Natural Product: NPC322503

Natural Product ID:  NPC322503
Common Name:   8-O-Cinnamoylmussaenosidic Acid
IUPAC Name:   (1S,4aS,7S,7aS)-7-methyl-7-[(E)-3-phenylprop-2-enoyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Synonyms:   8-O-Cinnamoylmussaenosidic Acid
Molecular Formula:   C25H30O11
Standard InCHIKey:  SKMCYGKNAPIRGG-GKBUEBNRSA-N
Standard InCHI:  InChI=1S/C25H30O11/c1-25(36-17(27)8-7-13-5-3-2-4-6-13)10-9-14-15(22(31)32)12-33-23(18(14)25)35-24-21(30)20(29)19(28)16(11-26)34-24/h2-8,12,14,16,18-21,23-24,26,28-30H,9-11H2,1H3,(H,31,32)/b8-7+/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@](C)(CC3)OC(=O)/C=C/c2ccccc2)C(=O)O)[C@@H]([C@H]([C@@H]1O)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
NPO10363 Anarrhinum orientale Species Plantaginaceae Eukaryota PMID[21506603]
NPO10363 Anarrhinum orientale Species Plantaginaceae Eukaryota Aerial parts PMID[21506603]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 109000 nM 21506603
NPT1644 Protein Family Trypsin Homo sapiens IC50 > 200000 nM 21506603

  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 NPC322503 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
1.0 High Similarity NPC470143
0.9403 High Similarity NPC284957
0.9008 High Similarity NPC17567
0.8992 High Similarity NPC276047
0.8992 High Similarity NPC267733
0.8984 High Similarity NPC145287
0.8873 High Similarity NPC240592
0.8873 High Similarity NPC117346
0.8864 High Similarity NPC319995
0.8864 High Similarity NPC289415
0.8811 High Similarity NPC289021
0.8811 High Similarity NPC158546
0.8803 High Similarity NPC96599
0.8779 High Similarity NPC175333
0.8714 High Similarity NPC202391
0.8714 High Similarity NPC296659
0.8582 High Similarity NPC184464
0.8582 High Similarity NPC251062
0.8552 High Similarity NPC475379
0.8542 High Similarity NPC478234
0.8542 High Similarity NPC478236
0.8514 High Similarity NPC475378
0.8511 High Similarity NPC186296
0.85 High Similarity NPC7518
0.85 High Similarity NPC159387
0.85 High Similarity NPC137501
0.85 High Similarity NPC154262
0.8446 Intermediate Similarity NPC475484
0.8444 Intermediate Similarity NPC305162
0.8367 Intermediate Similarity NPC194705
0.8367 Intermediate Similarity NPC478235
0.8333 Intermediate Similarity NPC119773
0.8333 Intermediate Similarity NPC475539
0.8333 Intermediate Similarity NPC474268
0.8333 Intermediate Similarity NPC143246
0.8311 Intermediate Similarity NPC229354
0.8286 Intermediate Similarity NPC475195
0.8278 Intermediate Similarity NPC179914
0.8264 Intermediate Similarity NPC475528
0.8261 Intermediate Similarity NPC38420
0.8261 Intermediate Similarity NPC136608
0.8258 Intermediate Similarity NPC140561
0.8258 Intermediate Similarity NPC141970
0.8255 Intermediate Similarity NPC478232
0.8243 Intermediate Similarity NPC469456
0.8227 Intermediate Similarity NPC31745
0.8227 Intermediate Similarity NPC220936
0.8227 Intermediate Similarity NPC49597
0.8222 Intermediate Similarity NPC231627
0.8214 Intermediate Similarity NPC27721
0.8194 Intermediate Similarity NPC77922
0.8194 Intermediate Similarity NPC473281
0.8182 Intermediate Similarity NPC109990
0.8162 Intermediate Similarity NPC226101
0.8162 Intermediate Similarity NPC237182
0.8151 Intermediate Similarity NPC473149
0.8148 Intermediate Similarity NPC290276
0.8148 Intermediate Similarity NPC10121
0.8148 Intermediate Similarity NPC124878
0.8148 Intermediate Similarity NPC35338
0.8148 Intermediate Similarity NPC63404
0.8148 Intermediate Similarity NPC198918
0.8148 Intermediate Similarity NPC204214
0.8148 Intermediate Similarity NPC10883
0.8148 Intermediate Similarity NPC231888
0.8148 Intermediate Similarity NPC92283
