity NPC89225
0.7765 Intermediate Similarity NPC477057
0.7753 Intermediate Similarity NPC166857
0.7753 Intermediate Similarity NPC173089
0.7753 Intermediate Similarity NPC158141
0.7753 Intermediate Similarity NPC96496
0.7742 Intermediate Similarity NPC148523
0.7727 Intermediate Similarity NPC164424
0.7722 Intermediate Similarity NPC94192
0.7717 Intermediate Similarity NPC298554
0.7717 Intermediate Similarity NPC38232
0.7717 Intermediate Similarity NPC118490
0.7717 Intermediate Similarity NPC131840
0.7711 Intermediate Similarity NPC104806
0.7711 Intermediate Similarity NPC89294
0.7708 Intermediate Similarity NPC476888
0.7708 Intermediate Similarity NPC93744
0.7701 Intermediate Similarity NPC200752
0.7701 Intermediate Similarity NPC132386
0.7701 Intermediate Similarity NPC476100
0.7692 Intermediate Similarity NPC148414
0.7692 Intermediate Similarity NPC470589
0.7692 Intermediate Similarity NPC126369
0.7692 Intermediate Similarity NPC111110
0.7692 Intermediate Similarity NPC175628
0.7692 Intermediate Similarity NPC111585
0.7692 Intermediate Similarity NPC130278
0.7684 Intermediate Similarity NPC174663
0.7683 Intermediate Similarity NPC91858
0.7683 Intermediate Similarity NPC166797
0.7674 Intermediate Similarity NPC267691
0.7674 Intermediate Similarity NPC274050
0.7674 Intermediate Similarity NPC48673
0.7674 Intermediate Similarity NPC20096
0.7674 Intermediate Similarity NPC471898
0.7674 Intermediate Similarity NPC195334
0.7674 Intermediate Similarity NPC162632
0.7674 Intermediate Similarity NPC290495
0.7674 Intermediate Similarity NPC263272
0.7674 Intermediate Similarity NPC147066
0.7674 Intermediate Similarity NPC221647
0.7674 Intermediate Similarity NPC170303
0.7667 Intermediate Similarity NPC52169
0.7667 Intermediate Similarity NPC246708
0.7667 Intermediate Similarity NPC48107
0.7667 Intermediate Similarity NPC1753
0.7667 Intermediate Similarity NPC474511
0.7667 Intermediate Similarity NPC40552
0.7667 Intermediate Similarity NPC182797
0.766 Intermediate Similarity NPC327179
0.766 Intermediate Similarity NPC472806
0.766 Intermediate Similarity NPC201657
0.766 Intermediate Similarity NPC167193
0.766 Intermediate Similarity NPC471153
0.7654 Intermediate Similarity NPC160817
0.7647 Intermediate Similarity NPC16394
0.7647 Intermediate Similarity NPC476438
0.7647 Intermediate Similarity NPC192999
0.764 Intermediate Similarity NPC322159
0.764 Intermediate Similarity NPC475753
0.764 Intermediate Similarity NPC476104
0.764 Intermediate Similarity NPC82979
0.7634 Intermediate Similarity NPC191412
0.7634 Intermediate Similarity NPC114159
0.7634 Intermediate Similarity NPC6818
0.7634 Intermediate Similarity NPC159410
0.7634 Intermediate Similarity NPC74751
0.7634 Intermediate Similarity NPC215700
0.7634 Intermediate Similarity NPC474529
0.7634 Intermediate Similarity NPC296164
0.7634 Intermediate Similarity NPC474963
0.7634 Intermediate Similarity NPC80365
0.7634 Intermediate Similarity NPC209868
0.7629 Intermediate Similarity NPC40918
0.7629 Intermediate Similarity NPC476890
0.7625 Intermediate Similarity NPC476431
0.7619 Intermediate Similarity NPC165711
0.7614 Intermediate Similarity NPC96095
0.7614 Intermediate Similarity NPC306951
0.7609 Intermediate Similarity NPC177641
0.7609 Intermediate Similarity NPC477574
0.7609 Intermediate Similarity NPC36491
0.7609 Intermediate Similarity NPC26888
0.7604 Intermediate Similarity NPC35751
0.7604 Intermediate Similarity NPC35239
0.759 Intermediate Similarity NPC476844
0.7586 Intermediate Similarity NPC69101
0.7586 Intermediate Similarity NPC251779

