Natural Product: NPC469792

Natural Product ID:  NPC469792
Common Name:   Racemosinine C
IUPAC Name:  
Synonyms:   Racemosinine C
Molecular Formula:   C35H32N2O7
Standard InCHIKey:  DTBYELYRIBFWEE-YNJTUNHHSA-N
Standard InCHI:  InChI=1S/C35H32N2O7/c1-37(40)13-11-22-17-30(41-2)31-19-25(22)27(37)15-21-6-9-28(38)29(16-21)43-24-7-4-20(5-8-24)14-26-33-23(10-12-36-26)18-32(42-3)34(39)35(33)44-31/h4-10,12,16-19,27,38-39H,11,13-15H2,1-3H3/t27-,37?/m1/s1
Canonical SMILES:  COc1cc2CCN(=O)([C@H]3c2cc1Oc1c(O)c(OC)cc2c1c(ncc2)Cc1ccc(Oc2cc(C3)ccc2O)cc1)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
NPO18410 Cyclea racemosa Species Menispermaceae Eukaryota roots PMID[20593839]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000 nM 22960697
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10000 nM Open TG-GATES in vivo data: Hematology
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000 nM 16872140

  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 NPC469792 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
0.9019 High Similarity NPC201508
0.8848 High Similarity NPC255800
0.8848 High Similarity NPC96584
0.8768 High Similarity NPC473822
0.8349 Intermediate Similarity NPC122463
0.8271 Intermediate Similarity NPC202605
0.8271 Intermediate Similarity NPC112206
0.8091 Intermediate Similarity NPC174049
0.8038 Intermediate Similarity NPC224928
0.8009 Intermediate Similarity NPC290689
0.7944 Intermediate Similarity NPC36229
0.7944 Intermediate Similarity NPC476581
0.7944 Intermediate Similarity NPC16452
0.792 Intermediate Similarity NPC476997
0.7885 Intermediate Similarity NPC476998
0.7885 Intermediate Similarity NPC476996
0.7857 Intermediate Similarity NPC471113
0.7847 Intermediate Similarity NPC195268
0.7847 Intermediate Similarity NPC133140
0.7841 Intermediate Similarity NPC476994
0.7814 Intermediate Similarity NPC469440
0.7804 Intermediate Similarity NPC31930
0.7778 Intermediate Similarity NPC61350
0.7758 Intermediate Similarity NPC173080
0.7714 Intermediate Similarity NPC469390
0.771 Intermediate Similarity NPC4071
0.771 Intermediate Similarity NPC476582
0.771 Intermediate Similarity NPC476578
0.7692 Intermediate Similarity NPC202768
0.7692 Intermediate Similarity NPC296482
0.7692 Intermediate Similarity NPC53069
0.7689 Intermediate Similarity NPC85381
0.7682 Intermediate Similarity NPC476995
0.7678 Intermediate Similarity NPC41122
0.7678 Intermediate Similarity NPC318805
0.7669 Intermediate Similarity NPC15406
0.7617 Intermediate Similarity NPC234318
0.7561 Intermediate Similarity NPC10871
0.7544 Intermediate Similarity NPC118121
0.7534 Intermediate Similarity NPC96405
0.7534 Intermediate Similarity NPC171409
0.7512 Intermediate Similarity NPC477019
0.7511 Intermediate Similarity NPC119134
0.7511 Intermediate Similarity NPC217554
0.749 Intermediate Similarity NPC284141
0.7488 Intermediate Similarity NPC473053
0.7468 Intermediate Similarity NPC476999
0.7466 Intermediate Similarity NPC313189
0.7458 Intermediate Similarity NPC107123
0.7455 Intermediate Similarity NPC137929
0.7455 Intermediate Similarity NPC164374
0.7438 Intermediate Similarity NPC134637
0.7426 Intermediate Similarity NPC11408
0.7407 Intermediate Similarity NPC77878
0.7406 Intermediate Similarity NPC249996
0.7395 Intermediate Similarity NPC289786
0.7393 Intermediate Similarity NPC476202
0.7378 Intermediate Similarity NPC251160
0.7373 Intermediate Similarity NPC90875
0.7368 Intermediate Similarity NPC204446
0.7362 Intermediate Similarity NPC233334
0.7349 Intermediate Similarity NPC141915
0.7349 Intermediate Similarity NPC280964
0.7349 Intermediate Similarity NPC114335
0.7346 Intermediate Similarity NPC195538
0.7345 Intermediate Similarity NPC266931
