NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.17
Volume:	234.285
LogP:	4.447
LogD:	3.549
LogS:	-3.907
# Rotatable Bonds:	6
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	2.564
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.542
MDCK Permeability:	1.6535548638785258e-05
Pgp-inhibitor:	0.852
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.684
Plasma Protein Binding (PPB):	94.6222915649414%
Volume Distribution (VD):	3.502
Pgp-substrate:	5.519339561462402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.404
CYP2C19-inhibitor:	0.385
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.381
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	13.589
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.905
Carcinogencity:	0.427
Eye Corrosion:	0.833
Eye Irritation:	0.975
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC185839

Natural Product ID:	NPC185839
*Common Name:**	6,10-Dimethylundeca-5,9-Dien-2-One
IUPAC Name:	6,10-dimethylundeca-5,9-dien-2-one
Synonyms:
Standard InCHIKey:	HNZUNIKWNYHEJJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3
SMILES:	CC(=CCCC(=O)C)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3184326
PubChem CID:	19633
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001127] Acyclic monoterpenoids

*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
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[10364842]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[12392098]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24996657]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[25767328]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	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	NP ID	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
Potency	11

Activity Type	# Activity
Individual Protein	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	7.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13868.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4364.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1096.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2197.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68868.7	nM	PubChem BioAssay data set

