NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	3.077
LogD:	2.895
LogS:	-4.46
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.696
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.629
MDCK Permeability:	1.9006620277650654e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	93.6362075805664%
Volume Distribution (VD):	0.73
Pgp-substrate:	6.681393146514893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.942
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	15.072
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.328
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.559
Skin Sensitization:	0.722
Carcinogencity:	0.674
Eye Corrosion:	0.017
Eye Irritation:	0.932
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC274750

Natural Product ID:	NPC274750
*Common Name:**	(2S,3R,6S,E)-2-Bromo-9-(Bromomethylene)-1,1-Dimethyl-5-Methylenespiro[5.5]Undec-7-En-3-Ol
IUPAC Name:	(3R,4S,6S,9E)-4-bromo-9-(bromomethylidene)-5,5-dimethyl-1-methylidenespiro[5.5]undec-10-en-3-ol
Synonyms:
Standard InCHIKey:	BERVNSMGLDGYPR-IGRCQTSTSA-N
Standard InCHI:	InChI=1S/C15H20Br2O/c1-10-8-12(18)13(17)14(2,3)15(10)6-4-11(9-16)5-7-15/h4,6,9,12-13,18H,1,5,7-8H2,2-3H3/b11-9-/t12-,13-,15-/m1/s1
SMILES:	C=C1C[C@H]([C@H](C(C)(C)[C@]21C=C/C(=C/Br)/CC2)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL113677
PubChem CID:	44576245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002517] Chamigranes

*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
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754610]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872159]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	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
IC50	3
Others	5

Activity Type	# Activity
NON-MOLECULAR	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3503	Organism	Nippostrongylus brasiliensis	Nippostrongylus brasiliensis	Activity	<	100.0	uM	PMID[548985]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>=	10000.0	nM	PMID[548986]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.0	%	PMID[548986]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.0	%	PMID[548986]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	34.0	%	PMID[548986]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	69.0	%	PMID[548986]

☑ 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 NPC274750 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	195
0.1-0.2	1524
0.2-0.3	8223
0.3-0.4	18934
0.4-0.5	9290
0.5-0.6	3759
0.6-0.7	684
0.7-0.8	74
0.8-0.85	4
0.85-0.9	4
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215307
0.9315	High Similarity	NPC474946
0.9315	High Similarity	NPC35397
0.9091	High Similarity	NPC311891
0.8961	High Similarity	NPC113024
0.859	High Similarity	NPC31330
0.8442	Intermediate Similarity	NPC61080
0.8214	Intermediate Similarity	NPC109900
0.7901	Intermediate Similarity	NPC83436
0.7805	Intermediate Similarity	NPC15714
0.7701	Intermediate Similarity	NPC188896
0.7614	Intermediate Similarity	NPC239453
0.7614	Intermediate Similarity	NPC224552
0.7595	Intermediate Similarity	NPC68443
0.7595	Intermediate Similarity	NPC476609
0.7586	Intermediate Similarity	NPC174273
0.7564	Intermediate Similarity	NPC145498
0.7564	Intermediate Similarity	NPC92801
0.7532	Intermediate Similarity	NPC96484
0.7532	Intermediate Similarity	NPC208999
0.7529	Intermediate Similarity	NPC97491