0.7342 Intermediate Similarity NPC295228
0.7336 Intermediate Similarity NPC183537
0.7325 Intermediate Similarity NPC473513
0.7309 Intermediate Similarity NPC135549
0.7301 Intermediate Similarity NPC316981
0.7298 Intermediate Similarity NPC129897
0.7297 Intermediate Similarity NPC210256
0.7293 Intermediate Similarity NPC100079
0.7293 Intermediate Similarity NPC23614
0.7273 Intermediate Similarity NPC234197
0.7269 Intermediate Similarity NPC474594
0.7269 Intermediate Similarity NPC162530
0.7261 Intermediate Similarity NPC148409
0.7237 Intermediate Similarity NPC235076
0.723 Intermediate Similarity NPC8836
0.723 Intermediate Similarity NPC222661
0.723 Intermediate Similarity NPC181796
0.723 Intermediate Similarity NPC328155
0.723 Intermediate Similarity NPC290582
0.723 Intermediate Similarity NPC258657
0.723 Intermediate Similarity NPC290005
0.723 Intermediate Similarity NPC90998
0.723 Intermediate Similarity NPC182052
0.723 Intermediate Similarity NPC239824
0.723 Intermediate Similarity NPC223690
0.723 Intermediate Similarity NPC285931
0.723 Intermediate Similarity NPC54654
0.723 Intermediate Similarity NPC279228
0.723 Intermediate Similarity NPC251735
0.723 Intermediate Similarity NPC7715
0.723 Intermediate Similarity NPC49075
0.723 Intermediate Similarity NPC185639
0.723 Intermediate Similarity NPC217748
0.723 Intermediate Similarity NPC229373
0.723 Intermediate Similarity NPC271013
0.723 Intermediate Similarity NPC311973
0.723 Intermediate Similarity NPC104196
0.723 Intermediate Similarity NPC42663
0.723 Intermediate Similarity NPC15414
0.7229 Intermediate Similarity NPC469439
0.7222 Intermediate Similarity NPC214980
0.722 Intermediate Similarity NPC47059
0.722 Intermediate Similarity NPC165349
0.722 Intermediate Similarity NPC274291
0.722 Intermediate Similarity NPC329708
0.722 Intermediate Similarity NPC264166
0.722 Intermediate Similarity NPC118832
0.7203 Intermediate Similarity NPC24019
0.7196 Intermediate Similarity NPC167116
0.7196 Intermediate Similarity NPC254441
0.7196 Intermediate Similarity NPC274716
0.7193 Intermediate Similarity NPC236668
0.7186 Intermediate Similarity NPC46451
0.7183 Intermediate Similarity NPC286119
0.7176 Intermediate Similarity NPC275680
0.7176 Intermediate Similarity NPC22115
0.717 Intermediate Similarity NPC470474
0.7167 Intermediate Similarity NPC280272
0.7162 Intermediate Similarity NPC146976
0.7155 Intermediate Similarity NPC54066
0.715 Intermediate Similarity NPC30779
0.7149 Intermediate Similarity NPC200888
0.7149 Intermediate Similarity NPC210296
0.7131 Intermediate Similarity NPC124313
0.713 Intermediate Similarity NPC116465
0.713 Intermediate Similarity NPC66815
0.713 Intermediate Similarity NPC212237
0.7129 Intermediate Similarity NPC204908
0.7129 Intermediate Similarity NPC83198
0.7119 Intermediate Similarity NPC84164
0.7119 Intermediate Similarity NPC207283
0.7118 Intermediate Similarity NPC271215
0.7118 Intermediate Similarity NPC149471
0.7111 Intermediate Similarity NPC470164
0.7111 Intermediate Similarity NPC323345
0.7089 Intermediate Similarity NPC246381
0.7083 Intermediate Similarity NPC16357
0.7083 Intermediate Similarity NPC277351
0.7083 Intermediate Similarity NPC95426
0.7083 Intermediate Similarity NPC302245
0.7083 Intermediate Similarity NPC66083
0.7078 Intermediate Similarity NPC99891
0.7078 Intermediate Similarity NPC279401
0.7078 Intermediate Similarity NPC79293
0.7074 Intermediate Similarity NPC203168
0.7064 Intermediate Similarity NPC82457
0.7064 Intermediate Similarity NPC175890
0.7064 Intermediate Similarity NPC206900
0.7064 Intermediate Similarity NPC48490
0.7064 Intermediate Similarity NPC11296
0.7064 Intermediate Similarity NPC274661
0.7061 Intermediate Similarity NPC219664