0.8143 Intermediate Similarity NPC202729
0.8134 Intermediate Similarity NPC87153
0.8134 Intermediate Similarity NPC162925
0.8129 Intermediate Similarity NPC28836
0.8129 Intermediate Similarity NPC311492
0.8117 Intermediate Similarity NPC145847
0.8116 Intermediate Similarity NPC239358
0.8116 Intermediate Similarity NPC233692
0.8112 Intermediate Similarity NPC46644
0.8074 Intermediate Similarity NPC28069
0.8074 Intermediate Similarity NPC77651
0.8069 Intermediate Similarity NPC63304
0.8058 Intermediate Similarity NPC472248
0.8058 Intermediate Similarity NPC159811
0.8054 Intermediate Similarity NPC474620
0.8047 Intermediate Similarity NPC474641
0.8041 Intermediate Similarity NPC161955
0.8031 Intermediate Similarity NPC470825
0.8029 Intermediate Similarity NPC471024
0.8028 Intermediate Similarity NPC473301
0.8 Intermediate Similarity NPC237872
0.8 Intermediate Similarity NPC244454
0.8 Intermediate Similarity NPC302286
0.8 Intermediate Similarity NPC475213
0.8 Intermediate Similarity NPC88754
0.8 Intermediate Similarity NPC116104
0.8 Intermediate Similarity NPC152796
0.8 Intermediate Similarity NPC476011
0.8 Intermediate Similarity NPC263397
0.8 Intermediate Similarity NPC293154
0.7987 Intermediate Similarity NPC35097
0.7987 Intermediate Similarity NPC474936
0.7987 Intermediate Similarity NPC138993
0.7986 Intermediate Similarity NPC233860
0.7984 Intermediate Similarity NPC29607
0.7975 Intermediate Similarity NPC21956
0.7973 Intermediate Similarity NPC476173
0.7972 Intermediate Similarity NPC473440
0.7959 Intermediate Similarity NPC212808
0.7959 Intermediate Similarity NPC473147
0.7956 Intermediate Similarity NPC471025
0.7953 Intermediate Similarity NPC43584
0.7945 Intermediate Similarity NPC478240
0.7945 Intermediate Similarity NPC194938
0.7943 Intermediate Similarity NPC169398
0.7943 Intermediate Similarity NPC200154
0.7937 Intermediate Similarity NPC184633
0.7926 Intermediate Similarity NPC138798
0.7922 Intermediate Similarity NPC165234
0.7922 Intermediate Similarity NPC475536
0.7917 Intermediate Similarity NPC242355
0.7917 Intermediate Similarity NPC325078
0.7902 Intermediate Similarity NPC156393
0.7891 Intermediate Similarity NPC210330
0.7885 Intermediate Similarity NPC206815
0.7883 Intermediate Similarity NPC147032
0.7883 Intermediate Similarity NPC477365
0.7883 Intermediate Similarity NPC471026
0.7881 Intermediate Similarity NPC471176
0.7871 Intermediate Similarity NPC475437
0.7871 Intermediate Similarity NPC475505
0.7871 Intermediate Similarity NPC473641
0.7871 Intermediate Similarity NPC475300
0.7871 Intermediate Similarity NPC473797
0.7871 Intermediate Similarity NPC475464
0.7857 Intermediate Similarity NPC187205
0.7857 Intermediate Similarity NPC254819
0.7857 Intermediate Similarity NPC329997
0.7852 Intermediate Similarity NPC120728
0.7852 Intermediate Similarity NPC189631
0.7848 Intermediate Similarity NPC301910
0.7848 Intermediate Similarity NPC130730
0.7843 Intermediate Similarity NPC476784
0.7838 Intermediate Similarity NPC37838
0.7832 Intermediate Similarity NPC472132
0.7829 Intermediate Similarity NPC257847
0.7826 Intermediate Similarity NPC477370
0.782 Intermediate Similarity NPC476096
0.7815 Intermediate Similarity NPC471135
0.781 Intermediate Similarity NPC477366
0.7794 Intermediate Similarity NPC473881
0.7793 Intermediate Similarity NPC77493
0.7793 Intermediate Similarity NPC475413
0.7793 Intermediate Similarity NPC474303
0.7786 Intermediate Similarity NPC475478
0.7785 Intermediate Similarity NPC18789
0.7778 Intermediate Similarity NPC65262
0.7778 Intermediate Similarity NPC101686
0.7778 Intermediate Similarity NPC469364
0.7771 Intermediate Similarity NPC477491
