NPASS Compound

Structure

NPC71274 OpenBabel07101718322D 29 30 0 0 1 0 0 0 0 0999 V2000 4.4945 4.4347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0055 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7626 -2.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 3.5686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0823 0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0334 0.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0823 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9945 3.5686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 1.8366 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0334 1.4706 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 18 1 0 0 0 0 2 19 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 20 3 1 6 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	440.549
LogP:	5.463
LogD:	4.857
LogS:	-4.645
# Rotatable Bonds:	11
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	3.463
Fsp3:	0.44
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:	-4.824
MDCK Permeability:	2.638650948938448e-05
Pgp-inhibitor:	0.567
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.447
20% Bioavailability (F20%):	0.162
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	98.2995376586914%
Volume Distribution (VD):	3.052
Pgp-substrate:	0.6577497124671936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.504
CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.7
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	5.913
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.487
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.839
Skin Sensitization:	0.647
Carcinogencity:	0.684
Eye Corrosion:	0.004
Eye Irritation:	0.44
Respiratory Toxicity:	0.814

Download Data

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

Natural Product: NPC71274

Natural Product ID:	NPC71274
*Common Name:**	(8E,13Z,18R,20Z)-Strobilinin
IUPAC Name:	(5Z)-5-[(2R,5Z,9E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-5,9-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:	(8E,13Z,18R,20Z)-Strobilinin
Standard InCHIKey:	IBYNQQZMPJJRJJ-QBZUXMSOSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h9-10,14-17,20,26H,5-8,11-13H2,1-4H3/b18-10-,19-9+,23-16-/t20-/m1/s1
SMILES:	C/C(=C/CC[C@@H](C)/C=C1/C(=C(C)C(=O)O1)O)/CC/C=C(C)/CCCc1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463350
PubChem CID:	54685522
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

☑ 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	5
IC50	2
Others	3

Activity Type	# Activity
Cell Line	5
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	10.5	ug ml-1	PMID[559640]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	7.5	ug ml-1	PMID[559640]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.8	ug ml-1	PMID[559640]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	8.7	ug ml-1	PMID[559640]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[559640]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	30.0	%	PMID[559640]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	60.0	%	PMID[559640]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	100.0	%	PMID[559640]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[559640]
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[559640]