0.7061 Intermediate Similarity NPC188420
0.7051 Intermediate Similarity NPC65312
0.7051 Intermediate Similarity NPC139783
0.7048 Intermediate Similarity NPC66573
0.7048 Intermediate Similarity NPC18348
0.7035 Intermediate Similarity NPC472111
0.7035 Intermediate Similarity NPC304183
0.7034 Intermediate Similarity NPC473449
0.7033 Intermediate Similarity NPC264850
0.7033 Intermediate Similarity NPC13916
0.7032 Intermediate Similarity NPC191132
0.7032 Intermediate Similarity NPC60295
0.7028 Intermediate Similarity NPC152680
0.7028 Intermediate Similarity NPC190783
0.7028 Intermediate Similarity NPC232386
0.7027 Intermediate Similarity NPC127085
0.7023 Intermediate Similarity NPC62069
0.7021 Intermediate Similarity NPC210434
0.7004 Intermediate Similarity NPC474595
0.7 Intermediate Similarity NPC478093
0.7 Intermediate Similarity NPC24260
0.6986 Remote Similarity NPC24465
0.6983 Remote Similarity NPC108342
0.6968 Remote Similarity NPC30182
0.6968 Remote Similarity NPC473589
0.6968 Remote Similarity NPC478092
0.6968 Remote Similarity NPC478091
0.6955 Remote Similarity NPC189903
0.6955 Remote Similarity NPC182907
0.6948 Remote Similarity NPC283152
0.6944 Remote Similarity NPC318068
0.6943 Remote Similarity NPC469589
0.6926 Remote Similarity NPC166722
0.692 Remote Similarity NPC302807
0.692 Remote Similarity NPC287437
0.6916 Remote Similarity NPC285558
0.6901 Remote Similarity NPC227060
0.6901 Remote Similarity NPC317439
0.6901 Remote Similarity NPC63646
0.6901 Remote Similarity NPC276890
0.6901 Remote Similarity NPC10908
0.6901 Remote Similarity NPC115284

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469792 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
0.7847 Intermediate Similarity NPD3922 Approved
0.7847 Intermediate Similarity NPD3923 Approved
0.7847 Intermediate Similarity NPD3921 Approved
0.7847 Intermediate Similarity NPD3924 Approved
0.7725 Intermediate Similarity NPD6361 Phase 2
0.7706 Intermediate Similarity NPD6494 Phase 2
0.7692 Intermediate Similarity NPD3815 Phase 1
0.7692 Intermediate Similarity NPD3816 Phase 1
0.7585 Intermediate Similarity NPD3386 Phase 2
0.7559 Intermediate Similarity NPD4551 Phase 2
0.7443 Intermediate Similarity NPD6477 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD7169 Suspended
0.7378 Intermediate Similarity NPD7069 Discontinued
0.7349 Intermediate Similarity NPD6569 Phase 2
0.7333 Intermediate Similarity NPD1483 Discontinued
0.7321 Intermediate Similarity NPD3920 Phase 2
0.7257 Intermediate Similarity NPD7558 Phase 2
0.7251 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD8054 Approved
0.723 Intermediate Similarity NPD8053 Approved
0.7222 Intermediate Similarity NPD2334 Discontinued
0.722 Intermediate Similarity NPD32 Approved
0.722 Intermediate Similarity NPD4033 Approved
0.722 Intermediate Similarity NPD4034 Approved
0.722 Intermediate Similarity NPD4122 Approved
0.722 Intermediate Similarity NPD4039 Approved
0.722 Intermediate Similarity NPD4038 Approved
0.722 Intermediate Similarity NPD4036 Approved
0.722 Intermediate Similarity NPD4037 Approved
0.722 Intermediate Similarity NPD4035 Approved
0.722 Intermediate Similarity NPD31 Approved
0.7195 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD3763 Approved
0.7168 Intermediate Similarity NPD4437 Phase 3
0.7166 Intermediate Similarity NPD7859 Phase 2
0.7156 Intermediate Similarity NPD7222 Phase 2
0.715 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD7675 Phase 3
0.7149 Intermediate Similarity NPD7674 Phase 3
0.7131 Intermediate Similarity NPD6230 Discontinued
0.713 Intermediate Similarity NPD5612 Discontinued
0.7119 Intermediate Similarity NPD4875 Phase 3
0.7119 Intermediate Similarity NPD4876 Phase 3
