Natural Product: NPC136801

Natural Product ID:  NPC136801
Common Name:   Fasciculol I
IUPAC Name:   (2R,3R,5R,10S,13R,14S,17R)-2,3-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,5,6,7,11,15,16,17-decahydrocyclopenta[a]phenanthren-12-one
Synonyms:  
Molecular Formula:   C30H50O6
Standard InCHIKey:  MNTGMRBOSQJGGX-ULBHAVAUSA-N
Standard InCHI:  InChI=1S/C30H50O6/c1-26(2)22-10-9-19-20(28(22,5)15-21(32)25(26)35)14-24(34)30(7)18(12-13-29(19,30)6)17(16-31)8-11-23(33)27(3,4)36/h17-18,21-23,25,31-33,35-36H,8-16H2,1-7H3/t17-,18+,21+,22-,23+,25-,28+,29-,30-/m0/s1
Canonical SMILES:  OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)C(=O)CC1=C2CC[C@@H]2[C@]1(C)C[C@@H](O)[C@@H](C2(C)C)O)C)CC[C@H](C(O)(C)C)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
NPO33351 naematoloma fasciculare Species Strophariaceae Eukaryota PMID[23634786]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 > 30000 nM 25437304
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 30000 nM 24215398
NPT81 Cell Line A549 Homo sapiens IC50 > 30000 nM 15711537
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 7980 nM 18591275

