NPASS Compound

Structure

CID24733 OpenBabel06191715352D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.7601 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 13 24 2 0 0 0 0 14 1 1 6 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 6 0 0 0 17 5 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 6 0 0 0 19 21 1 6 0 0 0 20 22 1 6 0 0 0 21 2 1 6 0 0 0 22 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.27
Volume:	363.006
LogP:	4.67
LogD:	4.035
LogS:	-4.878
# Rotatable Bonds:	1
TPSA:	24.39
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	5.362
Fsp3:	0.864
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:	-4.701
MDCK Permeability:	1.1046090548916254e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.788
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.792
Plasma Protein Binding (PPB):	75.50201416015625%
Volume Distribution (VD):	1.429
Pgp-substrate:	13.040020942687988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.493
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	9.997
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.557
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.455
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.948
Carcinogencity:	0.695
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC24733

Natural Product ID:	NPC24733
*Common Name:**	Conessidine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CHMBCKMSXBNZSX-QLPKIABKSA-N
Standard InCHI:	InChI=1S/C22H34N2/c1-14-18-6-7-20-17-5-4-15-12-16(23-3)8-10-21(15,2)19(17)9-11-22(18,20)13-24-14/h4,13-14,16-20,23H,5-12H2,1-3H3/t14-,16-,17+,18+,19-,20-,21-,22-/m0/s1
SMILES:	CN[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]24[C@H]3CC[C@@H]4[C@@H](N=C2)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2262847
PubChem CID:	22214027
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000091] Pyrrolines

*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
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1602299]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16880667]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21147	Anisocycla grandidieri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13898	Typhonium flagelliforme	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1421	Papaver hybrid	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8641	Haemanthus tigrinus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3577	Bambusa tulda	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11334	Rubus moluccanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10834	Protea compacta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11073	Alpinia formosana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9025	Croton balsamifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13993	Dimelaena thysanota	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12589	Heliotropium angiospermum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO805	Myrmicaria opaciventris	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14603	Flindersia australis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	2.29	ug.mL-1	PMID[568753]

