NPASS Compound

Structure

NPC291619 OpenBabel07101719252D 26 26 0 0 0 0 0 0 0 0999 V2000 7.9170 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9115 -3.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3292 -2.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3183 -2.6089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3347 -2.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7305 -1.7999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 -2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7360 -1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7524 -2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1482 -1.0954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 -1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5604 -0.2864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 -1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9726 0.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9781 0.4181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3903 1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3958 1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8080 1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9890 0.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 3 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 19 22 2 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.27
Volume:	410.996
LogP:	7.075
LogD:	3.613
LogS:	-5.764
# Rotatable Bonds:	16
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	2.43
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.003
MDCK Permeability:	1.935323962243274e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	97.23062896728516%
Volume Distribution (VD):	1.885
Pgp-substrate:	0.6915987730026245%

ADMET: Metabolism

CYP1A2-inhibitor:	0.319
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.392
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	3.335
Half-life (T1/2):	0.567

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.131
Skin Sensitization:	0.942
Carcinogencity:	0.172
Eye Corrosion:	0.69
Eye Irritation:	0.945
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC291619

Natural Product ID:	NPC291619
*Common Name:**	19-(2-Furyl)Nonadeca-5-Ynoic Acid
IUPAC Name:	19-(furan-2-yl)nonadec-5-ynoic acid
Synonyms:
Standard InCHIKey:	ONOHKAVRSPRSMW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H36O3/c24-23(25)20-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-18-22-19-17-21-26-22/h17,19,21H,1-9,11,13-16,18,20H2,(H,24,25)
SMILES:	OC(=O)CCCC#CCCCCCCCCCCCCCc1ccco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499558
PubChem CID:	11566680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	19.4	ug.mL-1	PMID[547541]

☑ 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 NPC291619 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	261
0.1-0.2	2129
0.2-0.3	6141
0.3-0.4	11854
0.4-0.5	7525
0.5-0.6	10648
0.6-0.7	3819
0.7-0.8	288
0.8-0.85	22
0.85-0.9	5
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254958
0.964	High Similarity	NPC476014
0.964	High Similarity	NPC474987
0.964	High Similarity	NPC476031
0.8957	High Similarity	NPC76844
0.887	High Similarity	NPC11821
0.8739	High Similarity	NPC42471
0.8644	High Similarity	NPC187547
0.8644	High Similarity	NPC21831
0.8403	Intermediate Similarity	NPC144745
0.8403	Intermediate Similarity	NPC208906
0.8374	Intermediate Similarity	NPC118853
0.8288	Intermediate Similarity	NPC156768
0.825	Intermediate Similarity	NPC312525
0.825	Intermediate Similarity	NPC217180
0.8235	Intermediate Similarity	NPC205523
0.8151	Intermediate Similarity	NPC292036
0.8115	Intermediate Similarity	NPC473969
0.8099	Intermediate Similarity	NPC227660
0.8095	Intermediate Similarity	NPC474260
0.8095	Intermediate Similarity	NPC329694