☑ 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 NPC185839 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	219
0.1-0.2	13996
0.2-0.3	19058
0.3-0.4	6844
0.4-0.5	1899
0.5-0.6	495
0.6-0.7	136
0.7-0.8	41
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC180840
0.9706	High Similarity	NPC38497
0.8649	High Similarity	NPC155880
0.8649	High Similarity	NPC92863
0.85	High Similarity	NPC301972
0.8293	Intermediate Similarity	NPC477686
0.8095	Intermediate Similarity	NPC191337
0.8056	Intermediate Similarity	NPC12889
0.8049	Intermediate Similarity	NPC216921
0.7907	Intermediate Similarity	NPC8610
0.7907	Intermediate Similarity	NPC262558
0.7907	Intermediate Similarity	NPC100380
0.7857	Intermediate Similarity	NPC25771
0.7838	Intermediate Similarity	NPC269641
0.7778	Intermediate Similarity	NPC266979
0.775	Intermediate Similarity	NPC111474
0.7674	Intermediate Similarity	NPC166788
0.7619	Intermediate Similarity	NPC106819
0.7619	Intermediate Similarity	NPC292463
0.7556	Intermediate Similarity	NPC145311
0.7556	Intermediate Similarity	NPC267110
0.75	Intermediate Similarity	NPC217923
0.75	Intermediate Similarity	NPC471752
0.7442	Intermediate Similarity	NPC471753
0.7391	Intermediate Similarity	NPC118788
0.7391	Intermediate Similarity	NPC15325
0.7391	Intermediate Similarity	NPC32351
0.7391	Intermediate Similarity	NPC225974
0.7333	Intermediate Similarity	NPC91962
0.7317	Intermediate Similarity	NPC101147
0.7317	Intermediate Similarity	NPC18205
0.7317	Intermediate Similarity	NPC12319
0.7234	Intermediate Similarity	NPC27438
0.7111	Intermediate Similarity	NPC195246
0.7111	Intermediate Similarity	NPC276009
0.7111	Intermediate Similarity	NPC22098
0.7021	Intermediate Similarity	NPC228776
0.7021	Intermediate Similarity	NPC176819
0.7021	Intermediate Similarity	NPC58970
0.7021	Intermediate Similarity	NPC163984
0.7	Intermediate Similarity	NPC24833
0.6944	Remote Similarity	NPC123965
0.6944	Remote Similarity	NPC138113
0.6944	Remote Similarity	NPC115959
0.6939	Remote Similarity	NPC45283
0.6939	Remote Similarity	NPC268564
0.6939	Remote Similarity	NPC296311
0.6939	Remote Similarity	NPC217188
0.6939	Remote Similarity	NPC37644
0.6905	Remote Similarity	NPC113082
0.6875	Remote Similarity	NPC64866
0.6809	Remote Similarity	NPC135698
0.68	Remote Similarity	NPC317796
0.68	Remote Similarity	NPC202850
0.68	Remote Similarity	NPC189677
0.68	Remote Similarity	NPC63396
0.6757	Remote Similarity	NPC60288
0.6744	Remote Similarity	NPC188596
0.6739	Remote Similarity	NPC236355
0.6739	Remote Similarity	NPC14917
0.6739	Remote Similarity	NPC4079
0.6735	Remote Similarity	NPC471751
0.6735	Remote Similarity	NPC151919
0.6667	Remote Similarity	NPC304079
0.6667	Remote Similarity	NPC267514
0.6667	Remote Similarity	NPC255042
0.6667	Remote Similarity	NPC288381
0.6667	Remote Similarity	NPC182840
0.6667	Remote Similarity	NPC27264
0.6667	Remote Similarity	NPC103213
0.6667	Remote Similarity	NPC20934
0.6667	Remote Similarity	NPC6963
0.6667	Remote Similarity	NPC275472
0.6667	Remote Similarity	NPC29091
0.6667	Remote Similarity	NPC145755
0.66	Remote Similarity	NPC474805
0.66	Remote Similarity	NPC23117
0.66	Remote Similarity	NPC474141
0.6596	Remote Similarity	NPC324812
0.6591	Remote Similarity	NPC51758
0.6591	Remote Similarity	NPC68889
0.6591	Remote Similarity	NPC180871
0.6591	Remote Similarity	NPC194586
0.6591	Remote Similarity	NPC67761
0.6591	Remote Similarity	NPC88079
0.6591	Remote Similarity	NPC108494
0.6591	Remote Similarity	NPC209279
0.6585	Remote Similarity	NPC254764
0.6585	Remote Similarity	NPC220061
0.6579	Remote Similarity	NPC471327
0.6579	Remote Similarity	NPC100879
0.6579	Remote Similarity	NPC3649
0.6579	Remote Similarity	NPC206088
0.6579	Remote Similarity	NPC66577
0.6538	Remote Similarity	NPC473733
0.6531	Remote Similarity	NPC477458
0.6531	Remote Similarity	NPC148056
0.6531	Remote Similarity	NPC178586
0.6531	Remote Similarity	NPC234829
0.6522	Remote Similarity	NPC474362
0.6522	Remote Similarity	NPC474202
0.6522	Remote Similarity	NPC26600
0.6522	Remote Similarity	NPC47946
0.6522	Remote Similarity	NPC117572
0.6522	Remote Similarity	NPC239754
0.6522	Remote Similarity	NPC270706
0.6512	Remote Similarity	NPC56917
0.6486	Remote Similarity	NPC155900
0.6458	Remote Similarity	NPC15912
0.6444	Remote Similarity	NPC270796
