NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	284.2
Volume:	306.624
LogP:	4.108
LogD:	2.64
LogS:	-3.451
# Rotatable Bonds:	9
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	3.965
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.525
MDCK Permeability:	3.0856317607685924e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	94.3201904296875%
Volume Distribution (VD):	1.259
Pgp-substrate:	4.277063369750977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.279
CYP2C9-substrate:	0.523
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.469
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	8.384
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.371
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.548
Carcinogencity:	0.069
Eye Corrosion:	0.028
Eye Irritation:	0.116
Respiratory Toxicity:	0.34

Download Data

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

Natural Product: NPC474959

Natural Product ID:	NPC474959
*Common Name:**	Litseakolide G
IUPAC Name:	(3Z,4R,5R)-3-decylidene-4-hydroxy-5-methoxy-5-methyloxolan-2-one
Synonyms:	Litseakolide G
Standard InCHIKey:	HYRMWBVOZFMSIF-MMDYRICWSA-N
Standard InCHI:	InChI=1S/C16H28O4/c1-4-5-6-7-8-9-10-11-12-13-14(17)16(2,19-3)20-15(13)18/h12,14,17H,4-11H2,1-3H3/b13-12-/t14-,16-/m1/s1
SMILES:	CCCCCCCCCC=C1C(C(OC1=O)(C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490274
PubChem CID:	10424025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO11602	Litsea acutivena	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754599]
NPO11602	Litsea acutivena	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22224304]
NPO11602	Litsea acutivena	Species	Lauraceae	Eukaryota	n.a.	twig	n.a.	PMID[22224304]
NPO11602	Litsea acutivena	Species	Lauraceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.97	ug ml-1	PMID[497258]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.73	ug ml-1	PMID[497258]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.94	ug ml-1	PMID[497258]

☑ 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 NPC474959 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	170
0.1-0.2	1556
0.2-0.3	6260
0.3-0.4	14913
0.4-0.5	11210
0.5-0.6	6033
0.6-0.7	1965
0.7-0.8	479
0.8-0.85	91
0.85-0.9	13
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC11383
1.0	High Similarity	NPC310450
1.0	High Similarity	NPC475046
0.987	High Similarity	NPC286770
0.987	High Similarity	NPC284472
0.987	High Similarity	NPC229799
0.8961	High Similarity	NPC301207
0.8875	High Similarity	NPC150502
0.8846	High Similarity	NPC51809
0.8846	High Similarity	NPC474818
0.8846	High Similarity	NPC125365
0.8846	High Similarity	NPC176329
0.8846	High Similarity	NPC49302
0.8734	High Similarity	NPC221095
0.8734	High Similarity	NPC473471
0.8734	High Similarity	NPC279214
0.8718	High Similarity	NPC209113
0.8718	High Similarity	NPC127118
0.8354	Intermediate Similarity	NPC161038
0.8333	Intermediate Similarity	NPC41856
0.8276	Intermediate Similarity	NPC139418
0.8182	Intermediate Similarity	NPC473904
0.8171	Intermediate Similarity	NPC99651
0.8148	Intermediate Similarity	NPC275530
0.814	Intermediate Similarity	NPC469910
0.8077	Intermediate Similarity	NPC202011
0.8068	Intermediate Similarity	NPC130359
0.8068	Intermediate Similarity	NPC14901
0.8046	Intermediate Similarity	NPC178215
0.8025	Intermediate Similarity	NPC68819
0.8025	Intermediate Similarity	NPC205615
0.8025	Intermediate Similarity	NPC256640
