NPASS Compound

Structure

CID252156 OpenBabel06191716052D 60 66 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 4 41 1 0 0 0 0 5 56 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 19 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 10 57 1 0 0 0 0 11 21 1 0 0 0 0 12 2 1 1 0 0 0 12 38 1 0 0 0 0 12 42 1 0 0 0 0 13 3 1 6 0 0 0 13 26 1 0 0 0 0 13 58 1 0 0 0 0 14 56 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 23 1 0 0 0 0 16 29 1 0 0 0 0 17 25 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 35 1 0 0 0 0 19 22 1 0 0 0 0 19 43 1 0 0 0 0 20 30 1 0 0 0 0 20 44 1 1 0 0 0 21 31 2 0 0 0 0 21 37 1 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 32 2 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 32 1 0 0 0 0 26 36 1 0 0 0 0 26 41 1 6 0 0 0 27 45 2 0 0 0 0 28 46 2 0 0 0 0 29 35 1 0 0 0 0 29 47 1 6 0 0 0 30 33 1 0 0 0 0 30 48 1 6 0 0 0 31 49 1 0 0 0 0 32 50 1 0 0 0 0 33 39 1 0 0 0 0 33 51 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 34 52 1 1 0 0 0 35 59 1 1 0 0 0 36 60 1 6 0 0 0 37 42 2 3 0 0 0 37 53 1 0 0 0 0 38 54 2 0 0 0 0 38 55 1 0 0 0 0 39 57 1 0 0 0 0 39 60 1 6 0 0 0 40 58 1 0 0 0 0 40 59 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	840.26
Volume:	786.444
LogP:	3.016
LogD:	1.04
LogS:	-4.617
# Rotatable Bonds:	10
TPSA:	326.88
# H-Bond Aceptor:	20
# H-Bond Donor:	13
# Rings:	7
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.056
Synthetic Accessibility Score:	5.615
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.768
MDCK Permeability:	4.748897936224239e-06
Pgp-inhibitor:	0.214
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.99
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	79.71375274658203%
Volume Distribution (VD):	0.776
Pgp-substrate:	50.18973922729492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.71
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.927
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.059

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC252156

Natural Product ID:	NPC252156
*Common Name:**	Pradimicin A
IUPAC Name:	(2R)-2-[[(5S,6S)-1,6,9,14-tetrahydroxy-5-[(2S,3R,4S,5S,6R)-3-hydroxy-6-methyl-5-(methylamino)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-11-methoxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carbonyl]amino]propanoic acid
Synonyms:	Pradimicin A; Pradimicin-A
Standard InCHIKey:	WPICPWIIIBCXCV-NJGWPHBESA-N
Standard InCHI:	InChI=1S/C40H44N2O18/c1-11-6-18-24(31(49)21(11)37(53)42-12(2)38(54)55)23-16(9-17-25(32(23)50)28(46)15-7-14(56-5)8-19(43)22(15)27(17)45)29(47)35(18)59-40-34(52)36(26(41-4)13(3)58-40)60-39-33(51)30(48)20(44)10-57-39/h6-9,12-13,20,26,29-30,33-36,39-41,43-44,47-52H,10H2,1-5H3,(H,42,53)(H,54,55)/t12-,13-,20-,26+,29+,30+,33-,34-,35+,36+,39+,40+/m1/s1
SMILES:	CN[C@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1[C@@H](O)c2cc3c(c(c2c2c1cc(C)c(c2O)C(=N[C@@H](C(=O)O)C)O)O)C(=O)c1c(C3=O)c(O)cc(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1673205
PubChem CID:	5479145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1021/jo00272a013]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21119678]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	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	NP ID	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
EC50	34
IC50	4
Kd	4
Others	57

Activity Type	# Activity
Cell Line	36
NON-MOLECULAR	4
Organism	45
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	>	95.0	%	PMID[458335]
NPT927	Cell Line	PBMC	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT492	Cell Line	Caco-2	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT3552	Cell Line	OST	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT112	Cell Line	MOLT-4	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT137	Cell Line	L1210	Mus musculus	CC50	>	50000.0	nM	PMID[458335]
NPT927	Cell Line	PBMC	Homo sapiens	CC50	>	250000.0	nM	PMID[458335]
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	50000.0	nM	PMID[458335]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	CC50	>	100000.0	nM	PMID[458335]
