Natural Product: NPC290261

Natural Product ID:  NPC290261
Common Name:   Gukulenin A
IUPAC Name:  
Synonyms:  
Molecular Formula:   C42H54O10
Standard InCHIKey:  WLDVYQCSQQXPRE-WSUXPNIVSA-N
Standard InCHI:  InChI=1S/C42H54O10/c1-19(2)26-10-12-40(8,31(18-43)51-23(7)44)34(26)28-15-25(16-30(46)36(47)21(28)5)42(50)17-24-14-29(45)37(48)22(6)32-33(24)38(52-42)39(49)41(9)13-11-27(20(3)4)35(32)41/h14-16,18-20,26-27,31,34-35,38-39,49-50H,10-13,17H2,1-9H3,(H,45,48)(H,46,47)/t26-,27-,31+,34-,35-,38-,39+,40+,41-,42+/m1/s1
Canonical SMILES:  O=C[C@@H]([C@]1(C)CC[C@@H]([C@@H]1c1cc(cc(c(=O)c1C)O)[C@]1(O)Cc2cc(O)c(=O)c(c3c2[C@@H](O1)[C@H](O)[C@]1([C@@H]3[C@H](CC1)C(C)C)C)C)C(C)C)OC(=O)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
NPO32543 phorbas gukulensis Species Hymedesmiidae Eukaryota PMID[20232859]
NPO32713 phorbas gukhulensis Species Hymedesmiidae Eukaryota Korea PMID[24025124]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1097 Cell Line MKN-45 Homo sapiens IC50 = 130 nM 2128518
NPT81 Cell Line A549 Homo sapiens LC50 = 320 nM 24597894
NPT2 Others Unspecified IC50 > 100000 nM 24597894
NPT368 Cell Line SN12C Homo sapiens IC50 = 92 nM 10.6019/CHEMBL1201861
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 62 nM 10.6019/CHEMBL1201861
NPT1216 Cell Line FaDu Homo sapiens IC50 = 57 nM 10.6019/CHEMBL1201861
NPT111 Cell Line K562 Homo sapiens LC50 = 260 nM 20061160
NPT2 Others Unspecified IC50 > 100000 nM 19008110
NPT2890 Protein Complex Sodium/potassium-transporting ATPase Homo sapiens IC50 > 100000 nM 15921413

