NPASS Compound

Structure

NPC474136 OpenBabel07101718292D 29 30 0 0 1 0 0 0 0 0999 V2000 -2.3022 5.8793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7473 5.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7520 1.6756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9202 4.7038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1796 3.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3473 2.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0067 4.2970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7293 4.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2841 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4518 3.9349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2661 3.0768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4338 2.5337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0724 0.8700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6656 -0.0435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4632 1.0392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1977 4.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6428 4.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1615 2.0823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3292 1.5392 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 -1.6092 -0.1691 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 -2.5873 0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6711 0.0610 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 1 0 0 0 0 10 18 2 0 0 0 0 11 19 2 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 1 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:	4.94
LogD:	4.542
LogS:	-4.731
# 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:	3.519
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:	-4.801
MDCK Permeability:	2.5653058401076123e-05
Pgp-inhibitor:	0.363
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.336
20% Bioavailability (F20%):	0.613
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	100.27391052246094%
Volume Distribution (VD):	3.734
Pgp-substrate:	0.5857941508293152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.421
CYP1A2-substrate:	0.876
CYP2C19-inhibitor:	0.663
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.805
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	7.415
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.636
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.522
Maximum Recommended Daily Dose:	0.642
Skin Sensitization:	0.792
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.329
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC474136

Natural Product ID:	NPC474136
*Common Name:**	(8Z,13Z,18R,20Z)-Strobilinin
IUPAC Name:	(5Z)-5-[(2R,5Z,10Z)-13-(furan-3-yl)-2,6,10-trimethyltrideca-5,10-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:	(8Z,13Z,18R,20Z)-Strobilinin
Standard InCHIKey:	UEPPLVMRPUYBQT-BHKQWKHBSA-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/h10-11,14-17,20,26H,5-9,12-13H2,1-4H3/b18-10-,19-11-,23-16-/t20-/m1/s1
SMILES:	CC1=C(C(=CC(C)CCC=C(C)CCCC(=CCCC2=COC=C2)C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462758
PubChem CID:	54726686
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

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[543571]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	14.1	ug ml-1	PMID[543571]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	14.4	ug ml-1	PMID[543571]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	20.3	ug ml-1	PMID[543571]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	16.0	ug ml-1	PMID[543571]