0.8025	Intermediate Similarity	NPC16279
0.8023	Intermediate Similarity	NPC286338
0.8023	Intermediate Similarity	NPC473478
0.8023	Intermediate Similarity	NPC473669
0.8023	Intermediate Similarity	NPC231009
0.8023	Intermediate Similarity	NPC283085
0.8023	Intermediate Similarity	NPC110710
0.8023	Intermediate Similarity	NPC103284
0.8023	Intermediate Similarity	NPC66346
0.8023	Intermediate Similarity	NPC1083
0.8023	Intermediate Similarity	NPC107986
0.8023	Intermediate Similarity	NPC82795
0.8023	Intermediate Similarity	NPC132496
0.8023	Intermediate Similarity	NPC473651
0.8023	Intermediate Similarity	NPC470755
0.8023	Intermediate Similarity	NPC223871
0.8	Intermediate Similarity	NPC473561
0.8	Intermediate Similarity	NPC475173
0.8	Intermediate Similarity	NPC476590
0.8	Intermediate Similarity	NPC473663
0.8	Intermediate Similarity	NPC473723
0.8	Intermediate Similarity	NPC114727
0.8	Intermediate Similarity	NPC469692
0.8	Intermediate Similarity	NPC11456
0.8	Intermediate Similarity	NPC469645
0.7978	Intermediate Similarity	NPC474232
0.7955	Intermediate Similarity	NPC21208
0.7955	Intermediate Similarity	NPC287089
0.7955	Intermediate Similarity	NPC280621
0.7955	Intermediate Similarity	NPC233551
0.7955	Intermediate Similarity	NPC48338
0.7955	Intermediate Similarity	NPC20339
0.7955	Intermediate Similarity	NPC40376
0.7955	Intermediate Similarity	NPC476803
0.7949	Intermediate Similarity	NPC475982
0.7931	Intermediate Similarity	NPC62118
0.7931	Intermediate Similarity	NPC134865
0.7931	Intermediate Similarity	NPC232555
0.7931	Intermediate Similarity	NPC103523
0.7931	Intermediate Similarity	NPC204686
0.7931	Intermediate Similarity	NPC210218
0.7931	Intermediate Similarity	NPC107717
0.7931	Intermediate Similarity	NPC134885
0.7931	Intermediate Similarity	NPC231096
0.7931	Intermediate Similarity	NPC473687
0.7931	Intermediate Similarity	NPC134807
0.7931	Intermediate Similarity	NPC114694
0.7931	Intermediate Similarity	NPC219498
0.7931	Intermediate Similarity	NPC69082
0.7931	Intermediate Similarity	NPC171174
0.7931	Intermediate Similarity	NPC142117
0.7931	Intermediate Similarity	NPC112685
0.7931	Intermediate Similarity	NPC475581
0.7931	Intermediate Similarity	NPC308412
0.7931	Intermediate Similarity	NPC240695
0.7931	Intermediate Similarity	NPC279267
0.7912	Intermediate Similarity	NPC121825
0.7907	Intermediate Similarity	NPC163093
0.7907	Intermediate Similarity	NPC158756
0.7901	Intermediate Similarity	NPC478192
0.7901	Intermediate Similarity	NPC478191
0.7901	Intermediate Similarity	NPC478194
0.7901	Intermediate Similarity	NPC478193
0.7901	Intermediate Similarity	NPC478196
0.7901	Intermediate Similarity	NPC478195
0.7889	Intermediate Similarity	NPC473707
0.7816	Intermediate Similarity	NPC477013
0.7816	Intermediate Similarity	NPC477014
0.7816	Intermediate Similarity	NPC120398
0.7816	Intermediate Similarity	NPC471567
0.7816	Intermediate Similarity	NPC470124
0.7816	Intermediate Similarity	NPC182383
0.7802	Intermediate Similarity	NPC295204
0.7802	Intermediate Similarity	NPC273579
0.7802	Intermediate Similarity	NPC288240
0.7802	Intermediate Similarity	NPC162205
0.7791	Intermediate Similarity	NPC40746
0.7791	Intermediate Similarity	NPC169575
0.7791	Intermediate Similarity	NPC116543
0.7778	Intermediate Similarity	NPC473311
0.7778	Intermediate Similarity	NPC239517
0.7766	Intermediate Similarity	NPC187268
0.7765	Intermediate Similarity	NPC297440
