Natural Product: NPC474268

Natural Product ID:  NPC474268
Common Name:   Acetylgaertneroside
IUPAC Name:   methyl (1R,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[hydroxy-(4-hydroxyphenyl)methyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Synonyms:   Acetylgaertneroside
Molecular Formula:   C28H30O14
Standard InCHIKey:  BDUPWFOFVQZENO-YNFGFELQSA-N
Standard InCHI:  InChI=1S/C28H30O14/c1-12(29)38-11-18-21(32)22(33)23(34)27(40-18)41-26-19-15(17(10-39-26)24(35)37-2)7-8-28(19)9-16(25(36)42-28)20(31)13-3-5-14(30)6-4-13/h3-10,15,18-23,26-27,30-34H,11H2,1-2H3/t15-,18-,19-,20?,21-,22+,23-,26-,27+,28-/m1/s1
Canonical SMILES:  COC(=O)C1=CO[C@@H]([C@H]2[C@@H]1C=C[C@@]12OC(=O)C(=C1)C(c1ccc(cc1)O)O)O[C@@H]1O[C@H](COC(=O)C)[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
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota PMID[12542353]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 71000 nM 10.6019/CHEMBL2113921
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 5.4 ug/ml PubChem BioAssay data set

  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 NPC474268 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 NPC475539
1.0 High Similarity NPC143246
1.0 High Similarity NPC119773
0.9928 High Similarity NPC475528
0.9712 High Similarity NPC63304
0.965 High Similarity NPC474620
0.9262 High Similarity NPC286919
0.9262 High Similarity NPC475663
0.9231 High Similarity NPC210330
0.92 High Similarity NPC469384
0.9195 High Similarity NPC475378
0.9161 High Similarity NPC296659
0.9161 High Similarity NPC202391
0.9078 High Similarity NPC220936
0.9078 High Similarity NPC31745
0.9071 High Similarity NPC472132
0.9048 High Similarity NPC240592
0.9048 High Similarity NPC117346
0.9034 High Similarity NPC212808
0.9028 High Similarity NPC473281
0.9028 High Similarity NPC77922
0.8986 High Similarity NPC289021
0.8986 High Similarity NPC158546
0.898 High Similarity NPC96599
0.8929 High Similarity NPC169398
0.8903 High Similarity NPC180586
0.8851 High Similarity NPC478236
0.8851 High Similarity NPC478234
0.8844 High Similarity NPC473149
0.8828 High Similarity NPC293154
0.8776 High Similarity NPC473147
0.8767 High Similarity NPC251062
0.8767 High Similarity NPC184464
0.8741 High Similarity NPC469364
0.8741 High Similarity NPC101686
0.8741 High Similarity NPC65262
0.8714 High Similarity NPC254819
0.8714 High Similarity NPC281798
0.8701 High Similarity NPC76211
0.8699 High Similarity NPC478250
0.8699 High Similarity NPC186296
0.8699 High Similarity NPC475213
0.8699 High Similarity NPC152796
0.869 High Similarity NPC154262
0.869 High Similarity NPC137501
0.869 High Similarity NPC159387
0.869 High Similarity NPC7518
0.8675 High Similarity NPC194705
0.863 High Similarity NPC296643
0.8627 High Similarity NPC475484
0.8609 High Similarity NPC475379
0.8592 High Similarity NPC114116
0.8571 High Similarity NPC469549
0.8553 High Similarity NPC478235
0.8552 High Similarity NPC49597
