Natural Product: NPC475528

Natural Product ID:  NPC475528
Common Name:   Gaertneric Acid
IUPAC Name:   (1R,4aS,7R,7aS)-4'-[hydroxy-(4-hydroxyphenyl)methyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
Synonyms:   Gaertneric Acid
Molecular Formula:   C25H26O13
Standard InCHIKey:  FTQHRAAKMDKGHW-DWTWZDHPSA-N
Standard InCHI:  InChI=1S/C25H26O13/c26-8-15-18(29)19(30)20(31)24(36-15)37-23-16-12(14(9-35-23)21(32)33)5-6-25(16)7-13(22(34)38-25)17(28)10-1-3-11(27)4-2-10/h1-7,9,12,15-20,23-24,26-31H,8H2,(H,32,33)/t12-,15-,16-,17?,18-,19+,20-,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@]2(C=C3)OC(=O)C(=C2)C(c2ccc(cc2)O)O)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
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
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 7.1 ug/ml 22871217
NPT2 Others Unspecified IC50 = 69000 nM 24720452

  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 NPC475528 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
0.9928 High Similarity NPC143246
0.9928 High Similarity NPC119773
0.9928 High Similarity NPC474268
0.9928 High Similarity NPC475539
0.964 High Similarity NPC63304
0.958 High Similarity NPC474620
0.9195 High Similarity NPC475663
0.9195 High Similarity NPC286919
0.9161 High Similarity NPC210330
0.9137 High Similarity NPC472132
0.9133 High Similarity NPC469384
0.9128 High Similarity NPC475378
0.9091 High Similarity NPC77922
0.9091 High Similarity NPC202391
0.9091 High Similarity NPC296659
0.9091 High Similarity NPC473281
0.9007 High Similarity NPC220936
0.9007 High Similarity NPC31745
0.898 High Similarity NPC117346
0.898 High Similarity NPC240592
0.8966 High Similarity NPC212808
0.8919 High Similarity NPC158546
0.8919 High Similarity NPC289021
0.8912 High Similarity NPC478236
0.8912 High Similarity NPC96599
0.8857 High Similarity NPC169398
0.8839 High Similarity NPC180586
0.8784 High Similarity NPC478234
0.8777 High Similarity NPC254819
0.8776 High Similarity NPC473149
0.8759 High Similarity NPC293154
0.8759 High Similarity NPC478250
0.8733 High Similarity NPC194705
0.8707 High Similarity NPC473147
0.8699 High Similarity NPC184464
0.8699 High Similarity NPC251062
0.8671 High Similarity NPC469364
0.8671 High Similarity NPC65262
0.8671 High Similarity NPC101686
0.8643 High Similarity NPC281798
0.8636 High Similarity NPC76211
0.863 High Similarity NPC186296
0.863 High Similarity NPC475213
0.863 High Similarity NPC152796
0.8621 High Similarity NPC7518
0.8621 High Similarity NPC137501
0.8621 High Similarity NPC154262
0.8621 High Similarity NPC159387
0.8609 High Similarity NPC478235
0.8601 High Similarity NPC471345
0.8571 High Similarity NPC194938
0.8571 High Similarity NPC17567
0.8562 High Similarity NPC475484
0.8562 High Similarity NPC296643
0.8553 High Similarity NPC229354
0.8543 High Similarity NPC475379
0.8521 High Similarity NPC114116
0.8511 High Similarity NPC478255