0.777 Intermediate Similarity NPC170668
0.777 Intermediate Similarity NPC301857
0.7756 Intermediate Similarity NPC208676
0.7756 Intermediate Similarity NPC130489
0.7755 Intermediate Similarity NPC478250
0.7754 Intermediate Similarity NPC114096
0.7748 Intermediate Similarity NPC69367
0.7748 Intermediate Similarity NPC147224
0.7742 Intermediate Similarity NPC286919
0.7742 Intermediate Similarity NPC475663
0.774 Intermediate Similarity NPC63737
0.7737 Intermediate Similarity NPC57607
0.7737 Intermediate Similarity NPC317163
0.7736 Intermediate Similarity NPC282551
0.7733 Intermediate Similarity NPC308178
0.7727 Intermediate Similarity NPC319404
0.7718 Intermediate Similarity NPC205389
0.7714 Intermediate Similarity NPC11025
0.7712 Intermediate Similarity NPC475638
0.7712 Intermediate Similarity NPC290683
0.7712 Intermediate Similarity NPC475548
0.7704 Intermediate Similarity NPC229600
0.7698 Intermediate Similarity NPC148026
0.7697 Intermediate Similarity NPC269914
0.7697 Intermediate Similarity NPC472657
0.7697 Intermediate Similarity NPC469477
0.7697 Intermediate Similarity NPC478249
0.7697 Intermediate Similarity NPC133430
0.7697 Intermediate Similarity NPC472658
0.7692 Intermediate Similarity NPC469384
0.7687 Intermediate Similarity NPC45307
0.7687 Intermediate Similarity NPC296643
0.7681 Intermediate Similarity NPC79608
0.7681 Intermediate Similarity NPC477363
0.7681 Intermediate Similarity NPC470816
0.7671 Intermediate Similarity NPC473497
0.7667 Intermediate Similarity NPC474564
0.7664 Intermediate Similarity NPC477362
0.7662 Intermediate Similarity NPC322048
0.7662 Intermediate Similarity NPC318447
0.7651 Intermediate Similarity NPC477737
0.7651 Intermediate Similarity NPC312393
0.7647 Intermediate Similarity NPC475328
0.7647 Intermediate Similarity NPC203664

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC322503 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
0.8321 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7685 Pre-registration
0.75 Intermediate Similarity NPD6685 Approved
0.7368 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD7799 Discontinued
0.7344 Intermediate Similarity NPD5909 Discontinued
0.7266 Intermediate Similarity NPD5765 Approved
0.7218 Intermediate Similarity NPD6912 Phase 3
0.7174 Intermediate Similarity NPD7503 Approved
0.7154 Intermediate Similarity NPD5048 Discontinued
0.7133 Intermediate Similarity NPD7266 Discontinued
0.7132 Intermediate Similarity NPD6647 Phase 2
0.7132 Intermediate Similarity NPD5738 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD7236 Approved
0.7081 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD2067 Discontinued
0.702 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6002 Phase 3
0.702 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6004 Phase 3
0.702 Intermediate Similarity NPD6005 Phase 3
0.7006 Intermediate Similarity NPD7239 Suspended
0.7 Intermediate Similarity NPD5126 Approved
0.7 Intermediate Similarity NPD5125 Phase 3
0.6993 Remote Similarity NPD4628 Phase 3
0.6986 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6972 Remote Similarity NPD7507 Approved
0.6951 Remote Similarity NPD7199 Phase 2
0.6948 Remote Similarity NPD6190 Approved
0.6934 Remote Similarity NPD690 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6686 Approved
0.6887 Remote Similarity NPD7033 Discontinued
0.6867 Remote Similarity NPD6653 Approved
0.6859 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6838 Remote Similarity NPD969 Suspended
0.6828 Remote Similarity NPD7319 Approved
0.6812 Remote Similarity NPD2629 Approved
0.679 Remote Similarity NPD8455 Phase 2
0.6788 Remote Similarity NPD7094 Approved