NPT927	Cell Line	PBMC	Homo sapiens	FC	=	4.0	n.a.	PMID[458335]
NPT927	Cell Line	PBMC	Homo sapiens	FC	=	2.0	n.a.	PMID[458335]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	>	50000.0	nM	PMID[458336]
NPT333	Cell Line	CEM	Homo sapiens	CC50	>	100000.0	nM	PMID[458338]
NPT333	Cell Line	CEM	Homo sapiens	CC50	>	100000.0	nM	PMID[458340]
NPT333	Cell Line	CEM	Homo sapiens	CC50	>	50000.0	nM	PMID[458341]
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	100000.0	nM	PMID[458342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	50000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5200.0	nM	PMID[458335]
NPT2	Others	Unspecified		Kd	=	14900.0	nM	PMID[458335]
NPT2	Others	Unspecified		Kd	=	410.0	nM	PMID[458335]
NPT2	Others	Unspecified		Kd	=	2.91	10'-2/s	PMID[458335]
NPT2	Others	Unspecified		Ka	=	1.96	10'3/M/s	PMID[458335]
NPT2	Others	Unspecified		Kd	=	6.1	10'-3/s	PMID[458335]
NPT2	Others	Unspecified		Ka	=	1.49	10'4/M/s	PMID[458335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3400.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5400.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	21000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	3500.0	nM	PMID[458335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4300.0	nM	PMID[458335]
NPT27	Others	Unspecified		CC50	>	50000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Ratio	=	2.0	n.a.	PMID[458335]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	=	4300.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2200.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2600.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1600.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6700.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	8000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4700.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	10000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5900.0	nM	PMID[458335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	5500.0	nM	PMID[458335]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	5000.0	nM	PMID[458335]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	5200.0	nM	PMID[458335]
NPT35	Others	n.a.		Activity	=	50.0	uM	PMID[458335]
NPT35	Others	n.a.		Solubility	>	20000.0	nM	PMID[458335]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5200.0	nM	PMID[458336]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	5900.0	nM	PMID[458336]
NPT35	Others	n.a.		Solubility	=	20.0	ug.mL-1	PMID[458337]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3300.0	nM	PMID[458338]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	5900.0	nM	PMID[458338]
NPT2	Others	Unspecified		Activity	=	0.57	molar ratio	PMID[458339]
NPT2	Others	Unspecified		Activity	=	1.08	molar ratio	PMID[458339]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3300.0	nM	PMID[458340]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	5900.0	nM	PMID[458340]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3400.0	nM	PMID[458341]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3300.0	nM	PMID[458342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5900.0	nM	PMID[458342]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	30.3	n.a.	PMID[458342]
NPT20	Organism	Candida albicans	Candida albicans	PD50	=	8.9	mg kg-1	PMID[458343]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC252156 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	1390
0.2-0.3	4112
0.3-0.4	9953
0.4-0.5	8794
0.5-0.6	7986
0.6-0.7	8444
0.7-0.8	1687
0.8-0.85	33
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8473	Intermediate Similarity	NPC313274
0.8465	Intermediate Similarity	NPC315351
0.8465	Intermediate Similarity	NPC316412
0.8429	Intermediate Similarity	NPC315253
0.8398	Intermediate Similarity	NPC314941
0.8382	Intermediate Similarity	NPC261012
0.8382	Intermediate Similarity	NPC314738
0.8382	Intermediate Similarity	NPC109403
0.8365	Intermediate Similarity	NPC315889
0.8333	Intermediate Similarity	NPC42286
0.8259	Intermediate Similarity	NPC87583
