NPASS Compound

Natural Product: NPC51141

Natural Product ID	NPC51141
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MONIRWNCXRAPAW-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318084
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 85 91 0 0 0 0 0 0 0 0999 V2000 3.8477 -4.4928 -1.7803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2497 -3.3826 -1.1539 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9959 -2.8442 -0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1944 -1.8996 0.7859 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9939 -1.4014 0.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0601 -0.6565 0.8929 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2154 -0.4864 0.4840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7312 -1.0244 -0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2502 -1.7436 -1.4372 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5066 -1.8686 -1.0046 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 -2.4055 -1.9374 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -1.3075 -2.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9757 -0.2292 -1.6060 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3365 -0.2725 -1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8394 0.6142 -0.1153 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9597 1.4599 0.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6857 1.5781 -0.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1584 0.7648 -0.9826 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8889 2.6101 0.5985 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7982 2.9903 0.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8996 2.9733 1.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1454 2.9399 2.0208 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0104 3.3695 1.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5928 3.5861 -0.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7398 3.4153 -0.8088 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3341 3.2529 1.6321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2347 2.3345 0.7528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3792 0.9446 1.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7381 0.3589 0.8949 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8709 1.2674 0.8014 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6445 2.6777 0.4793 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3257 3.0521 0.2660 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0823 3.5158 -1.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8917 -0.9537 0.9502 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9265 -1.8460 1.1233 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 -1.3475 1.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4650 -0.0582 1.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 0.3513 1.3023 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6921 -2.3769 1.4286 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1525 -3.2159 1.1515 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4199 -3.7600 1.0200 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3430 2.3111 1.4131 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4438 2.3467 2.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.0759 -1.1082 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4590 -1.9990 -2.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7104 -4.0815 -2.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2357 -5.1503 -2.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3870 -5.0488 -0.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3168 -3.7657 0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 -2.5153 -0.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7614 -2.6647 1.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7832 -1.1540 1.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4871 -0.2446 1.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0910 -2.1055 -2.3489 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1006 -2.8899 -2.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2863 -1.0166 -3.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5106 -1.9638 -2.6923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0389 -0.9275 -1.5998 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8778 0.4727 0.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1316 0.8887 -1.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0709 2.1952 0.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0936 2.7767 3.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3596 3.9248 -0.7998 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 3.5615 -1.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3487 2.7689 2.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9303 4.2354 1.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5124 2.2954 -0.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5094 1.1776 1.7563 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5630 0.8016 0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2261 2.9496 -0.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1745 3.3238 1.2567 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9395 3.2534 -1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9130 4.5850 -1.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2123 2.9753 -1.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9671 -1.3308 0.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7382 -3.2178 0.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9861 -3.8193 1.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0111 -3.1920 0.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2577 -4.8419 0.6798 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1143 2.2946 3.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0805 1.3846 2.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0834 3.2062 2.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7066 -2.8927 -2.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3234 -2.5816 -1.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7605 -1.7331 -3.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 29 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 36 39 1 0 35 40 1 0 40 41 1 0 16 42 1 0 42 43 1 0 8 44 1 0 44 45 1 0 11 2 1 0 18 13 2 0 25 20 1 0 32 27 1 0 10 5 1 0 37 28 1 0 38 7 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 9 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 14 58 1 0 15 59 1 0 18 60 1 0 21 61 1 0 22 62 1 0 24 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 27 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 31 71 1 0 33 72 1 0 33 73 1 0 33 74 1 0 34 75 1 0 39 76 1 0 41 77 1 0 41 78 1 0 41 79 1 0 43 80 1 0 43 81 1 0 43 82 1 0 45 83 1 0 45 84 1 0 45 85 1 0 M END

Standard InCHIKey	MONIRWNCXRAPAW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C37H40N2O6/c1-38-14-12-24-19-33-31(42-4)21-27(24)28(38)17-23-8-11-30(41-3)32(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3
SMILES	CN1CCc2cc3c(cc2C1Cc1ccc(c(c1)Oc1ccc(cc1)CC1c2c(CCN1C)cc(c(c2O3)O)OC)OC)OC

