NPASS Compound

Natural Product: NPC481043

Natural Product ID	NPC481043
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PIUYQFXGNHWGBD-JTLUYSSBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44566588
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-glycosides

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 59 62 0 0 0 0 0 0 0 0999 V2000 1.0636 -3.8820 2.5258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1034 -3.0898 1.9060 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3453 -1.9402 1.1950 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5865 -1.4110 0.9978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7958 -0.2458 0.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7012 0.3646 -0.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6263 -0.1252 -0.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7583 -1.2810 0.6440 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0246 -1.8612 0.8657 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4400 -2.8856 -0.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 0.5689 -0.6428 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9696 0.4380 -0.6142 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7284 1.7473 -0.3741 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1455 1.3423 -0.0262 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5471 0.0451 -0.6542 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7781 -0.2999 -1.8828 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2865 0.4308 -3.1114 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6548 -0.1350 -4.2167 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4252 -0.1295 -1.8228 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5332 -1.0315 0.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0568 2.3495 -0.3348 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1662 2.3165 0.7788 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1588 0.2806 0.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5710 0.7173 -1.1466 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7988 1.1981 -1.3371 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6922 1.2938 -0.3925 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9565 1.8107 -0.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8934 1.9065 0.3294 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5513 1.4856 1.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2940 0.9771 1.8692 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3473 0.8742 0.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0672 0.3614 1.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7577 -0.0153 2.2590 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9869 0.5696 3.1416 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1806 2.4179 0.0984 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6279 -3.3816 3.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5381 -4.7804 2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7464 -4.3034 1.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4562 -1.9002 1.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8174 1.2766 -0.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1299 -2.4973 -1.0667 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5310 -2.9118 -0.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9346 -3.8349 0.1340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3417 -0.2337 0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6683 2.4209 -1.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2299 1.1973 1.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6283 0.1447 -0.9703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 -1.3951 -2.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0376 1.4940 -2.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3796 0.3409 -3.2387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2214 0.5799 -4.7379 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2256 -0.9448 0.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8105 2.3212 0.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2295 3.3109 0.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 0.6552 -1.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2257 2.1399 -1.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2909 1.5651 2.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1261 1.2121 3.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5722 2.3617 -0.8367 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 7 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 1 0 17 18 1 0 16 19 1 0 15 20 1 0 14 21 1 0 13 22 1 0 5 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 30 34 1 0 28 35 1 0 8 3 1 0 19 12 1 0 32 23 1 0 31 26 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 6 40 1 0 10 41 1 0 10 42 1 0 10 43 1 0 12 44 1 1 13 45 1 6 14 46 1 1 15 47 1 6 16 48 1 6 17 49 1 0 17 50 1 0 18 51 1 0 20 52 1 0 21 53 1 0 22 54 1 0 24 55 1 0 27 56 1 0 29 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	PIUYQFXGNHWGBD-JTLUYSSBSA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-14-3-9(11-8-33-13-6-10(25)5-12(26)17(13)18(11)27)4-15(22(14)32-2)34-23-21(30)20(29)19(28)16(7-24)35-23/h3-6,8,16,19-21,23-26,28-30H,7H2,1-2H3/t16-,19-,20+,21-,23-/m1/s1
SMILES	COc1cc(cc(c1OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c1coc2cc(cc(c2c1=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	0.619 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.175 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.899 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	188.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.002	Fsp³:	0.348
MCE-18:	89.71 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.508	Fluc inhibitor:	0.169 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.853 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.818 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.096	Promiscuous compounds:	0.675

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.137	MDCK Permeability:	-5.356
Pgp-inhibitor:	0.0	Pgp-substrate:	0.487
PAMPA:	0.92 ? 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):	0.214
20% Bioavailability (F20%):	0.118	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022	MRP1:	0.414
Plasma Protein Binding (PPB):	87.471%	Volume Distribution (VD):	-0.15
Fu:	10.661% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.826
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.535	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.959
HLM stability:	0.103 ? 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):

2.665

Half-life (T1/2):

3.274

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.146
Human Hepatotoxicity (H-HT):	0.71	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.263	Skin Sensitization:	0.974
Carcinogencity:	0.444	Eye Corrosion:	0.0
Eye Irritation:	0.311	Respiratory Toxicity:	0.064
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.855
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	0.472
Genotoxicity:	0.969	RPMI-8226 Immunitoxicity:	0.139
A549 Cytotoxicity:	0.404	Hek293 Cytotoxicity:	0.567
BCF:	0.397 ? 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:	3.066 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.409 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.608 ? 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
NPO12485	Ceiba pentandra	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8133294]
NPO12485	Ceiba pentandra	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461647]
NPO12485	Ceiba pentandra	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12485	Ceiba pentandra	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12485	Ceiba pentandra	Species	Malvaceae	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
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1665	Individual protein	Cyclooxygenase-1	Bos taurus	IC50	=	381000.0	nM	PMID[9461647]
NPT325	Individual protein	Cyclooxygenase-2	Ovis aries	IC50	=	1200000.0	nM	PMID[9461647]

