NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	266.474
LogP:	2.602
LogD:	2.721
LogS:	-3.563
# Rotatable Bonds:	6
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	3.511
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.623
MDCK Permeability:	1.9204306227038614e-05
Pgp-inhibitor:	0.379
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	65.663818359375%
Volume Distribution (VD):	0.751
Pgp-substrate:	35.98500061035156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.579
CYP2D6-inhibitor:	0.177
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	8.52
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.535
Skin Sensitization:	0.199
Carcinogencity:	0.634
Eye Corrosion:	0.04
Eye Irritation:	0.434
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC474141

Natural Product ID:	NPC474141
*Common Name:**	Mandassidione
IUPAC Name:	3-methyl-2-(5-oxo-2-prop-1-en-2-ylhexyl)cyclopent-2-en-1-one
Synonyms:	Mandassidione
Standard InCHIKey:	VALJTPGALJMVTL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-10(2)13(7-6-12(4)16)9-14-11(3)5-8-15(14)17/h13H,1,5-9H2,2-4H3
SMILES:	CC1=C(C(=O)CC1)CC(CCC(=O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462896
PubChem CID:	14109869
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones

*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
NPO7630	Cyperus longus	Species	Cyperaceae	Eukaryota	n.a.	Egyptian herbal medicine	n.a.	PMID[15104485]
NPO7630	Cyperus longus	Species	Cyperaceae	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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	7.7	%	PMID[513097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-0.1	%	PMID[513097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	14.7	%	PMID[513097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	21.6	%	PMID[513097]

☑ 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 NPC474141 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	207
0.1-0.2	3338
0.2-0.3	17419
0.3-0.4	12567
0.4-0.5	6203
0.5-0.6	2410
0.6-0.7	428
0.7-0.8	101
0.8-0.85	16
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9057	High Similarity	NPC20603
0.8868	High Similarity	NPC275472
0.8846	High Similarity	NPC45283
0.8654	High Similarity	NPC471751
0.8596	High Similarity	NPC97322
0.8571	High Similarity	NPC259261
0.8545	High Similarity	NPC193695
0.8491	Intermediate Similarity	NPC296311
0.8448	Intermediate Similarity	NPC167256
0.8431	Intermediate Similarity	NPC145311
0.8393	Intermediate Similarity	NPC266295
0.8393	Intermediate Similarity	NPC94991
0.8333	Intermediate Similarity	NPC63396
0.8333	Intermediate Similarity	NPC202850
0.8269	Intermediate Similarity	NPC32351
0.8246	Intermediate Similarity	NPC143834
0.8167	Intermediate Similarity	NPC474304
0.8167	Intermediate Similarity	NPC474329
0.8148	Intermediate Similarity	NPC268564
0.8113	Intermediate Similarity	NPC27438
0.8103	Intermediate Similarity	NPC25853
0.807	Intermediate Similarity	NPC56905
0.807	Intermediate Similarity	NPC27610
0.807	Intermediate Similarity	NPC30215
0.8039	Intermediate Similarity	NPC100380
0.8039	Intermediate Similarity	NPC8610
0.8039	Intermediate Similarity	NPC14917
0.8039	Intermediate Similarity	NPC262558
0.8039	Intermediate Similarity	NPC4079
0.8039	Intermediate Similarity	NPC236355
0.8	Intermediate Similarity	NPC473902
0.8	Intermediate Similarity	NPC212210
0.7966	Intermediate Similarity	NPC213152
0.7966	Intermediate Similarity	NPC475795
0.7931	Intermediate Similarity	NPC472304