  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 NPC290261 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
0.9375 High Similarity NPC82759
0.9375 High Similarity NPC136922
0.824 Intermediate Similarity NPC262845
0.824 Intermediate Similarity NPC68293
0.7672 Intermediate Similarity NPC303559
0.7667 Intermediate Similarity NPC475065
0.7656 Intermediate Similarity NPC3381
0.7647 Intermediate Similarity NPC475176
0.7607 Intermediate Similarity NPC155332
0.7607 Intermediate Similarity NPC114540
0.7607 Intermediate Similarity NPC32577
0.76 Intermediate Similarity NPC473828
0.76 Intermediate Similarity NPC473617
0.76 Intermediate Similarity NPC311554
0.76 Intermediate Similarity NPC257457
0.7589 Intermediate Similarity NPC80738
0.7586 Intermediate Similarity NPC266955
0.7583 Intermediate Similarity NPC318363
0.7583 Intermediate Similarity NPC473482
0.7583 Intermediate Similarity NPC475418
0.7563 Intermediate Similarity NPC173172
0.7563 Intermediate Similarity NPC266570
0.7563 Intermediate Similarity NPC475414
0.7541 Intermediate Similarity NPC475668
0.7541 Intermediate Similarity NPC473921
0.7541 Intermediate Similarity NPC475480
0.7521 Intermediate Similarity NPC115899
0.752 Intermediate Similarity NPC471854
0.7519 Intermediate Similarity NPC145238
0.75 Intermediate Similarity NPC147912
0.75 Intermediate Similarity NPC108368
0.75 Intermediate Similarity NPC57079
0.75 Intermediate Similarity NPC67259
0.75 Intermediate Similarity NPC329048
0.75 Intermediate Similarity NPC473284
0.75 Intermediate Similarity NPC330011
0.748 Intermediate Similarity NPC109607
0.748 Intermediate Similarity NPC69291
0.748 Intermediate Similarity NPC107338
0.7459 Intermediate Similarity NPC475134
0.7459 Intermediate Similarity NPC475563
0.744 Intermediate Similarity NPC478216
0.7438 Intermediate Similarity NPC220155
0.7424 Intermediate Similarity NPC471407
0.7422 Intermediate Similarity NPC52839
0.7419 Intermediate Similarity NPC472926
0.7417 Intermediate Similarity NPC189863
0.7414 Intermediate Similarity NPC202705
0.7414 Intermediate Similarity NPC253826
0.7402 Intermediate Similarity NPC9674
0.7402 Intermediate Similarity NPC476529
0.7402 Intermediate Similarity NPC475775
0.7402 Intermediate Similarity NPC19028
0.7398 Intermediate Similarity NPC474315
0.7395 Intermediate Similarity NPC176883
0.7395 Intermediate Similarity NPC476237
0.7391 Intermediate Similarity NPC25887
0.7385 Intermediate Similarity NPC470922
0.7381 Intermediate Similarity NPC140055
0.7381 Intermediate Similarity NPC167606
0.7381 Intermediate Similarity NPC20302
0.7381 Intermediate Similarity NPC286528
0.7377 Intermediate Similarity NPC10064
0.7377 Intermediate Similarity NPC170221
0.7377 Intermediate Similarity NPC228477
0.7377 Intermediate Similarity NPC137911
0.7373 Intermediate Similarity NPC168319
0.7373 Intermediate Similarity NPC194028
0.7373 Intermediate Similarity NPC472643
0.7364 Intermediate Similarity NPC162009
0.7364 Intermediate Similarity NPC257017
0.736 Intermediate Similarity NPC178289
0.736 Intermediate Similarity NPC475163
0.7355 Intermediate Similarity NPC475294
0.7355 Intermediate Similarity NPC131665
0.7355 Intermediate Similarity NPC255387
0.7348 Intermediate Similarity NPC270109
0.7344 Intermediate Similarity NPC472759
0.7344 Intermediate Similarity NPC157252
0.7344 Intermediate Similarity NPC470312
0.7344 Intermediate Similarity NPC329080
0.7344 Intermediate Similarity NPC19336
0.7344 Intermediate Similarity NPC471126
0.7344 Intermediate Similarity NPC471128
0.7344 Intermediate Similarity NPC185876
0.7344 Intermediate Similarity NPC145182
0.7344 Intermediate Similarity NPC475885
0.7339 Intermediate Similarity NPC264634
0.7339 Intermediate Similarity NPC470063
0.7333 Intermediate Similarity NPC472868
0.7328 Intermediate Similarity NPC15095
0.7328 Intermediate Similarity NPC250757
0.7328 Intermediate Similarity NPC222307
0.7328 Intermediate Similarity NPC473153
0.7328 Intermediate Similarity NPC301534
0.7323 Intermediate Similarity NPC50774
0.7323 Intermediate Similarity NPC709
0.7317 Intermediate Similarity NPC473627
0.7317 Intermediate Similarity NPC37116