0.8095	Intermediate Similarity	NPC329922
0.8095	Intermediate Similarity	NPC81912
0.8031	Intermediate Similarity	NPC474830
0.8016	Intermediate Similarity	NPC71274
0.8016	Intermediate Similarity	NPC474829
0.8016	Intermediate Similarity	NPC75557
0.8	Intermediate Similarity	NPC476351
0.8	Intermediate Similarity	NPC473982
0.7983	Intermediate Similarity	NPC26157
0.7983	Intermediate Similarity	NPC1811
0.797	Intermediate Similarity	NPC170604
0.797	Intermediate Similarity	NPC215109
0.7969	Intermediate Similarity	NPC474438
0.7969	Intermediate Similarity	NPC474279
0.7951	Intermediate Similarity	NPC131801
0.7937	Intermediate Similarity	NPC243269
0.7928	Intermediate Similarity	NPC146316
0.7917	Intermediate Similarity	NPC311987
0.7899	Intermediate Similarity	NPC105249
0.7891	Intermediate Similarity	NPC476016
0.7857	Intermediate Similarity	NPC475818
0.7852	Intermediate Similarity	NPC202260
0.784	Intermediate Similarity	NPC474136
0.7815	Intermediate Similarity	NPC229387
0.7797	Intermediate Similarity	NPC473356
0.7797	Intermediate Similarity	NPC471521
0.7795	Intermediate Similarity	NPC188377
0.7795	Intermediate Similarity	NPC65735
0.7794	Intermediate Similarity	NPC148374
0.7787	Intermediate Similarity	NPC28054
0.7786	Intermediate Similarity	NPC475092
0.7778	Intermediate Similarity	NPC270807
0.7778	Intermediate Similarity	NPC289911
0.7778	Intermediate Similarity	NPC272487
0.7778	Intermediate Similarity	NPC283284
0.7778	Intermediate Similarity	NPC174915
0.776	Intermediate Similarity	NPC474817
0.7752	Intermediate Similarity	NPC473355
0.7752	Intermediate Similarity	NPC471573
0.7752	Intermediate Similarity	NPC471501
0.7752	Intermediate Similarity	NPC471554
0.7748	Intermediate Similarity	NPC233791
0.7744	Intermediate Similarity	NPC106247
0.7742	Intermediate Similarity	NPC206007
0.7739	Intermediate Similarity	NPC217226
0.7734	Intermediate Similarity	NPC471559
0.7731	Intermediate Similarity	NPC209111
0.7731	Intermediate Similarity	NPC177331
0.7712	Intermediate Similarity	NPC219969
0.7704	Intermediate Similarity	NPC473268
0.7687	Intermediate Similarity	NPC159786
0.7686	Intermediate Similarity	NPC22678
0.768	Intermediate Similarity	NPC137710
0.768	Intermediate Similarity	NPC244293
0.768	Intermediate Similarity	NPC67345
0.768	Intermediate Similarity	NPC4898
0.768	Intermediate Similarity	NPC244862
0.7674	Intermediate Similarity	NPC138139
0.7674	Intermediate Similarity	NPC46536
0.7661	Intermediate Similarity	NPC107482
0.7652	Intermediate Similarity	NPC17681
0.7652	Intermediate Similarity	NPC477645
0.7638	Intermediate Similarity	NPC477967
0.763	Intermediate Similarity	NPC303217
0.7627	Intermediate Similarity	NPC298087
0.7615	Intermediate Similarity	NPC83178
0.76	Intermediate Similarity	NPC243704
0.7597	Intermediate Similarity	NPC471074
0.7597	Intermediate Similarity	NPC221798
0.7597	Intermediate Similarity	NPC473885
0.7594	Intermediate Similarity	NPC45358
0.7594	Intermediate Similarity	NPC97740
0.7581	Intermediate Similarity	NPC328451
0.7574	Intermediate Similarity	NPC307401
0.7574	Intermediate Similarity	NPC278832
0.7574	Intermediate Similarity	NPC64157
0.7559	Intermediate Similarity	NPC79557
0.7559	Intermediate Similarity	NPC1848
0.7557	Intermediate Similarity	NPC112706
0.7557	Intermediate Similarity	NPC207294
0.7557	Intermediate Similarity	NPC329707
0.7556	Intermediate Similarity	NPC265793
0.7538	Intermediate Similarity	NPC216810
0.7537	Intermediate Similarity	NPC474425
0.7537	Intermediate Similarity	NPC474407
0.7537	Intermediate Similarity	NPC474426
0.7536	Intermediate Similarity	NPC201370
0.7536	Intermediate Similarity	NPC473983
0.7519	Intermediate Similarity	NPC136340
0.7519	Intermediate Similarity	NPC89133
0.75	Intermediate Similarity	NPC263870
0.75	Intermediate Similarity	NPC473379