0.8182	Intermediate Similarity	NPC314946
0.8168	Intermediate Similarity	NPC221140
0.8168	Intermediate Similarity	NPC475352
0.8168	Intermediate Similarity	NPC229817
0.8168	Intermediate Similarity	NPC473686
0.8168	Intermediate Similarity	NPC475220
0.8109	Intermediate Similarity	NPC477860
0.8109	Intermediate Similarity	NPC475161
0.8098	Intermediate Similarity	NPC264302
0.8069	Intermediate Similarity	NPC473631
0.8069	Intermediate Similarity	NPC475662
0.8069	Intermediate Similarity	NPC473717
0.8069	Intermediate Similarity	NPC293227
0.806	Intermediate Similarity	NPC277710
0.806	Intermediate Similarity	NPC299149
0.806	Intermediate Similarity	NPC153578
0.806	Intermediate Similarity	NPC114257
0.805	Intermediate Similarity	NPC46958
0.8039	Intermediate Similarity	NPC105591
0.8	Intermediate Similarity	NPC68381
0.799	Intermediate Similarity	NPC316164
0.798	Intermediate Similarity	NPC313452
0.796	Intermediate Similarity	NPC475246
0.7951	Intermediate Similarity	NPC65489
0.795	Intermediate Similarity	NPC472054
0.7936	Intermediate Similarity	NPC313582
0.7931	Intermediate Similarity	NPC315221
0.7931	Intermediate Similarity	NPC470452
0.7931	Intermediate Similarity	NPC470448
0.7931	Intermediate Similarity	NPC164047
0.7931	Intermediate Similarity	NPC470453
0.791	Intermediate Similarity	NPC3718
0.791	Intermediate Similarity	NPC63105
0.79	Intermediate Similarity	NPC111536
0.79	Intermediate Similarity	NPC5029
0.79	Intermediate Similarity	NPC271385
0.79	Intermediate Similarity	NPC30432
0.79	Intermediate Similarity	NPC76128
0.7892	Intermediate Similarity	NPC329790
0.7882	Intermediate Similarity	NPC84494
0.7882	Intermediate Similarity	NPC245059
0.7874	Intermediate Similarity	NPC31208
0.7874	Intermediate Similarity	NPC472721
0.7874	Intermediate Similarity	NPC472724
0.7874	Intermediate Similarity	NPC160543
0.7874	Intermediate Similarity	NPC93065
0.7874	Intermediate Similarity	NPC469652
0.7874	Intermediate Similarity	NPC314672
0.7874	Intermediate Similarity	NPC472720
0.7871	Intermediate Similarity	NPC289876
0.7867	Intermediate Similarity	NPC174140
0.7861	Intermediate Similarity	NPC85368
0.7861	Intermediate Similarity	NPC213052
0.7861	Intermediate Similarity	NPC203751
0.7854	Intermediate Similarity	NPC231254
0.785	Intermediate Similarity	NPC298778
0.7843	Intermediate Similarity	NPC85316
0.7843	Intermediate Similarity	NPC197357
0.783	Intermediate Similarity	NPC319774
0.7826	Intermediate Similarity	NPC240200
0.7826	Intermediate Similarity	NPC290289
0.7826	Intermediate Similarity	NPC158214
0.7826	Intermediate Similarity	NPC223534
0.7821	Intermediate Similarity	NPC314743
0.7816	Intermediate Similarity	NPC241847
0.7811	Intermediate Similarity	NPC477836
0.781	Intermediate Similarity	NPC316274
0.781	Intermediate Similarity	NPC470196
0.781	Intermediate Similarity	NPC470198
0.781	Intermediate Similarity	NPC470195
0.781	Intermediate Similarity	NPC470193
0.781	Intermediate Similarity	NPC470194
0.781	Intermediate Similarity	NPC282474
0.781	Intermediate Similarity	NPC470197
0.781	Intermediate Similarity	NPC470200
0.7804	Intermediate Similarity	NPC314596
0.7794	Intermediate Similarity	NPC58538
0.7794	Intermediate Similarity	NPC212290
0.7789	Intermediate Similarity	NPC477835
0.7788	Intermediate Similarity	NPC187632
0.7783	Intermediate Similarity	NPC472723
0.7783	Intermediate Similarity	NPC76112
0.7783	Intermediate Similarity	NPC475233
0.7783	Intermediate Similarity	NPC92403
0.7783	Intermediate Similarity	NPC170018
0.7783	Intermediate Similarity	NPC102053
0.7783	Intermediate Similarity	NPC66820
0.7783	Intermediate Similarity	NPC170101
0.7778	Intermediate Similarity	NPC260521
0.7778	Intermediate Similarity	NPC469649
0.7767	Intermediate Similarity	NPC292706
0.7767	Intermediate Similarity	NPC224557
0.7762	Intermediate Similarity	NPC477082
0.7751	Intermediate Similarity	NPC40078
0.7751	Intermediate Similarity	NPC471091
0.7751	Intermediate Similarity	NPC48474
0.7751	Intermediate Similarity	NPC97924
0.774	Intermediate Similarity	NPC205721
0.7734	Intermediate Similarity	NPC477992