☑ 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 NPC71274 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	232
0.1-0.2	1208
0.2-0.3	3763
0.3-0.4	9151
0.4-0.5	10836
0.5-0.6	9747
0.6-0.7	7107
0.7-0.8	557
0.8-0.85	44
0.85-0.9	29
0.9-0.95	11
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC75557
0.9829	High Similarity	NPC476351
0.975	High Similarity	NPC474438
0.975	High Similarity	NPC474279
0.9748	High Similarity	NPC329694
0.9748	High Similarity	NPC81912
0.9748	High Similarity	NPC329922
0.9748	High Similarity	NPC474260
0.9744	High Similarity	NPC289911
0.9744	High Similarity	NPC283284
0.9658	High Similarity	NPC474136
0.9504	High Similarity	NPC476016
0.9496	High Similarity	NPC475818
0.9344	High Similarity	NPC474830
0.9322	High Similarity	NPC473969
0.9244	High Similarity	NPC474817
0.918	High Similarity	NPC474829
0.9153	High Similarity	NPC131801
0.9153	High Similarity	NPC208906
0.9153	High Similarity	NPC144745
0.907	High Similarity	NPC170604
0.907	High Similarity	NPC215109
0.8976	High Similarity	NPC97740
0.8915	High Similarity	NPC14650
0.8898	High Similarity	NPC17681
0.8871	High Similarity	NPC471559
0.8837	High Similarity	NPC288209
0.8828	High Similarity	NPC45358
0.8803	High Similarity	NPC105249
0.879	High Similarity	NPC243269
0.876	High Similarity	NPC474425
0.876	High Similarity	NPC474407
0.876	High Similarity	NPC474426
0.873	High Similarity	NPC471573
0.873	High Similarity	NPC471501
0.873	High Similarity	NPC137570
0.873	High Similarity	NPC473355
0.873	High Similarity	NPC471554
0.8729	High Similarity	NPC1811
0.8729	High Similarity	NPC26157
0.8629	High Similarity	NPC471549
0.8629	High Similarity	NPC473379
0.8561	High Similarity	NPC303217
0.8547	High Similarity	NPC471521
0.8547	High Similarity	NPC473356
0.8512	High Similarity	NPC28054
0.8492	Intermediate Similarity	NPC65735
0.8492	Intermediate Similarity	NPC118853
0.8492	Intermediate Similarity	NPC188377
0.8467	Intermediate Similarity	NPC218712
0.8467	Intermediate Similarity	NPC267004
0.8467	Intermediate Similarity	NPC307346
0.8467	Intermediate Similarity	NPC261733
0.8455	Intermediate Similarity	NPC21831
0.8455	Intermediate Similarity	NPC187547
0.84	Intermediate Similarity	NPC1848
0.8387	Intermediate Similarity	NPC4898
0.8372	Intermediate Similarity	NPC207294
0.8372	Intermediate Similarity	NPC112706
0.837	Intermediate Similarity	NPC107571
0.8359	Intermediate Similarity	NPC138139
0.8359	Intermediate Similarity	NPC46536
0.8333	Intermediate Similarity	NPC477967
0.8321	Intermediate Similarity	NPC89133
0.8319	Intermediate Similarity	NPC177331
0.8295	Intermediate Similarity	NPC83178
0.8281	Intermediate Similarity	NPC179354
0.8268	Intermediate Similarity	NPC16922
0.8226	Intermediate Similarity	NPC312525
0.8226	Intermediate Similarity	NPC217180
0.8222	Intermediate Similarity	NPC473268
0.8209	Intermediate Similarity	NPC159786
0.8203	Intermediate Similarity	NPC477965
0.8203	Intermediate Similarity	NPC477038
0.8189	Intermediate Similarity	NPC263870
0.8189	Intermediate Similarity	NPC317217
0.816	Intermediate Similarity	NPC243704
0.8145	Intermediate Similarity	NPC45536
0.812	Intermediate Similarity	NPC471545
0.812	Intermediate Similarity	NPC473344
0.812	Intermediate Similarity	NPC471817
0.812	Intermediate Similarity	NPC471544
0.8102	Intermediate Similarity	NPC90953
0.808	Intermediate Similarity	NPC227660
0.8077	Intermediate Similarity	NPC74612
0.8077	Intermediate Similarity	NPC23086
0.8065	Intermediate Similarity	NPC150895
0.8065	Intermediate Similarity	NPC205523
0.806	Intermediate Similarity	NPC470740
0.8045	Intermediate Similarity	NPC298190
0.8045	Intermediate Similarity	NPC136340
0.8016	Intermediate Similarity	NPC291619
0.8016	Intermediate Similarity	NPC254958
0.8015	Intermediate Similarity	NPC319140
0.8015	Intermediate Similarity	NPC95567
0.8	Intermediate Similarity	NPC80635
0.8	Intermediate Similarity	NPC476031
0.8	Intermediate Similarity	NPC476014
0.8	Intermediate Similarity	NPC254198
0.7985	Intermediate Similarity	NPC473982
0.7969	Intermediate Similarity	NPC79557