0.7117 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD4375 Approved
0.7105 Intermediate Similarity NPD4131 Phase 3
0.7085 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6963 Approved
0.7083 Intermediate Similarity NPD6964 Approved
0.7075 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7046 Intermediate Similarity NPD6553 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5930 Phase 3
0.6991 Remote Similarity NPD4889 Approved
0.6984 Remote Similarity NPD8091 Phase 3
0.6983 Remote Similarity NPD8510 Clinical (unspecified phase)
0.6982 Remote Similarity NPD1622 Discontinued
0.6974 Remote Similarity NPD5863 Clinical (unspecified phase)
0.6967 Remote Similarity NPD7885 Phase 2
0.6967 Remote Similarity NPD7886 Phase 2
0.696 Remote Similarity NPD5530 Phase 1
0.6934 Remote Similarity NPD1923 Clinical (unspecified phase)
0.6934 Remote Similarity NPD5602 Clinical (unspecified phase)
0.693 Remote Similarity NPD7453 Approved
0.693 Remote Similarity NPD7452 Approved
0.6905 Remote Similarity NPD8442 Discontinued
0.6901 Remote Similarity NPD8251 Approved
0.6901 Remote Similarity NPD8099 Discontinued
0.6901 Remote Similarity NPD8252 Approved
0.69 Remote Similarity NPD5658 Approved
0.6898 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6895 Remote Similarity NPD4021 Phase 2
0.6892 Remote Similarity NPD3395 Approved
0.6892 Remote Similarity NPD3396 Approved
0.689 Remote Similarity NPD7955 Approved
0.689 Remote Similarity NPD7956 Approved
0.6889 Remote Similarity NPD6219 Discontinued
0.6869 Remote Similarity NPD8156 Discontinued
0.6862 Remote Similarity NPD7426 Phase 1
0.686 Remote Similarity NPD6773 Clinical (unspecified phase)
0.6856 Remote Similarity NPD1392 Approved
0.6855 Remote Similarity NPD4350 Approved
0.6855 Remote Similarity NPD4349 Approved
0.6852 Remote Similarity NPD4203 Approved
0.6852 Remote Similarity NPD4204 Approved
0.6851 Remote Similarity NPD6568 Discontinued
0.6842 Remote Similarity NPD4795 Phase 2
0.6835 Remote Similarity NPD6298 Discontinued
0.683 Remote Similarity NPD2952 Discontinued
0.6816 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6812 Remote Similarity NPD4305 Clinical (unspecified phase)
0.681 Remote Similarity NPD4502 Phase 2
0.6795 Remote Similarity NPD5902 Approved
0.6795 Remote Similarity NPD5903 Approved
0.6792 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3477 Phase 2
0.6786 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7134 Clinical (unspecified phase)
0.6773 Remote Similarity NPD8350 Clinical (unspecified phase)
0.677 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5147 Discontinued
0.6757 Remote Similarity NPD7803 Approved
0.6754 Remote Similarity NPD7123 Suspended
0.6753 Remote Similarity NPD2739 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5601 Phase 2
0.6735 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7708 Approved
0.673 Remote Similarity NPD7682 Approved
0.673 Remote Similarity NPD7684 Approved
0.6723 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6722 Remote Similarity NPD5640 Discontinued
0.671 Remote Similarity NPD7263 Phase 2
0.6697 Remote Similarity NPD1034 Phase 3
0.6697 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6696 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6696 Remote Similarity NPD1038 Approved
0.6694 Remote Similarity NPD5905 Phase 1
0.6681 Remote Similarity NPD5944 Phase 1
0.6681 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6681 Remote Similarity NPD5945 Phase 1
0.6667 Remote Similarity NPD7417 Discontinued
0.6667 Remote Similarity NPD4989 Phase 2
0.6667 Remote Similarity NPD4418 Discontinued
0.6667 Remote Similarity NPD1740 Approved
0.6667 Remote Similarity NPD1739 Approved
0.6667 Remote Similarity NPD3003 Approved