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20426456]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392886]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC51141 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	28850
0.1-0.2	19544
0.2-0.3	1196
0.3-0.4	123
0.4-0.5	38
0.5-0.6	44
0.6-0.7	29
0.7-0.8	2
0.8-0.85	7
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC290582
0.9403	High Similarity	NPC217748
0.9403	High Similarity	NPC182052
0.9403	High Similarity	NPC271013
0.9403	High Similarity	NPC42663
0.9403	High Similarity	NPC15414
0.8986	High Similarity	NPC279228
0.8108	Intermediate Similarity	NPC229373
0.8	Intermediate Similarity	NPC181796
0.8	Intermediate Similarity	NPC54654
0.8	Intermediate Similarity	NPC7715
0.8	Intermediate Similarity	NPC328155
0.8	Intermediate Similarity	NPC222661
0.8	Intermediate Similarity	NPC285931
0.7763	Intermediate Similarity	NPC290005
0.7746	Intermediate Similarity	NPC276890
0.7576	Intermediate Similarity	NPC104196
0.7397	Intermediate Similarity	NPC603603
0.7368	Intermediate Similarity	NPC311973
0.7361	Intermediate Similarity	NPC76682
0.7361	Intermediate Similarity	NPC10908
0.7361	Intermediate Similarity	NPC63646
0.7361	Intermediate Similarity	NPC317145
0.7361	Intermediate Similarity	NPC198498
0.7361	Intermediate Similarity	NPC115284
0.7313	Intermediate Similarity	NPC247639
0.7313	Intermediate Similarity	NPC25084
0.7273	Intermediate Similarity	NPC254441
0.7108	Intermediate Similarity	NPC11296
0.7108	Intermediate Similarity	NPC274661
0.7067	Intermediate Similarity	NPC12424
0.7067	Intermediate Similarity	NPC129518
0.7067	Intermediate Similarity	NPC251580
0.7051	Intermediate Similarity	NPC116465
0.6923	Remote Similarity	NPC239824
0.6883	Remote Similarity	NPC73492
0.6883	Remote Similarity	NPC299990
0.6829	Remote Similarity	NPC8836
0.6829	Remote Similarity	NPC275680
0.6829	Remote Similarity	NPC22115
0.6753	Remote Similarity	NPC603853
0.6709	Remote Similarity	NPC286119
0.6706	Remote Similarity	NPC82457
0.6625	Remote Similarity	NPC185639
0.6625	Remote Similarity	NPC251735
0.6625	Remote Similarity	NPC49075
0.6625	Remote Similarity	NPC599951
0.6494	Remote Similarity	NPC227060
0.6486	Remote Similarity	NPC30779
0.6456	Remote Similarity	NPC480587
0.642	Remote Similarity	NPC223690
0.642	Remote Similarity	NPC9532
0.6235	Remote Similarity	NPC24260
0.6154	Remote Similarity	NPC175890
0.6145	Remote Similarity	NPC274716
0.6145	Remote Similarity	NPC167116
0.6145	Remote Similarity	NPC609821
0.6133	Remote Similarity	NPC317272
0.6133	Remote Similarity	NPC268503
0.6118	Remote Similarity	NPC212237
0.6047	Remote Similarity	NPC611658
0.6026	Remote Similarity	NPC480592
0.6	Remote Similarity	NPC240841
0.5949	Remote Similarity	NPC41376
0.5897	Remote Similarity	NPC256012
0.5897	Remote Similarity	NPC610965
0.587	Remote Similarity	NPC48490
0.5843	Remote Similarity	NPC480586
0.5843	Remote Similarity	NPC480590
0.5783	Remote Similarity	NPC608819
0.5714	Remote Similarity	NPC475393
0.5694	Remote Similarity	NPC317439
0.5632	Remote Similarity	NPC16357
0.5632	Remote Similarity	NPC302245
0.5632	Remote Similarity	NPC195538
0.5568	Remote Similarity	NPC475479
0.5568	Remote Similarity	NPC243454
0.5568	Remote Similarity	NPC323537
0.5507	Remote Similarity	NPC213206
0.5507	Remote Similarity	NPC188163
0.5507	Remote Similarity	NPC328750
0.5479	Remote Similarity	NPC135538
0.5479	Remote Similarity	NPC24233
0.5422	Remote Similarity	NPC610959
0.5385	Remote Similarity	NPC10871
0.5385	Remote Similarity	NPC239584
0.5362	Remote Similarity	NPC314682
0.5333	Remote Similarity	NPC485712
0.5333	Remote Similarity	NPC249996
0.5278	Remote Similarity	NPC185838
0.5269	Remote Similarity	NPC281581
0.5263	Remote Similarity	NPC41122
0.5263	Remote Similarity	NPC318805
0.5222	Remote Similarity	NPC139783
0.5222	Remote Similarity	NPC65312
0.5222	Remote Similarity	NPC611798
0.5176	Remote Similarity	NPC480591
0.5172	Remote Similarity	NPC600054
0.5172	Remote Similarity	NPC600872
0.5172	Remote Similarity	NPC601504
0.5135	Remote Similarity	NPC147390
0.5135	Remote Similarity	NPC428
0.5106	Remote Similarity	NPC206900
0.5106	Remote Similarity	NPC254581
0.5055	Remote Similarity	NPC601489
0.5055	Remote Similarity	NPC604804
0.5053	Remote Similarity	NPC485711

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4594
0.1-0.2	4438
0.2-0.3	103
0.3-0.4	8
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7361	Intermediate Similarity	NPD8099	Discontinued
0.72	Intermediate Similarity	NPD8156	Discontinued
0.6667	Remote Similarity	NPD8095	Phase 1
0.5638	Remote Similarity	NPD8054	Phase 4
0.5507	Remote Similarity	NPD4664	Clinical (unspecified phase)

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data