NPASS Compound

Natural Product: NPC601139

Natural Product ID	NPC601139
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XLPAINGDLCDYQV-SDTWUMECSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479910
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 79 82 0 0 0 0 0 0 0 0999 V2000 6.8187 -2.4540 -0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7835 -1.1176 0.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0499 -0.4739 0.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6227 -0.5091 0.3400 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3213 -1.0954 -0.0551 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5264 -0.3583 -1.0472 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0483 1.0015 -0.8185 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1920 1.9374 -0.5832 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1633 2.6306 0.4614 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2672 2.0842 -1.4369 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 1.2943 0.0803 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0058 0.9474 1.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5536 1.1510 2.0126 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2384 1.4583 0.7935 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2717 2.9509 0.5875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5947 0.8536 0.7320 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0949 0.6940 -0.4874 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3788 1.0788 -1.7262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1003 1.1503 -1.6288 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5834 0.7540 -0.2879 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4618 -0.7149 -0.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4639 0.1098 -0.6478 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3955 1.3029 -0.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5776 -0.6556 -1.9220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8246 -1.4805 -2.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9881 -2.2943 -0.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1201 -3.4978 -0.8990 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9808 -1.5585 0.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2549 -0.8384 0.7715 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8401 -2.6462 1.5720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7484 -0.7288 0.5571 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6790 0.1159 1.8136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2366 0.4982 2.0029 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8511 -2.8406 -0.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3918 -2.4354 -1.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2855 -3.2239 0.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8539 -0.5833 -0.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3918 -1.0154 1.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9052 0.5788 0.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6476 0.4573 0.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6179 -2.0732 -0.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7831 -1.4906 0.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 -1.0644 -1.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2065 -0.2918 -1.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6663 1.3491 -1.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8884 2.8834 -1.4472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7936 2.4330 0.0536 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2444 -0.0706 1.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6063 1.7132 2.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4857 2.0370 2.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2078 0.3023 2.5986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1921 3.2728 -0.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2697 3.3276 0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4819 3.4727 1.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7364 2.0901 -2.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6983 0.3786 -2.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5176 2.1351 -1.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5312 0.4118 -2.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3696 -1.1924 -1.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4999 -0.9646 0.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2682 -1.2127 0.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0890 1.8227 -1.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2594 2.0408 0.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4486 1.0078 -0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7191 -1.3198 -2.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6743 0.1082 -2.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7425 -0.8683 -2.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7413 -2.0979 -2.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1489 0.1616 1.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9159 -1.4079 1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8876 -0.7465 -0.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1795 -2.2913 2.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4017 -3.5682 1.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7828 -2.9639 1.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8795 -1.4486 0.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3002 1.0078 1.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9782 -0.5504 2.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7018 -0.2827 2.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2340 1.4229 2.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 17 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 20 11 1 0 31 22 1 0 20 14 1 0 33 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 7 45 1 6 10 46 1 0 11 47 1 1 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 1 32 76 1 0 32 77 1 0 33 78 1 0 33 79 1 0 M END

Standard InCHIKey	XLPAINGDLCDYQV-SDTWUMECSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,28+,29-,30+/m0/s1
SMILES	CC(C)=CCC[C@H](C(=O)O)[C@@H]1CC[C@]2(C)C3=C(CC[C@@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	509.035 ? Van der Waals volume.
Dense:	0.893	LogP:	4.252 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.261 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.867 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.432	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.655	Fsp³:	0.8
MCE-18:	80.593 ? 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:	0.706	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.624	Promiscuous compounds:	0.188

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.811	MDCK Permeability:	-4.84
Pgp-inhibitor:	0.745	Pgp-substrate:	0.0
PAMPA:	0.917 ? 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):	0.0
20% Bioavailability (F20%):	0.007	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.474

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05	MRP1:	0.994
Plasma Protein Binding (PPB):	96.066%	Volume Distribution (VD):	0.195
Fu:	4.04% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.014
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.244	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.981	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.0 ? 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):

4.653

Half-life (T1/2):

0.571

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.059
Human Hepatotoxicity (H-HT):	0.698	Drug-induced Liver Injury (DILI):	0.42
AMES Toxicity:	0.151	Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.309	Skin Sensitization:	0.945
Carcinogencity:	0.644	Eye Corrosion:	0.19
Eye Irritation:	0.736	Respiratory Toxicity:	0.768
Drug-induced Neurotoxicity:	0.193	Ototoxicity:	0.528
Hematotoxicity:	0.676	Drug-induced Nephrotoxicity:	0.872
Genotoxicity:	0.399	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.064	Hek293 Cytotoxicity:	0.072
BCF:	1.545 ? 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:	4.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.555 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.156 ? 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
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730241]
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61135	Trattinnickia burserifolia	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10628	Boswellia papyrifera	Species	Burseraceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	IC50	=	13160.0	nM	PMID[25466185]

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 NPC601139 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	25742
0.1-0.2	21791
0.2-0.3	2026
0.3-0.4	217
0.4-0.5	46
0.5-0.6	23
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201912
1.0	High Similarity	NPC38350
0.7302	Intermediate Similarity	NPC289213
0.6719	Remote Similarity	NPC83569
0.6719	Remote Similarity	NPC233836
0.6719	Remote Similarity	NPC159046
0.6719	Remote Similarity	NPC187376
0.6667	Remote Similarity	NPC148414
0.6667	Remote Similarity	NPC111585
0.6667	Remote Similarity	NPC175628
0.6364	Remote Similarity	NPC147066
0.597	Remote Similarity	NPC142253
0.597	Remote Similarity	NPC3511
0.5634	Remote Similarity	NPC482518
0.5571	Remote Similarity	NPC69279
0.5571	Remote Similarity	NPC54689
0.5493	Remote Similarity	NPC243866
0.5493	Remote Similarity	NPC206810
0.5493	Remote Similarity	NPC489792
0.5417	Remote Similarity	NPC479661
0.5342	Remote Similarity	NPC96496
0.5294	Remote Similarity	NPC474083
0.5286	Remote Similarity	NPC141178
0.527	Remote Similarity	NPC42042
0.527	Remote Similarity	NPC69982
0.5143	Remote Similarity	NPC55309
0.5143	Remote Similarity	NPC28252
0.5143	Remote Similarity	NPC260956
0.5143	Remote Similarity	NPC482576
0.5139	Remote Similarity	NPC474889
0.5072	Remote Similarity	NPC606148
0.507	Remote Similarity	NPC469400
0.5068	Remote Similarity	NPC66429
0.5065	Remote Similarity	NPC474570

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC601139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6652
0.1-0.2	2411
0.2-0.3	87
0.3-0.4	0
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