0.7931	Intermediate Similarity	NPC96551
0.7931	Intermediate Similarity	NPC285594
0.7931	Intermediate Similarity	NPC276764
0.7895	Intermediate Similarity	NPC49575
0.7895	Intermediate Similarity	NPC115385
0.7895	Intermediate Similarity	NPC267626
0.7895	Intermediate Similarity	NPC55004
0.7895	Intermediate Similarity	NPC230823
0.7895	Intermediate Similarity	NPC192427
0.7833	Intermediate Similarity	NPC165695
0.7833	Intermediate Similarity	NPC32285
0.7797	Intermediate Similarity	NPC127582
0.7719	Intermediate Similarity	NPC473733
0.7705	Intermediate Similarity	NPC150162
0.7692	Intermediate Similarity	NPC471752
0.7656	Intermediate Similarity	NPC256846
0.7656	Intermediate Similarity	NPC67608
0.7619	Intermediate Similarity	NPC475523
0.7593	Intermediate Similarity	NPC176819
0.7593	Intermediate Similarity	NPC116906
0.7593	Intermediate Similarity	NPC163984
0.7593	Intermediate Similarity	NPC58970
0.7581	Intermediate Similarity	NPC251118
0.7547	Intermediate Similarity	NPC91962
0.7541	Intermediate Similarity	NPC288253
0.7541	Intermediate Similarity	NPC472306
0.7538	Intermediate Similarity	NPC246722
0.7538	Intermediate Similarity	NPC151045
0.75	Intermediate Similarity	NPC476614
0.7458	Intermediate Similarity	NPC311852
0.7455	Intermediate Similarity	NPC64866
0.7455	Intermediate Similarity	NPC236623
0.7424	Intermediate Similarity	NPC29328
0.7419	Intermediate Similarity	NPC285371
0.7419	Intermediate Similarity	NPC6697
0.7419	Intermediate Similarity	NPC475124
0.7385	Intermediate Similarity	NPC162867
0.7385	Intermediate Similarity	NPC139397
0.7385	Intermediate Similarity	NPC61702
0.7377	Intermediate Similarity	NPC260573
0.7377	Intermediate Similarity	NPC60565
0.7344	Intermediate Similarity	NPC476626
0.7308	Intermediate Similarity	NPC25771
0.7302	Intermediate Similarity	NPC470329
0.7273	Intermediate Similarity	NPC2634
0.7273	Intermediate Similarity	NPC260040
0.7273	Intermediate Similarity	NPC265782
0.7273	Intermediate Similarity	NPC307176
0.7273	Intermediate Similarity	NPC251929
0.7273	Intermediate Similarity	NPC228776
0.7241	Intermediate Similarity	NPC188789
0.7231	Intermediate Similarity	NPC469679
0.7231	Intermediate Similarity	NPC87141
0.7231	Intermediate Similarity	NPC469688
0.7231	Intermediate Similarity	NPC155198
0.7231	Intermediate Similarity	NPC188292
0.7231	Intermediate Similarity	NPC260474
0.7206	Intermediate Similarity	NPC7382
0.7188	Intermediate Similarity	NPC197089
0.717	Intermediate Similarity	NPC166788
0.7167	Intermediate Similarity	NPC308108
0.7167	Intermediate Similarity	NPC170799
0.7164	Intermediate Similarity	NPC181204
0.7164	Intermediate Similarity	NPC469737
0.7164	Intermediate Similarity	NPC54123
0.7143	Intermediate Similarity	NPC477458
0.7143	Intermediate Similarity	NPC4638
0.7121	Intermediate Similarity	NPC469914
0.7121	Intermediate Similarity	NPC477448
0.7121	Intermediate Similarity	NPC477449
0.7115	Intermediate Similarity	NPC292463
0.7115	Intermediate Similarity	NPC301972
0.7101	Intermediate Similarity	NPC473171
0.7101	Intermediate Similarity	NPC89374
0.7101	Intermediate Similarity	NPC469669
0.7101	Intermediate Similarity	NPC474011
0.7101	Intermediate Similarity	NPC469678
0.7101	Intermediate Similarity	NPC475771
0.7101	Intermediate Similarity	NPC216791
0.7069	Intermediate Similarity	NPC100809
0.7069	Intermediate Similarity	NPC250539
0.7069	Intermediate Similarity	NPC209431
0.7059	Intermediate Similarity	NPC474228
0.7059	Intermediate Similarity	NPC300940
0.7059	Intermediate Similarity	NPC303613