0.8543 High Similarity NPC35097
0.8543 High Similarity NPC69367
0.8542 High Similarity NPC471345
0.8533 High Similarity NPC473428
0.8533 High Similarity NPC189631
0.8514 High Similarity NPC194938
0.8511 High Similarity NPC17567
0.8497 Intermediate Similarity NPC229354
0.8471 Intermediate Similarity NPC477627
0.8462 Intermediate Similarity NPC179914
0.8451 Intermediate Similarity NPC478255
0.8442 Intermediate Similarity NPC478232
0.8435 Intermediate Similarity NPC46644
0.8431 Intermediate Similarity NPC203664
0.8429 Intermediate Similarity NPC288416
0.8429 Intermediate Similarity NPC106677
0.8425 Intermediate Similarity NPC220942
0.8411 Intermediate Similarity NPC120728
0.84 Intermediate Similarity NPC291153
0.84 Intermediate Similarity NPC473867
0.8397 Intermediate Similarity NPC187205
0.8378 Intermediate Similarity NPC469623
0.8378 Intermediate Similarity NPC148080
0.8365 Intermediate Similarity NPC109990
0.8357 Intermediate Similarity NPC471157
0.8357 Intermediate Similarity NPC252114
0.8355 Intermediate Similarity NPC161955
0.8354 Intermediate Similarity NPC117943
0.8354 Intermediate Similarity NPC293568
0.8344 Intermediate Similarity NPC470330
0.8333 Intermediate Similarity NPC164172
0.8333 Intermediate Similarity NPC52097
0.8333 Intermediate Similarity NPC470143
0.8333 Intermediate Similarity NPC322503
0.8323 Intermediate Similarity NPC472127
0.8323 Intermediate Similarity NPC472128
0.8322 Intermediate Similarity NPC235294
0.8322 Intermediate Similarity NPC46137
0.8313 Intermediate Similarity NPC294722
0.8312 Intermediate Similarity NPC106818
0.8311 Intermediate Similarity NPC80098
0.831 Intermediate Similarity NPC253595
0.8302 Intermediate Similarity NPC476011
0.8302 Intermediate Similarity NPC145847
0.8301 Intermediate Similarity NPC12006
0.8298 Intermediate Similarity NPC45224
0.8298 Intermediate Similarity NPC471881
0.8298 Intermediate Similarity NPC173150
0.8298 Intermediate Similarity NPC35288
0.8298 Intermediate Similarity NPC471882
0.8298 Intermediate Similarity NPC156692
0.8291 Intermediate Similarity NPC138993
0.8289 Intermediate Similarity NPC23677
0.8288 Intermediate Similarity NPC470572
0.8286 Intermediate Similarity NPC83218
0.8286 Intermediate Similarity NPC126991
0.8286 Intermediate Similarity NPC123704
0.828 Intermediate Similarity NPC226759
0.8276 Intermediate Similarity NPC471029
0.8264 Intermediate Similarity NPC471095
0.8264 Intermediate Similarity NPC471066
0.8261 Intermediate Similarity NPC11724
0.8261 Intermediate Similarity NPC469419
0.8258 Intermediate Similarity NPC87403
0.8258 Intermediate Similarity NPC257847
0.8252 Intermediate Similarity NPC289415
0.8252 Intermediate Similarity NPC319995
0.8252 Intermediate Similarity NPC470122
0.8252 Intermediate Similarity NPC17968
0.8252 Intermediate Similarity NPC469705
0.8239 Intermediate Similarity NPC158673
0.8239 Intermediate Similarity NPC225307
0.8235 Intermediate Similarity NPC478242