0.7734	Intermediate Similarity	NPC474345
0.7734	Intermediate Similarity	NPC146803
0.7734	Intermediate Similarity	NPC199533
0.7734	Intermediate Similarity	NPC470454
0.7734	Intermediate Similarity	NPC477991
0.7729	Intermediate Similarity	NPC469650
0.7729	Intermediate Similarity	NPC261623
0.7729	Intermediate Similarity	NPC111490
0.7714	Intermediate Similarity	NPC314459
0.7714	Intermediate Similarity	NPC470199
0.7711	Intermediate Similarity	NPC259905
0.7711	Intermediate Similarity	NPC222455
0.77	Intermediate Similarity	NPC178851
0.7696	Intermediate Similarity	NPC477816
0.7689	Intermediate Similarity	NPC3474
0.7689	Intermediate Similarity	NPC108487
0.7685	Intermediate Similarity	NPC98776
0.7685	Intermediate Similarity	NPC470336
0.7685	Intermediate Similarity	NPC470335
0.7681	Intermediate Similarity	NPC75574
0.7673	Intermediate Similarity	NPC76047
0.767	Intermediate Similarity	NPC208069
0.7662	Intermediate Similarity	NPC472058
0.7662	Intermediate Similarity	NPC234497
0.7662	Intermediate Similarity	NPC470341
0.7662	Intermediate Similarity	NPC324522
0.7662	Intermediate Similarity	NPC105414
0.7662	Intermediate Similarity	NPC249977
0.7659	Intermediate Similarity	NPC267549
0.7659	Intermediate Similarity	NPC470334
0.7656	Intermediate Similarity	NPC477083
0.7656	Intermediate Similarity	NPC473618
0.7656	Intermediate Similarity	NPC477081
0.7656	Intermediate Similarity	NPC269046
0.765	Intermediate Similarity	NPC478022
0.765	Intermediate Similarity	NPC478020
0.7647	Intermediate Similarity	NPC321226
0.7647	Intermediate Similarity	NPC478046
0.7647	Intermediate Similarity	NPC470667
0.7647	Intermediate Similarity	NPC180210
0.7647	Intermediate Similarity	NPC314914
0.7647	Intermediate Similarity	NPC328856
0.7647	Intermediate Similarity	NPC478047
0.7647	Intermediate Similarity	NPC186800
0.7644	Intermediate Similarity	NPC112380
0.7642	Intermediate Similarity	NPC313453
0.7633	Intermediate Similarity	NPC129533
0.7633	Intermediate Similarity	NPC132111
0.7633	Intermediate Similarity	NPC123259
0.763	Intermediate Similarity	NPC204580
0.7621	Intermediate Similarity	NPC80956
0.7621	Intermediate Similarity	NPC472726
0.7621	Intermediate Similarity	NPC472725
0.7619	Intermediate Similarity	NPC201814
0.7617	Intermediate Similarity	NPC131405
0.7613	Intermediate Similarity	NPC316368
0.7613	Intermediate Similarity	NPC284236
0.761	Intermediate Similarity	NPC67629
0.761	Intermediate Similarity	NPC297574
0.761	Intermediate Similarity	NPC79736
0.7608	Intermediate Similarity	NPC179947
0.7608	Intermediate Similarity	NPC237202
0.7606	Intermediate Similarity	NPC133775
0.7602	Intermediate Similarity	NPC478048
0.7598	Intermediate Similarity	NPC25724
0.7598	Intermediate Similarity	NPC168789
0.7598	Intermediate Similarity	NPC199357
0.7596	Intermediate Similarity	NPC49690
0.7596	Intermediate Similarity	NPC318119
0.7594	Intermediate Similarity	NPC476358
0.7594	Intermediate Similarity	NPC83019
0.7586	Intermediate Similarity	NPC470272
0.7585	Intermediate Similarity	NPC208797
0.7585	Intermediate Similarity	NPC53680
0.7585	Intermediate Similarity	NPC8940
0.7585	Intermediate Similarity	NPC469371
0.7574	Intermediate Similarity	NPC470271
0.7574	Intermediate Similarity	NPC190204
0.7574	Intermediate Similarity	NPC43918
0.7574	Intermediate Similarity	NPC311389
0.7574	Intermediate Similarity	NPC261411
0.7573	Intermediate Similarity	NPC472387
0.7571	Intermediate Similarity	NPC173872
0.7571	Intermediate Similarity	NPC7839
0.7571	Intermediate Similarity	NPC119094
0.7571	Intermediate Similarity	NPC142291
0.7569	Intermediate Similarity	NPC46990
0.7562	Intermediate Similarity	NPC178281
0.7562	Intermediate Similarity	NPC7752
0.7559	Intermediate Similarity	NPC314687

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	586
0.2-0.3	1410
0.3-0.4	2443
0.4-0.5	2596
0.5-0.6	1445
0.6-0.7	399
0.7-0.8	57
0.8-0.85	25
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9343	High Similarity	NPD8151	Discontinued
0.8689	High Similarity	NPD7801	Approved
0.8585	High Similarity	NPD8155	Clinical (unspecified phase)
0.8578	High Similarity	NPD7871	Phase 2