  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 NPC136801 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
0.9643 High Similarity NPC138756
0.9545 High Similarity NPC200702
0.9091 High Similarity NPC289213
0.8824 High Similarity NPC7988
0.8764 High Similarity NPC32830
0.875 High Similarity NPC99909
0.8723 High Similarity NPC316964
0.866 High Similarity NPC323834
0.8652 High Similarity NPC131470
0.8652 High Similarity NPC193360
0.8652 High Similarity NPC143767
0.8652 High Similarity NPC44181
0.8646 High Similarity NPC191892
0.8636 High Similarity NPC72133
0.8636 High Similarity NPC89077
0.8588 High Similarity NPC22403
0.8571 High Similarity NPC233116
0.8571 High Similarity NPC189520
0.8557 High Similarity NPC209502
0.8557 High Similarity NPC204833
0.8556 High Similarity NPC275740
0.8556 High Similarity NPC86319
0.8556 High Similarity NPC250592
0.8556 High Similarity NPC77263
0.8539 High Similarity NPC241875
0.8539 High Similarity NPC90652
0.8539 High Similarity NPC469314
0.8539 High Similarity NPC469317
0.8495 Intermediate Similarity NPC48330
0.8495 Intermediate Similarity NPC127063
0.8495 Intermediate Similarity NPC297199
0.8469 Intermediate Similarity NPC48733
0.8469 Intermediate Similarity NPC202167
0.8469 Intermediate Similarity NPC149047
0.8469 Intermediate Similarity NPC171137
0.8469 Intermediate Similarity NPC152695
0.8469 Intermediate Similarity NPC296945
0.8469 Intermediate Similarity NPC260268
0.8469 Intermediate Similarity NPC476027
0.8469 Intermediate Similarity NPC85829
0.8469 Intermediate Similarity NPC302607
0.8469 Intermediate Similarity NPC319077
0.8469 Intermediate Similarity NPC97202
0.8469 Intermediate Similarity NPC214264
0.8469 Intermediate Similarity NPC150531
0.8469 Intermediate Similarity NPC50692
0.8469 Intermediate Similarity NPC49958
0.8462 Intermediate Similarity NPC469400
0.8462 Intermediate Similarity NPC183283
0.8444 Intermediate Similarity NPC471724
0.8444 Intermediate Similarity NPC470417
0.8444 Intermediate Similarity NPC471722
0.8444 Intermediate Similarity NPC242864
0.8427 Intermediate Similarity NPC94755
0.8427 Intermediate Similarity NPC55309
0.8427 Intermediate Similarity NPC28252
0.8404 Intermediate Similarity NPC249954
0.8404 Intermediate Similarity NPC173272
0.8404 Intermediate Similarity NPC7124
0.8387 Intermediate Similarity NPC111015
0.8387 Intermediate Similarity NPC196485
0.8387 Intermediate Similarity NPC245972
0.8387 Intermediate Similarity NPC166906
0.8384 Intermediate Similarity NPC475060
0.8384 Intermediate Similarity NPC83744
0.8384 Intermediate Similarity NPC165873
0.8384 Intermediate Similarity NPC477916
0.8384 Intermediate Similarity NPC220229
0.837 Intermediate Similarity NPC63748
0.837 Intermediate Similarity NPC155304
0.8352 Intermediate Similarity NPC474245
0.8352 Intermediate Similarity NPC186688
0.8351 Intermediate Similarity NPC473424
0.8351 Intermediate Similarity NPC477915
0.8333 Intermediate Similarity NPC187376
0.8333 Intermediate Similarity NPC159046
0.8333 Intermediate Similarity NPC110149
0.8333 Intermediate Similarity NPC233836
0.8316 Intermediate Similarity NPC122294
0.8316 Intermediate Similarity NPC320306
0.8316 Intermediate Similarity NPC170978
0.8316 Intermediate Similarity NPC190554
0.8315 Intermediate Similarity NPC197823
0.83 Intermediate Similarity NPC65941
0.83 Intermediate Similarity NPC217201
0.83 Intermediate Similarity NPC329417
0.8298 Intermediate Similarity NPC271195
0.8298 Intermediate Similarity NPC255809
0.8298 Intermediate Similarity NPC317586
0.8298 Intermediate Similarity NPC473170
0.8298 Intermediate Similarity NPC472485
0.8298 Intermediate Similarity NPC259286
0.8298 Intermediate Similarity NPC470016
0.8295 Intermediate Similarity NPC86370
0.8283 Intermediate Similarity NPC166607
0.828 Intermediate Similarity NPC206810
0.828 Intermediate Similarity NPC69454
0.8265 Intermediate Similarity NPC55954
0.8265 Intermediate Similarity NPC218513
0.8261 Intermediate Similarity NPC191684
0.8261 Intermediate Similarity NPC20388