0.7529	Intermediate Similarity	NPC273356
0.75	Intermediate Similarity	NPC131453
0.75	Intermediate Similarity	NPC477138
0.75	Intermediate Similarity	NPC243342
0.747	Intermediate Similarity	NPC129501
0.7468	Intermediate Similarity	NPC242001
0.7407	Intermediate Similarity	NPC291503
0.7407	Intermediate Similarity	NPC476605
0.7403	Intermediate Similarity	NPC45782
0.7391	Intermediate Similarity	NPC257510
0.7391	Intermediate Similarity	NPC299714
0.7375	Intermediate Similarity	NPC471799
0.7375	Intermediate Similarity	NPC182717
0.7349	Intermediate Similarity	NPC307965
0.7349	Intermediate Similarity	NPC76931
0.7349	Intermediate Similarity	NPC18603
0.7317	Intermediate Similarity	NPC265588
0.7317	Intermediate Similarity	NPC106432
0.7284	Intermediate Similarity	NPC91858
0.7284	Intermediate Similarity	NPC471797
0.7273	Intermediate Similarity	NPC149680
0.725	Intermediate Similarity	NPC110799
0.725	Intermediate Similarity	NPC164022
0.7241	Intermediate Similarity	NPC282598
0.7237	Intermediate Similarity	NPC225415
0.7237	Intermediate Similarity	NPC290367
0.7229	Intermediate Similarity	NPC471798
0.7215	Intermediate Similarity	NPC476604
0.7195	Intermediate Similarity	NPC69383
0.7195	Intermediate Similarity	NPC66566
0.7195	Intermediate Similarity	NPC171148
0.7195	Intermediate Similarity	NPC313179
0.7195	Intermediate Similarity	NPC477923
0.7143	Intermediate Similarity	NPC205455
0.7143	Intermediate Similarity	NPC318136
0.7143	Intermediate Similarity	NPC186191
0.7128	Intermediate Similarity	NPC156912
0.7126	Intermediate Similarity	NPC237795
0.7126	Intermediate Similarity	NPC82538
0.7125	Intermediate Similarity	NPC49422
0.7125	Intermediate Similarity	NPC9161
0.7108	Intermediate Similarity	NPC250621
0.7108	Intermediate Similarity	NPC129165
0.7108	Intermediate Similarity	NPC134330
0.7108	Intermediate Similarity	NPC113733
0.7108	Intermediate Similarity	NPC253190
0.7108	Intermediate Similarity	NPC274079
0.7108	Intermediate Similarity	NPC476606
0.7108	Intermediate Similarity	NPC470362
0.7108	Intermediate Similarity	NPC477925
0.7108	Intermediate Similarity	NPC476607
0.7089	Intermediate Similarity	NPC216460
0.7089	Intermediate Similarity	NPC32055
0.7089	Intermediate Similarity	NPC471238
0.7073	Intermediate Similarity	NPC329090
0.7073	Intermediate Similarity	NPC100334
0.7073	Intermediate Similarity	NPC27395
0.7059	Intermediate Similarity	NPC476603
0.7059	Intermediate Similarity	NPC476610
0.7053	Intermediate Similarity	NPC34732
0.7053	Intermediate Similarity	NPC92231
0.7051	Intermediate Similarity	NPC202017
0.7045	Intermediate Similarity	NPC238485
0.7037	Intermediate Similarity	NPC242992
0.7037	Intermediate Similarity	NPC477792
0.7037	Intermediate Similarity	NPC475077
0.7037	Intermediate Similarity	NPC167706
0.7024	Intermediate Similarity	NPC477924
0.7024	Intermediate Similarity	NPC91594
0.7013	Intermediate Similarity	NPC144650
0.7011	Intermediate Similarity	NPC201852
0.7	Intermediate Similarity	NPC476431
0.7	Intermediate Similarity	NPC474248
0.7	Intermediate Similarity	NPC167272
0.7	Intermediate Similarity	NPC269877
0.6988	Remote Similarity	NPC471723
0.6988	Remote Similarity	NPC288035
0.6988	Remote Similarity	NPC141071
0.6988	Remote Similarity	NPC162742
0.6988	Remote Similarity	NPC136188
0.6988	Remote Similarity	NPC28657
0.6988	Remote Similarity	NPC22105
0.6988	Remote Similarity	NPC230301