0.6667 Remote Similarity NPD1954 Phase 1
0.6667 Remote Similarity NPD1856 Discontinued
0.6653 Remote Similarity NPD6856 Discontinued
0.6652 Remote Similarity NPD4372 Phase 1
0.664 Remote Similarity NPD5833 Phase 1
0.6639 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6636 Remote Similarity NPD1032 Phase 2
0.6626 Remote Similarity NPD4984 Phase 2
0.6623 Remote Similarity NPD4052 Clinical (unspecified phase)
0.6623 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6612 Remote Similarity NPD7719 Discontinued
0.6611 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6605 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6599 Remote Similarity NPD2757 Phase 2
0.6597 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6596 Remote Similarity NPD5067 Phase 2
0.6596 Remote Similarity NPD5066 Phase 2
0.6593 Remote Similarity NPD3810 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7967 Discontinued
0.6585 Remote Similarity NPD7796 Approved
0.6585 Remote Similarity NPD7797 Approved
0.6579 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6577 Remote Similarity NPD5256 Discontinued
0.6571 Remote Similarity NPD8512 Phase 3
0.6571 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6564 Remote Similarity NPD6550 Discontinued
0.6561 Remote Similarity NPD7313 Approved
0.6561 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6561 Remote Similarity NPD7312 Approved
0.6561 Remote Similarity NPD7311 Approved
0.6561 Remote Similarity NPD7310 Approved
0.6556 Remote Similarity NPD5506 Approved
0.6556 Remote Similarity NPD5507 Approved
0.6553 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6552 Remote Similarity NPD3397 Phase 2
0.655 Remote Similarity NPD5999 Phase 2
0.655 Remote Similarity NPD1768 Approved
0.6549 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6542 Remote Similarity NPD7194 Discontinued
0.6542 Remote Similarity NPD6501 Approved
0.6542 Remote Similarity NPD6500 Approved
0.654 Remote Similarity NPD7673 Phase 3
0.6538 Remote Similarity NPD7672 Approved
0.6538 Remote Similarity NPD7671 Approved
0.6535 Remote Similarity NPD7948 Phase 1
0.6532 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6532 Remote Similarity NPD7309 Approved
0.6531 Remote Similarity NPD7555 Discontinued
0.6529 Remote Similarity NPD6824 Clinical (unspecified phase)
0.652 Remote Similarity NPD6491 Clinical (unspecified phase)
0.6513 Remote Similarity NPD6140 Clinical (unspecified phase)
0.6509 Remote Similarity NPD4044 Discontinued
0.65 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6494 Remote Similarity NPD2929 Clinical (unspecified phase)
0.6494 Remote Similarity NPD6592 Clinical (unspecified phase)
0.6492 Remote Similarity NPD4080 Discontinued
0.6489 Remote Similarity NPD8063 Discontinued
0.6484 Remote Similarity NPD6243 Phase 3
0.6484 Remote Similarity NPD6244 Phase 3
0.6484 Remote Similarity NPD4072 Approved
0.6484 Remote Similarity NPD4071 Approved
0.6482 Remote Similarity NPD7620 Phase 2
0.6481 Remote Similarity NPD6071 Discontinued
0.6481 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6478 Remote Similarity NPD2175 Phase 3
0.6478 Remote Similarity NPD4996 Approved
0.6478 Remote Similarity NPD2176 Approved
0.6478 Remote Similarity NPD2177 Approved
0.6478 Remote Similarity NPD4995 Approved
0.6475 Remote Similarity NPD7586 Clinical (unspecified phase)
0.6473 Remote Similarity NPD4926 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   46872350
ChEMBL   CHEMBL1172572
ZINC  

Physicochemical Properties

Molecular Weight:  592.22
ALogP:  
MLogP:  4.32
XLogP:  
# Rotatable Bonds:  7
Polar Surface Area:  106.81
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  44

Download Data

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