0.8231 Intermediate Similarity NPC469696
0.8231 Intermediate Similarity NPC302583
0.8231 Intermediate Similarity NPC100558
0.8231 Intermediate Similarity NPC84789
0.8231 Intermediate Similarity NPC310252
0.8227 Intermediate Similarity NPC61181
0.8219 Intermediate Similarity NPC182217
0.8219 Intermediate Similarity NPC70680
0.8219 Intermediate Similarity NPC233350
0.8217 Intermediate Similarity NPC478055
0.8207 Intermediate Similarity NPC254398
0.82 Intermediate Similarity NPC237872
0.82 Intermediate Similarity NPC469367
0.82 Intermediate Similarity NPC263397
0.82 Intermediate Similarity NPC88754
0.82 Intermediate Similarity NPC302286
0.82 Intermediate Similarity NPC116104
0.8199 Intermediate Similarity NPC475979
0.8199 Intermediate Similarity NPC265600
0.8194 Intermediate Similarity NPC225384
0.8194 Intermediate Similarity NPC134819
0.8194 Intermediate Similarity NPC138777
0.8194 Intermediate Similarity NPC476407
0.8194 Intermediate Similarity NPC246869
0.8188 Intermediate Similarity NPC79908
0.8188 Intermediate Similarity NPC476872
0.8182 Intermediate Similarity NPC267469
0.8182 Intermediate Similarity NPC182350
0.8182 Intermediate Similarity NPC87630
0.8182 Intermediate Similarity NPC179128
0.8182 Intermediate Similarity NPC116292
0.8176 Intermediate Similarity NPC62800
0.8176 Intermediate Similarity NPC328273
0.8176 Intermediate Similarity NPC130489
0.8176 Intermediate Similarity NPC474936
0.8176 Intermediate Similarity NPC324262
0.8176 Intermediate Similarity NPC171134
0.8176 Intermediate Similarity NPC321184
0.8176 Intermediate Similarity NPC208676
0.8176 Intermediate Similarity NPC321638
0.817 Intermediate Similarity NPC28776
0.817 Intermediate Similarity NPC473138
0.8169 Intermediate Similarity NPC103533
0.8165 Intermediate Similarity NPC40920
0.8165 Intermediate Similarity NPC4747
0.8165 Intermediate Similarity NPC43638
0.8165 Intermediate Similarity NPC104275
0.8165 Intermediate Similarity NPC223335
0.8165 Intermediate Similarity NPC478226
0.816 Intermediate Similarity NPC21956
0.8158 Intermediate Similarity NPC208293
0.8158 Intermediate Similarity NPC320734
0.8153 Intermediate Similarity NPC172920
0.8153 Intermediate Similarity NPC10205
0.8153 Intermediate Similarity NPC156624
0.8151 Intermediate Similarity NPC34456
0.8151 Intermediate Similarity NPC287597
0.8151 Intermediate Similarity NPC68517
0.8151 Intermediate Similarity NPC886
0.8151 Intermediate Similarity NPC34293
0.8148 Intermediate Similarity NPC301910
0.8148 Intermediate Similarity NPC469459
0.8148 Intermediate Similarity NPC130730
0.8148 Intermediate Similarity NPC469458
0.8148 Intermediate Similarity NPC88176
0.8148 Intermediate Similarity NPC149002
0.8148 Intermediate Similarity NPC469396
0.8146 Intermediate Similarity NPC478240
0.8141 Intermediate Similarity NPC157898
0.8141 Intermediate Similarity NPC44730
0.8138 Intermediate Similarity NPC473285
0.8138 Intermediate Similarity NPC473924

