NPASS Compound

Natural Product: NPC603856

Natural Product ID	NPC603856
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CPPNFWGIJSYTAL-VREZJPALSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4866440
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 72 76 0 0 0 0 0 0 0 0999 V2000 4.8768 -3.1931 1.1985 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6753 -1.9771 1.2590 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7954 -1.0427 1.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6637 0.2533 1.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7305 1.2170 0.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0264 0.8610 0.4973 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0041 1.8395 0.2749 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7183 3.1852 0.3503 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6755 4.1662 0.1325 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4200 3.5381 0.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1171 4.9067 0.7358 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4538 2.5737 0.8761 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4326 -1.5209 1.5585 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2408 -2.1172 1.8097 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5098 -2.6943 0.6768 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1285 -1.7415 -0.3080 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1133 -2.1796 -0.8126 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4532 -1.4389 -1.9286 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5444 -0.5966 -2.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 -0.3645 -1.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5414 0.5043 -1.1618 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3671 0.6793 -0.1690 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4342 1.4771 -0.1951 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2779 1.5901 0.9718 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9244 0.8388 2.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6555 0.8716 3.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7790 1.6561 3.3687 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5386 1.7018 4.5540 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1443 2.4001 2.2765 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2780 3.1924 2.3771 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3877 2.3526 1.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6372 2.1418 -1.3748 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7017 2.9986 -1.5412 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7939 2.0059 -2.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9976 2.6225 -3.5533 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7236 1.1605 -2.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8230 0.9428 -3.3776 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0746 1.6470 -4.5625 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7794 0.1015 -3.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8839 -0.1039 -4.2545 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0795 -3.6491 -1.0316 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8417 -4.3749 -0.0880 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2642 -4.2741 -1.1449 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8898 -3.8708 -2.3431 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1722 -3.8461 -0.0008 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3438 -4.9362 0.8450 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7630 -1.4596 0.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6720 0.6309 1.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2829 -0.1820 0.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0240 1.5380 0.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5040 3.9944 -0.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3258 5.4268 1.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4351 2.8849 1.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5724 -1.4508 2.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4418 -2.9824 2.5343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5389 -3.1196 1.1050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -2.0130 0.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3534 -0.8569 -0.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0330 0.2025 2.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3857 0.2913 4.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5527 1.6464 4.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1855 4.2027 2.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7218 2.9534 0.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0866 3.2336 -2.4472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8650 2.6492 -4.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0497 0.4941 -4.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6095 -3.9170 -2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7680 -4.5023 -0.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1892 -5.3917 -1.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6734 -4.4683 -2.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1206 -3.5486 -0.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9735 -5.7601 0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 8 10 1 0 10 11 1 0 10 12 2 0 2 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 2 0 23 32 2 0 32 33 1 0 32 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 37 39 2 0 39 40 1 0 17 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 12 5 1 0 45 15 1 0 39 19 1 0 36 21 2 0 31 24 1 0 3 47 1 0 4 48 1 0 6 49 1 0 7 50 1 0 9 51 1 0 11 52 1 0 12 53 1 0 14 54 1 0 14 55 1 0 15 56 1 1 17 57 1 1 20 58 1 0 25 59 1 0 26 60 1 0 28 61 1 0 30 62 1 0 31 63 1 0 33 64 1 0 38 65 1 0 40 66 1 0 41 67 1 6 42 68 1 0 43 69 1 6 44 70 1 0 45 71 1 6 46 72 1 0 M END

Standard InCHIKey	CPPNFWGIJSYTAL-VREZJPALSA-N
Standard InCHI	InChI=1S/C30H26O16/c31-13-4-1-11(7-15(13)33)2-6-20(35)43-10-19-23(37)26(40)28(42)30(46-19)45-18-9-17-21(24(38)22(18)36)25(39)27(41)29(44-17)12-3-5-14(32)16(34)8-12/h1-9,19,23,26,28,30-34,36-38,40-42H,10H2/b6-2+/t19-,23-,26+,28-,30-/m1/s1
SMILES	O=C(/C=C/c1ccc(O)c(O)c1)OC[C@H]1O[C@@H](Oc2cc3oc(-c4ccc(O)c(O)c4)c(O)c(=O)c3c(O)c2O)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	642.12	Volume:	591.023 ? Van der Waals volume.
Dense:	1.086	LogP:	0.955 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.033 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.046 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	277.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.076	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.456	Fsp³:	0.2
MCE-18:	114.722 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.824	Fluc inhibitor:	0.719 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.937 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.813 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.883