0.85 High Similarity NPC469549
0.8493 Intermediate Similarity NPC46644
0.8489 Intermediate Similarity NPC288416
0.8483 Intermediate Similarity NPC49597
0.8477 Intermediate Similarity NPC35097
0.8477 Intermediate Similarity NPC69367
0.8467 Intermediate Similarity NPC120728
0.8467 Intermediate Similarity NPC189631
0.8467 Intermediate Similarity NPC473428
0.8456 Intermediate Similarity NPC473867
0.8452 Intermediate Similarity NPC187205
0.8435 Intermediate Similarity NPC148080
0.8435 Intermediate Similarity NPC469623
0.8417 Intermediate Similarity NPC252114
0.8408 Intermediate Similarity NPC477627
0.8397 Intermediate Similarity NPC179914
0.8394 Intermediate Similarity NPC52097
0.8392 Intermediate Similarity NPC164172
0.8377 Intermediate Similarity NPC478232
0.8369 Intermediate Similarity NPC253595
0.8367 Intermediate Similarity NPC80098
0.8366 Intermediate Similarity NPC203664
0.8357 Intermediate Similarity NPC106677
0.8356 Intermediate Similarity NPC220942
0.8355 Intermediate Similarity NPC12006
0.8345 Intermediate Similarity NPC123704
0.8345 Intermediate Similarity NPC126991
0.8345 Intermediate Similarity NPC470572
0.8345 Intermediate Similarity NPC83218
0.8344 Intermediate Similarity NPC138993
0.8333 Intermediate Similarity NPC291153
0.8322 Intermediate Similarity NPC471095
0.8322 Intermediate Similarity NPC471066
0.8321 Intermediate Similarity NPC11724
0.831 Intermediate Similarity NPC319995
0.831 Intermediate Similarity NPC17968
0.831 Intermediate Similarity NPC289415
0.831 Intermediate Similarity NPC470122
0.831 Intermediate Similarity NPC469705
0.8302 Intermediate Similarity NPC109990
0.8298 Intermediate Similarity NPC158673
0.8298 Intermediate Similarity NPC225307
0.8291 Intermediate Similarity NPC293568
0.8291 Intermediate Similarity NPC117943
0.8289 Intermediate Similarity NPC161955
0.8288 Intermediate Similarity NPC84789
0.8288 Intermediate Similarity NPC310252
0.8288 Intermediate Similarity NPC302583
0.8288 Intermediate Similarity NPC469696
0.8288 Intermediate Similarity NPC100558
0.8286 Intermediate Similarity NPC471157
0.8278 Intermediate Similarity NPC470330
0.8264 Intermediate Similarity NPC322503
0.8264 Intermediate Similarity NPC470143
0.8258 Intermediate Similarity NPC472128
0.8258 Intermediate Similarity NPC472127
0.8252 Intermediate Similarity NPC46137
0.8252 Intermediate Similarity NPC235294
0.8252 Intermediate Similarity NPC476407
0.825 Intermediate Similarity NPC294722
0.8248 Intermediate Similarity NPC476872
0.8247 Intermediate Similarity NPC106818
0.8239 Intermediate Similarity NPC145847
0.8239 Intermediate Similarity NPC476011
0.8231 Intermediate Similarity NPC171134
0.8231 Intermediate Similarity NPC321638
0.8231 Intermediate Similarity NPC328273
0.8231 Intermediate Similarity NPC321184
0.8227 Intermediate Similarity NPC35288
0.8227 Intermediate Similarity NPC45224
0.8227 Intermediate Similarity NPC156692