0.7037	Intermediate Similarity	NPC276009
0.7037	Intermediate Similarity	NPC195246
0.7037	Intermediate Similarity	NPC22098
0.7031	Intermediate Similarity	NPC61473
0.7015	Intermediate Similarity	NPC35734
0.7015	Intermediate Similarity	NPC282593
0.7015	Intermediate Similarity	NPC280256
0.7015	Intermediate Similarity	NPC159577
0.7	Intermediate Similarity	NPC473223
0.6984	Remote Similarity	NPC197238
0.6984	Remote Similarity	NPC202118
0.6984	Remote Similarity	NPC322457
0.6981	Remote Similarity	NPC471753
0.697	Remote Similarity	NPC310992
0.6964	Remote Similarity	NPC474391
0.6957	Remote Similarity	NPC474796
0.6957	Remote Similarity	NPC474797
0.6957	Remote Similarity	NPC309852
0.6957	Remote Similarity	NPC469691
0.6957	Remote Similarity	NPC329866
0.6957	Remote Similarity	NPC167049
0.6949	Remote Similarity	NPC200258
0.6912	Remote Similarity	NPC474562
0.6912	Remote Similarity	NPC21944
0.6912	Remote Similarity	NPC133253
0.6912	Remote Similarity	NPC115023
0.6912	Remote Similarity	NPC190035
0.6912	Remote Similarity	NPC288667
0.6912	Remote Similarity	NPC5701
0.6901	Remote Similarity	NPC472014
0.6901	Remote Similarity	NPC195785
0.6901	Remote Similarity	NPC86917
0.6901	Remote Similarity	NPC15975
0.6897	Remote Similarity	NPC23117
0.6897	Remote Similarity	NPC37644
0.6875	Remote Similarity	NPC469662
0.6866	Remote Similarity	NPC296522
0.6866	Remote Similarity	NPC261398
0.6866	Remote Similarity	NPC144511
0.6866	Remote Similarity	NPC469677
0.6866	Remote Similarity	NPC474060
0.6857	Remote Similarity	NPC77501
0.6857	Remote Similarity	NPC251435
0.6852	Remote Similarity	NPC191337
0.6842	Remote Similarity	NPC234829
0.6825	Remote Similarity	NPC174560
0.6825	Remote Similarity	NPC125312
0.6818	Remote Similarity	NPC4370
0.6818	Remote Similarity	NPC278895
0.6818	Remote Similarity	NPC290350
0.6812	Remote Similarity	NPC470045
0.6812	Remote Similarity	NPC130016
0.6812	Remote Similarity	NPC470044
0.6812	Remote Similarity	NPC109576
0.6812	Remote Similarity	NPC56747
0.6812	Remote Similarity	NPC251705
0.6812	Remote Similarity	NPC180015
0.6806	Remote Similarity	NPC476627
0.6806	Remote Similarity	NPC299235
0.6806	Remote Similarity	NPC19443
0.68	Remote Similarity	NPC223315
0.678	Remote Similarity	NPC95581
0.6765	Remote Similarity	NPC318766
0.6761	Remote Similarity	NPC469793
0.6761	Remote Similarity	NPC472967
0.6761	Remote Similarity	NPC469646
0.6761	Remote Similarity	NPC69408
0.6761	Remote Similarity	NPC266159
0.6761	Remote Similarity	NPC469796
0.6724	Remote Similarity	NPC216407
0.6724	Remote Similarity	NPC22182
0.6716	Remote Similarity	NPC20610
0.6714	Remote Similarity	NPC255021
0.6714	Remote Similarity	NPC20025
0.6712	Remote Similarity	NPC472013
0.6712	Remote Similarity	NPC476624
0.6667	Remote Similarity	NPC126899
0.6667	Remote Similarity	NPC84790
0.6667	Remote Similarity	NPC323005
0.6667	Remote Similarity	NPC15325

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 NPC474141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	3345
0.2-0.3	4055
0.3-0.4	1106
0.4-0.5	311
0.5-0.6	118
0.6-0.7	13
0.7-0.8	3
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
0.7385	Intermediate Similarity	NPD4137	Phase 3
0.7273	Intermediate Similarity	NPD4691	Approved
0.7273	Intermediate Similarity	NPD4747	Approved
0.7188	Intermediate Similarity	NPD7331	Phase 2
0.7167	Intermediate Similarity	NPD287	Approved
0.7164	Intermediate Similarity	NPD5276	Approved
0.7031	Intermediate Similarity	NPD7341	Phase 2
0.6957	Remote Similarity	NPD4058	Approved