0.8578	High Similarity	NPD7870	Phase 2
0.8571	High Similarity	NPD6823	Phase 2
0.8529	High Similarity	NPD7698	Approved
0.8529	High Similarity	NPD7696	Phase 3
0.8529	High Similarity	NPD7697	Approved
0.851	High Similarity	NPD7783	Phase 2
0.851	High Similarity	NPD7782	Clinical (unspecified phase)
0.8454	Intermediate Similarity	NPD7701	Phase 2
0.8398	Intermediate Similarity	NPD8320	Phase 1
0.8398	Intermediate Similarity	NPD8319	Approved
0.8382	Intermediate Similarity	NPD6780	Approved
0.8382	Intermediate Similarity	NPD6781	Approved
0.8382	Intermediate Similarity	NPD6779	Approved
0.8382	Intermediate Similarity	NPD6782	Approved
0.8382	Intermediate Similarity	NPD6778	Approved
0.8382	Intermediate Similarity	NPD6777	Approved
0.8382	Intermediate Similarity	NPD6776	Approved
0.8373	Intermediate Similarity	NPD7874	Approved
0.8373	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7699	Phase 2
0.8284	Intermediate Similarity	NPD7700	Phase 2
0.8219	Intermediate Similarity	NPD8059	Phase 3
0.8219	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD7435	Discontinued
0.8137	Intermediate Similarity	NPD6535	Approved
0.8137	Intermediate Similarity	NPD6534	Approved
0.8047	Intermediate Similarity	NPD7930	Approved
0.784	Intermediate Similarity	NPD7999	Approved
0.781	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD8313	Approved
0.7783	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8150	Discontinued
0.7656	Intermediate Similarity	NPD6212	Phase 3
0.7656	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6213	Phase 3
0.7593	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7584	Approved
0.7456	Intermediate Similarity	NPD8491	Approved
0.7443	Intermediate Similarity	NPD7585	Approved
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7434	Intermediate Similarity	NPD8366	Approved
0.7413	Intermediate Similarity	NPD6959	Discontinued
0.7397	Intermediate Similarity	NPD7583	Approved
0.7387	Intermediate Similarity	NPD7827	Phase 1
0.7376	Intermediate Similarity	NPD6232	Discontinued
0.7366	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8469	Approved
0.7343	Intermediate Similarity	NPD6559	Discontinued
0.733	Intermediate Similarity	NPD7074	Phase 3
0.733	Intermediate Similarity	NPD7472	Approved
0.7315	Intermediate Similarity	NPD7565	Approved
0.7315	Intermediate Similarity	NPD8285	Discontinued
0.7308	Intermediate Similarity	NPD7808	Phase 3
0.7303	Intermediate Similarity	NPD8152	Approved
0.7303	Intermediate Similarity	NPD8153	Approved
0.7291	Intermediate Similarity	NPD5710	Approved
0.7291	Intermediate Similarity	NPD5711	Approved
0.7282	Intermediate Similarity	NPD7054	Approved
0.726	Intermediate Similarity	NPD7251	Discontinued
0.7212	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6797	Phase 2
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5844	Phase 1
0.7178	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7228	Approved
0.7136	Intermediate Similarity	NPD5006	Approved
0.7136	Intermediate Similarity	NPD5005	Approved
0.7123	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7819	Suspended
0.7067	Intermediate Similarity	NPD3818	Discontinued
0.7064	Intermediate Similarity	NPD7282	Approved
0.7062	Intermediate Similarity	NPD5026	Approved
0.7062	Intermediate Similarity	NPD5034	Approved
0.7062	Intermediate Similarity	NPD4954	Approved
0.7062	Intermediate Similarity	NPD5028	Approved
0.7062	Intermediate Similarity	NPD36	Approved
0.7062	Intermediate Similarity	NPD4955	Approved
0.7062	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8163	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8162	Phase 2
0.7053	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6166	Phase 2
0.7053	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4380	Phase 2
0.7044	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8067	Phase 3
0.7031	Intermediate Similarity	NPD8404	Phase 2
0.703	Intermediate Similarity	NPD8455	Phase 2
0.7024	Intermediate Similarity	NPD6746	Phase 2
0.7021	Intermediate Similarity	NPD7654	Discontinued
0.7014	Intermediate Similarity	NPD5030	Phase 2
