NPASS Compound

Natural Product: NPC489647

Natural Product ID	NPC489647
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KHIDSVXJRBGIHK-DUTCEVNASA-N
IUPAC Name	n.a.
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 71 0 0 0 0 0 0 0 0999 V2000 3.6597 -1.8029 -2.1642 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6580 -0.9942 -1.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1336 0.0252 -0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5954 0.3313 -0.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0760 0.2358 0.7522 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5154 0.5245 0.8537 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7046 1.6085 1.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 2.0924 1.9620 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2443 3.1444 2.6688 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4330 1.2572 1.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5804 -0.3072 0.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2033 -1.3273 -1.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4174 -0.3596 -0.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0568 -0.5902 -0.5728 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8457 0.3765 0.2718 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4722 0.3070 1.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5925 1.7928 -0.1845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6821 2.3137 -1.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0172 2.3786 -0.4574 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2255 1.2076 0.5392 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0847 1.7202 1.9117 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6673 0.7871 0.3552 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1096 -0.2129 1.1620 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3215 0.1379 0.0577 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7108 -1.2762 0.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9321 -2.1641 -0.5755 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4396 -2.0311 -0.4319 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0150 -2.7074 0.7966 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9987 -2.6750 -1.6231 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1921 -1.2053 -2.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1161 -2.5989 -2.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3465 -2.3344 -1.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5132 0.6715 -0.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7366 1.3424 -1.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1820 -0.3881 -1.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8293 -0.7676 1.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6533 2.0651 1.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6226 -1.2782 0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5553 0.2190 0.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2937 -0.4942 -0.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1661 -2.3562 -0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9300 -1.4530 -2.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4376 0.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7072 0.6430 -0.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4108 -0.3394 -1.6281 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5354 1.3099 2.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0278 -0.4804 2.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4043 0.0400 1.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6636 1.9383 -0.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5111 2.5170 0.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3767 3.3646 -1.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6740 1.7785 -2.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7855 2.3405 -1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1907 3.3311 0.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4840 2.6529 1.9332 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1034 2.1161 2.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8374 0.9891 2.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8899 0.6029 -0.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2992 1.6971 0.5861 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6442 -0.3435 1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4080 0.1626 -1.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5735 -1.5525 1.4325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7673 -1.5112 0.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1970 -1.7857 -1.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2600 -3.2254 -0.4940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7825 -3.7859 0.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1062 -2.3223 1.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7943 -2.7680 1.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4102 -2.1467 -2.3592 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 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 6 11 1 0 2 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 6 10 5 1 0 27 14 1 0 24 15 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 7 37 1 0 11 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 6 16 46 1 0 16 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 18 52 1 0 19 53 1 0 19 54 1 0 21 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 24 61 1 6 25 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 M END

Standard InCHIKey	KHIDSVXJRBGIHK-DUTCEVNASA-N
Standard InCHI	InChI=1S/C25H40O4/c1-17(7-9-19-18(2)15-22(27)29-19)8-10-21-24(4)13-6-12-23(3,16-26)20(24)11-14-25(21,5)28/h7,15,19-21,26,28H,6,8-14,16H2,1-5H3/b17-7+/t19?,20-,21+,23-,24-,25+/m0/s1
SMILES	C/C(=CCC1C(=CC(=O)O1)C)/CC[C@@H]1[C@@]2(C)CCC[C@@](C)(CO)[C@@H]2CC[C@@]1(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	404.29	Volume:	442.538 ? Van der Waals volume.
Dense:	0.914	LogP:	3.228 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.609 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.486	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.794	Fsp³:	0.8
MCE-18:	59.733 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.119	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.522	Promiscuous compounds:	0.264

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.409	MDCK Permeability:	-5.147
Pgp-inhibitor:	0.269	Pgp-substrate:	0.005
PAMPA:	0.999 ? 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):	0.005
20% Bioavailability (F20%):	0.052	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.345
Plasma Protein Binding (PPB):	74.032%	Volume Distribution (VD):	-0.16
Fu:	23.51% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.571	BCRP inhibitor:	0.497
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.913	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.03
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.012
HLM stability:	0.008 ? 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):

8.926

Half-life (T1/2):

0.666

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.278
Human Hepatotoxicity (H-HT):	0.692	Drug-induced Liver Injury (DILI):	0.47
AMES Toxicity:	0.229	Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.76	Skin Sensitization:	0.998
Carcinogencity:	0.681	Eye Corrosion:	0.007
Eye Irritation:	0.699	Respiratory Toxicity:	0.634
Drug-induced Neurotoxicity:	0.185	Ototoxicity:	0.54
Hematotoxicity:	0.601	Drug-induced Nephrotoxicity:	0.947
Genotoxicity:	0.583	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.175	Hek293 Cytotoxicity:	0.354
BCF:	1.191 ? 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:	3.865 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.639 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.711 ? 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
NPO40338	Salvia tingitana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32182064]

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
MIC	22

Activity Type	# Activity
Organism	22

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
NPT4427	Organism	Staphylococcus simulans	Staphylococcus simulans	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT3599	Organism	Staphylococcus capitis	Staphylococcus capitis	MIC	=	317000.0	nM	PMID[32182064]
NPT5312	Organism	Staphylococcus warneri	Staphylococcus warneri	MIC	=	317000.0	nM	PMID[32182064]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	=	158000.0	nM	PMID[32182064]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	158000.0	nM	PMID[32182064]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	317000.0	nM	PMID[32182064]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	317000.0	nM	PMID[32182064]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	317000.0	nM	PMID[32182064]
NPT4025	Organism	Staphylococcus hominis	Staphylococcus hominis	MIC	=	317000.0	nM	PMID[32182064]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	317000.0	nM	PMID[32182064]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	79200.0	nM	PMID[32182064]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	158000.0	nM	PMID[32182064]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	128.0	ug.mL-1	PMID[32182064]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	317000.0	nM	PMID[32182064]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	158000.0	nM	PMID[32182064]
NPT23872	Organism	Enterococcus casseliflavus	Enterococcus casseliflavus	MIC	=	158000.0	nM	PMID[32182064]

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 NPC489647 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	15038
0.1-0.2	26569
0.2-0.3	7871
0.3-0.4	327
0.4-0.5	37
0.5-0.6	6
0.6-0.7	4
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
0.7797	Intermediate Similarity	NPC489641
0.7458	Intermediate Similarity	NPC276110
0.6406	Remote Similarity	NPC120321
0.6308	Remote Similarity	NPC222927
0.6212	Remote Similarity	NPC489648
0.6119	Remote Similarity	NPC489646
0.5942	Remote Similarity	NPC489644
0.5857	Remote Similarity	NPC120009
0.5821	Remote Similarity	NPC489642
0.5634	Remote Similarity	NPC476081
0.5606	Remote Similarity	NPC38855
0.5079	Remote Similarity	NPC488957

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6308
0.1-0.2	2664
0.2-0.3	177
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