0.6429	Remote Similarity	NPC130923
0.6415	Remote Similarity	NPC299369
0.6415	Remote Similarity	NPC193695
0.6415	Remote Similarity	NPC268185
0.6415	Remote Similarity	NPC55004
0.6415	Remote Similarity	NPC224103
0.6415	Remote Similarity	NPC230823
0.6415	Remote Similarity	NPC49575
0.6415	Remote Similarity	NPC200831
0.6415	Remote Similarity	NPC267626
0.6415	Remote Similarity	NPC283502
0.641	Remote Similarity	NPC213749
0.64	Remote Similarity	NPC216407
0.64	Remote Similarity	NPC137396
0.64	Remote Similarity	NPC170167
0.6383	Remote Similarity	NPC110234
0.6383	Remote Similarity	NPC197467
0.6383	Remote Similarity	NPC308331
0.6383	Remote Similarity	NPC163751
0.6383	Remote Similarity	NPC128280
0.6383	Remote Similarity	NPC44363
0.6364	Remote Similarity	NPC33489
0.6364	Remote Similarity	NPC269823
0.6364	Remote Similarity	NPC270170
0.6364	Remote Similarity	NPC7754
0.6327	Remote Similarity	NPC236338
0.6327	Remote Similarity	NPC474391
0.6327	Remote Similarity	NPC220191
0.6327	Remote Similarity	NPC116906
0.6304	Remote Similarity	NPC12907
0.6296	Remote Similarity	NPC30215
0.6296	Remote Similarity	NPC94991
0.6296	Remote Similarity	NPC266295
0.6296	Remote Similarity	NPC311852
0.6279	Remote Similarity	NPC33761
0.6275	Remote Similarity	NPC284224
0.6275	Remote Similarity	NPC14002
0.6275	Remote Similarity	NPC61177
0.625	Remote Similarity	NPC99088
0.625	Remote Similarity	NPC91495
0.625	Remote Similarity	NPC173592
0.625	Remote Similarity	NPC305759
0.6226	Remote Similarity	NPC20603
0.6222	Remote Similarity	NPC187922
0.6222	Remote Similarity	NPC208936
0.6222	Remote Similarity	NPC287397
0.6222	Remote Similarity	NPC67920
0.6222	Remote Similarity	NPC256766
0.6222	Remote Similarity	NPC213538
0.6222	Remote Similarity	NPC298710
0.6216	Remote Similarity	NPC262789
0.6216	Remote Similarity	NPC64176
0.6216	Remote Similarity	NPC138325
0.6216	Remote Similarity	NPC288991
0.62	Remote Similarity	NPC48162
0.62	Remote Similarity	NPC244452
0.62	Remote Similarity	NPC30433
0.62	Remote Similarity	NPC22329
0.619	Remote Similarity	NPC279300
0.6182	Remote Similarity	NPC276764
0.6182	Remote Similarity	NPC278202
0.6182	Remote Similarity	NPC38455
0.6182	Remote Similarity	NPC143834
0.6182	Remote Similarity	NPC472304
0.6182	Remote Similarity	NPC96551
0.6182	Remote Similarity	NPC285594
0.6182	Remote Similarity	NPC259261
0.6154	Remote Similarity	NPC300121
0.6154	Remote Similarity	NPC322461
0.6154	Remote Similarity	NPC95581
0.6154	Remote Similarity	NPC474127
0.6154	Remote Similarity	NPC5626
0.6136	Remote Similarity	NPC123357
0.6136	Remote Similarity	NPC323278
0.6122	Remote Similarity	NPC149821
0.6122	Remote Similarity	NPC5413
0.6122	Remote Similarity	NPC91765
0.6111	Remote Similarity	NPC71755
0.6111	Remote Similarity	NPC281230
0.6111	Remote Similarity	NPC192843
0.6111	Remote Similarity	NPC115385
0.6087	Remote Similarity	NPC116934
0.6071	Remote Similarity	NPC25853
0.6071	Remote Similarity	NPC127582
0.6071	Remote Similarity	NPC79756
0.6053	Remote Similarity	NPC34671
0.6047	Remote Similarity	NPC40434
0.6047	Remote Similarity	NPC34873
0.6042	Remote Similarity	NPC42304
0.6038	Remote Similarity	NPC297280

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 NPC185839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	5741
0.2-0.3	2705
0.3-0.4	423
0.4-0.5	53
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD5783	Phase 3
0.6531	Remote Similarity	NPD6927	Phase 3
0.6522	Remote Similarity	NPD4222	Approved
0.6522	Remote Similarity	NPD3174	Discontinued
0.6522	Remote Similarity	NPD39	Approved
0.6444	Remote Similarity	NPD5326	Phase 3
0.6415	Remote Similarity	NPD8779	Phase 3
0.6304	Remote Similarity	NPD6096	Approved
0.6304	Remote Similarity	NPD6097	Approved
0.625	Remote Similarity	NPD5343	Approved
0.6154	Remote Similarity	NPD539	Approved
0.6122	Remote Similarity	NPD4220	Pre-registration
0.6122	Remote Similarity	NPD3173	Approved
0.6	Remote Similarity	NPD287	Approved
0.5882	Remote Similarity	NPD29	Approved
0.5882	Remote Similarity	NPD28	Approved
0.5833	Remote Similarity	NPD4265	Approved
0.5814	Remote Similarity	NPD319	Phase 1
0.5778	Remote Similarity	NPD1153	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.566	Remote Similarity	NPD3172	Approved

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