0.8227 Intermediate Similarity NPC173150
0.8227 Intermediate Similarity NPC471881
0.8227 Intermediate Similarity NPC471882
0.8224 Intermediate Similarity NPC23677
0.8224 Intermediate Similarity NPC28776
0.8224 Intermediate Similarity NPC473138
0.8217 Intermediate Similarity NPC226759
0.8207 Intermediate Similarity NPC68517
0.8207 Intermediate Similarity NPC886
0.8207 Intermediate Similarity NPC287597
0.8207 Intermediate Similarity NPC471029
0.8207 Intermediate Similarity NPC34293
0.8199 Intermediate Similarity NPC469419
0.8194 Intermediate Similarity NPC87403
0.8194 Intermediate Similarity NPC473924
0.8194 Intermediate Similarity NPC257847
0.8182 Intermediate Similarity NPC140151
0.817 Intermediate Similarity NPC478242
0.8158 Intermediate Similarity NPC18789
0.8156 Intermediate Similarity NPC61181
0.8153 Intermediate Similarity NPC478055
0.8153 Intermediate Similarity NPC149368
0.8153 Intermediate Similarity NPC265480
0.8151 Intermediate Similarity NPC476870
0.8151 Intermediate Similarity NPC70680
0.8151 Intermediate Similarity NPC123988
0.8151 Intermediate Similarity NPC182217
0.8151 Intermediate Similarity NPC233350
0.8141 Intermediate Similarity NPC185103
0.8138 Intermediate Similarity NPC254398
0.8137 Intermediate Similarity NPC475979
0.8137 Intermediate Similarity NPC265600
0.8133 Intermediate Similarity NPC40305
0.8133 Intermediate Similarity NPC302286
0.8133 Intermediate Similarity NPC116104
0.8133 Intermediate Similarity NPC88754
0.8133 Intermediate Similarity NPC469367
0.8133 Intermediate Similarity NPC237872
0.8133 Intermediate Similarity NPC263397
0.8129 Intermediate Similarity NPC134819
0.8125 Intermediate Similarity NPC246869
0.8125 Intermediate Similarity NPC225384
0.8125 Intermediate Similarity NPC219677
0.8125 Intermediate Similarity NPC138777
0.8121 Intermediate Similarity NPC79908
0.8117 Intermediate Similarity NPC267469
0.8117 Intermediate Similarity NPC87630
0.8117 Intermediate Similarity NPC179128
0.8117 Intermediate Similarity NPC116292
0.8117 Intermediate Similarity NPC182350
0.8113 Intermediate Similarity NPC130489
0.8113 Intermediate Similarity NPC474936
0.8113 Intermediate Similarity NPC271479
0.8113 Intermediate Similarity NPC208676
0.8113 Intermediate Similarity NPC328093
0.8112 Intermediate Similarity NPC477294
0.8112 Intermediate Similarity NPC477293
0.8112 Intermediate Similarity NPC229784
0.8108 Intermediate Similarity NPC24295
0.8108 Intermediate Similarity NPC62800
0.8108 Intermediate Similarity NPC324262
0.8108 Intermediate Similarity NPC283560
0.8101 Intermediate Similarity NPC122809
0.8101 Intermediate Similarity NPC258035
0.8101 Intermediate Similarity NPC40920
0.8101 Intermediate Similarity NPC4747
0.8101 Intermediate Similarity NPC49173
0.8101 Intermediate Similarity NPC223335
0.8101 Intermediate Similarity NPC161749
0.8101 Intermediate Similarity NPC197896
0.8101 Intermediate Similarity NPC43638