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474268 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
0.8054 Intermediate Similarity NPD7266 Discontinued
0.805 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7685 Pre-registration
0.7843 Intermediate Similarity NPD6190 Approved
0.777 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD4380 Phase 2
0.7665 Intermediate Similarity NPD3818 Discontinued
0.7662 Intermediate Similarity NPD4628 Phase 3
0.7619 Intermediate Similarity NPD7054 Approved
0.7619 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7472 Approved
0.7544 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6797 Phase 2
0.75 Intermediate Similarity NPD7075 Discontinued
0.7485 Intermediate Similarity NPD6559 Discontinued
0.7485 Intermediate Similarity NPD7251 Discontinued
0.7471 Intermediate Similarity NPD7074 Phase 3
0.7465 Intermediate Similarity NPD9545 Approved
0.7456 Intermediate Similarity NPD7228 Approved
0.7455 Intermediate Similarity NPD6234 Discontinued
0.7451 Intermediate Similarity NPD7033 Discontinued
0.7442 Intermediate Similarity NPD7808 Phase 3
0.7439 Intermediate Similarity NPD4966 Approved
0.7439 Intermediate Similarity NPD4967 Phase 2
0.7439 Intermediate Similarity NPD4965 Approved
0.7438 Intermediate Similarity NPD1653 Approved
0.7423 Intermediate Similarity NPD8455 Phase 2
0.7401 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD7199 Phase 2
0.7362 Intermediate Similarity NPD6801 Discontinued
0.7362 Intermediate Similarity NPD37 Approved
0.7358 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD8312 Approved
0.7299 Intermediate Similarity NPD8313 Approved
0.7285 Intermediate Similarity NPD3764 Approved
0.7255 Intermediate Similarity NPD230 Phase 1
0.7229 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6799 Approved
0.7178 Intermediate Similarity NPD7458 Discontinued
0.7176 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD3817 Phase 2
0.716 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5403 Approved
0.7152 Intermediate Similarity NPD1934 Approved
0.7151 Intermediate Similarity NPD3751 Discontinued
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD1091 Approved
0.7133 Intermediate Similarity NPD5647 Approved
0.7124 Intermediate Similarity NPD6233 Phase 2
0.7115 Intermediate Similarity NPD1510 Phase 2
0.7108 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7819 Suspended
0.7091 Intermediate Similarity NPD7411 Suspended
0.7089 Intermediate Similarity NPD1549 Phase 2
0.7086 Intermediate Similarity NPD7240 Approved
0.7066 Intermediate Similarity NPD5402 Approved
0.7066 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD7799 Discontinued
0.7051 Intermediate Similarity NPD7097 Phase 1
0.7051 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5401 Approved
0.7035 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6166 Phase 2
0.7035 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6599 Discontinued
0.7025 Intermediate Similarity NPD6005 Phase 3
0.7025 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6004 Phase 3
0.7025 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6002 Phase 3
0.7025 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3787 Discontinued
0.7006 Intermediate Similarity NPD2801 Approved
0.7005 Intermediate Similarity NPD7435 Discontinued
0.7 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8166 Discontinued
0.6995 Remote Similarity NPD7930 Approved
0.6987 Remote Similarity NPD6653 Approved
0.6983 Remote Similarity NPD8150 Discontinued
0.6983 Remote Similarity NPD8434 Phase 2
0.6972 Remote Similarity NPD969 Suspended
0.6968 Remote Similarity NPD8319 Approved
0.6968 Remote Similarity NPD8320 Phase 1
0.6962 Remote Similarity NPD2796 Approved
0.6962 Remote Similarity NPD2935 Discontinued
0.6954 Remote Similarity NPD2797 Approved
0.6948 Remote Similarity NPD3268 Approved
0.6948 Remote Similarity NPD6798 Discontinued
0.694 Remote Similarity NPD6534 Approved
0.694 Remote Similarity NPD6535 Approved
0.6937 Remote Similarity NPD1652 Phase 2
0.6936 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6777 Approved
0.6935 Remote Similarity NPD6782 Approved
0.6935 Remote Similarity NPD6780 Approved
0.6935 Remote Similarity NPD6781 Approved
0.6935 Remote Similarity NPD6776 Approved
