NPASS Compound

Natural Product: NPC34910

Natural Product ID	NPC34910
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oxalicumone D
IUPAC Name	(2R,4S)-2,4-dihydroxy-4-[(2S)-5-hydroxy-7-methyl-4-oxo-2,3-dihydrothieno[2,3-b]chromen-2-yl]-5-methoxy-5-oxopentanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3263077
PubChem CID	90676612
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

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 46 48 0 0 0 0 0 0 0 0999 V2000 7.4484 0.8078 0.5266 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0820 0.3183 0.1843 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8708 -0.6296 -0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5949 -1.0611 -1.0877 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4642 -0.5748 -0.4239 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6836 0.3714 0.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9699 0.8011 0.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6376 0.8397 1.1864 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4141 0.4360 0.9169 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1017 -0.4959 -0.0308 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3258 -0.8331 -0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1429 0.3766 0.1462 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5537 0.0526 0.5678 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1971 -0.6897 -0.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6280 -1.0742 -0.2906 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1541 -1.7827 -1.4690 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1204 -1.3145 -2.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5770 -2.9673 -1.8741 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3741 0.0805 -0.0928 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2464 1.3465 0.7979 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6941 1.5908 1.9452 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4297 2.3059 -0.1820 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1031 3.5415 0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5234 -0.6922 1.7188 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1847 0.9224 1.6351 S 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 -1.0290 -0.7422 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0226 -1.8942 -1.6367 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3491 -2.0171 -2.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8747 0.1942 1.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3361 1.8535 0.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0504 0.7361 -0.3992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7242 -1.0263 -1.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1477 1.5470 1.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5084 -1.1084 -1.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6195 -1.6571 0.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0920 1.1748 -0.5907 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1725 -0.0364 -1.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5805 -1.5866 -0.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7125 -1.6667 0.6419 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0533 -3.6452 -2.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9762 0.2421 -0.8582 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0476 3.8091 1.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1159 3.5601 -0.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5130 4.3209 -0.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4164 -1.6637 1.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0807 -1.7833 -3.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 6 8 1 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 1 0 15 16 1 0 16 17 2 0 16 18 1 0 15 19 1 0 13 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 13 24 1 1 12 25 1 0 10 26 1 0 26 27 2 0 4 28 1 0 7 2 1 0 25 9 1 0 26 5 1 0 1 29 1 0 1 30 1 0 1 31 1 0 3 32 1 0 7 33 1 0 11 34 1 0 11 35 1 0 12 36 1 6 14 37 1 0 14 38 1 0 15 39 1 1 18 40 1 0 19 41 1 0 23 42 1 0 23 43 1 0 23 44 1 0 24 45 1 0 28 46 1 0 M END

Standard InCHIKey	ROHDJYQMXQAIJT-GDAOTKPNSA-N
Standard InCHI	InChI=1S/C18H18O9S/c1-7-3-9(19)13-11(4-7)27-16-8(14(13)21)5-12(28-16)18(25,17(24)26-2)6-10(20)15(22)23/h3-4,10,12,19-20,25H,5-6H2,1-2H3,(H,22,23)/t10-,12+,18-/m1/s1
SMILES	Cc1cc(c2c(c1)oc1c(C[C@@H]([C@](C[C@H](C(=O)O)O)(C(=O)OC)O)S1)c2=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	410.07	Volume:	373.381 ? Van der Waals volume.
Dense:	1.098	LogP:	1.876 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.907 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.624 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	154.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.514	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.473	Fsp³:	0.389
MCE-18:	72.68 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.389	Fluc inhibitor:	0.123 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.168 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.261 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.525	Promiscuous compounds:	0.195

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.426	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.0	Pgp-substrate:	0.747
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.15
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048	MRP1:	0.996
Plasma Protein Binding (PPB):	94.935%	Volume Distribution (VD):	-0.282
Fu:	3.757% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.831	BCRP inhibitor:	0.011
BSEP inhibitor:	0.52

ADMET: Metabolism

CYP1A2-inhibitor:	0.018	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.919	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.969	CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.688 ? 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):

2.039

Half-life (T1/2):

2.03

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.764
AMES Toxicity:	0.258	Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.799	Skin Sensitization:	0.865
Carcinogencity:	0.347	Eye Corrosion:	0.018
Eye Irritation:	0.605	Respiratory Toxicity:	0.679
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.425
Hematotoxicity:	0.256	Drug-induced Nephrotoxicity:	0.8
Genotoxicity:	0.951	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.075
BCF:	0.581 ? 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:	3.318 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.8 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.025 ? 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
NPO12404	Trigonostemon chinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611050]
NPO33528	Penicillium oxalicum SCSGAF 0023	Species	Aspergillaceae	Eukaryota	isolated from gorgonian Muricella flexuosa	South China Sea, Sanya (1811N, 10925E), Hainan Province, China	n.a.	PMID[24767845]
NPO10023	Francoeuria undulata	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[28032767]
NPO678	Streptomyces spiroverticillatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13302	Streptomyces nanchangensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10023	Francoeuria undulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33528	Penicillium oxalicum SCSGAF 0023	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12404	Trigonostemon chinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13202	Pseudodistoma kanoko	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4866	Diospyros rotundifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6632	Lunaria biennis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12220	Hemerocallis thunbergii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12220	Hemerocallis thunbergii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4866	Diospyros rotundifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8232	Sclerocarya caffra	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13302	Streptomyces nanchangensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8648	Gorgonia mariae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14605	Glochidion thomsonii	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12404	Trigonostemon chinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10620	Monochoria elata	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO897	Pinus gerardi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12220	Hemerocallis thunbergii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6632	Lunaria biennis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13202	Pseudodistoma kanoko	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10023	Francoeuria undulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO678	Streptomyces spiroverticillatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11338	Muricella flexuosa	Species	Acanthogorgiidae	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
IC50	2

Activity Type	# Activity
Cell line	1
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
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	5740.0	nM	PMID[24767845]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	10100.0	nM	PMID[24767845]

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 NPC34910 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	11320
0.1-0.2	36828
0.2-0.3	1693
0.3-0.4	10
0.4-0.5	3
0.5-0.6	1
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	Natural Product ID
0.7971	Intermediate Similarity	NPC284918
0.7671	Intermediate Similarity	NPC264756
0.7671	Intermediate Similarity	NPC477677
0.55	Remote Similarity	NPC272550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC34910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2518
0.1-0.2	6549
0.2-0.3	82
0.3-0.4	1
0.4-0.5	0
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