0.6988	Remote Similarity	NPC328104
0.6988	Remote Similarity	NPC471468
0.6988	Remote Similarity	NPC285893
0.6988	Remote Similarity	NPC257347
0.6988	Remote Similarity	NPC134847
0.6988	Remote Similarity	NPC319090
0.6988	Remote Similarity	NPC304309
0.6977	Remote Similarity	NPC96362
0.6977	Remote Similarity	NPC287749
0.6966	Remote Similarity	NPC313115
0.6962	Remote Similarity	NPC96962
0.6962	Remote Similarity	NPC476650
0.6962	Remote Similarity	NPC197805
0.6951	Remote Similarity	NPC220939
0.6951	Remote Similarity	NPC265485
0.6941	Remote Similarity	NPC72507
0.6941	Remote Similarity	NPC275910
0.6941	Remote Similarity	NPC470396
0.6941	Remote Similarity	NPC83351
0.6941	Remote Similarity	NPC167891
0.6941	Remote Similarity	NPC99168
0.6941	Remote Similarity	NPC474989
0.6941	Remote Similarity	NPC22955
0.6941	Remote Similarity	NPC476314
0.6932	Remote Similarity	NPC470384
0.6914	Remote Similarity	NPC34834
0.6905	Remote Similarity	NPC107059
0.6905	Remote Similarity	NPC122418
0.6905	Remote Similarity	NPC290598
0.6905	Remote Similarity	NPC321381
0.6905	Remote Similarity	NPC189883
0.6905	Remote Similarity	NPC46160
0.6905	Remote Similarity	NPC315261
0.6905	Remote Similarity	NPC265328
0.6905	Remote Similarity	NPC30590
0.6905	Remote Similarity	NPC96319
0.6905	Remote Similarity	NPC27765
0.6905	Remote Similarity	NPC120098
0.6905	Remote Similarity	NPC240604
0.6905	Remote Similarity	NPC321016
0.6905	Remote Similarity	NPC106364
0.6905	Remote Similarity	NPC300324
0.6905	Remote Similarity	NPC202642
0.6897	Remote Similarity	NPC142163
0.6897	Remote Similarity	NPC476646
0.6883	Remote Similarity	NPC83200
0.6867	Remote Similarity	NPC306727
0.6867	Remote Similarity	NPC469534
0.6867	Remote Similarity	NPC469533
0.6867	Remote Similarity	NPC469593
0.686	Remote Similarity	NPC291379
0.686	Remote Similarity	NPC53744
0.686	Remote Similarity	NPC100906
0.6854	Remote Similarity	NPC231310
0.6854	Remote Similarity	NPC474493
0.6835	Remote Similarity	NPC476039
0.6835	Remote Similarity	NPC286669
0.6835	Remote Similarity	NPC473929
0.6835	Remote Similarity	NPC222366
0.6829	Remote Similarity	NPC471271
0.6829	Remote Similarity	NPC471272
0.6829	Remote Similarity	NPC471268
0.6829	Remote Similarity	NPC23954
0.6824	Remote Similarity	NPC198968
0.6824	Remote Similarity	NPC34177
0.6824	Remote Similarity	NPC318495
0.6824	Remote Similarity	NPC214570
0.6824	Remote Similarity	NPC90979
0.6824	Remote Similarity	NPC157996
0.6824	Remote Similarity	NPC40394
0.6824	Remote Similarity	NPC283619
0.6824	Remote Similarity	NPC101475
0.6824	Remote Similarity	NPC34019
0.6824	Remote Similarity	NPC155986
0.6824	Remote Similarity	NPC472805
0.6818	Remote Similarity	NPC202389
0.6795	Remote Similarity	NPC323424
0.6795	Remote Similarity	NPC68656
0.6795	Remote Similarity	NPC96793
0.679	Remote Similarity	NPC9942
0.679	Remote Similarity	NPC471560
0.6786	Remote Similarity	NPC138374
0.6786	Remote Similarity	NPC34700
0.6786	Remote Similarity	NPC322353
0.6786	Remote Similarity	NPC118508
0.6786	Remote Similarity	NPC121744
0.6782	Remote Similarity	NPC164840
0.6782	Remote Similarity	NPC209944
0.6782	Remote Similarity	NPC234193
0.6782	Remote Similarity	NPC241290
0.6778	Remote Similarity	NPC109528
0.6753	Remote Similarity	NPC282694
0.6753	Remote Similarity	NPC225342
0.6753	Remote Similarity	NPC475251
0.6753	Remote Similarity	NPC194208
0.6753	Remote Similarity	NPC79576