0.7958	Intermediate Similarity	NPC104924
0.7956	Intermediate Similarity	NPC186626
0.7955	Intermediate Similarity	NPC477123
0.7955	Intermediate Similarity	NPC477039
0.7955	Intermediate Similarity	NPC477966
0.7955	Intermediate Similarity	NPC477040
0.7941	Intermediate Similarity	NPC92941
0.7941	Intermediate Similarity	NPC476947
0.7926	Intermediate Similarity	NPC218838
0.7917	Intermediate Similarity	NPC234494
0.791	Intermediate Similarity	NPC475092
0.7887	Intermediate Similarity	NPC34056
0.7883	Intermediate Similarity	NPC146872
0.7877	Intermediate Similarity	NPC33938
0.7874	Intermediate Similarity	NPC293424
0.7868	Intermediate Similarity	NPC106247
0.7842	Intermediate Similarity	NPC202260
0.7836	Intermediate Similarity	NPC21460
0.7836	Intermediate Similarity	NPC476925
0.7826	Intermediate Similarity	NPC470742
0.782	Intermediate Similarity	NPC476917
0.782	Intermediate Similarity	NPC327527
0.7817	Intermediate Similarity	NPC137295
0.7803	Intermediate Similarity	NPC88403
0.7803	Intermediate Similarity	NPC216810
0.7801	Intermediate Similarity	NPC121158
0.7793	Intermediate Similarity	NPC125182
0.7793	Intermediate Similarity	NPC69647
0.7786	Intermediate Similarity	NPC130275
0.7786	Intermediate Similarity	NPC56197
0.7778	Intermediate Similarity	NPC255414
0.7778	Intermediate Similarity	NPC61788
0.7778	Intermediate Similarity	NPC477645
0.777	Intermediate Similarity	NPC236532
0.7769	Intermediate Similarity	NPC36255
0.7762	Intermediate Similarity	NPC195920
0.7761	Intermediate Similarity	NPC223063
0.7761	Intermediate Similarity	NPC208389
0.7761	Intermediate Similarity	NPC120836
0.7755	Intermediate Similarity	NPC294511
0.7755	Intermediate Similarity	NPC121615
0.7755	Intermediate Similarity	NPC474378
0.7755	Intermediate Similarity	NPC474219
0.7746	Intermediate Similarity	NPC22248
0.7746	Intermediate Similarity	NPC267632
0.7746	Intermediate Similarity	NPC476946
0.7744	Intermediate Similarity	NPC474476
0.7744	Intermediate Similarity	NPC290955
0.774	Intermediate Similarity	NPC470997
0.774	Intermediate Similarity	NPC228842
0.7727	Intermediate Similarity	NPC473885
0.7727	Intermediate Similarity	NPC230979
0.7727	Intermediate Similarity	NPC471074
0.7724	Intermediate Similarity	NPC7388
0.7717	Intermediate Similarity	NPC76844
0.7717	Intermediate Similarity	NPC474987
0.7708	Intermediate Similarity	NPC346
0.7703	Intermediate Similarity	NPC253201
0.7703	Intermediate Similarity	NPC237259
0.7703	Intermediate Similarity	NPC34421
0.7703	Intermediate Similarity	NPC302054
0.7703	Intermediate Similarity	NPC98206
0.7698	Intermediate Similarity	NPC42400
0.7698	Intermediate Similarity	NPC310830
0.7698	Intermediate Similarity	NPC64157
0.7698	Intermediate Similarity	NPC307401
0.7698	Intermediate Similarity	NPC278832
0.7692	Intermediate Similarity	NPC251865
0.7692	Intermediate Similarity	NPC476944
0.7687	Intermediate Similarity	NPC329707
0.7687	Intermediate Similarity	NPC279877
0.7687	Intermediate Similarity	NPC26532
0.768	Intermediate Similarity	NPC22678
0.7674	Intermediate Similarity	NPC137710
0.7667	Intermediate Similarity	NPC472778
0.7667	Intermediate Similarity	NPC472776
0.7667	Intermediate Similarity	NPC472777
0.766	Intermediate Similarity	NPC282973
0.766	Intermediate Similarity	NPC148374
0.7655	Intermediate Similarity	NPC71821
0.7655	Intermediate Similarity	NPC250228
0.7655	Intermediate Similarity	NPC471174
0.7655	Intermediate Similarity	NPC216755
0.7652	Intermediate Similarity	NPC83115
0.7651	Intermediate Similarity	NPC155939
0.7651	Intermediate Similarity	NPC141538
0.7651	Intermediate Similarity	NPC296807
0.7643	Intermediate Similarity	NPC476943
0.7643	Intermediate Similarity	NPC220094
0.7638	Intermediate Similarity	NPC11821
0.7635	Intermediate Similarity	NPC44577
0.7635	Intermediate Similarity	NPC472672
0.7635	Intermediate Similarity	NPC268905
0.763	Intermediate Similarity	NPC198904
0.7626	Intermediate Similarity	NPC204592
0.7623	Intermediate Similarity	NPC42471
0.7622	Intermediate Similarity	NPC110305
0.7622	Intermediate Similarity	NPC223415
0.7616	Intermediate Similarity	NPC472779

