NPASS Compound

Natural Product: NPC113639

Natural Product ID	NPC113639
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QPIUBKNTZMBLLI-ASFQSAAXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1689087
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

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 61 62 0 0 0 0 0 0 0 0999 V2000 3.2234 -0.3928 2.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4366 -1.1277 1.5409 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3306 -0.4440 0.5187 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8824 0.8891 0.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4015 0.9445 -0.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8547 0.7840 -1.4256 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8713 0.5302 -2.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4360 0.7635 -1.8049 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6410 0.8573 -0.8227 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1251 -0.2117 0.0130 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4045 -0.9128 -0.3331 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5077 -1.9636 0.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1825 -1.9598 1.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2715 -1.4110 0.3575 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2385 -2.4748 -0.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9736 -1.1108 1.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1743 -1.4839 0.7846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6877 -0.1828 -0.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7726 -1.2795 -0.6574 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8816 0.7739 -1.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0846 0.3581 0.8675 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1888 1.9465 0.0547 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7442 3.1684 0.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7136 3.4580 -0.5770 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1380 4.1542 1.0964 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2010 0.1167 3.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0860 -1.1135 3.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4798 0.3989 2.8174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9274 -2.0987 1.7652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3658 -0.3399 0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4006 -1.1374 -0.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1879 1.7269 0.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3880 1.0921 -0.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8444 1.2296 0.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2730 0.4300 -3.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4389 -0.3835 -2.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5065 1.4203 -2.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3213 1.6738 -2.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2912 -0.0604 -2.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5313 1.3698 -1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3595 0.2290 1.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3433 -1.4207 -1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2550 -1.6217 1.5534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7600 -2.9594 0.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8499 -2.9668 1.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1516 -1.2626 2.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9811 -3.3150 -0.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 -2.1447 -1.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7178 -3.0195 -0.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8596 -0.4693 1.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3744 -2.1271 -0.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0451 -1.8088 0.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3654 -1.8908 -1.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6834 -0.7723 -1.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7743 1.8226 -1.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9826 0.7427 -1.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3290 0.4865 -2.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8128 1.3300 0.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9275 4.8399 1.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6797 4.6962 0.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2932 3.6346 1.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 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 11 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 9 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 17 2 1 0 14 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 1 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 7 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 9 40 1 6 10 41 1 1 11 42 1 6 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 15 47 1 0 15 48 1 0 15 49 1 0 16 50 1 0 17 51 1 0 19 52 1 0 19 53 1 0 19 54 1 0 20 55 1 0 20 56 1 0 20 57 1 0 21 58 1 0 25 59 1 0 25 60 1 0 25 61 1 0 M END

Standard InCHIKey	QPIUBKNTZMBLLI-ASFQSAAXSA-N
Standard InCHI	InChI=1S/C22H36O3/c1-15-8-7-9-16(2)14-19(25-17(3)23)20-18(21(4,5)24)11-13-22(20,6)12-10-15/h9-10,12,15,18-20,24H,7-8,11,13-14H2,1-6H3/b12-10+,16-9+/t15-,18-,19+,20-,22+/m1/s1
SMILES	C[C@@H]1CC/C=C(C)/C[C@@H]([C@H]2[C@@H](CC[C@]2(C)/C=C/1)C(C)(C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	348.27	Volume:	390.417 ? Van der Waals volume.
Dense:	0.892	LogP:	3.83 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.596 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.061 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	16.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.561	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.016	Fsp³:	0.773
MCE-18:	45.231 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.477	Fluc inhibitor:	0.203 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.691	Promiscuous compounds:	0.521

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973	MDCK Permeability:	-4.847
Pgp-inhibitor:	0.996	Pgp-substrate:	0.018
PAMPA:	0.011 ? 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%):	0.086	30% Bioavailability (F30%):	0.46
50% Bioavailability (F50%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.586
Plasma Protein Binding (PPB):	96.269%	Volume Distribution (VD):	-0.228
Fu:	4.869% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.262
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.902	CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.983	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.065	CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.043	CYP2D6-substrate:	0.478
CYP3A4-inhibitor:	0.142	CYP3A4-substrate:	0.068
CYP2B6-substrate:	0.004	CYP2C8-inhibitor:	0.97
HLM stability:	0.916 ? 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):

7.56

Half-life (T1/2):

0.353

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.685	Drug-induced Liver Injury (DILI):	0.328
AMES Toxicity:	0.297	Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.194	Skin Sensitization:	0.988
Carcinogencity:	0.633	Eye Corrosion:	0.179
Eye Irritation:	0.898	Respiratory Toxicity:	0.282
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.367
Hematotoxicity:	0.441	Drug-induced Nephrotoxicity:	0.796
Genotoxicity:	0.132	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.071	Hek293 Cytotoxicity:	0.232
BCF:	1.463 ? 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:	3.921 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.553 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.904 ? 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
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11325249]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	at a depth of 0.1-1 m, Elafonissos Island (3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	Elafonissos Island (GPS coordinates 3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16565	Lindera oldhami	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21494	Eryngium maritimum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20488	Abies homolepis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17330	Pseudopotamilla occelata	Species	Sabellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19911	Arachniodes festina	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27967	Betula glandulosa	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20420	Helenium brevifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20221	Maytenus truncata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20558	Pseudevernia ericetorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17838	Aster flaccidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20838	Cleome pentaphylla	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16565	Lindera oldhami	Species	Tineidae	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
MIC	6

Activity Type	# Activity
Organism	6

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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[21190330]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[21190330]

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 NPC113639 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	17493
0.1-0.2	26333
0.2-0.3	5940
0.3-0.4	89
0.4-0.5	2
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	Natural Product ID
0.5472	Remote Similarity	NPC323153

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC113639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6491
0.1-0.2	2580
0.2-0.3	79
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