0.6957	Remote Similarity	NPD5733	Approved
0.6957	Remote Similarity	NPD4687	Approved
0.6716	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5783	Phase 3
0.6234	Remote Similarity	NPD4223	Phase 3
0.6234	Remote Similarity	NPD4221	Approved
0.6212	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4695	Discontinued
0.6176	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3617	Approved
0.6125	Remote Similarity	NPD4623	Approved
0.6125	Remote Similarity	NPD4519	Discontinued
0.6076	Remote Similarity	NPD3133	Approved
0.6076	Remote Similarity	NPD4197	Approved
0.6076	Remote Similarity	NPD3665	Phase 1
0.6076	Remote Similarity	NPD3666	Approved
0.6026	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD28	Approved
0.6	Remote Similarity	NPD29	Approved
0.6	Remote Similarity	NPD5329	Approved
0.5926	Remote Similarity	NPD5280	Approved
0.5926	Remote Similarity	NPD7521	Approved
0.5926	Remote Similarity	NPD4690	Approved
0.5926	Remote Similarity	NPD7146	Approved
0.5926	Remote Similarity	NPD4693	Phase 3
0.5926	Remote Similarity	NPD6409	Approved
0.5926	Remote Similarity	NPD5205	Approved
0.5926	Remote Similarity	NPD4689	Approved
0.5926	Remote Similarity	NPD4138	Approved
0.5926	Remote Similarity	NPD4694	Approved
0.5926	Remote Similarity	NPD5330	Approved
0.5926	Remote Similarity	NPD5279	Phase 3
0.5926	Remote Similarity	NPD6684	Approved
0.5926	Remote Similarity	NPD7334	Approved
0.5926	Remote Similarity	NPD4688	Approved
0.5926	Remote Similarity	NPD5690	Phase 2
0.5926	Remote Similarity	NPD3618	Phase 1
0.5921	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8028	Phase 2
0.5862	Remote Similarity	NPD345	Approved
0.5862	Remote Similarity	NPD343	Approved
0.5862	Remote Similarity	NPD344	Approved
0.5823	Remote Similarity	NPD5209	Approved
0.5823	Remote Similarity	NPD3667	Approved
0.5823	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD4193	Approved
0.5821	Remote Similarity	NPD4191	Approved
0.5821	Remote Similarity	NPD4192	Approved
0.5821	Remote Similarity	NPD4194	Approved
0.5806	Remote Similarity	NPD3172	Approved
0.5802	Remote Similarity	NPD1694	Approved
0.5802	Remote Similarity	NPD5363	Approved
0.5797	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6672	Approved
0.5783	Remote Similarity	NPD5208	Approved
0.5783	Remote Similarity	NPD5737	Approved
0.5783	Remote Similarity	NPD6903	Approved
0.5783	Remote Similarity	NPD4518	Approved
0.5769	Remote Similarity	NPD5368	Approved
0.5769	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5362	Discontinued
0.575	Remote Similarity	NPD7154	Phase 3
0.5732	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD539	Approved
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD9298	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD3704	Approved
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5696	Remote Similarity	NPD5369	Approved
0.5696	Remote Similarity	NPD857	Phase 3
0.569	Remote Similarity	NPD3174	Discontinued
0.5679	Remote Similarity	NPD3668	Phase 3
0.5679	Remote Similarity	NPD4786	Approved
0.5663	Remote Similarity	NPD3573	Approved
0.566	Remote Similarity	NPD319	Phase 1
0.5647	Remote Similarity	NPD5692	Phase 3
0.5647	Remote Similarity	NPD5207	Approved
0.5647	Remote Similarity	NPD4096	Approved
0.5632	Remote Similarity	NPD5282	Discontinued
0.5625	Remote Similarity	NPD4270	Approved
0.5625	Remote Similarity	NPD6435	Approved
0.5625	Remote Similarity	NPD4269	Approved
0.561	Remote Similarity	NPD1733	Clinical (unspecified phase)

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