0.6788 Remote Similarity NPD6858 Approved
0.6781 Remote Similarity NPD5647 Approved
0.6766 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3818 Discontinued
0.6739 Remote Similarity NPD6010 Discontinued
0.6738 Remote Similarity NPD7741 Discontinued
0.6736 Remote Similarity NPD6637 Approved
0.6728 Remote Similarity NPD37 Approved
0.6709 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4380 Phase 2
0.6707 Remote Similarity NPD7058 Phase 2
0.6707 Remote Similarity NPD4965 Approved
0.6707 Remote Similarity NPD4967 Phase 2
0.6707 Remote Similarity NPD4966 Approved
0.6707 Remote Similarity NPD7057 Phase 3
0.6706 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6706 Remote Similarity NPD7804 Clinical (unspecified phase)
0.669 Remote Similarity NPD8513 Phase 3
0.6667 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6085 Phase 2
0.6647 Remote Similarity NPD7228 Approved
0.6642 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6641 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6234 Discontinued
0.6609 Remote Similarity NPD8313 Approved
0.6609 Remote Similarity NPD8312 Approved
0.6608 Remote Similarity NPD7054 Approved
0.6597 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6594 Remote Similarity NPD6053 Discontinued
0.659 Remote Similarity NPD6559 Discontinued
0.6584 Remote Similarity NPD1653 Approved
0.6581 Remote Similarity NPD5762 Approved
0.6581 Remote Similarity NPD5763 Approved
0.6579 Remote Similarity NPD6355 Discontinued
0.6573 Remote Similarity NPD8516 Approved
0.6573 Remote Similarity NPD8517 Approved
0.6573 Remote Similarity NPD8515 Approved
0.657 Remote Similarity NPD7472 Approved
0.657 Remote Similarity NPD7074 Phase 3
0.6566 Remote Similarity NPD7075 Discontinued
0.6552 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6552 Remote Similarity NPD1091 Approved
0.6548 Remote Similarity NPD8127 Discontinued
0.6543 Remote Similarity NPD7458 Discontinued
0.6532 Remote Similarity NPD6797 Phase 2
0.6525 Remote Similarity NPD4198 Discontinued
0.6524 Remote Similarity NPD6801 Discontinued
0.6522 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6522 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6519 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6516 Remote Similarity NPD7137 Phase 2
0.6515 Remote Similarity NPD7798 Approved
0.6506 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6503 Remote Similarity NPD9545 Approved
0.6503 Remote Similarity NPD7028 Phase 2
0.6494 Remote Similarity NPD8368 Discontinued
0.6494 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6494 Remote Similarity NPD7251 Discontinued
0.649 Remote Similarity NPD3268 Approved
0.649 Remote Similarity NPD3764 Approved
0.6486 Remote Similarity NPD6362 Approved
0.6486 Remote Similarity NPD2797 Approved
0.6485 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6479 Remote Similarity NPD7328 Approved
0.6479 Remote Similarity NPD7327 Approved
0.6479 Remote Similarity NPD694 Clinical (unspecified phase)
0.6477 Remote Similarity NPD8407 Phase 2
0.6471 Remote Similarity NPD6412 Phase 2
0.646 Remote Similarity NPD6273 Approved
0.6457 Remote Similarity NPD7808 Phase 3
0.6456 Remote Similarity NPD2575 Approved
0.6456 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6456 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6447 Remote Similarity NPD7961 Discontinued
0.6447 Remote Similarity NPD6663 Approved
0.6439 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6434 Remote Similarity NPD7516 Approved
0.642 Remote Similarity NPD5403 Approved
0.6414 Remote Similarity NPD5305 Approved
0.6414 Remote Similarity NPD5306 Approved