0.7317 Intermediate Similarity NPC181298
0.7317 Intermediate Similarity NPC6206
0.7317 Intermediate Similarity NPC238850
0.7317 Intermediate Similarity NPC16270
0.7313 Intermediate Similarity NPC471855
0.7311 Intermediate Similarity NPC473596
0.7295 Intermediate Similarity NPC306265
0.7295 Intermediate Similarity NPC88701
0.7293 Intermediate Similarity NPC476966
0.7288 Intermediate Similarity NPC472644
0.7288 Intermediate Similarity NPC201406
0.7287 Intermediate Similarity NPC202051
0.728 Intermediate Similarity NPC73050
0.728 Intermediate Similarity NPC472929
0.7279 Intermediate Similarity NPC158350
0.7273 Intermediate Similarity NPC477125
0.7266 Intermediate Similarity NPC275696
0.7266 Intermediate Similarity NPC473270
0.7266 Intermediate Similarity NPC5991
0.7266 Intermediate Similarity NPC471108
0.7266 Intermediate Similarity NPC255081
0.7266 Intermediate Similarity NPC180640
0.7266 Intermediate Similarity NPC473274
0.7266 Intermediate Similarity NPC22628
0.7266 Intermediate Similarity NPC156745
0.7266 Intermediate Similarity NPC475041
0.7266 Intermediate Similarity NPC5989
0.7266 Intermediate Similarity NPC236918
0.7266 Intermediate Similarity NPC264954
0.7265 Intermediate Similarity NPC141401
0.7265 Intermediate Similarity NPC471815
0.7265 Intermediate Similarity NPC110937
0.7265 Intermediate Similarity NPC208094
0.7258 Intermediate Similarity NPC100329
0.7258 Intermediate Similarity NPC247031
0.7258 Intermediate Similarity NPC132790
0.7258 Intermediate Similarity NPC97939
0.725 Intermediate Similarity NPC180204
0.725 Intermediate Similarity NPC475050
0.725 Intermediate Similarity NPC112009
0.725 Intermediate Similarity NPC475526
0.725 Intermediate Similarity NPC329345
0.725 Intermediate Similarity NPC473283
0.725 Intermediate Similarity NPC72151
0.7244 Intermediate Similarity NPC473968
0.7244 Intermediate Similarity NPC183580
0.7244 Intermediate Similarity NPC243065
0.7244 Intermediate Similarity NPC312824
0.7244 Intermediate Similarity NPC473656
0.7244 Intermediate Similarity NPC470492
0.7244 Intermediate Similarity NPC472927
0.7244 Intermediate Similarity NPC470493
0.7244 Intermediate Similarity NPC10721
0.7244 Intermediate Similarity NPC284068
0.7239 Intermediate Similarity NPC196921
0.7239 Intermediate Similarity NPC220757
0.7236 Intermediate Similarity NPC475274
0.7231 Intermediate Similarity NPC23786
0.7231 Intermediate Similarity NPC470265
0.7231 Intermediate Similarity NPC269642
0.7227 Intermediate Similarity NPC99411
0.7218 Intermediate Similarity NPC245094
0.7214 Intermediate Similarity NPC470426
0.7213 Intermediate Similarity NPC469853
0.7209 Intermediate Similarity NPC474370
0.7206 Intermediate Similarity NPC471234
0.7206 Intermediate Similarity NPC182266
0.7206 Intermediate Similarity NPC471137
0.7206 Intermediate Similarity NPC475154
0.7206 Intermediate Similarity NPC471136
0.7206 Intermediate Similarity NPC475500
0.7206 Intermediate Similarity NPC100017
0.7206 Intermediate Similarity NPC473548
0.7206 Intermediate Similarity NPC223356
0.7203 Intermediate Similarity NPC471610
0.72 Intermediate Similarity NPC236217
0.72 Intermediate Similarity NPC285956
0.72 Intermediate Similarity NPC221144
0.72 Intermediate Similarity NPC317687
0.72 Intermediate Similarity NPC100267
0.72 Intermediate Similarity NPC328074
0.72 Intermediate Similarity NPC191620
0.72 Intermediate Similarity NPC475970
0.72 Intermediate Similarity NPC321272
0.72 Intermediate Similarity NPC475524
0.72 Intermediate Similarity NPC317460
0.72 Intermediate Similarity NPC147180
0.72 Intermediate Similarity NPC470025
0.72 Intermediate Similarity NPC476801
0.7197 Intermediate Similarity NPC159499
0.7194 Intermediate Similarity NPC476825
0.719 Intermediate Similarity NPC473577
0.719 Intermediate Similarity NPC118911
0.719 Intermediate Similarity NPC475585
0.719 Intermediate Similarity NPC272632
0.719 Intermediate Similarity NPC474550
0.7188 Intermediate Similarity NPC146280
0.7188 Intermediate Similarity NPC146786
0.7188 Intermediate Similarity NPC124676
0.7188 Intermediate Similarity NPC472758
0.7188 Intermediate Similarity NPC171905