☑ 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 NPC24733 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	357
0.1-0.2	8918
0.2-0.3	17670
0.3-0.4	12559
0.4-0.5	2768
0.5-0.6	321
0.6-0.7	80
0.7-0.8	16
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC283277
0.8554	High Similarity	NPC329782
0.8554	High Similarity	NPC118329
0.8554	High Similarity	NPC152039
0.8452	Intermediate Similarity	NPC472312
0.8434	Intermediate Similarity	NPC12035
0.8125	Intermediate Similarity	NPC21773
0.8095	Intermediate Similarity	NPC211322
0.7952	Intermediate Similarity	NPC7214
0.7927	Intermediate Similarity	NPC476904
0.7907	Intermediate Similarity	NPC474122
0.7683	Intermediate Similarity	NPC265789
0.7604	Intermediate Similarity	NPC167419
0.7347	Intermediate Similarity	NPC140685
0.7333	Intermediate Similarity	NPC171639
0.7283	Intermediate Similarity	NPC166458
0.7222	Intermediate Similarity	NPC215474
0.7209	Intermediate Similarity	NPC125828
0.7174	Intermediate Similarity	NPC152684
0.7143	Intermediate Similarity	NPC21667
0.7126	Intermediate Similarity	NPC259989
0.7126	Intermediate Similarity	NPC174803
0.7087	Intermediate Similarity	NPC230677
0.6979	Remote Similarity	NPC84171
0.6951	Remote Similarity	NPC469970
0.6857	Remote Similarity	NPC25340
0.6842	Remote Similarity	NPC43308
0.6829	Remote Similarity	NPC53276
0.6796	Remote Similarity	NPC58200
0.6768	Remote Similarity	NPC476754
0.6739	Remote Similarity	NPC257962
0.6733	Remote Similarity	NPC474164
0.6731	Remote Similarity	NPC474583
0.6729	Remote Similarity	NPC175585
0.6707	Remote Similarity	NPC472544
0.6706	Remote Similarity	NPC271640
0.6667	Remote Similarity	NPC476752
0.6667	Remote Similarity	NPC476753
0.6635	Remote Similarity	NPC152718
0.6635	Remote Similarity	NPC471083
0.6632	Remote Similarity	NPC147513
0.6632	Remote Similarity	NPC75810
0.6604	Remote Similarity	NPC233256
0.6604	Remote Similarity	NPC195841
0.6602	Remote Similarity	NPC135799
0.6562	Remote Similarity	NPC157479
0.6562	Remote Similarity	NPC56107
0.6556	Remote Similarity	NPC476308
0.6545	Remote Similarity	NPC56796
0.6531	Remote Similarity	NPC249312
0.6526	Remote Similarity	NPC471867
0.6514	Remote Similarity	NPC472313
0.6476	Remote Similarity	NPC226509
0.6476	Remote Similarity	NPC176012
0.6476	Remote Similarity	NPC50815
0.6471	Remote Similarity	NPC37792
0.6455	Remote Similarity	NPC474459
0.6455	Remote Similarity	NPC79238
0.6442	Remote Similarity	NPC275686
0.6437	Remote Similarity	NPC184919
0.6437	Remote Similarity	NPC138409
0.6396	Remote Similarity	NPC474452
0.6389	Remote Similarity	NPC169375
0.6386	Remote Similarity	NPC219621
0.6381	Remote Similarity	NPC118275
0.6355	Remote Similarity	NPC469958
0.6341	Remote Similarity	NPC21781
0.633	Remote Similarity	NPC159367
0.6321	Remote Similarity	NPC247060
0.6316	Remote Similarity	NPC471868
0.6311	Remote Similarity	NPC476903
0.6292	Remote Similarity	NPC476329
0.6289	Remote Similarity	NPC311769
0.6289	Remote Similarity	NPC182106
0.6275	Remote Similarity	NPC280710
0.6275	Remote Similarity	NPC243985
0.6265	Remote Similarity	NPC311809
0.6262	Remote Similarity	NPC90538
0.625	Remote Similarity	NPC184033
0.625	Remote Similarity	NPC124384
0.625	Remote Similarity	NPC245223
0.622	Remote Similarity	NPC472830
0.6211	Remote Similarity	NPC90150
0.6196	Remote Similarity	NPC25110
0.617	Remote Similarity	NPC57599
0.6132	Remote Similarity	NPC239768
0.6132	Remote Similarity	NPC128698
0.6126	Remote Similarity	NPC85001
0.6126	Remote Similarity	NPC147835
0.6126	Remote Similarity	NPC253645
0.6126	Remote Similarity	NPC95920
0.6118	Remote Similarity	NPC145715
0.61	Remote Similarity	NPC259252
0.6095	Remote Similarity	NPC240650
0.6071	Remote Similarity	NPC317778
0.6067	Remote Similarity	NPC472831
0.6055	Remote Similarity	NPC119329
0.6049	Remote Similarity	NPC123194
0.6047	Remote Similarity	NPC473959
0.6038	Remote Similarity	NPC91604
0.6024	Remote Similarity	NPC469769
0.6019	Remote Similarity	NPC93027
0.6018	Remote Similarity	NPC66862
0.6	Remote Similarity	NPC55462
0.6	Remote Similarity	NPC86906
0.6	Remote Similarity	NPC472543
0.6	Remote Similarity	NPC247220
0.5979	Remote Similarity	NPC224072
0.5963	Remote Similarity	NPC98765
0.5952	Remote Similarity	NPC472827
0.5932	Remote Similarity	NPC35037
0.593	Remote Similarity	NPC474086
0.5929	Remote Similarity	NPC72753
0.5929	Remote Similarity	NPC472359
0.5926	Remote Similarity	NPC474582
0.5909	Remote Similarity	NPC474456
0.5905	Remote Similarity	NPC311164
0.5905	Remote Similarity	NPC272732
0.5904	Remote Similarity	NPC474415
0.5904	Remote Similarity	NPC475696
0.5904	Remote Similarity	NPC474528
0.5902	Remote Similarity	NPC237286
0.5843	Remote Similarity	NPC476135
0.5833	Remote Similarity	NPC324944
0.5818	Remote Similarity	NPC241879
0.5818	Remote Similarity	NPC45365
0.5818	Remote Similarity	NPC293299
0.5816	Remote Similarity	NPC39966
0.5812	Remote Similarity	NPC304646
0.5812	Remote Similarity	NPC28280
0.5794	Remote Similarity	NPC140300
0.5784	Remote Similarity	NPC34754
0.5784	Remote Similarity	NPC324405
0.5765	Remote Similarity	NPC474420
0.5765	Remote Similarity	NPC474455
0.5765	Remote Similarity	NPC152211
0.5765	Remote Similarity	NPC28755
0.5765	Remote Similarity	NPC474454
0.5765	Remote Similarity	NPC475716
0.5747	Remote Similarity	NPC477740
0.5714	Remote Similarity	NPC470369
0.5714	Remote Similarity	NPC477292
0.5714	Remote Similarity	NPC173815
0.5714	Remote Similarity	NPC470370
0.5714	Remote Similarity	NPC474695
0.5714	Remote Similarity	NPC474457
0.5696	Remote Similarity	NPC22765
0.5696	Remote Similarity	NPC17518
0.569	Remote Similarity	NPC80834
0.569	Remote Similarity	NPC469968
0.5682	Remote Similarity	NPC476682
0.5667	Remote Similarity	NPC176107
0.5664	Remote Similarity	NPC476756
0.5664	Remote Similarity	NPC244982
0.5664	Remote Similarity	NPC46981
0.5663	Remote Similarity	NPC469770
0.5652	Remote Similarity	NPC120167
0.5652	Remote Similarity	NPC473442
0.5636	Remote Similarity	NPC34193
0.5636	Remote Similarity	NPC474001
0.5625	Remote Similarity	NPC212874
0.5625	Remote Similarity	NPC200129
0.561	Remote Similarity	NPC472828
0.561	Remote Similarity	NPC127944
0.5604	Remote Similarity	NPC20610
0.56	Remote Similarity	NPC161344

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 NPC24733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	830
0.2-0.3	4690
0.3-0.4	2901
0.4-0.5	456
0.5-0.6	56
0.6-0.7	5
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
0.7059	Intermediate Similarity	NPD5365	Phase 2
0.6744	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6939	Phase 2
0.6275	Remote Similarity	NPD5771	Approved
0.5962	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7335	Phase 2
0.5826	Remote Similarity	NPD7336	Phase 2
0.5826	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.566	Remote Similarity	NPD3980	Approved
0.566	Remote Similarity	NPD3982	Approved
0.5614	Remote Similarity	NPD2207	Approved
0.5614	Remote Similarity	NPD2206	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