0.75	Intermediate Similarity	NPC471549
0.7481	Intermediate Similarity	NPC137570
0.7481	Intermediate Similarity	NPC141059
0.7464	Intermediate Similarity	NPC107571
0.7463	Intermediate Similarity	NPC15083
0.746	Intermediate Similarity	NPC293424
0.7447	Intermediate Similarity	NPC218712
0.7447	Intermediate Similarity	NPC267004
0.7447	Intermediate Similarity	NPC261733
0.7447	Intermediate Similarity	NPC307346
0.7444	Intermediate Similarity	NPC238309
0.7442	Intermediate Similarity	NPC291189
0.7442	Intermediate Similarity	NPC69403
0.7442	Intermediate Similarity	NPC16922
0.744	Intermediate Similarity	NPC45536
0.7422	Intermediate Similarity	NPC97566
0.7413	Intermediate Similarity	NPC308799
0.7407	Intermediate Similarity	NPC293253
0.7405	Intermediate Similarity	NPC83301
0.7391	Intermediate Similarity	NPC130976
0.7391	Intermediate Similarity	NPC472376
0.7388	Intermediate Similarity	NPC183348
0.7388	Intermediate Similarity	NPC282230
0.7379	Intermediate Similarity	NPC212257
0.7368	Intermediate Similarity	NPC59502
0.7361	Intermediate Similarity	NPC93666
0.7361	Intermediate Similarity	NPC61284
0.7361	Intermediate Similarity	NPC113428
0.7348	Intermediate Similarity	NPC474476
0.7348	Intermediate Similarity	NPC246392
0.7348	Intermediate Similarity	NPC290955
0.7333	Intermediate Similarity	NPC471817
0.7333	Intermediate Similarity	NPC470976
0.7333	Intermediate Similarity	NPC104854
0.7333	Intermediate Similarity	NPC470977
0.7333	Intermediate Similarity	NPC196979
0.7328	Intermediate Similarity	NPC179354
0.7313	Intermediate Similarity	NPC66246
0.7313	Intermediate Similarity	NPC170546
0.7305	Intermediate Similarity	NPC263337
0.7302	Intermediate Similarity	NPC79202
0.7302	Intermediate Similarity	NPC470860
0.7302	Intermediate Similarity	NPC59035
0.7299	Intermediate Similarity	NPC14650
0.7293	Intermediate Similarity	NPC279877
0.7293	Intermediate Similarity	NPC26532
0.7293	Intermediate Similarity	NPC161322
0.7287	Intermediate Similarity	NPC115859
0.728	Intermediate Similarity	NPC252004
0.7279	Intermediate Similarity	NPC470740
0.7279	Intermediate Similarity	NPC294511
0.7279	Intermediate Similarity	NPC121615
0.7273	Intermediate Similarity	NPC247221
0.7273	Intermediate Similarity	NPC74612
0.7273	Intermediate Similarity	NPC23086
0.7266	Intermediate Similarity	NPC264976
0.726	Intermediate Similarity	NPC228842
0.7254	Intermediate Similarity	NPC254198
0.7252	Intermediate Similarity	NPC477965
0.7252	Intermediate Similarity	NPC477038
0.7246	Intermediate Similarity	NPC204592
0.7244	Intermediate Similarity	NPC240664
0.7239	Intermediate Similarity	NPC50583
0.7239	Intermediate Similarity	NPC208389
0.7239	Intermediate Similarity	NPC2596
0.7236	Intermediate Similarity	NPC476003
0.7231	Intermediate Similarity	NPC317217
0.7222	Intermediate Similarity	NPC150895
0.7222	Intermediate Similarity	NPC104924
0.7222	Intermediate Similarity	NPC51345
0.7218	Intermediate Similarity	NPC319140
0.7218	Intermediate Similarity	NPC95567
0.7218	Intermediate Similarity	NPC184391
0.7218	Intermediate Similarity	NPC475236
0.7209	Intermediate Similarity	NPC474874
0.7209	Intermediate Similarity	NPC246214
0.7185	Intermediate Similarity	NPC939
0.7176	Intermediate Similarity	NPC311219
0.7172	Intermediate Similarity	NPC71821
0.7165	Intermediate Similarity	NPC316062
0.7163	Intermediate Similarity	NPC282973
0.7154	Intermediate Similarity	NPC234639
0.7153	Intermediate Similarity	NPC56731
0.7143	Intermediate Similarity	NPC470858
0.7143	Intermediate Similarity	NPC52035
0.7133	Intermediate Similarity	NPC41880
0.7132	Intermediate Similarity	NPC61779

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 NPC291619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1141
0.2-0.3	2124
0.3-0.4	2834
0.4-0.5	1819
0.5-0.6	789
0.6-0.7	205
0.7-0.8	7
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