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.842	MDCK Permeability:	-4.792
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.746
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.043
Plasma Protein Binding (PPB):	84.636%	Volume Distribution (VD):	-0.063
Fu:	11.796% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.781
BSEP inhibitor:	0.013

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.78 ? 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):

3.851

Half-life (T1/2):

4.21

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.597
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.977
AMES Toxicity:	0.768	Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.397	Skin Sensitization:	1.0
Carcinogencity:	0.069	Eye Corrosion:	0.0
Eye Irritation:	0.768	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.899
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.097
Genotoxicity:	0.952	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.973	Hek293 Cytotoxicity:	0.325
BCF:	0.648 ? 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:	3.619 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.863 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.539 ? 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
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27892	Eupatorium glandulosum	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	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
Unchecked	2

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
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	790.0	nM	PMID[33857371]

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 NPC603856 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	18472
0.1-0.2	27260
0.2-0.3	3084
0.3-0.4	784
0.4-0.5	204
0.5-0.6	41
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC599948
0.7065	Intermediate Similarity	NPC477848
0.6869	Remote Similarity	NPC80068
0.6832	Remote Similarity	NPC81042
0.6635	Remote Similarity	NPC480796
0.6593	Remote Similarity	NPC245014
0.6505	Remote Similarity	NPC214621
0.6505	Remote Similarity	NPC34267
0.6296	Remote Similarity	NPC139571
0.625	Remote Similarity	NPC223426
0.5962	Remote Similarity	NPC270675
0.5962	Remote Similarity	NPC195685
0.5941	Remote Similarity	NPC233994
0.5922	Remote Similarity	NPC488364
0.5905	Remote Similarity	NPC85751
0.5905	Remote Similarity	NPC19240
0.5895	Remote Similarity	NPC84265
0.5877	Remote Similarity	NPC488078
0.5769	Remote Similarity	NPC211532
0.5729	Remote Similarity	NPC291296
0.5728	Remote Similarity	NPC476871
0.5727	Remote Similarity	NPC472993
0.5701	Remote Similarity	NPC36138
0.5699	Remote Similarity	NPC157898
0.5676	Remote Similarity	NPC217520
0.5648	Remote Similarity	NPC472994
0.5636	Remote Similarity	NPC470416
0.5612	Remote Similarity	NPC476864
0.5607	Remote Similarity	NPC477629
0.56	Remote Similarity	NPC476870
0.5586	Remote Similarity	NPC477895
0.5534	Remote Similarity	NPC67105
0.5421	Remote Similarity	NPC476620
0.5347	Remote Similarity	NPC476868
0.5339	Remote Similarity	NPC488079
0.5327	Remote Similarity	NPC470443
0.5253	Remote Similarity	NPC58716
0.5204	Remote Similarity	NPC238376
0.52	Remote Similarity	NPC476867
0.5192	Remote Similarity	NPC254540
0.5189	Remote Similarity	NPC133984
0.5152	Remote Similarity	NPC277205
0.5152	Remote Similarity	NPC37919
0.5149	Remote Similarity	NPC157816
0.5143	Remote Similarity	NPC488081
0.5098	Remote Similarity	NPC476866
0.5096	Remote Similarity	NPC116864
0.5096	Remote Similarity	NPC244776
0.5089	Remote Similarity	NPC484301
0.505	Remote Similarity	NPC117260
0.5049	Remote Similarity	NPC488082

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC603856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4451
0.1-0.2	4641
0.2-0.3	46
0.3-0.4	9
0.4-0.5	3
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