0.7753	Intermediate Similarity	NPC242364
0.7753	Intermediate Similarity	NPC261952
0.7753	Intermediate Similarity	NPC234077
0.7753	Intermediate Similarity	NPC172821
0.7753	Intermediate Similarity	NPC169511
0.7753	Intermediate Similarity	NPC191929
0.7753	Intermediate Similarity	NPC274446
0.7753	Intermediate Similarity	NPC100454
0.7753	Intermediate Similarity	NPC476805
0.7753	Intermediate Similarity	NPC475819
0.7753	Intermediate Similarity	NPC133730
0.7753	Intermediate Similarity	NPC39754
0.7753	Intermediate Similarity	NPC287164
0.7753	Intermediate Similarity	NPC320569
0.7753	Intermediate Similarity	NPC151403
0.7753	Intermediate Similarity	NPC81045
0.7753	Intermediate Similarity	NPC61257
0.7753	Intermediate Similarity	NPC171135
0.7742	Intermediate Similarity	NPC477921
0.7727	Intermediate Similarity	NPC469483
0.7727	Intermediate Similarity	NPC305475
0.7727	Intermediate Similarity	NPC47937
0.7727	Intermediate Similarity	NPC475461
0.7727	Intermediate Similarity	NPC477015
0.7701	Intermediate Similarity	NPC156804
0.7692	Intermediate Similarity	NPC9447
0.7692	Intermediate Similarity	NPC473321
0.7683	Intermediate Similarity	NPC260396
0.7674	Intermediate Similarity	NPC473712
0.7674	Intermediate Similarity	NPC73310
0.7674	Intermediate Similarity	NPC475159
0.7674	Intermediate Similarity	NPC145914
0.7674	Intermediate Similarity	NPC329829
0.7674	Intermediate Similarity	NPC180363
0.7674	Intermediate Similarity	NPC473529
0.7674	Intermediate Similarity	NPC131002
0.7674	Intermediate Similarity	NPC473780
0.7674	Intermediate Similarity	NPC65930
0.7674	Intermediate Similarity	NPC94875
0.7674	Intermediate Similarity	NPC11332
0.7667	Intermediate Similarity	NPC42598
0.7667	Intermediate Similarity	NPC477011
0.7667	Intermediate Similarity	NPC81778
0.7667	Intermediate Similarity	NPC91067
0.7667	Intermediate Similarity	NPC318963
0.7667	Intermediate Similarity	NPC79027
0.7667	Intermediate Similarity	NPC473504
0.7667	Intermediate Similarity	NPC20621
0.7667	Intermediate Similarity	NPC280612
0.7667	Intermediate Similarity	NPC93794
0.7667	Intermediate Similarity	NPC40066
0.7662	Intermediate Similarity	NPC19769
0.7662	Intermediate Similarity	NPC470123
0.7647	Intermediate Similarity	NPC47653
0.764	Intermediate Similarity	NPC475037
0.7634	Intermediate Similarity	NPC477922
0.7634	Intermediate Similarity	NPC471142
0.7619	Intermediate Similarity	NPC318481
0.7619	Intermediate Similarity	NPC93763
0.7619	Intermediate Similarity	NPC108816
0.7619	Intermediate Similarity	NPC182292
0.7614	Intermediate Similarity	NPC329615
0.7614	Intermediate Similarity	NPC475034
0.7614	Intermediate Similarity	NPC21469
0.7614	Intermediate Similarity	NPC255307
0.7614	Intermediate Similarity	NPC322529
0.7614	Intermediate Similarity	NPC329838
0.7609	Intermediate Similarity	NPC475912
0.7609	Intermediate Similarity	NPC473520
0.7604	Intermediate Similarity	NPC110443
0.7604	Intermediate Similarity	NPC128733
0.7604	Intermediate Similarity	NPC46998
0.7604	Intermediate Similarity	NPC185141
0.7604	Intermediate Similarity	NPC133907
0.759	Intermediate Similarity	NPC470705
0.759	Intermediate Similarity	NPC190400
0.759	Intermediate Similarity	NPC49392
0.7586	Intermediate Similarity	NPC473390
0.7586	Intermediate Similarity	NPC161045
0.7586	Intermediate Similarity	NPC131669
0.7586	Intermediate Similarity	NPC253801
0.7586	Intermediate Similarity	NPC144415
0.7582	Intermediate Similarity	NPC473619
