NPASS Compound

Natural Product: NPC537382

Natural Product ID	NPC537382
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{S},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{S},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 69 73 0 0 0 0 0 0 0 0999 V2000 4.3808 -4.6737 -0.0577 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4552 -3.4303 -0.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6657 -2.7768 -0.2982 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7448 -1.4089 -0.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9966 -0.7065 -0.5475 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1939 -1.3440 -0.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3717 -0.6244 -0.9845 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3765 0.7409 -0.9891 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5603 1.4554 -1.2087 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1976 1.3979 -0.7740 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1581 2.7963 -0.7707 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0427 0.6810 -0.5596 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6480 -0.7184 -0.1139 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4710 -1.2928 0.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3943 -0.4649 0.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1178 -0.9769 0.5380 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1205 -0.0571 0.7204 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2020 -0.4006 0.9664 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9551 0.1872 -0.0464 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6481 1.3079 0.3021 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0048 2.0440 -0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7728 1.2708 -1.8216 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9790 0.8644 -1.2915 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9326 -0.5502 -1.2611 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9574 -1.0619 -0.4819 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3197 -0.6361 -0.8947 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1100 -0.5809 0.2779 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4168 0.6869 -1.5548 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3786 0.5901 -2.5864 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1637 1.2040 -2.1731 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8987 0.5963 -3.4205 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6737 2.2400 1.0281 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1950 3.5287 1.1145 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4942 1.6553 2.4073 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2446 2.0268 2.9398 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5509 0.1739 2.3279 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8277 -0.2565 2.6476 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0121 -2.3381 0.5600 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0987 -3.1967 0.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9514 -4.5706 0.3906 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3323 -2.6528 0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5445 -3.3532 -0.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2803 -2.3991 -0.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2965 -1.1428 -1.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1098 1.7152 -0.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4764 3.3496 0.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1252 1.2184 -0.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5285 0.5949 0.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3134 -1.4947 0.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5153 1.1777 0.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0333 2.2223 -1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4252 3.0339 -0.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1575 1.2282 -0.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7678 -0.8155 0.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 -2.1673 -0.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8127 -1.4394 -1.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7890 0.2576 0.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8124 1.4895 -0.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3499 1.4473 -3.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2791 2.3022 -2.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4932 -0.1986 -3.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6864 2.2597 0.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1724 3.4203 1.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2771 2.1012 3.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2523 2.6092 2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8601 -0.2492 3.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1347 0.0147 3.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0621 -2.8050 0.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5324 -5.1059 -0.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 2 0 4 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 20 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 16 38 2 0 38 39 1 0 39 40 1 0 39 41 2 0 41 2 1 0 12 5 1 0 41 14 1 0 36 18 1 0 30 23 1 0 3 42 1 0 6 43 1 0 7 44 1 0 9 45 1 0 11 46 1 0 12 47 1 0 15 48 1 0 18 49 1 1 20 50 1 1 21 51 1 0 21 52 1 0 23 53 1 1 25 54 1 0 25 55 1 0 26 56 1 6 27 57 1 0 28 58 1 1 29 59 1 0 30 60 1 6 31 61 1 0 32 62 1 6 33 63 1 0 34 64 1 1 35 65 1 0 36 66 1 1 37 67 1 0 38 68 1 0 40 69 1 0 M END

Standard InCHIKey	QOYOSTICCWYNER-QFHSPVPESA-N
Standard InCHI	InChI=1S/C26H28O15/c27-11-2-1-9(3-12(11)28)16-6-14(30)19-13(29)4-10(5-17(19)40-16)39-26-24(36)22(34)21(33)18(41-26)8-38-25-23(35)20(32)15(31)7-37-25/h1-6,15,18,20-29,31-36H,7-8H2/t15-,18-,20+,21-,22+,23+,24-,25+,26-/m1/s1
SMILES	O=C1C=C(C2=CC=C(O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4OC[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12

