NPASS Compound

Natural Product: NPC473867

Natural Product ID	NPC473867
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-P-Hydroxybenzoyl-Beta-D-Apiofuranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4R,5R,6S)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] 3,4-dihydroxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL453796
PubChem CID	44558991
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl 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 55 57 0 0 0 0 0 0 0 0999 V2000 -6.9735 -1.0600 -0.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8663 -0.2388 -0.1665 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 0.6648 -1.3633 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8984 1.5047 -1.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6092 -0.1915 -2.5979 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3281 -0.6535 -2.4020 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5658 0.3530 -1.8680 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4892 1.4088 -1.3235 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5632 2.4905 -2.2065 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7902 -0.1082 -0.8061 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4342 0.0895 -1.0891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5672 -0.4051 0.0537 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7750 -0.1967 -0.2537 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4891 -0.2941 0.9331 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8727 -0.0765 0.7522 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5790 0.9481 1.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9741 1.7622 2.0593 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0178 1.1197 1.0939 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6971 2.1640 1.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0645 2.3218 1.4639 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7595 1.4440 0.6580 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0941 0.3971 0.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7324 0.2557 0.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7826 -0.4981 -0.7546 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1316 1.6305 0.4574 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 -1.6264 1.5577 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4117 -2.5512 0.6898 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8474 -1.8734 0.2277 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9117 -2.0824 1.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1342 -3.0065 -0.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5401 -1.4733 2.7694 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5059 -0.8963 0.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9629 -0.8930 -0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7938 0.3088 0.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0646 1.9350 -0.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3221 -1.0362 -2.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6427 0.4700 -3.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8990 0.7637 -2.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2723 1.7124 -0.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4236 3.0011 -2.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1246 -0.4925 -1.9852 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2184 1.1781 -1.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8339 0.1808 0.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1279 0.5121 1.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1584 2.8606 2.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6067 3.1208 1.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1893 -0.5583 -0.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7578 -0.6560 -0.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4747 2.5877 0.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1962 -2.1258 1.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0886 -3.4072 1.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1269 -2.2886 -0.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5458 -2.3332 2.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8692 -3.9285 -0.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 -2.2343 3.3854 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 14 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 8 3 1 0 28 12 1 0 23 18 1 0 1 32 1 0 2 33 1 0 2 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 7 38 1 6 8 39 1 1 9 40 1 0 11 41 1 0 11 42 1 0 12 43 1 1 14 44 1 1 19 45 1 0 20 46 1 0 23 47 1 0 24 48 1 0 25 49 1 0 26 50 1 1 27 51 1 1 28 52 1 6 29 53 1 0 30 54 1 0 31 55 1 0 M END

Standard InCHIKey	JQKKLIRCVDZHKC-NMPWBNDMSA-N
Standard InCHI	InChI=1S/C18H24O13/c19-5-18(27)6-29-17(14(18)25)28-4-10-11(22)12(23)13(24)16(30-10)31-15(26)7-1-2-8(20)9(21)3-7/h1-3,10-14,16-17,19-25,27H,4-6H2/t10-,11-,12+,13-,14+,16+,17-,18-/m0/s1
SMILES	OC[C@]1(O)CO[C@@H]([C@H]1O)OC[C@@H]1O[C@H](OC(=O)c2ccc(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.12	Volume:	397.942 ? Van der Waals volume.
Dense:	1.126	LogP:	-0.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.339 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	18.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	3.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.157	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.43	Fsp³:	0.611
MCE-18:	83.276 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.357	Fluc inhibitor:	0.328 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.128 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.024 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.228	Promiscuous compounds:	0.522

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.532	MDCK Permeability:	-5.21
Pgp-inhibitor:	0.0	Pgp-substrate:	0.422
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.612
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088	MRP1:	0.688
Plasma Protein Binding (PPB):	41.119%	Volume Distribution (VD):	-0.518
Fu:	65.119% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.968
OATP1B3 inhibitor:	0.844	BCRP inhibitor:	0.103
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.502
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.839
HLM stability:	0.048 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.432

Half-life (T1/2):

2.543

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.303
Human Hepatotoxicity (H-HT):	0.386	Drug-induced Liver Injury (DILI):	0.675
AMES Toxicity:	0.827	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.017	Skin Sensitization:	0.998
Carcinogencity:	0.112	Eye Corrosion:	0.0
Eye Irritation:	0.895	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.881
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.687
Genotoxicity:	0.407	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.349	Hek293 Cytotoxicity:	0.067
BCF:	0.324 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	2.777 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.417 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.705 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33321838]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36987013]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37176852]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37751472]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836125]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	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

Activity Type	# Activity
Activity	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.78	n.a.	PMID[10096857]

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 NPC473867 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	13943
0.1-0.2	31088
0.2-0.3	4155
0.3-0.4	546
0.4-0.5	101
0.5-0.6	23
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7273	Intermediate Similarity	NPC473924
0.6818	Remote Similarity	NPC90318
0.5968	Remote Similarity	NPC92117
0.5775	Remote Similarity	NPC476448
0.5775	Remote Similarity	NPC469548
0.5775	Remote Similarity	NPC476445
0.5763	Remote Similarity	NPC219040
0.5758	Remote Similarity	NPC264784
0.5753	Remote Similarity	NPC195196
0.5676	Remote Similarity	NPC164172
0.5658	Remote Similarity	NPC252833
0.5625	Remote Similarity	NPC114096
0.5556	Remote Similarity	NPC289438
0.5541	Remote Similarity	NPC6836
0.5493	Remote Similarity	NPC287429
0.5467	Remote Similarity	NPC34965
0.5405	Remote Similarity	NPC242756
0.5395	Remote Similarity	NPC470881
0.5395	Remote Similarity	NPC602810
0.5325	Remote Similarity	NPC232454
0.5325	Remote Similarity	NPC470907
0.5325	Remote Similarity	NPC178449
0.527	Remote Similarity	NPC229784
0.5152	Remote Similarity	NPC472026
0.5065	Remote Similarity	NPC470510

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4895
0.1-0.2	4154
0.2-0.3	93
0.3-0.4	7
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

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