0.8242 Intermediate Similarity NPC280556
0.8242 Intermediate Similarity NPC328539
0.8242 Intermediate Similarity NPC53911
0.8229 Intermediate Similarity NPC16021
0.8222 Intermediate Similarity NPC472494
0.8222 Intermediate Similarity NPC473168
0.8222 Intermediate Similarity NPC472491
0.8218 Intermediate Similarity NPC11710
0.8211 Intermediate Similarity NPC305483
0.8211 Intermediate Similarity NPC49371
0.8211 Intermediate Similarity NPC95565
0.8211 Intermediate Similarity NPC328162
0.8211 Intermediate Similarity NPC96859
0.8202 Intermediate Similarity NPC221758
0.8202 Intermediate Similarity NPC59453
0.8202 Intermediate Similarity NPC473246
0.8191 Intermediate Similarity NPC318332
0.8182 Intermediate Similarity NPC160843
0.8182 Intermediate Similarity NPC471293
0.8182 Intermediate Similarity NPC477812
0.8172 Intermediate Similarity NPC297265
0.8172 Intermediate Similarity NPC473166
0.8172 Intermediate Similarity NPC73457
0.8172 Intermediate Similarity NPC168027
0.8172 Intermediate Similarity NPC185936
0.8172 Intermediate Similarity NPC23434
0.8172 Intermediate Similarity NPC107690
0.8172 Intermediate Similarity NPC19114
0.8163 Intermediate Similarity NPC296879
0.8163 Intermediate Similarity NPC471119
0.8152 Intermediate Similarity NPC229871
0.8152 Intermediate Similarity NPC469319
0.8152 Intermediate Similarity NPC474889
0.8152 Intermediate Similarity NPC84271
0.8152 Intermediate Similarity NPC1015
0.8152 Intermediate Similarity NPC102414
0.8152 Intermediate Similarity NPC475921
0.8152 Intermediate Similarity NPC31985
0.8152 Intermediate Similarity NPC77168
0.8152 Intermediate Similarity NPC474704
0.8144 Intermediate Similarity NPC144660
0.8144 Intermediate Similarity NPC327431
0.8144 Intermediate Similarity NPC307954
0.8144 Intermediate Similarity NPC15390
0.8144 Intermediate Similarity NPC83709
0.8144 Intermediate Similarity NPC299971
0.8144 Intermediate Similarity NPC154072
0.8137 Intermediate Similarity NPC76084
0.8132 Intermediate Similarity NPC474684
0.8132 Intermediate Similarity NPC142361
0.8132 Intermediate Similarity NPC475740
0.8125 Intermediate Similarity NPC108078
0.8111 Intermediate Similarity NPC474083
0.8111 Intermediate Similarity NPC478127
0.8111 Intermediate Similarity NPC470574
0.8105 Intermediate Similarity NPC279974
0.8105 Intermediate Similarity NPC472824
0.809 Intermediate Similarity NPC278648
0.809 Intermediate Similarity NPC476082
0.8085 Intermediate Similarity NPC477855
0.8085 Intermediate Similarity NPC470254
0.8085 Intermediate Similarity NPC475255
0.8085 Intermediate Similarity NPC274046
0.8085 Intermediate Similarity NPC198074
0.8085 Intermediate Similarity NPC291373
0.8085 Intermediate Similarity NPC472930
0.8081 Intermediate Similarity NPC117185
0.8081 Intermediate Similarity NPC55872
0.8081 Intermediate Similarity NPC471005
0.8081 Intermediate Similarity NPC251017
0.8068 Intermediate Similarity NPC6707
0.8065 Intermediate Similarity NPC111585
0.8065 Intermediate Similarity NPC219495
0.8065 Intermediate Similarity NPC175628
0.8065 Intermediate Similarity NPC46758
0.8065 Intermediate Similarity NPC148414
0.8041 Intermediate Similarity NPC114274
0.8041 Intermediate Similarity NPC477854
0.8041 Intermediate Similarity NPC191565
0.8022 Intermediate Similarity NPC51014
0.8022 Intermediate Similarity NPC31564
0.8022 Intermediate Similarity NPC475022
0.8022 Intermediate Similarity NPC474778
0.8022 Intermediate Similarity NPC94462
0.8022 Intermediate Similarity NPC222613
0.8022 Intermediate Similarity NPC145879
0.8022 Intermediate Similarity NPC474732
0.8022 Intermediate Similarity NPC474733
0.8022 Intermediate Similarity NPC118648
0.8021 Intermediate Similarity NPC91439
0.8021 Intermediate Similarity NPC117133
0.8021 Intermediate Similarity NPC471463
0.8021 Intermediate Similarity NPC477853
0.802 Intermediate Similarity NPC473037
0.8 Intermediate Similarity NPC240617
0.8 Intermediate Similarity NPC8993
0.8 Intermediate Similarity NPC85774
0.8 Intermediate Similarity NPC184870
0.8 Intermediate Similarity NPC82902