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC290261 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
0.7381 Intermediate Similarity NPD7115 Discovery
0.72 Intermediate Similarity NPD8297 Approved
0.7068 Intermediate Similarity NPD7507 Approved
0.7063 Intermediate Similarity NPD6882 Approved
0.7059 Intermediate Similarity NPD4225 Approved
0.7016 Intermediate Similarity NPD7320 Approved
0.6912 Remote Similarity NPD7319 Approved
0.688 Remote Similarity NPD6899 Approved
0.688 Remote Similarity NPD6881 Approved
0.688 Remote Similarity NPD6686 Approved
0.686 Remote Similarity NPD7639 Approved
0.686 Remote Similarity NPD7640 Approved
0.6855 Remote Similarity NPD7128 Approved
0.6855 Remote Similarity NPD6675 Approved
0.6855 Remote Similarity NPD6402 Approved
0.6855 Remote Similarity NPD5739 Approved
0.685 Remote Similarity NPD6650 Approved
0.685 Remote Similarity NPD8130 Phase 1
0.685 Remote Similarity NPD6649 Approved
0.6825 Remote Similarity NPD6373 Approved
0.6825 Remote Similarity NPD6372 Approved
0.68 Remote Similarity NPD5697 Approved
0.6777 Remote Similarity NPD7638 Approved
0.6772 Remote Similarity NPD7290 Approved
0.6772 Remote Similarity NPD6883 Approved
0.6772 Remote Similarity NPD7102 Approved
0.6772 Remote Similarity NPD6371 Approved
0.6767 Remote Similarity NPD7503 Approved
0.6765 Remote Similarity NPD7078 Approved
0.6746 Remote Similarity NPD6011 Approved
0.6741 Remote Similarity NPD7492 Approved
0.6719 Remote Similarity NPD6617 Approved
0.6719 Remote Similarity NPD6869 Approved
0.6719 Remote Similarity NPD6847 Approved
0.6718 Remote Similarity NPD6009 Approved
0.6715 Remote Similarity NPD7736 Approved
0.6694 Remote Similarity NPD6084 Phase 2
0.6694 Remote Similarity NPD6083 Phase 2
0.6693 Remote Similarity NPD6013 Approved
0.6693 Remote Similarity NPD6014 Approved
0.6693 Remote Similarity NPD6012 Approved
0.6692 Remote Similarity NPD6319 Approved
0.6692 Remote Similarity NPD6054 Approved
0.6691 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5701 Approved
0.6642 Remote Similarity NPD8293 Discontinued
0.6642 Remote Similarity NPD8033 Approved
0.6617 Remote Similarity NPD7516 Approved
0.6615 Remote Similarity NPD4632 Approved
0.6612 Remote Similarity NPD4697 Phase 3
0.661 Remote Similarity NPD5785 Approved
0.6593 Remote Similarity NPD6370 Approved
0.6589 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6581 Remote Similarity NPD6672 Approved
0.6581 Remote Similarity NPD5737 Approved
0.6567 Remote Similarity NPD8294 Approved
0.6567 Remote Similarity NPD6059 Approved
0.6567 Remote Similarity NPD8377 Approved
0.6552 Remote Similarity NPD5279 Phase 3
0.6541 Remote Similarity NPD7328 Approved
0.6541 Remote Similarity NPD7327 Approved
0.6538 Remote Similarity NPD6053 Discontinued
0.6529 Remote Similarity NPD5695 Phase 3
0.6519 Remote Similarity NPD6016 Approved
0.6519 Remote Similarity NPD6015 Approved
0.6519 Remote Similarity NPD8380 Approved
0.6519 Remote Similarity NPD8379 Approved
0.6519 Remote Similarity NPD8296 Approved
0.6519 Remote Similarity NPD8335 Approved
0.6519 Remote Similarity NPD8378 Approved
0.6515 Remote Similarity NPD6868 Approved
0.6504 Remote Similarity NPD8029 Clinical (unspecified phase)
0.65 Remote Similarity NPD6399 Phase 3
0.648 Remote Similarity NPD5211 Phase 2
0.6475 Remote Similarity NPD5222 Approved
0.6475 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6475 Remote Similarity NPD5221 Approved
0.6471 Remote Similarity NPD5988 Approved
0.6462 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6454 Remote Similarity NPD7260 Phase 2
0.6446 Remote Similarity NPD7748 Approved
0.6423 Remote Similarity NPD5173 Approved
0.6423 Remote Similarity NPD7604 Phase 2
0.6423 Remote Similarity NPD8328 Phase 3
0.6418 Remote Similarity NPD6335 Approved
0.6417 Remote Similarity NPD6050 Approved
0.6417 Remote Similarity NPD5693 Phase 1
0.6417 Remote Similarity NPD7637 Suspended
0.6417 Remote Similarity NPD6079 Approved
0.64 Remote Similarity NPD5344 Discontinued
0.6397 Remote Similarity NPD8513 Phase 3
0.6397 Remote Similarity NPD5983 Phase 2
0.6391 Remote Similarity NPD6274 Approved
0.6387 Remote Similarity NPD5328 Approved
0.6378 Remote Similarity NPD5141 Approved
0.6371 Remote Similarity NPD5696 Approved
0.637 Remote Similarity NPD7100 Approved
0.637 Remote Similarity NPD7101 Approved
0.6356 Remote Similarity NPD7524 Approved
0.6349 Remote Similarity NPD7632 Discontinued
0.6348 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6343 Remote Similarity NPD6317 Approved
0.6333 Remote Similarity NPD6698 Approved