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 NPC71274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	969
0.2-0.3	1947
0.3-0.4	2750
0.4-0.5	1957
0.5-0.6	1019
0.6-0.7	280
0.7-0.8	11
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
0.7589	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7372	Intermediate Similarity	NPD6832	Phase 2
0.7357	Intermediate Similarity	NPD6355	Discontinued
0.7313	Intermediate Similarity	NPD9717	Approved
0.7226	Intermediate Similarity	NPD5647	Approved
0.7154	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7078	Intermediate Similarity	NPD5761	Phase 2
0.7078	Intermediate Similarity	NPD5760	Phase 2
0.7077	Intermediate Similarity	NPD1241	Discontinued
0.7063	Intermediate Similarity	NPD6653	Approved
0.7047	Intermediate Similarity	NPD6799	Approved
0.7029	Intermediate Similarity	NPD1203	Approved
0.7021	Intermediate Similarity	NPD3268	Approved
0.7008	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD7843	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6992	Remote Similarity	NPD9092	Discovery
0.6978	Remote Similarity	NPD1019	Discontinued
0.6977	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4062	Phase 3
0.6972	Remote Similarity	NPD6233	Phase 2
0.6966	Remote Similarity	NPD4308	Phase 3
0.6953	Remote Similarity	NPD2684	Approved
0.694	Remote Similarity	NPD9545	Approved
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9494	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6913	Remote Similarity	NPD3887	Approved
0.6913	Remote Similarity	NPD2354	Approved
0.6912	Remote Similarity	NPD3496	Discontinued
0.6908	Remote Similarity	NPD5403	Approved
0.6901	Remote Similarity	NPD2313	Discontinued
0.6883	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD1933	Approved
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD2344	Approved
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6005	Phase 3
0.6871	Remote Similarity	NPD6002	Phase 3
0.6867	Remote Similarity	NPD7440	Discontinued
0.6861	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD8434	Phase 2
0.6842	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD7157	Approved
0.6835	Remote Similarity	NPD7075	Discontinued
0.6818	Remote Similarity	NPD7458	Discontinued
0.6815	Remote Similarity	NPD1894	Discontinued
0.6812	Remote Similarity	NPD1608	Approved
0.6806	Remote Similarity	NPD4307	Phase 2
0.6803	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD920	Approved
0.6795	Remote Similarity	NPD6801	Discontinued
0.6791	Remote Similarity	NPD9493	Approved
0.6786	Remote Similarity	NPD6362	Approved
0.6786	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3266	Approved
0.6786	Remote Similarity	NPD3267	Approved
0.6783	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD411	Approved
0.6776	Remote Similarity	NPD5401	Approved
0.6769	Remote Similarity	NPD2067	Discontinued
0.6759	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2353	Approved
0.6757	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6765	Approved
0.6747	Remote Similarity	NPD6764	Approved
0.6747	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4110	Phase 3
0.6732	Remote Similarity	NPD5049	Phase 3
0.6715	Remote Similarity	NPD17	Approved
0.6714	Remote Similarity	NPD1876	Approved
0.6713	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7095	Approved
0.6711	Remote Similarity	NPD5958	Discontinued
0.671	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2182	Approved
0.6691	Remote Similarity	NPD1481	Phase 2
0.6691	Remote Similarity	NPD3972	Approved
0.669	Remote Similarity	NPD4060	Phase 1
0.6689	Remote Similarity	NPD2309	Approved
0.6689	Remote Similarity	NPD2239	Approved
0.6689	Remote Similarity	NPD2240	Approved
0.6687	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4662	Approved
0.6646	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2346	Discontinued
