NPASS Compound

Structure

NPC192034 OpenBabel06302216212D 64 69 0 0 1 0 0 0 0 0999 V2000 -0.2756 -5.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7244 -5.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2244 -5.1086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2190 -5.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4269 -4.0260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5608 -3.5260 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8177 -4.1951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3628 -3.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0596 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4245 -3.1122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4314 -2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5714 -2.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1871 -1.6488 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3373 -1.7898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0460 -2.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0510 -2.8300 0.0000 N 0 5 0 0 0 0 0 0 0 0 0 0 0.7838 -1.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3251 -1.2827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8880 -1.3279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3967 -1.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7822 -1.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9927 -2.5101 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9997 -3.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8022 -3.6039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4739 -2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3651 -2.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4180 -2.0317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7225 -3.5567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7754 -3.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6622 -1.8350 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1101 -1.8931 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7034 -2.8066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2911 -2.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8789 -2.1021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8735 -2.2066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4722 -1.1886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0600 -0.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6532 0.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2410 1.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2355 1.2385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 2.2566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4221 3.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0153 3.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6031 4.7881 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5976 4.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1964 5.7017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7842 6.5107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3774 7.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9652 8.2333 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9597 8.1287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5585 9.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 9.9558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7395 10.8694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3273 11.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3218 11.5739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9206 12.5919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -2.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4450 -0.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4107 -0.4229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2627 0.0238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0048 0.9900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5371 -1.7727 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 -1.2843 -3.6228 0.0000 C 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 7 1 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 4 64 1 0 0 0 0 5 24 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 10 63 1 0 0 0 0 11 15 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 12 62 1 0 0 0 0 13 14 1 0 0 0 0 13 58 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 17 31 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 25 26 2 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 28 29 2 0 0 0 0 30 31 1 0 0 0 0 30 57 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 34 35 2 0 0 0 0 34 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 38 39 2 0 0 0 0 39 40 1 0 0 0 0 39 41 1 0 0 0 0 41 42 1 0 0 0 0 42 43 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 44 46 1 0 0 0 0 46 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 49 50 1 0 0 0 0 49 51 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 0 0 0 0 54 55 1 0 0 0 0 54 56 1 0 0 0 0 58 59 2 0 0 0 0 58 60 1 0 0 0 0 60 61 1 0 0 0 0 M CHG 2 16 -1 62 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	870.57
Volume:	956.888
LogP:	11.977
LogD:	8.042
LogS:	-5.836
# Rotatable Bonds:	21
TPSA:	132.83
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	7.48
Fsp3:	0.509
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.707
MDCK Permeability:	6.8028548412257805e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	102.14122009277344%
Volume Distribution (VD):	3.087
Pgp-substrate:	0.7750639915466309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.546
CYP1A2-substrate:	0.793
CYP2C19-inhibitor:	0.599
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.958
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	2.781
Half-life (T1/2):	0.01

ADMET: Toxicity

hERG Blockers:	0.801
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.938
Carcinogencity:	0.774
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC192034

Natural Product ID:	NPC192034
*Common Name:**	ATNHDLDRLWWWCB-UHFFFAOYSA-M
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATNHDLDRLWWWCB-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C55H73N4O5.Mg/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42;/h13,26,28-33,37,41,51H,1,14-25,27H2,2-12H3,(H-,56,57,58,59,61);/q-1;+2/p-1
SMILES:	C=Cc1c(C)c2=CC3=NC(=C4C(C(=O)C5=C(C)C(=Cc6c(CC)c(C)c(C=c1[nH]2)[n-]6)N=C45)C(=O)OC)C(CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C3C.[Mg+2]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5086910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001455] Tetrapyrroles and derivatives [CHEMONTID:0000716] Chlorins

*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
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1021/jf970571j]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Himeji City, Japan	n.a.	PMID[15053555]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764147]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23132311]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[240326]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[USDA]

☑ 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
NPO27617	NPC192034	Other	Fruit	20.5	0	41	mg/100g	Database [DUKE]
NPO16230	NPC192034	Raw	Fruit	0.05	0	0.1	mg/100g	Database [DUKE]
NPO31303	NPC192034	Raw	Fruit	1.65	0.3	3	mg/100g	Database [DUKE]

☑ 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 NPC192034 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	343
0.1-0.2	2079
0.2-0.3	8876
0.3-0.4	20404
0.4-0.5	6837
0.5-0.6	2805
0.6-0.7	1261
0.7-0.8	83
0.8-0.85	1
0.85-0.9	6
0.9-0.95	2
0.95-1	0

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 NPC192034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	632
0.2-0.3	784
0.3-0.4	2220
0.4-0.5	3234
0.5-0.6	1756
0.6-0.7	271
0.7-0.8	13
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
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