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475528 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
0.8101 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7266 Discontinued
0.7895 Intermediate Similarity NPD6190 Approved
0.7844 Intermediate Similarity NPD7685 Pre-registration
0.7722 Intermediate Similarity NPD4380 Phase 2
0.7711 Intermediate Similarity NPD3818 Discontinued
0.7703 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD4628 Phase 3
0.7588 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7054 Approved
0.7558 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7472 Approved
0.7484 Intermediate Similarity NPD1653 Approved
0.7471 Intermediate Similarity NPD6797 Phase 2
0.7469 Intermediate Similarity NPD8455 Phase 2
0.7439 Intermediate Similarity NPD7075 Discontinued
0.7427 Intermediate Similarity NPD7251 Discontinued
0.7427 Intermediate Similarity NPD6559 Discontinued
0.7412 Intermediate Similarity NPD7074 Phase 3
0.7396 Intermediate Similarity NPD7228 Approved
0.7394 Intermediate Similarity NPD6234 Discontinued
0.7394 Intermediate Similarity NPD9545 Approved
0.7386 Intermediate Similarity NPD7033 Discontinued
0.7384 Intermediate Similarity NPD7808 Phase 3
0.7378 Intermediate Similarity NPD4965 Approved
0.7378 Intermediate Similarity NPD4966 Approved
0.7378 Intermediate Similarity NPD4967 Phase 2
0.7345 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD8313 Approved
0.7341 Intermediate Similarity NPD8312 Approved
0.7333 Intermediate Similarity NPD3764 Approved
0.7305 Intermediate Similarity NPD7199 Phase 2
0.7301 Intermediate Similarity NPD6801 Discontinued
0.7301 Intermediate Similarity NPD37 Approved
0.7296 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD5403 Approved
0.7193 Intermediate Similarity NPD3751 Discontinued
0.7192 Intermediate Similarity NPD1091 Approved
0.719 Intermediate Similarity NPD230 Phase 1
0.7161 Intermediate Similarity NPD1510 Phase 2
0.7134 Intermediate Similarity NPD1549 Phase 2
0.7125 Intermediate Similarity NPD6799 Approved
0.7118 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7458 Discontinued
0.7108 Intermediate Similarity NPD5402 Approved
0.7108 Intermediate Similarity NPD3817 Phase 2
0.7099 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD1934 Approved
0.7081 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5401 Approved
0.7078 Intermediate Similarity NPD6355 Discontinued
0.707 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD5647 Approved
0.7059 Intermediate Similarity NPD3787 Discontinued
0.7059 Intermediate Similarity NPD6233 Phase 2
0.7048 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7819 Suspended
0.703 Intermediate Similarity NPD7411 Suspended
0.7029 Intermediate Similarity NPD7240 Approved
0.7021 Intermediate Similarity NPD969 Suspended
0.7006 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7799 Discontinued
0.6993 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6987 Remote Similarity NPD7097 Phase 1
0.6981 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6166 Phase 2
0.6977 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4378 Clinical (unspecified phase)
0.697 Remote Similarity NPD6599 Discontinued
0.6962 Remote Similarity NPD6002 Phase 3
0.6962 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6962 Remote Similarity NPD6004 Phase 3
0.6962 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6962 Remote Similarity NPD6005 Phase 3
0.6952 Remote Similarity NPD7435 Discontinued
0.6946 Remote Similarity NPD2801 Approved
0.6943 Remote Similarity NPD7930 Approved
0.6937 Remote Similarity NPD3750 Approved
0.6937 Remote Similarity NPD8166 Discontinued
0.6937 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6927 Remote Similarity NPD8150 Discontinued
0.6927 Remote Similarity NPD8434 Phase 2
0.6923 Remote Similarity NPD3749 Approved
0.6923 Remote Similarity NPD6653 Approved
0.6915 Remote Similarity NPD8320 Phase 1
0.6915 Remote Similarity NPD8319 Approved
0.6914 Remote Similarity NPD1511 Approved
0.6899 Remote Similarity NPD2796 Approved
0.6899 Remote Similarity NPD2935 Discontinued
0.6887 Remote Similarity NPD2797 Approved
0.6885 Remote Similarity NPD6535 Approved
0.6885 Remote Similarity NPD6534 Approved
0.6883 Remote Similarity NPD6798 Discontinued
0.6883 Remote Similarity NPD3268 Approved
0.6882 Remote Similarity NPD6780 Approved
0.6882 Remote Similarity NPD6776 Approved