0.7661	Intermediate Similarity	NPD9092	Discovery
0.7591	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD1241	Discontinued
0.7176	Intermediate Similarity	NPD9717	Approved
0.7054	Intermediate Similarity	NPD1894	Discontinued
0.7015	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5647	Approved
0.695	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD9545	Approved
0.6901	Remote Similarity	NPD1551	Phase 2
0.6889	Remote Similarity	NPD2797	Approved
0.6889	Remote Similarity	NPD6362	Approved
0.6853	Remote Similarity	NPD2344	Approved
0.6849	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7440	Discontinued
0.6838	Remote Similarity	NPD1019	Discontinued
0.6828	Remote Similarity	NPD4628	Phase 3
0.6825	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3134	Approved
0.6769	Remote Similarity	NPD9493	Approved
0.6763	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3268	Approved
0.6757	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6355	Discontinued
0.6736	Remote Similarity	NPD6005	Phase 3
0.6736	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6004	Phase 3
0.6736	Remote Similarity	NPD6002	Phase 3
0.6715	Remote Similarity	NPD2798	Approved
0.6713	Remote Similarity	NPD4308	Phase 3
0.6711	Remote Similarity	NPD6273	Approved
0.6692	Remote Similarity	NPD1778	Approved
0.6689	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD454	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6643	Remote Similarity	NPD6798	Discontinued
0.6643	Remote Similarity	NPD411	Approved
0.6642	Remote Similarity	NPD3496	Discontinued
0.6621	Remote Similarity	NPD2346	Discontinued
0.662	Remote Similarity	NPD447	Suspended
0.662	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3750	Approved
0.6599	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6233	Phase 2
0.6596	Remote Similarity	NPD4062	Phase 3
0.6593	Remote Similarity	NPD1535	Discovery
0.6587	Remote Similarity	NPD1358	Approved
0.6569	Remote Similarity	NPD1876	Approved
0.656	Remote Similarity	NPD9697	Approved
0.6557	Remote Similarity	NPD1238	Approved
0.6556	Remote Similarity	NPD5403	Approved
0.6554	Remote Similarity	NPD3887	Approved
0.6554	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD2935	Discontinued
0.6549	Remote Similarity	NPD4307	Phase 2
0.6547	Remote Similarity	NPD9494	Approved
0.6535	Remote Similarity	NPD2182	Approved
0.6533	Remote Similarity	NPD5401	Approved
0.6531	Remote Similarity	NPD1243	Approved
0.6525	Remote Similarity	NPD3764	Approved
0.6525	Remote Similarity	NPD9365	Approved
0.6522	Remote Similarity	NPD3266	Approved
0.6522	Remote Similarity	NPD3267	Approved
0.6516	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7819	Suspended
0.6503	Remote Similarity	NPD1933	Approved
0.65	Remote Similarity	NPD2614	Approved
0.6494	Remote Similarity	NPD7411	Suspended
0.6493	Remote Similarity	NPD5585	Approved
0.6486	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD3748	Approved
0.6471	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1549	Phase 2
0.6458	Remote Similarity	NPD6653	Approved
0.6449	Remote Similarity	NPD3225	Approved
0.6444	Remote Similarity	NPD17	Approved
0.6438	Remote Similarity	NPD2796	Approved
0.6438	Remote Similarity	NPD4477	Approved
0.6438	Remote Similarity	NPD4476	Approved
0.6429	Remote Similarity	NPD6599	Discontinued
0.6424	Remote Similarity	NPD6765	Approved
0.6424	Remote Similarity	NPD6764	Approved
0.6412	Remote Similarity	NPD9069	Phase 1
0.6406	Remote Similarity	NPD2684	Approved
0.6397	Remote Similarity	NPD3847	Discontinued
0.6395	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1471	Phase 3
0.6395	Remote Similarity	NPD2353	Approved
0.6395	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7075	Discontinued
0.6392	Remote Similarity	NPD3749	Approved