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
NPO62895	Halenia corniculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC537382 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	24907
0.1-0.2	21445
0.2-0.3	2477
0.3-0.4	582
0.4-0.5	289
0.5-0.6	107
0.6-0.7	34
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8537	High Similarity	NPC210073
0.8235	Intermediate Similarity	NPC65711
0.7765	Intermediate Similarity	NPC44931
0.7333	Intermediate Similarity	NPC229409
0.7284	Intermediate Similarity	NPC19709
0.7195	Intermediate Similarity	NPC189142
0.7195	Intermediate Similarity	NPC77660
0.7143	Intermediate Similarity	NPC209296
0.7093	Intermediate Similarity	NPC190003
0.7079	Intermediate Similarity	NPC473512
0.7079	Intermediate Similarity	NPC22062
0.7079	Intermediate Similarity	NPC473634
0.7079	Intermediate Similarity	NPC138811
0.6966	Remote Similarity	NPC67105
0.6915	Remote Similarity	NPC101636
0.6889	Remote Similarity	NPC129827
0.6739	Remote Similarity	NPC64051
0.6596	Remote Similarity	NPC473623
0.6593	Remote Similarity	NPC67326
0.6562	Remote Similarity	NPC298171
0.6548	Remote Similarity	NPC331652
0.6526	Remote Similarity	NPC270675
0.6526	Remote Similarity	NPC488089
0.6526	Remote Similarity	NPC195685
0.6484	Remote Similarity	NPC473657
0.6471	Remote Similarity	NPC39360
0.6471	Remote Similarity	NPC29763
0.6471	Remote Similarity	NPC210003
0.6452	Remote Similarity	NPC186816
0.6437	Remote Similarity	NPC27942
0.6374	Remote Similarity	NPC8856
0.6374	Remote Similarity	NPC254540
0.6353	Remote Similarity	NPC473043
0.6327	Remote Similarity	NPC472994
0.6304	Remote Similarity	NPC295613
0.6237	Remote Similarity	NPC275454
0.6237	Remote Similarity	NPC227508
0.6211	Remote Similarity	NPC46202
0.6211	Remote Similarity	NPC475497
0.6211	Remote Similarity	NPC488074
0.6129	Remote Similarity	NPC471079
0.6105	Remote Similarity	NPC115674
0.6092	Remote Similarity	NPC261866
0.6078	Remote Similarity	NPC472993
0.6064	Remote Similarity	NPC15358
0.6042	Remote Similarity	NPC284277
0.6	Remote Similarity	NPC20505
0.5978	Remote Similarity	NPC276377
0.5955	Remote Similarity	NPC181712
0.5934	Remote Similarity	NPC22832
0.5934	Remote Similarity	NPC601144
0.5909	Remote Similarity	NPC238376
0.587	Remote Similarity	NPC311830
0.5843	Remote Similarity	NPC95090
0.5843	Remote Similarity	NPC277205
0.5843	Remote Similarity	NPC27408
0.5843	Remote Similarity	NPC37919
0.5773	Remote Similarity	NPC204693
0.5769	Remote Similarity	NPC108406
0.5745	Remote Similarity	NPC172807
0.5728	Remote Similarity	NPC11468
0.5714	Remote Similarity	NPC480441
0.567	Remote Similarity	NPC203259
0.567	Remote Similarity	NPC33054
0.567	Remote Similarity	NPC176740
0.567	Remote Similarity	NPC471725
0.567	Remote Similarity	NPC134532
0.567	Remote Similarity	NPC156869
0.567	Remote Similarity	NPC602582
0.5667	Remote Similarity	NPC136042
0.5604	Remote Similarity	NPC58716
0.5604	Remote Similarity	NPC84362
0.5604	Remote Similarity	NPC271692
0.5604	Remote Similarity	NPC45638
0.56	Remote Similarity	NPC483707
0.5596	Remote Similarity	NPC298666
0.5591	Remote Similarity	NPC243930
0.5545	Remote Similarity	NPC486577