0.6882 Remote Similarity NPD6781 Approved
0.6882 Remote Similarity NPD6778 Approved
0.6882 Remote Similarity NPD6777 Approved
0.6882 Remote Similarity NPD6779 Approved
0.6882 Remote Similarity NPD6782 Approved
0.6879 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1652 Phase 2
0.6871 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2534 Approved
0.6871 Remote Similarity NPD2532 Approved
0.6871 Remote Similarity NPD2533 Approved
0.6864 Remote Similarity NPD3882 Suspended
0.686 Remote Similarity NPD6232 Discontinued
0.6859 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6859 Remote Similarity NPD5124 Phase 1
0.6857 Remote Similarity NPD5844 Phase 1
0.6857 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6851 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2798 Approved
0.6839 Remote Similarity NPD7473 Discontinued
0.6839 Remote Similarity NPD6663 Approved
0.6829 Remote Similarity NPD1512 Approved
0.6813 Remote Similarity NPD2424 Discontinued
0.6802 Remote Similarity NPD8127 Discontinued
0.68 Remote Similarity NPD1608 Approved
0.6795 Remote Similarity NPD1240 Approved
0.6792 Remote Similarity NPD1551 Phase 2
0.6789 Remote Similarity NPD7999 Approved
0.6781 Remote Similarity NPD9493 Approved
0.6774 Remote Similarity NPD7699 Phase 2
0.6774 Remote Similarity NPD7700 Phase 2
0.6765 Remote Similarity NPD7768 Phase 2
0.6759 Remote Similarity NPD690 Clinical (unspecified phase)
0.6754 Remote Similarity NPD7584 Approved
0.6752 Remote Similarity NPD1933 Approved
0.6752 Remote Similarity NPD4340 Discontinued
0.6748 Remote Similarity NPD5058 Phase 3
0.6746 Remote Similarity NPD1465 Phase 2
0.6744 Remote Similarity NPD5494 Approved
0.6736 Remote Similarity NPD7874 Approved
0.6736 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4062 Phase 3
0.673 Remote Similarity NPD2799 Discontinued
0.6728 Remote Similarity NPD3400 Discontinued
0.6719 Remote Similarity NPD7585 Approved
0.6711 Remote Similarity NPD3225 Approved
0.6711 Remote Similarity NPD5126 Approved
0.6711 Remote Similarity NPD5125 Phase 3
0.671 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6709 Remote Similarity NPD1607 Approved
0.6708 Remote Similarity NPD5958 Discontinued
0.6701 Remote Similarity NPD7783 Phase 2
0.6701 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6689 Remote Similarity NPD9269 Phase 2
0.6688 Remote Similarity NPD2861 Phase 2
0.6688 Remote Similarity NPD5736 Approved
0.6684 Remote Similarity NPD8151 Discontinued
0.6684 Remote Similarity NPD7697 Approved
0.6684 Remote Similarity NPD7696 Phase 3
0.6684 Remote Similarity NPD7698 Approved
0.6667 Remote Similarity NPD2313 Discontinued
0.6667 Remote Similarity NPD7028 Phase 2
0.6667 Remote Similarity NPD1203 Approved
0.6667 Remote Similarity NPD7583 Approved
0.6649 Remote Similarity NPD7871 Phase 2
0.6649 Remote Similarity NPD6213 Phase 3
0.6649 Remote Similarity NPD7870 Phase 2
0.6649 Remote Similarity NPD6212 Phase 3
0.6649 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6649 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6645 Remote Similarity NPD6832 Phase 2
0.6643 Remote Similarity NPD2067 Discontinued
0.6632 Remote Similarity NPD7701 Phase 2
0.6632 Remote Similarity NPD6823 Phase 2
0.6627 Remote Similarity NPD6273 Approved
0.6626 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6626 Remote Similarity NPD4110 Phase 3
0.6625 Remote Similarity NPD3748 Approved
0.6623 Remote Similarity NPD422 Phase 1
0.6623 Remote Similarity NPD3705 Approved
0.6623 Remote Similarity NPD1535 Discovery
0.662 Remote Similarity NPD1358 Approved
0.6615 Remote Similarity NPD7801 Approved
0.6609 Remote Similarity NPD6959 Discontinued
0.6607 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6607 Remote Similarity NPD3226 Approved
0.6603 Remote Similarity NPD3027 Phase 3
0.6603 Remote Similarity NPD7095 Approved
0.66 Remote Similarity NPD17 Approved
0.6597 Remote Similarity NPD7680 Approved
0.6596 Remote Similarity NPD5048 Discontinued
0.6595 Remote Similarity NPD7296 Approved
0.6587 Remote Similarity NPD920 Approved

Structure

External Identifiers

PubChem CID   44559440
ChEMBL   CHEMBL507310
ZINC  

Physicochemical Properties

Molecular Weight:  534.14
ALogP:  -3.7617
MLogP:  2.78
XLogP:  -0.202
# Rotatable Bonds:  13
Polar Surface Area:  212.67
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  38

Download Data

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