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC473592 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
0.7634 Intermediate Similarity NPD7748 Approved
0.7609 Intermediate Similarity NPD6411 Approved
0.7556 Intermediate Similarity NPD3573 Approved
0.7444 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7645 Phase 2
0.7419 Intermediate Similarity NPD7515 Phase 2
0.7396 Intermediate Similarity NPD6084 Phase 2
0.7396 Intermediate Similarity NPD6083 Phase 2
0.7396 Intermediate Similarity NPD7902 Approved
0.7391 Intermediate Similarity NPD6101 Approved
0.7391 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD6399 Phase 3
0.7262 Intermediate Similarity NPD4784 Approved
0.7262 Intermediate Similarity NPD4785 Approved
0.7255 Intermediate Similarity NPD6899 Approved
0.7255 Intermediate Similarity NPD6881 Approved
0.7253 Intermediate Similarity NPD6098 Approved
0.7241 Intermediate Similarity NPD4195 Approved
0.7229 Intermediate Similarity NPD4243 Approved
0.7228 Intermediate Similarity NPD6402 Approved
0.7228 Intermediate Similarity NPD5739 Approved
0.7228 Intermediate Similarity NPD7128 Approved
0.7228 Intermediate Similarity NPD6675 Approved
0.7204 Intermediate Similarity NPD6904 Approved
0.7204 Intermediate Similarity NPD6673 Approved
0.7204 Intermediate Similarity NPD6080 Approved
0.7188 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5695 Phase 3
0.7159 Intermediate Similarity NPD7525 Registered
0.7157 Intermediate Similarity NPD5697 Approved
0.7143 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD5696 Approved
0.7143 Intermediate Similarity NPD4225 Approved
0.7115 Intermediate Similarity NPD7290 Approved
0.7115 Intermediate Similarity NPD6883 Approved
0.7115 Intermediate Similarity NPD7102 Approved
0.7097 Intermediate Similarity NPD5737 Approved
0.7097 Intermediate Similarity NPD6672 Approved
0.7087 Intermediate Similarity NPD7320 Approved
0.7083 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7900 Approved
0.7071 Intermediate Similarity NPD7639 Approved
0.7071 Intermediate Similarity NPD7640 Approved
0.7065 Intermediate Similarity NPD6684 Approved
0.7065 Intermediate Similarity NPD7521 Approved
0.7065 Intermediate Similarity NPD7334 Approved
0.7065 Intermediate Similarity NPD6409 Approved
0.7065 Intermediate Similarity NPD7146 Approved
0.7065 Intermediate Similarity NPD5330 Approved
0.7053 Intermediate Similarity NPD5284 Approved
0.7053 Intermediate Similarity NPD7637 Suspended
0.7053 Intermediate Similarity NPD5281 Approved
0.7048 Intermediate Similarity NPD6869 Approved
0.7048 Intermediate Similarity NPD6650 Approved
0.7048 Intermediate Similarity NPD6847 Approved
0.7048 Intermediate Similarity NPD6649 Approved
0.7048 Intermediate Similarity NPD8130 Phase 1
0.7048 Intermediate Similarity NPD6617 Approved
0.7037 Intermediate Similarity NPD7115 Discovery
0.7021 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6051 Approved
0.7019 Intermediate Similarity NPD6012 Approved
0.7019 Intermediate Similarity NPD6373 Approved
0.7019 Intermediate Similarity NPD6372 Approved
0.7019 Intermediate Similarity NPD6013 Approved
0.7019 Intermediate Similarity NPD6014 Approved
0.7 Intermediate Similarity NPD4221 Approved
0.7 Intermediate Similarity NPD4223 Phase 3
0.699 Remote Similarity NPD5701 Approved
0.6981 Remote Similarity NPD8297 Approved
0.6981 Remote Similarity NPD6882 Approved
0.6979 Remote Similarity NPD5779 Approved
0.6979 Remote Similarity NPD5778 Approved
0.6966 Remote Similarity NPD4695 Discontinued
0.6957 Remote Similarity NPD5329 Approved
0.6923 Remote Similarity NPD6011 Approved
0.6915 Remote Similarity NPD5208 Approved
0.6915 Remote Similarity NPD6903 Approved
0.6915 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6907 Remote Similarity NPD6001 Approved
0.6882 Remote Similarity NPD4623 Approved
0.6882 Remote Similarity NPD3618 Phase 1
0.6882 Remote Similarity NPD4519 Discontinued
0.6875 Remote Similarity NPD6079 Approved
0.6875 Remote Similarity NPD5693 Phase 1
0.6875 Remote Similarity NPD6050 Approved
0.6875 Remote Similarity NPD8035 Phase 2
0.6875 Remote Similarity NPD8034 Phase 2
0.6875 Remote Similarity NPD5694 Approved
0.6848 Remote Similarity NPD4786 Approved
0.6848 Remote Similarity NPD4197 Approved
0.6842 Remote Similarity NPD4753 Phase 2
0.6842 Remote Similarity NPD5328 Approved
0.6813 Remote Similarity NPD3667 Approved
0.6782 Remote Similarity NPD5275 Approved
0.6782 Remote Similarity NPD4190 Phase 3
0.6782 Remote Similarity NPD7339 Approved
0.6782 Remote Similarity NPD6942 Approved
0.6774 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6771 Remote Similarity NPD5207 Approved