0.6333 Remote Similarity NPD7838 Discovery
0.6333 Remote Similarity NPD46 Approved
0.6333 Remote Similarity NPD5692 Phase 3
0.6331 Remote Similarity NPD6336 Discontinued
0.6325 Remote Similarity NPD1694 Approved
0.632 Remote Similarity NPD5285 Approved
0.632 Remote Similarity NPD4696 Approved
0.632 Remote Similarity NPD5286 Approved
0.632 Remote Similarity NPD6648 Approved
0.6308 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6903 Approved
0.6296 Remote Similarity NPD6314 Approved
0.6296 Remote Similarity NPD6313 Approved
0.6294 Remote Similarity NPD6845 Suspended
0.6293 Remote Similarity NPD5362 Discontinued
0.629 Remote Similarity NPD7902 Approved
0.629 Remote Similarity NPD4755 Approved
0.6283 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6281 Remote Similarity NPD7515 Phase 2
0.6281 Remote Similarity NPD5694 Approved
0.6279 Remote Similarity NPD6412 Phase 2
0.6277 Remote Similarity NPD8517 Approved
0.6277 Remote Similarity NPD8515 Approved
0.6277 Remote Similarity NPD8516 Approved
0.6271 Remote Similarity NPD3618 Phase 1
0.627 Remote Similarity NPD5223 Approved
0.626 Remote Similarity NPD1698 Clinical (unspecified phase)
0.625 Remote Similarity NPD6673 Approved
0.625 Remote Similarity NPD6904 Approved
0.625 Remote Similarity NPD6080 Approved
0.6241 Remote Similarity NPD6033 Approved
0.6241 Remote Similarity NPD8133 Approved
0.6239 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4786 Approved
0.623 Remote Similarity NPD5779 Approved
0.623 Remote Similarity NPD5778 Approved
0.622 Remote Similarity NPD5225 Approved
0.622 Remote Similarity NPD4633 Approved
0.622 Remote Similarity NPD5224 Approved
0.622 Remote Similarity NPD5226 Approved
0.619 Remote Similarity NPD4700 Approved
0.6186 Remote Similarity NPD5363 Approved
0.6183 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6174 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6172 Remote Similarity NPD5174 Approved
0.6172 Remote Similarity NPD5175 Approved
0.6159 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6159 Remote Similarity NPD6909 Approved
0.6159 Remote Similarity NPD6908 Approved
0.6148 Remote Similarity NPD7983 Approved
0.6148 Remote Similarity NPD8034 Phase 2
0.6148 Remote Similarity NPD8035 Phase 2
0.6148 Remote Similarity NPD6411 Approved
0.6136 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4634 Approved
0.6134 Remote Similarity NPD6684 Approved
0.6134 Remote Similarity NPD5330 Approved
0.6134 Remote Similarity NPD7334 Approved
0.6134 Remote Similarity NPD6409 Approved
0.6134 Remote Similarity NPD7521 Approved
0.6134 Remote Similarity NPD7146 Approved
0.6129 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6116 Remote Similarity NPD4753 Phase 2
0.6116 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6107 Remote Similarity NPD4730 Approved
0.6107 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6107 Remote Similarity NPD4729 Approved
0.6103 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6098 Remote Similarity NPD4202 Approved
0.608 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6077 Remote Similarity NPD6008 Approved
0.6077 Remote Similarity NPD4767 Approved
0.6077 Remote Similarity NPD4768 Approved
0.6068 Remote Similarity NPD3667 Approved
0.6056 Remote Similarity NPD8074 Phase 3
0.6053 Remote Similarity NPD4756 Discovery
0.605 Remote Similarity NPD7520 Clinical (unspecified phase)
0.605 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7900 Approved
0.6048 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6047 Remote Similarity NPD4754 Approved
0.6034 Remote Similarity NPD4695 Discontinued
0.6033 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6017 Remote Similarity NPD5332 Approved
0.6017 Remote Similarity NPD5331 Approved
0.6017 Remote Similarity NPD6695 Phase 3
0.6017 Remote Similarity NPD7154 Phase 3
0.6016 Remote Similarity NPD5284 Approved
0.6016 Remote Similarity NPD5281 Approved
0.6015 Remote Similarity NPD5250 Approved
0.6015 Remote Similarity NPD5251 Approved
0.6015 Remote Similarity NPD5249 Phase 3
0.6015 Remote Similarity NPD5248 Approved
0.6015 Remote Similarity NPD5247 Approved
0.6014 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6 Remote Similarity NPD5654 Approved

Structure

External Identifiers

PubChem CID   46210048
ChEMBL   CHEMBL1098258
ZINC  

Physicochemical Properties

Molecular Weight:  718.37
ALogP:  1.255
MLogP:  4.98
XLogP:  6.152
# Rotatable Bonds:  21
Polar Surface Area:  167.66
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  52

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs