NPASS Compound

Structure

NPC301384 OpenBabel06302216012D 31 34 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 2.5981 -1.5000 0.0000 C 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 1.7321 1.0000 0.0000 C 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 17 18 1 0 0 0 0 19 18 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 22 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 27 1 6 0 0 0 23 24 1 1 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 30 31 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.17
Volume:	578.977
LogP:	5.885
LogD:	3.454
LogS:	-7.35
# Rotatable Bonds:	6
TPSA:	140.98
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	3.799
Fsp3:	0.212
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.933
MDCK Permeability:	1.6702560969861224e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.136

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.7138671875%
Volume Distribution (VD):	0.338
Pgp-substrate:	1.6635321378707886%

ADMET: Metabolism

CYP1A2-inhibitor:	0.165
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.942
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	3.472
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.688
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.343
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.834
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC301384

Natural Product ID:	NPC301384
*Common Name:**	ASQHVCDULHERIH-JNHRPPPUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ASQHVCDULHERIH-JNHRPPPUSA-N
Standard InCHI:	InChI=1S/C21H20O10/c22-6-13-17(26)19(28)20(29)21(31-13)30-7-8-4-10-15(12(24)5-8)18(27)14-9(16(10)25)2-1-3-11(14)23/h1-5,13,17,19-24,26,28-29H,6-7H2/t13-,17-,19+,20-,21-/m1/s1
SMILES:	c1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	147295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978210]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19012276]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25593390]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14800	Oophaga granulifera	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19512	Gleichenia quadripartita	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17568	Balanophora laxiflora	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16572	Rhododendron dahuricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19232	Anchusa azurea	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21112	Chaetomium carinthiacum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19671	Dipsacus azureus	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17856	Anaphalis lactea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20353	Degenia velebitica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19395	Nepeta granatensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14932.1	Dalbergia lanceolaria subsp. paniculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21564	Senecio behnii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27737	Penicillium shearii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19913	Rhynchophorus ferrugineus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20560	Polyporus betulinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24407	Bipolaris heveae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20947	Tagetes filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13246	Pinalia stricta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20625	Delphinium virgatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21376	Lupinus corymbosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20844	Sphaerella rosigena	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18867	Stephanitis takeyai	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13754	Tanacetum coccineum	Species	Asteraceae	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	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC301384 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	385
0.1-0.2	1403
0.2-0.3	2967
0.3-0.4	6961
0.4-0.5	10294
0.5-0.6	6058
0.6-0.7	6782
0.7-0.8	7156
0.8-0.85	549
0.85-0.9	95
0.9-0.95	42
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID

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 NPC301384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	841
0.2-0.3	1561
0.3-0.4	2705
0.4-0.5	2081
0.5-0.6	1118
0.6-0.7	362
0.7-0.8	118
0.8-0.85	25
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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