0.6404 Remote Similarity NPD8434 Phase 2
0.6403 Remote Similarity NPD8413 Clinical (unspecified phase)
0.64 Remote Similarity NPD6764 Approved
0.64 Remote Similarity NPD7240 Approved
0.64 Remote Similarity NPD5736 Approved
0.64 Remote Similarity NPD6765 Approved
0.6395 Remote Similarity NPD1608 Approved
0.6392 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6391 Remote Similarity NPD2066 Phase 3
0.6389 Remote Similarity NPD8294 Approved
0.6389 Remote Similarity NPD8377 Approved
0.6387 Remote Similarity NPD7097 Phase 1
0.6386 Remote Similarity NPD5761 Phase 2
0.6386 Remote Similarity NPD5760 Phase 2
0.6377 Remote Similarity NPD2182 Approved
0.6364 Remote Similarity NPD230 Phase 1
0.6364 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5124 Phase 1
0.6358 Remote Similarity NPD2613 Approved
0.6358 Remote Similarity NPD3751 Discontinued
0.6357 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6347 Remote Similarity NPD5402 Approved
0.6346 Remote Similarity NPD7305 Phase 1
0.6345 Remote Similarity NPD8296 Approved
0.6345 Remote Similarity NPD8335 Approved
0.6345 Remote Similarity NPD8380 Approved
0.6345 Remote Similarity NPD8033 Approved
0.6345 Remote Similarity NPD8378 Approved
0.6345 Remote Similarity NPD8379 Approved
0.634 Remote Similarity NPD6233 Phase 2
0.6328 Remote Similarity NPD689 Discontinued
0.6327 Remote Similarity NPD4807 Approved
0.6327 Remote Similarity NPD4806 Approved
0.6322 Remote Similarity NPD5844 Phase 1
0.6316 Remote Similarity NPD9495 Approved
0.6313 Remote Similarity NPD8150 Discontinued
0.6309 Remote Similarity NPD7736 Approved
0.6301 Remote Similarity NPD6370 Approved
0.6299 Remote Similarity NPD1282 Approved
0.6296 Remote Similarity NPD5401 Approved
0.6294 Remote Similarity NPD6009 Approved
0.6291 Remote Similarity NPD3662 Phase 3
0.6291 Remote Similarity NPD3663 Approved
0.6291 Remote Similarity NPD3664 Approved
0.6291 Remote Similarity NPD3661 Approved
0.6287 Remote Similarity NPD7819 Suspended
0.6284 Remote Similarity NPD6535 Approved
0.6284 Remote Similarity NPD6534 Approved
0.6279 Remote Similarity NPD3673 Approved
0.6279 Remote Similarity NPD3672 Approved
0.6277 Remote Similarity NPD7435 Discontinued
0.6276 Remote Similarity NPD6319 Approved
0.6276 Remote Similarity NPD7009 Phase 2
0.6275 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6798 Discontinued
0.6268 Remote Similarity NPD2652 Approved
0.6268 Remote Similarity NPD2650 Approved
0.6265 Remote Similarity NPD7411 Suspended
0.6259 Remote Similarity NPD4106 Approved
0.6259 Remote Similarity NPD4135 Approved
0.6259 Remote Similarity NPD4136 Approved
0.6257 Remote Similarity NPD6785 Approved
0.6257 Remote Similarity NPD6784 Approved
0.625 Remote Similarity NPD3817 Phase 2
0.625 Remote Similarity NPD5201 Approved
0.625 Remote Similarity NPD1929 Approved
0.625 Remote Similarity NPD8166 Discontinued
0.625 Remote Similarity NPD7055 Discontinued
0.625 Remote Similarity NPD5203 Approved
0.625 Remote Similarity NPD1931 Clinical (unspecified phase)
0.625 Remote Similarity NPD4620 Approved
0.625 Remote Similarity NPD1930 Approved
0.625 Remote Similarity NPD4617 Approved
0.6243 Remote Similarity NPD8361 Approved
0.6243 Remote Similarity NPD8320 Phase 1
0.6243 Remote Similarity NPD8360 Approved
0.6243 Remote Similarity NPD8319 Approved
0.6242 Remote Similarity NPD6591 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   10744170
ChEMBL   CHEMBL1782503
ZINC  

Physicochemical Properties

Molecular Weight:  506.18
ALogP:  -2.1223
MLogP:  3
XLogP:  3.431
# Rotatable Bonds:  14
Polar Surface Area:  172.21
# H-Bond Aceptor:  11
# 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  
Similar NPs/Drugs