In vitro activity

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

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 NPC481043 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	19210
0.1-0.2	26570
0.2-0.3	2779
0.3-0.4	960
0.4-0.5	259
0.5-0.6	63
0.6-0.7	12
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
0.7733	Intermediate Similarity	NPC156457
0.7089	Intermediate Similarity	NPC138540
0.6765	Remote Similarity	NPC78341
0.6667	Remote Similarity	NPC205076
0.6585	Remote Similarity	NPC224462
0.6353	Remote Similarity	NPC48773
0.6341	Remote Similarity	NPC73511
0.6235	Remote Similarity	NPC307518
0.6234	Remote Similarity	NPC78697
0.622	Remote Similarity	NPC197896
0.622	Remote Similarity	NPC105511
0.622	Remote Similarity	NPC313163
0.6047	Remote Similarity	NPC88023
0.6047	Remote Similarity	NPC309025
0.5833	Remote Similarity	NPC258035
0.5814	Remote Similarity	NPC80140
0.5783	Remote Similarity	NPC135345
0.5698	Remote Similarity	NPC472459
0.5698	Remote Similarity	NPC100720
0.5698	Remote Similarity	NPC325555
0.5698	Remote Similarity	NPC226304
0.5647	Remote Similarity	NPC234739
0.5632	Remote Similarity	NPC479401
0.56	Remote Similarity	NPC200316
0.5568	Remote Similarity	NPC120099
0.5568	Remote Similarity	NPC609478
0.5529	Remote Similarity	NPC143851
0.5526	Remote Similarity	NPC481044
0.5506	Remote Similarity	NPC607201
0.5467	Remote Similarity	NPC239363
0.5465	Remote Similarity	NPC64305
0.5465	Remote Similarity	NPC161749
0.5444	Remote Similarity	NPC203050
0.5444	Remote Similarity	NPC225434
0.5444	Remote Similarity	NPC479407
0.5412	Remote Similarity	NPC45165
0.5393	Remote Similarity	NPC229729
0.5349	Remote Similarity	NPC19388
0.5349	Remote Similarity	NPC240431
0.5349	Remote Similarity	NPC77672
0.5349	Remote Similarity	NPC55786
0.5349	Remote Similarity	NPC133671
0.5349	Remote Similarity	NPC135391
0.5349	Remote Similarity	NPC78263
0.5349	Remote Similarity	NPC250069
0.5341	Remote Similarity	NPC21100
0.5333	Remote Similarity	NPC479406
0.5333	Remote Similarity	NPC294409
0.5333	Remote Similarity	NPC490701
0.5319	Remote Similarity	NPC479405
0.5287	Remote Similarity	NPC145038
0.5287	Remote Similarity	NPC56077
0.5287	Remote Similarity	NPC281131
0.5287	Remote Similarity	NPC253662
0.5287	Remote Similarity	NPC179950
0.5287	Remote Similarity	NPC88789
0.5287	Remote Similarity	NPC491374
0.5287	Remote Similarity	NPC603782
0.5281	Remote Similarity	NPC191306
0.5281	Remote Similarity	NPC60735
0.5281	Remote Similarity	NPC26230
0.5263	Remote Similarity	NPC479404
0.5256	Remote Similarity	NPC254702
0.5244	Remote Similarity	NPC268059
0.5222	Remote Similarity	NPC197285
0.5222	Remote Similarity	NPC601710
0.5181	Remote Similarity	NPC479305
0.5172	Remote Similarity	NPC259070
0.5172	Remote Similarity	NPC112755
0.5172	Remote Similarity	NPC170675
0.5172	Remote Similarity	NPC348541
0.5128	Remote Similarity	NPC194653
0.5122	Remote Similarity	NPC268668
0.5111	Remote Similarity	NPC479402
0.5065	Remote Similarity	NPC19980
0.5057	Remote Similarity	NPC160515
0.5055	Remote Similarity	NPC601607

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5234
0.1-0.2	3836
0.2-0.3	67
0.3-0.4	8
0.4-0.5	4
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	Drug ID	Developmental Stage
0.5465	Remote Similarity	NPD4381	Clinical (unspecified phase)

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