0.6935 Remote Similarity NPD6779 Approved
0.6935 Remote Similarity NPD6778 Approved
0.6933 Remote Similarity NPD2532 Approved
0.6933 Remote Similarity NPD2534 Approved
0.6933 Remote Similarity NPD2533 Approved
0.6933 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3882 Suspended
0.6923 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5124 Phase 1
0.6919 Remote Similarity NPD6232 Discontinued
0.6914 Remote Similarity NPD5844 Phase 1
0.6908 Remote Similarity NPD2798 Approved
0.6906 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6663 Approved
0.6897 Remote Similarity NPD7473 Discontinued
0.6894 Remote Similarity NPD3750 Approved
0.6882 Remote Similarity NPD3749 Approved
0.6875 Remote Similarity NPD2424 Discontinued
0.6871 Remote Similarity NPD1511 Approved
0.6867 Remote Similarity NPD1608 Approved
0.686 Remote Similarity NPD8127 Discontinued
0.6859 Remote Similarity NPD1240 Approved
0.6849 Remote Similarity NPD9493 Approved
0.6842 Remote Similarity NPD7999 Approved
0.6836 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6828 Remote Similarity NPD690 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7700 Phase 2
0.6828 Remote Similarity NPD7699 Phase 2
0.6824 Remote Similarity NPD7768 Phase 2
0.6815 Remote Similarity NPD1933 Approved
0.681 Remote Similarity NPD5058 Phase 3
0.6809 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7584 Approved
0.6802 Remote Similarity NPD5494 Approved
0.6795 Remote Similarity NPD4062 Phase 3
0.6792 Remote Similarity NPD2799 Discontinued
0.6788 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7874 Approved
0.6788 Remote Similarity NPD1512 Approved
0.6779 Remote Similarity NPD5126 Approved
0.6779 Remote Similarity NPD5125 Phase 3
0.6774 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1607 Approved
0.6771 Remote Similarity NPD7585 Approved
0.6753 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6753 Remote Similarity NPD5736 Approved
0.6753 Remote Similarity NPD7783 Phase 2
0.675 Remote Similarity NPD1551 Phase 2
0.6737 Remote Similarity NPD7698 Approved
0.6737 Remote Similarity NPD7697 Approved
0.6737 Remote Similarity NPD7696 Phase 3
0.6736 Remote Similarity NPD8151 Discontinued
0.6726 Remote Similarity NPD7028 Phase 2
0.6719 Remote Similarity NPD7583 Approved
0.6713 Remote Similarity NPD2067 Discontinued
0.671 Remote Similarity NPD6832 Phase 2
0.6709 Remote Similarity NPD4340 Discontinued
0.6706 Remote Similarity NPD1465 Phase 2
0.6703 Remote Similarity NPD6212 Phase 3
0.6703 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6703 Remote Similarity NPD6213 Phase 3
0.6702 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7870 Phase 2
0.6702 Remote Similarity NPD7871 Phase 2
0.669 Remote Similarity NPD1358 Approved
0.6689 Remote Similarity NPD422 Phase 1
0.6689 Remote Similarity NPD3705 Approved
0.6687 Remote Similarity NPD6273 Approved
0.6687 Remote Similarity NPD3400 Discontinued
0.6687 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6687 Remote Similarity NPD4110 Phase 3
0.6684 Remote Similarity NPD6823 Phase 2
0.6684 Remote Similarity NPD7701 Phase 2
0.6667 Remote Similarity NPD7095 Approved
0.6667 Remote Similarity NPD3226 Approved
0.6667 Remote Similarity NPD7801 Approved
0.6667 Remote Similarity NPD6959 Discontinued
0.6667 Remote Similarity NPD5048 Discontinued
0.6667 Remote Similarity NPD3027 Phase 3
0.6667 Remote Similarity NPD17 Approved
0.6667 Remote Similarity NPD3225 Approved
0.6667 Remote Similarity NPD5958 Discontinued
0.6649 Remote Similarity NPD7680 Approved
0.6649 Remote Similarity NPD7296 Approved
0.6647 Remote Similarity NPD920 Approved
0.6646 Remote Similarity NPD6100 Approved
0.6646 Remote Similarity NPD4060 Phase 1
0.6646 Remote Similarity NPD6099 Approved
0.6646 Remote Similarity NPD2438 Suspended
0.6645 Remote Similarity NPD9269 Phase 2
0.6645 Remote Similarity NPD2861 Phase 2
0.6645 Remote Similarity NPD9494 Approved

Structure

External Identifiers

PubChem CID   44559437
ChEMBL   CHEMBL464502
ZINC  

Physicochemical Properties

Molecular Weight:  590.16
ALogP:  -3.1316
MLogP:  3
XLogP:  0.43
# Rotatable Bonds:  16
Polar Surface Area:  207.74
# H-Bond Aceptor:  13
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  42

Download Data

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