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC136801 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
0.8352 Intermediate Similarity NPD5328 Approved
0.8202 Intermediate Similarity NPD4786 Approved
0.8172 Intermediate Similarity NPD6079 Approved
0.8022 Intermediate Similarity NPD3618 Phase 1
0.7978 Intermediate Similarity NPD3667 Approved
0.7938 Intermediate Similarity NPD4755 Approved
0.7895 Intermediate Similarity NPD4202 Approved
0.7835 Intermediate Similarity NPD5222 Approved
0.7835 Intermediate Similarity NPD4697 Phase 3
0.7835 Intermediate Similarity NPD5221 Approved
0.7835 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD4634 Approved
0.7778 Intermediate Similarity NPD5285 Approved
0.7778 Intermediate Similarity NPD5286 Approved
0.7778 Intermediate Similarity NPD4700 Approved
0.7778 Intermediate Similarity NPD4696 Approved
0.7755 Intermediate Similarity NPD5173 Approved
0.77 Intermediate Similarity NPD5223 Approved
0.7667 Intermediate Similarity NPD4692 Approved
0.7667 Intermediate Similarity NPD4139 Approved
0.7634 Intermediate Similarity NPD5279 Phase 3
0.7624 Intermediate Similarity NPD5224 Approved
0.7624 Intermediate Similarity NPD5226 Approved
0.7624 Intermediate Similarity NPD5225 Approved
0.7624 Intermediate Similarity NPD5211 Phase 2
0.7624 Intermediate Similarity NPD4633 Approved
0.7609 Intermediate Similarity NPD3666 Approved
0.7609 Intermediate Similarity NPD3665 Phase 1
0.7609 Intermediate Similarity NPD3133 Approved
0.7586 Intermediate Similarity NPD3703 Phase 2
0.7579 Intermediate Similarity NPD4753 Phase 2
0.7573 Intermediate Similarity NPD7128 Approved
0.7573 Intermediate Similarity NPD5739 Approved
0.7573 Intermediate Similarity NPD6675 Approved
0.7573 Intermediate Similarity NPD6402 Approved
0.757 Intermediate Similarity NPD4632 Approved
0.7556 Intermediate Similarity NPD7525 Registered
0.7549 Intermediate Similarity NPD4754 Approved
0.7549 Intermediate Similarity NPD5174 Approved
0.7549 Intermediate Similarity NPD5175 Approved
0.7528 Intermediate Similarity NPD6118 Approved
0.7528 Intermediate Similarity NPD6697 Approved
0.7528 Intermediate Similarity NPD6115 Approved
0.7528 Intermediate Similarity NPD6114 Approved
0.7527 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6399 Phase 3
0.7476 Intermediate Similarity NPD5141 Approved
0.7447 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6899 Approved
0.7429 Intermediate Similarity NPD7320 Approved
0.7429 Intermediate Similarity NPD6881 Approved
0.7423 Intermediate Similarity NPD7515 Phase 2
0.7419 Intermediate Similarity NPD3668 Phase 3
0.7404 Intermediate Similarity NPD4767 Approved
0.7404 Intermediate Similarity NPD4768 Approved
0.7391 Intermediate Similarity NPD4221 Approved
0.7391 Intermediate Similarity NPD4223 Phase 3
0.7363 Intermediate Similarity NPD4748 Discontinued
0.7358 Intermediate Similarity NPD6373 Approved
0.7358 Intermediate Similarity NPD6372 Approved
0.7358 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD5329 Approved
0.7333 Intermediate Similarity NPD3617 Approved
0.7333 Intermediate Similarity NPD5701 Approved
0.7333 Intermediate Similarity NPD5697 Approved
0.7315 Intermediate Similarity NPD8297 Approved
0.7312 Intermediate Similarity NPD4788 Approved
0.7303 Intermediate Similarity NPD6117 Approved
0.729 Intermediate Similarity NPD7102 Approved
0.729 Intermediate Similarity NPD7290 Approved
0.729 Intermediate Similarity NPD6883 Approved
0.7264 Intermediate Similarity NPD6011 Approved
0.7264 Intermediate Similarity NPD4729 Approved
0.7264 Intermediate Similarity NPD5128 Approved
0.7264 Intermediate Similarity NPD4730 Approved
0.7263 Intermediate Similarity NPD5690 Phase 2
0.7263 Intermediate Similarity NPD5280 Approved
0.7263 Intermediate Similarity NPD4694 Approved
0.7234 Intermediate Similarity NPD4197 Approved
0.7228 Intermediate Similarity NPD6083 Phase 2
0.7228 Intermediate Similarity NPD6084 Phase 2
0.7222 Intermediate Similarity NPD6116 Phase 1
0.7222 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6869 Approved
0.7222 Intermediate Similarity NPD8130 Phase 1
0.7222 Intermediate Similarity NPD6847 Approved
0.7222 Intermediate Similarity NPD6649 Approved
0.7222 Intermediate Similarity NPD6617 Approved
0.7222 Intermediate Similarity NPD6650 Approved
0.7209 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD6009 Approved
0.72 Intermediate Similarity NPD4629 Approved
0.72 Intermediate Similarity NPD5695 Phase 3
0.72 Intermediate Similarity NPD5210 Approved
0.7196 Intermediate Similarity NPD6014 Approved
0.7196 Intermediate Similarity NPD6012 Approved
0.7196 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD6013 Approved
0.7191 Intermediate Similarity NPD6942 Approved