0.7564	Intermediate Similarity	NPC248125
0.7564	Intermediate Similarity	NPC276299

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 NPC474959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2271
0.2-0.3	4058
0.3-0.4	1886
0.4-0.5	578
0.5-0.6	166
0.6-0.7	40
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
0.7396	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6698	Approved
0.7021	Intermediate Similarity	NPD46	Approved
0.6923	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD7838	Discovery
0.6771	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD4252	Approved
0.6452	Remote Similarity	NPD7154	Phase 3
0.6444	Remote Similarity	NPD4271	Approved
0.6444	Remote Similarity	NPD4268	Approved
0.6421	Remote Similarity	NPD4249	Approved
0.6404	Remote Similarity	NPD8516	Approved
0.6404	Remote Similarity	NPD8513	Phase 3
0.6404	Remote Similarity	NPD8515	Approved
0.6404	Remote Similarity	NPD8517	Approved
0.6354	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4250	Approved
0.6344	Remote Similarity	NPD4269	Approved
0.6344	Remote Similarity	NPD4270	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.6333	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4820	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6296	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.625	Remote Similarity	NPD69	Approved
0.625	Remote Similarity	NPD9119	Approved
0.625	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD5786	Approved
0.619	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7839	Suspended
0.6134	Remote Similarity	NPD8074	Phase 3
0.6125	Remote Similarity	NPD9118	Approved
0.6105	Remote Similarity	NPD5362	Discontinued
0.61	Remote Similarity	NPD7637	Suspended
0.6071	Remote Similarity	NPD3197	Phase 1
0.6064	Remote Similarity	NPD5369	Approved
0.6061	Remote Similarity	NPD5370	Suspended
0.6049	Remote Similarity	NPD6109	Phase 1
0.6049	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5778	Approved
0.604	Remote Similarity	NPD5779	Approved
0.6017	Remote Similarity	NPD7829	Approved
0.6017	Remote Similarity	NPD7642	Approved
0.6017	Remote Similarity	NPD7830	Approved
0.5974	Remote Similarity	NPD6927	Phase 3
0.5941	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5332	Approved
0.5938	Remote Similarity	NPD6110	Phase 1
0.5938	Remote Similarity	NPD5331	Approved
0.5914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1695	Approved
0.5895	Remote Similarity	NPD4790	Discontinued
0.5893	Remote Similarity	NPD2204	Approved
0.5849	Remote Similarity	NPD6648	Approved
0.5849	Remote Similarity	NPD7639	Approved
0.5849	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6435	Approved
0.5827	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5282	Discontinued
0.5816	Remote Similarity	NPD1694	Approved
0.5772	Remote Similarity	NPD7319	Approved
0.5755	Remote Similarity	NPD7638	Approved
0.5752	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6101	Approved
0.5743	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7641	Discontinued
0.5714	Remote Similarity	NPD9120	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6412	Phase 2
0.5656	Remote Similarity	NPD8451	Approved
0.5656	Remote Similarity	NPD7507	Approved
0.5641	Remote Similarity	NPD7500	Approved
0.5631	Remote Similarity	NPD6411	Approved
0.5625	Remote Similarity	NPD5368	Approved
0.561	Remote Similarity	NPD8448	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