0.5543	Remote Similarity	NPC201292
0.5534	Remote Similarity	NPC484301
0.5534	Remote Similarity	NPC253685
0.5532	Remote Similarity	NPC607707
0.5521	Remote Similarity	NPC606546
0.551	Remote Similarity	NPC65003
0.551	Remote Similarity	NPC479405
0.551	Remote Similarity	NPC303913
0.55	Remote Similarity	NPC470443
0.5495	Remote Similarity	NPC168822
0.549	Remote Similarity	NPC80068
0.5484	Remote Similarity	NPC282169
0.5481	Remote Similarity	NPC14187
0.5463	Remote Similarity	NPC488087
0.5455	Remote Similarity	NPC198199
0.5455	Remote Similarity	NPC479404
0.5421	Remote Similarity	NPC473644
0.5421	Remote Similarity	NPC25523
0.5417	Remote Similarity	NPC211594
0.5408	Remote Similarity	NPC301683
0.5385	Remote Similarity	NPC249281
0.5385	Remote Similarity	NPC108831
0.5385	Remote Similarity	NPC182634
0.537	Remote Similarity	NPC311850
0.5368	Remote Similarity	NPC605784
0.5364	Remote Similarity	NPC488086
0.5347	Remote Similarity	NPC479403
0.534	Remote Similarity	NPC473073
0.5326	Remote Similarity	NPC297987
0.5326	Remote Similarity	NPC323593
0.5326	Remote Similarity	NPC203500
0.5321	Remote Similarity	NPC488083
0.531	Remote Similarity	NPC120952
0.53	Remote Similarity	NPC122809
0.5294	Remote Similarity	NPC51326
0.5269	Remote Similarity	NPC46420
0.5258	Remote Similarity	NPC116864
0.5258	Remote Similarity	NPC244776
0.5253	Remote Similarity	NPC173582
0.5253	Remote Similarity	NPC265885
0.5253	Remote Similarity	NPC181465
0.5253	Remote Similarity	NPC215710
0.5253	Remote Similarity	NPC473438
0.5253	Remote Similarity	NPC253788
0.5248	Remote Similarity	NPC488073
0.5248	Remote Similarity	NPC126784
0.5248	Remote Similarity	NPC241423
0.5248	Remote Similarity	NPC475366
0.5243	Remote Similarity	NPC142142
0.5238	Remote Similarity	NPC179862
0.5225	Remote Similarity	NPC68592
0.5204	Remote Similarity	NPC156977
0.52	Remote Similarity	NPC218488
0.52	Remote Similarity	NPC150164
0.5192	Remote Similarity	NPC231194
0.5192	Remote Similarity	NPC475382
0.5192	Remote Similarity	NPC477629
0.5152	Remote Similarity	NPC236191
0.5152	Remote Similarity	NPC51774
0.514	Remote Similarity	NPC121703
0.5102	Remote Similarity	NPC52353
0.51	Remote Similarity	NPC39834
0.5094	Remote Similarity	NPC135358
0.5062	Remote Similarity	NPC234133
0.5052	Remote Similarity	NPC116458
0.5052	Remote Similarity	NPC293004
0.5052	Remote Similarity	NPC246943
0.505	Remote Similarity	NPC233994
0.505	Remote Similarity	NPC65563
0.505	Remote Similarity	NPC470949
0.505	Remote Similarity	NPC3583
0.505	Remote Similarity	NPC607513
0.5048	Remote Similarity	NPC195257
0.5046	Remote Similarity	NPC292019
0.5046	Remote Similarity	NPC202908
0.5046	Remote Similarity	NPC480796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC537382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5820
0.1-0.2	3268
0.2-0.3	49
0.3-0.4	7
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD7054	Phase 4
0.6458	Remote Similarity	NPD7251	Phase 2
0.567	Remote Similarity	NPD6797	Phase 2
0.5429	Remote Similarity	NPD7472	Pre-clinical
0.5429	Remote Similarity	NPD7808	Phase 3

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