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 NPC274750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1849
0.2-0.3	4344
0.3-0.4	2064
0.4-0.5	528
0.5-0.6	119
0.6-0.7	38
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
0.725	Intermediate Similarity	NPD7151	Approved
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD7152	Approved
0.7195	Intermediate Similarity	NPD8264	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7125	Intermediate Similarity	NPD7144	Approved
0.7073	Intermediate Similarity	NPD6924	Approved
0.7073	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD6923	Approved
0.7	Intermediate Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6942	Approved
0.6988	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD6933	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6628	Remote Similarity	NPD6932	Approved
0.6591	Remote Similarity	NPD6930	Phase 2
0.6591	Remote Similarity	NPD6931	Approved
0.6552	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7145	Approved
0.6444	Remote Similarity	NPD3667	Approved
0.6437	Remote Similarity	NPD6925	Approved
0.6437	Remote Similarity	NPD5776	Phase 2
0.6404	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7514	Phase 3
0.6404	Remote Similarity	NPD7332	Phase 2
0.6374	Remote Similarity	NPD6695	Phase 3
0.6333	Remote Similarity	NPD6902	Approved
0.6316	Remote Similarity	NPD4219	Approved
0.6304	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4786	Approved
0.6292	Remote Similarity	NPD6683	Phase 2
0.6279	Remote Similarity	NPD4784	Approved
0.6279	Remote Similarity	NPD4785	Approved
0.6237	Remote Similarity	NPD6893	Approved
0.6222	Remote Similarity	NPD4748	Discontinued
0.6186	Remote Similarity	NPD6411	Approved
0.617	Remote Similarity	NPD5279	Phase 3
0.617	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD6898	Phase 1
0.6105	Remote Similarity	NPD7524	Approved
0.6105	Remote Similarity	NPD7750	Discontinued
0.6105	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4243	Approved
0.602	Remote Similarity	NPD6079	Approved
0.5979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6101	Approved
0.5979	Remote Similarity	NPD5328	Approved
0.5977	Remote Similarity	NPD4732	Discontinued
0.5974	Remote Similarity	NPD342	Phase 1
0.5957	Remote Similarity	NPD3666	Approved
0.5957	Remote Similarity	NPD3665	Phase 1
0.5957	Remote Similarity	NPD3133	Approved
0.5926	Remote Similarity	NPD368	Approved
0.5895	Remote Similarity	NPD1696	Phase 3
0.5859	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD7087	Discontinued
0.5843	Remote Similarity	NPD4190	Phase 3
0.5843	Remote Similarity	NPD5275	Approved
0.58	Remote Similarity	NPD4202	Approved
0.58	Remote Similarity	NPD5778	Approved
0.58	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD3668	Phase 3
0.5784	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5222	Approved
0.5784	Remote Similarity	NPD5221	Approved
0.5761	Remote Similarity	NPD4195	Approved
0.5758	Remote Similarity	NPD7136	Phase 2
0.5728	Remote Similarity	NPD5173	Approved
0.57	Remote Similarity	NPD7637	Suspended
0.5699	Remote Similarity	NPD4695	Discontinued
0.5673	Remote Similarity	NPD5290	Discontinued
0.5644	Remote Similarity	NPD6399	Phase 3
0.5631	Remote Similarity	NPD4697	Phase 3
0.5619	Remote Similarity	NPD5286	Approved
0.5619	Remote Similarity	NPD5285	Approved
0.5619	Remote Similarity	NPD4696	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