0.7014	Intermediate Similarity	NPD7038	Approved
0.7014	Intermediate Similarity	NPD7039	Approved
0.701	Intermediate Similarity	NPD7075	Discontinued
0.7009	Intermediate Similarity	NPD5037	Approved
0.7009	Intermediate Similarity	NPD5038	Approved
0.6996	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8485	Approved
0.6981	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5036	Approved
0.6955	Remote Similarity	NPD4420	Approved
0.6948	Remote Similarity	NPD5035	Approved
0.6934	Remote Similarity	NPD7240	Approved
0.692	Remote Similarity	NPD8461	Discontinued
0.6916	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7177	Discontinued
0.6878	Remote Similarity	NPD7768	Phase 2
0.6866	Remote Similarity	NPD8360	Approved
0.6866	Remote Similarity	NPD8361	Approved
0.6863	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4666	Phase 3
0.6854	Remote Similarity	NPD8368	Discontinued
0.6847	Remote Similarity	NPD7411	Suspended
0.684	Remote Similarity	NPD8492	Approved
0.6837	Remote Similarity	NPD8407	Phase 2
0.6834	Remote Similarity	NPD7390	Discontinued
0.6832	Remote Similarity	NPD7458	Discontinued
0.6829	Remote Similarity	NPD5353	Approved
0.6825	Remote Similarity	NPD3751	Discontinued
0.6825	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4360	Phase 2
0.6818	Remote Similarity	NPD4363	Phase 3
0.6815	Remote Similarity	NPD8367	Approved
0.6814	Remote Similarity	NPD37	Approved
0.6812	Remote Similarity	NPD6234	Discontinued
0.6812	Remote Similarity	NPD5709	Phase 3
0.6806	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2532	Approved
0.68	Remote Similarity	NPD2534	Approved
0.68	Remote Similarity	NPD2533	Approved
0.6796	Remote Similarity	NPD4967	Phase 2
0.6796	Remote Similarity	NPD4965	Approved
0.6796	Remote Similarity	NPD4966	Approved
0.6792	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8435	Approved
0.678	Remote Similarity	NPD1465	Phase 2
0.6776	Remote Similarity	NPD5027	Approved
0.6776	Remote Similarity	NPD5031	Approved
0.6776	Remote Similarity	NPD5029	Approved
0.6771	Remote Similarity	NPD7810	Phase 3
0.6771	Remote Similarity	NPD7811	Phase 3
0.6766	Remote Similarity	NPD7907	Approved
0.6762	Remote Similarity	NPD5242	Approved
0.6749	Remote Similarity	NPD2649	Approved
0.6749	Remote Similarity	NPD2651	Approved
0.6732	Remote Similarity	NPD1934	Approved
0.6732	Remote Similarity	NPD6801	Discontinued
0.673	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3823	Discontinued
0.6726	Remote Similarity	NPD7497	Discontinued
0.6714	Remote Similarity	NPD3787	Discontinued
0.6699	Remote Similarity	NPD5494	Approved
0.6697	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3749	Approved
0.6683	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6677	Suspended
0.6681	Remote Similarity	NPD6863	Phase 2
0.6667	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD7693	Approved
0.6667	Remote Similarity	NPD6843	Phase 3
0.6667	Remote Similarity	NPD6842	Approved
0.6652	Remote Similarity	NPD5968	Phase 3
0.6637	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4361	Phase 2
0.6637	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4661	Approved
0.6634	Remote Similarity	NPD4662	Approved
0.6626	Remote Similarity	NPD6625	Approved
0.6626	Remote Similarity	NPD7922	Phase 1
0.6621	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7685	Pre-registration
0.661	Remote Similarity	NPD4111	Phase 1
0.661	Remote Similarity	NPD4665	Approved
0.6603	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6386	Approved
0.6602	Remote Similarity	NPD6385	Approved
0.6602	Remote Similarity	NPD7708	Approved
0.6593	Remote Similarity	NPD4914	Approved
0.659	Remote Similarity	NPD5032	Approved
0.6589	Remote Similarity	NPD2163	Approved
0.6589	Remote Similarity	NPD6620	Discovery
0.6588	Remote Similarity	NPD7199	Phase 2
0.6587	Remote Similarity	NPD5402	Approved
0.6587	Remote Similarity	NPD3817	Phase 2
0.6579	Remote Similarity	NPD7680	Approved
0.6573	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3451	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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