0.6642	Remote Similarity	NPD5585	Approved
0.6624	Remote Similarity	NPD7411	Suspended
0.6623	Remote Similarity	NPD7003	Approved
0.6623	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3750	Approved
0.6622	Remote Similarity	NPD7033	Discontinued
0.662	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1535	Discovery
0.6617	Remote Similarity	NPD5535	Approved
0.6604	Remote Similarity	NPD5402	Approved
0.66	Remote Similarity	NPD4534	Discontinued
0.6594	Remote Similarity	NPD1778	Approved
0.6588	Remote Similarity	NPD6784	Approved
0.6588	Remote Similarity	NPD6785	Approved
0.6584	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3140	Approved
0.6575	Remote Similarity	NPD3142	Approved
0.6562	Remote Similarity	NPD3882	Suspended
0.6562	Remote Similarity	NPD7768	Phase 2
0.6562	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1243	Approved
0.6547	Remote Similarity	NPD3847	Discontinued
0.6541	Remote Similarity	NPD7819	Suspended
0.6533	Remote Similarity	NPD1471	Phase 3
0.6533	Remote Similarity	NPD5763	Approved
0.6533	Remote Similarity	NPD5762	Approved
0.6531	Remote Similarity	NPD4618	Approved
0.6531	Remote Similarity	NPD4340	Discontinued
0.6531	Remote Similarity	NPD4622	Approved
0.6528	Remote Similarity	NPD2614	Approved
0.6519	Remote Similarity	NPD958	Approved
0.6519	Remote Similarity	NPD6677	Suspended
0.6513	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3748	Approved
0.6507	Remote Similarity	NPD8032	Phase 2
0.65	Remote Similarity	NPD3817	Phase 2
0.65	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1549	Phase 2
0.6489	Remote Similarity	NPD290	Approved
0.6485	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD1283	Approved
0.6479	Remote Similarity	NPD3225	Approved
0.6475	Remote Similarity	NPD4626	Approved
0.6474	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4477	Approved
0.6467	Remote Similarity	NPD2796	Approved
0.6467	Remote Similarity	NPD2438	Suspended
0.6467	Remote Similarity	NPD4476	Approved
0.6463	Remote Similarity	NPD2979	Phase 3
0.6462	Remote Similarity	NPD9697	Approved
0.6458	Remote Similarity	NPD454	Approved
0.6457	Remote Similarity	NPD1238	Approved
0.6452	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5688	Approved
0.6443	Remote Similarity	NPD5689	Approved
0.6439	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD987	Approved
0.6429	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.642	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3749	Approved
0.642	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD230	Phase 1
0.6408	Remote Similarity	NPD4359	Approved
0.6408	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD8166	Discontinued
0.6403	Remote Similarity	NPD5691	Approved
0.6402	Remote Similarity	NPD8127	Discontinued
0.6397	Remote Similarity	NPD2629	Approved
0.6392	Remote Similarity	NPD3226	Approved
0.6392	Remote Similarity	NPD2649	Approved
0.6392	Remote Similarity	NPD2651	Approved
0.6385	Remote Similarity	NPD164	Approved
0.6385	Remote Similarity	NPD5909	Discontinued
0.6383	Remote Similarity	NPD1281	Approved
0.6382	Remote Similarity	NPD2897	Discontinued
0.6382	Remote Similarity	NPD2424	Discontinued
0.6382	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD1934	Approved
0.6375	Remote Similarity	NPD7577	Discontinued
0.6369	Remote Similarity	NPD3873	Phase 3
0.6369	Remote Similarity	NPD3869	Phase 3
0.6364	Remote Similarity	NPD6808	Phase 2
0.6358	Remote Similarity	NPD6032	Approved
0.6358	Remote Similarity	NPD5712	Approved
0.6358	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD4380	Phase 2
0.6351	Remote Similarity	NPD1240	Approved
0.6346	Remote Similarity	NPD2534	Approved
0.6346	Remote Similarity	NPD2533	Approved
0.6346	Remote Similarity	NPD2532	Approved
0.6346	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD957	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