0.7191 Intermediate Similarity NPD7339 Approved
0.717 Intermediate Similarity NPD6412 Phase 2
0.7168 Intermediate Similarity NPD6054 Approved
0.7168 Intermediate Similarity NPD6059 Approved
0.7168 Intermediate Similarity NPD6319 Approved
0.7157 Intermediate Similarity NPD7638 Approved
0.7156 Intermediate Similarity NPD6882 Approved
0.713 Intermediate Similarity NPD5249 Phase 3
0.713 Intermediate Similarity NPD5251 Approved
0.713 Intermediate Similarity NPD5250 Approved
0.713 Intermediate Similarity NPD5169 Approved
0.713 Intermediate Similarity NPD5247 Approved
0.713 Intermediate Similarity NPD5248 Approved
0.713 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5135 Approved
0.7103 Intermediate Similarity NPD5168 Approved
0.71 Intermediate Similarity NPD7748 Approved
0.7093 Intermediate Similarity NPD5360 Phase 3
0.7093 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7639 Approved
0.7087 Intermediate Similarity NPD7640 Approved
0.7083 Intermediate Similarity NPD4693 Phase 3
0.7083 Intermediate Similarity NPD4689 Approved
0.7083 Intermediate Similarity NPD4688 Approved
0.7083 Intermediate Similarity NPD4138 Approved
0.7083 Intermediate Similarity NPD5205 Approved
0.7083 Intermediate Similarity NPD4690 Approved
0.7079 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6008 Approved
0.7071 Intermediate Similarity NPD8035 Phase 2
0.7071 Intermediate Similarity NPD8034 Phase 2
0.7071 Intermediate Similarity NPD5281 Approved
0.7071 Intermediate Similarity NPD5284 Approved
0.7064 Intermediate Similarity NPD5127 Approved
0.7064 Intermediate Similarity NPD5215 Approved
0.7064 Intermediate Similarity NPD5216 Approved
0.7064 Intermediate Similarity NPD5217 Approved
0.7054 Intermediate Similarity NPD7115 Discovery
0.7043 Intermediate Similarity NPD6370 Approved
0.7011 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7604 Phase 2
0.6957 Remote Similarity NPD5983 Phase 2
0.6957 Remote Similarity NPD6016 Approved
0.6957 Remote Similarity NPD6015 Approved
0.6952 Remote Similarity NPD7632 Discontinued
0.6941 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6672 Approved
0.6939 Remote Similarity NPD5737 Approved
0.6932 Remote Similarity NPD4789 Approved
0.6932 Remote Similarity NPD4244 Approved
0.6932 Remote Similarity NPD4245 Approved
0.6923 Remote Similarity NPD6933 Approved
0.6923 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7492 Approved
0.6907 Remote Similarity NPD6684 Approved
0.6907 Remote Similarity NPD7146 Approved
0.6907 Remote Similarity NPD7334 Approved
0.6907 Remote Similarity NPD6409 Approved
0.6907 Remote Similarity NPD7521 Approved
0.6907 Remote Similarity NPD5330 Approved
0.6897 Remote Similarity NPD5988 Approved
0.6893 Remote Similarity NPD7902 Approved
0.6875 Remote Similarity NPD5167 Approved
0.6864 Remote Similarity NPD6336 Discontinued
0.6864 Remote Similarity NPD6616 Approved
0.6863 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6335 Approved
0.6837 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7524 Approved
0.6832 Remote Similarity NPD5133 Approved
0.6827 Remote Similarity NPD5696 Approved
0.6818 Remote Similarity NPD3698 Phase 2
0.6818 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6814 Remote Similarity NPD6868 Approved
0.6814 Remote Similarity NPD6274 Approved
0.6807 Remote Similarity NPD8293 Discontinued
0.6807 Remote Similarity NPD7078 Approved
0.68 Remote Similarity NPD4096 Approved
0.6789 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6783 Remote Similarity NPD7100 Approved
0.6783 Remote Similarity NPD7101 Approved
0.6768 Remote Similarity NPD6903 Approved
0.6768 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6754 Remote Similarity NPD6317 Approved
0.675 Remote Similarity NPD6033 Approved
0.675 Remote Similarity NPD7736 Approved
0.6735 Remote Similarity NPD6098 Approved
0.6733 Remote Similarity NPD6050 Approved
0.6733 Remote Similarity NPD6411 Approved
0.6723 Remote Similarity NPD7507 Approved
0.6703 Remote Similarity NPD6926 Approved
0.6703 Remote Similarity NPD6924 Approved
0.6703 Remote Similarity NPD5733 Approved
0.6702 Remote Similarity NPD7645 Phase 2
0.6702 Remote Similarity NPD4195 Approved
0.67 Remote Similarity NPD6080 Approved
0.67 Remote Similarity NPD6673 Approved
0.67 Remote Similarity NPD6904 Approved

Structure

External Identifiers

PubChem CID   72714437
ChEMBL   CHEMBL2375643
ZINC  

Physicochemical Properties

Molecular Weight:  506.36
ALogP:  -0.0739
MLogP:  4.1
XLogP:  2.57
# Rotatable Bonds:  18
Polar Surface Area:  118.22
# H-Bond Aceptor:  6
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  36

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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