0.6771 Remote Similarity NPD5692 Phase 3
0.6733 Remote Similarity NPD5285 Approved
0.6733 Remote Similarity NPD5286 Approved
0.6733 Remote Similarity NPD4696 Approved
0.6729 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6705 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4693 Phase 3
0.6702 Remote Similarity NPD4138 Approved
0.6702 Remote Similarity NPD4688 Approved
0.6702 Remote Similarity NPD4690 Approved
0.6702 Remote Similarity NPD5690 Phase 2
0.6702 Remote Similarity NPD4689 Approved
0.6702 Remote Similarity NPD5205 Approved
0.67 Remote Similarity NPD4755 Approved
0.6696 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD4629 Approved
0.6667 Remote Similarity NPD3666 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD5210 Approved
0.6633 Remote Similarity NPD4202 Approved
0.663 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7492 Approved
0.6607 Remote Similarity NPD7101 Approved
0.6607 Remote Similarity NPD7100 Approved
0.6604 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6602 Remote Similarity NPD5225 Approved
0.6602 Remote Similarity NPD5224 Approved
0.6602 Remote Similarity NPD5211 Phase 2
0.6602 Remote Similarity NPD5226 Approved
0.6602 Remote Similarity NPD4633 Approved
0.66 Remote Similarity NPD5221 Approved
0.66 Remote Similarity NPD5222 Approved
0.66 Remote Similarity NPD7614 Phase 1
0.66 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6569 Remote Similarity NPD4700 Approved
0.6566 Remote Similarity NPD5707 Approved
0.6559 Remote Similarity NPD6695 Phase 3
0.6556 Remote Similarity NPD3617 Approved
0.6552 Remote Similarity NPD6616 Approved
0.6549 Remote Similarity NPD6054 Approved
0.6538 Remote Similarity NPD5174 Approved
0.6538 Remote Similarity NPD5175 Approved
0.6535 Remote Similarity NPD5173 Approved
0.6526 Remote Similarity NPD5280 Approved
0.6526 Remote Similarity NPD4694 Approved
0.6518 Remote Similarity NPD6335 Approved
0.6505 Remote Similarity NPD5223 Approved
0.6496 Remote Similarity NPD7078 Approved
0.6489 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3668 Phase 3
0.6486 Remote Similarity NPD6274 Approved
0.6486 Remote Similarity NPD6868 Approved
0.6481 Remote Similarity NPD4634 Approved
0.6477 Remote Similarity NPD6924 Approved
0.6477 Remote Similarity NPD6926 Approved
0.6476 Remote Similarity NPD5141 Approved
0.6455 Remote Similarity NPD4632 Approved
0.6442 Remote Similarity NPD7632 Discontinued
0.6441 Remote Similarity NPD7736 Approved
0.6436 Remote Similarity NPD4697 Phase 3
0.6435 Remote Similarity NPD6370 Approved
0.6429 Remote Similarity NPD6317 Approved
0.6421 Remote Similarity NPD1694 Approved
0.6415 Remote Similarity NPD6008 Approved
0.6404 Remote Similarity NPD6059 Approved
0.6389 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6389 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6381 Remote Similarity NPD6052 Approved
0.6379 Remote Similarity NPD8328 Phase 3
0.6372 Remote Similarity NPD6313 Approved
0.6372 Remote Similarity NPD6314 Approved
0.6356 Remote Similarity NPD8293 Discontinued
0.6355 Remote Similarity NPD6614 Approved
0.6355 Remote Similarity NPD6412 Phase 2
0.6348 Remote Similarity NPD6909 Approved
0.6348 Remote Similarity NPD6908 Approved
0.6348 Remote Similarity NPD6015 Approved
0.6348 Remote Similarity NPD7503 Approved
0.6348 Remote Similarity NPD6016 Approved
0.6344 Remote Similarity NPD4139 Approved
0.6344 Remote Similarity NPD4692 Approved
0.6344 Remote Similarity NPD5369 Approved
0.6337 Remote Similarity NPD5654 Approved
0.6333 Remote Similarity NPD6933 Approved
0.633 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6296 Remote Similarity NPD6686 Approved
0.6296 Remote Similarity NPD4729 Approved
0.6296 Remote Similarity NPD4730 Approved
0.6293 Remote Similarity NPD5988 Approved
0.6289 Remote Similarity NPD7750 Discontinued
0.6289 Remote Similarity NPD7524 Approved
0.6283 Remote Similarity NPD6009 Approved
0.6283 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6275 Remote Similarity NPD7732 Phase 3
0.6264 Remote Similarity NPD6932 Approved
0.6262 Remote Similarity NPD4767 Approved
0.6262 Remote Similarity NPD4768 Approved
0.6239 Remote Similarity NPD7604 Phase 2
0.6237 Remote Similarity NPD6930 Phase 2

Structure

External Identifiers

PubChem CID   44566223
ChEMBL   CHEMBL446724
ZINC  

Physicochemical Properties

Molecular Weight:  360.23
ALogP:  2.2258
MLogP:  3.44
XLogP:  6.14
# Rotatable Bonds:  9
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  26

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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