0.6382	Remote Similarity	NPD5049	Phase 3
0.6376	Remote Similarity	NPD7003	Approved
0.637	Remote Similarity	NPD7033	Discontinued
0.6369	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8032	Phase 2
0.6364	Remote Similarity	NPD7458	Discontinued
0.6364	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD919	Approved
0.6351	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5958	Discontinued
0.634	Remote Similarity	NPD3873	Phase 3
0.634	Remote Similarity	NPD3869	Phase 3
0.6338	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7843	Approved
0.6336	Remote Similarity	NPD5535	Approved
0.6331	Remote Similarity	NPD8434	Phase 2
0.6331	Remote Similarity	NPD1283	Approved
0.6329	Remote Similarity	NPD7768	Phase 2
0.6328	Remote Similarity	NPD9267	Approved
0.6328	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD9263	Approved
0.6328	Remote Similarity	NPD9264	Approved
0.6325	Remote Similarity	NPD6559	Discontinued
0.6319	Remote Similarity	NPD1240	Approved
0.6316	Remote Similarity	NPD4661	Approved
0.6316	Remote Similarity	NPD4662	Approved
0.6309	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD9266	Approved
0.6279	Remote Similarity	NPD74	Approved
0.6276	Remote Similarity	NPD4618	Approved
0.6276	Remote Similarity	NPD4622	Approved
0.6272	Remote Similarity	NPD6784	Approved
0.6272	Remote Similarity	NPD6785	Approved
0.6267	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4110	Phase 3
0.6267	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD5402	Approved
0.6259	Remote Similarity	NPD4359	Approved
0.6259	Remote Similarity	NPD1510	Phase 2
0.6258	Remote Similarity	NPD3226	Approved
0.625	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.625	Remote Similarity	NPD968	Approved
0.625	Remote Similarity	NPD5691	Approved
0.625	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4534	Discontinued
0.6242	Remote Similarity	NPD6280	Approved
0.6242	Remote Similarity	NPD6279	Approved
0.6242	Remote Similarity	NPD6801	Discontinued
0.6242	Remote Similarity	NPD7577	Discontinued
0.6242	Remote Similarity	NPD6844	Discontinued
0.6241	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6808	Phase 2
0.6233	Remote Similarity	NPD1607	Approved
0.6232	Remote Similarity	NPD422	Phase 1
0.6226	Remote Similarity	NPD3882	Suspended
0.6224	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5163	Phase 2
0.6224	Remote Similarity	NPD7095	Approved
0.622	Remote Similarity	NPD164	Approved
0.6216	Remote Similarity	NPD2240	Approved
0.6216	Remote Similarity	NPD2239	Approved
0.6216	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD196	Phase 1
0.6212	Remote Similarity	NPD821	Approved
0.6209	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4626	Approved
0.6203	Remote Similarity	NPD5761	Phase 2
0.6203	Remote Similarity	NPD5760	Phase 2
0.6202	Remote Similarity	NPD290	Approved
0.6194	Remote Similarity	NPD7157	Approved
0.619	Remote Similarity	NPD5688	Approved
0.619	Remote Similarity	NPD5689	Approved
0.619	Remote Similarity	NPD291	Approved
0.619	Remote Similarity	NPD7097	Phase 1
0.6182	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD958	Approved
0.6169	Remote Similarity	NPD2186	Approved
0.6167	Remote Similarity	NPD9256	Approved
0.6167	Remote Similarity	NPD9258	Approved
0.6164	Remote Similarity	NPD3817	Phase 2
0.6164	Remote Similarity	NPD1184	Approved
0.6164	Remote Similarity	NPD2296	Approved
0.6159	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2649	Approved
0.6154	Remote Similarity	NPD2651	Approved
0.6154	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6647	Phase 2
0.6142	Remote Similarity	NPD9261	Approved
0.6133	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD1670	Discontinued
0.6129	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4868	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