☑ 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 NPC474136 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	222
0.1-0.2	1314
0.2-0.3	4578
0.3-0.4	10571
0.4-0.5	9726
0.5-0.6	11229
0.6-0.7	4654
0.7-0.8	336
0.8-0.85	32
0.85-0.9	17
0.9-0.95	10
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC289911
0.9912	High Similarity	NPC283284
0.9826	High Similarity	NPC476351
0.9658	High Similarity	NPC75557
0.9658	High Similarity	NPC71274
0.9655	High Similarity	NPC475818
0.9565	High Similarity	NPC474817
0.9417	High Similarity	NPC474279
0.9417	High Similarity	NPC474438
0.9412	High Similarity	NPC474260
0.9412	High Similarity	NPC81912
0.9412	High Similarity	NPC329694
0.9412	High Similarity	NPC329922
0.9304	High Similarity	NPC131801
0.9174	High Similarity	NPC476016
0.9145	High Similarity	NPC473969
0.9035	High Similarity	NPC1811
0.9035	High Similarity	NPC26157
0.9016	High Similarity	NPC474830
0.8968	High Similarity	NPC288209
0.8947	High Similarity	NPC105249
0.8898	High Similarity	NPC14650
0.8852	High Similarity	NPC474829
0.885	High Similarity	NPC471521
0.885	High Similarity	NPC473356
0.8814	High Similarity	NPC208906
0.8814	High Similarity	NPC144745
0.876	High Similarity	NPC170604
0.876	High Similarity	NPC215109
0.8739	High Similarity	NPC21831
0.8739	High Similarity	NPC187547
0.8699	High Similarity	NPC471559
0.8667	High Similarity	NPC4898
0.8661	High Similarity	NPC97740
0.8609	High Similarity	NPC177331
0.8583	High Similarity	NPC17681
0.856	High Similarity	NPC471501
0.856	High Similarity	NPC473355
0.856	High Similarity	NPC471554
0.856	High Similarity	NPC471573
0.8525	High Similarity	NPC1848
0.8516	High Similarity	NPC45358
0.8468	Intermediate Similarity	NPC243269
0.8455	Intermediate Similarity	NPC473379
0.8455	Intermediate Similarity	NPC471549
0.845	Intermediate Similarity	NPC474426
0.845	Intermediate Similarity	NPC474407
0.845	Intermediate Similarity	NPC474425
0.8413	Intermediate Similarity	NPC137570
0.8306	Intermediate Similarity	NPC263870
0.8258	Intermediate Similarity	NPC303217
0.8182	Intermediate Similarity	NPC28054
0.8175	Intermediate Similarity	NPC218712
0.8175	Intermediate Similarity	NPC261733
0.8175	Intermediate Similarity	NPC118853
0.8175	Intermediate Similarity	NPC65735
0.8175	Intermediate Similarity	NPC307346
0.8175	Intermediate Similarity	NPC188377
0.8175	Intermediate Similarity	NPC267004
0.8074	Intermediate Similarity	NPC107571
0.8062	Intermediate Similarity	NPC112706
0.8062	Intermediate Similarity	NPC207294
0.8049	Intermediate Similarity	NPC312525
0.8049	Intermediate Similarity	NPC217180
0.8047	Intermediate Similarity	NPC138139
0.8047	Intermediate Similarity	NPC46536
0.8016	Intermediate Similarity	NPC477967
0.8015	Intermediate Similarity	NPC89133
0.7984	Intermediate Similarity	NPC83178
0.7969	Intermediate Similarity	NPC179354
0.7953	Intermediate Similarity	NPC16922
0.7926	Intermediate Similarity	NPC473268
0.791	Intermediate Similarity	NPC159786
0.7903	Intermediate Similarity	NPC227660
0.7891	Intermediate Similarity	NPC477038
0.7891	Intermediate Similarity	NPC477965
0.7886	Intermediate Similarity	NPC205523
0.7874	Intermediate Similarity	NPC317217
0.784	Intermediate Similarity	NPC291619
0.784	Intermediate Similarity	NPC254958
0.784	Intermediate Similarity	NPC243704
0.7823	Intermediate Similarity	NPC476031
0.7823	Intermediate Similarity	NPC45536
0.7823	Intermediate Similarity	NPC476014
0.782	Intermediate Similarity	NPC473344
0.782	Intermediate Similarity	NPC471817
0.782	Intermediate Similarity	NPC471545
0.782	Intermediate Similarity	NPC471544
0.781	Intermediate Similarity	NPC90953
0.7805	Intermediate Similarity	NPC292036
0.7769	Intermediate Similarity	NPC23086
0.7769	Intermediate Similarity	NPC74612
0.7761	Intermediate Similarity	NPC470740
0.7744	Intermediate Similarity	NPC136340
0.7744	Intermediate Similarity	NPC298190
0.7742	Intermediate Similarity	NPC150895
0.7734	Intermediate Similarity	NPC270807
0.7734	Intermediate Similarity	NPC174915
0.7714	Intermediate Similarity	NPC80635
0.7714	Intermediate Similarity	NPC254198
0.771	Intermediate Similarity	NPC319140
0.771	Intermediate Similarity	NPC95567
0.7698	Intermediate Similarity	NPC293424
0.7687	Intermediate Similarity	NPC473982
0.7676	Intermediate Similarity	NPC104924
0.7667	Intermediate Similarity	NPC140688
0.7664	Intermediate Similarity	NPC186626
0.7656	Intermediate Similarity	NPC79557
0.7652	Intermediate Similarity	NPC477040
0.7652	Intermediate Similarity	NPC477123
0.7652	Intermediate Similarity	NPC477966
0.7652	Intermediate Similarity	NPC477039
0.7647	Intermediate Similarity	NPC92941
0.7647	Intermediate Similarity	NPC476947
0.7639	Intermediate Similarity	NPC234494
0.7638	Intermediate Similarity	NPC67345
0.7638	Intermediate Similarity	NPC244862
0.7634	Intermediate Similarity	NPC88403
0.7634	Intermediate Similarity	NPC216810
0.763	Intermediate Similarity	NPC218838
0.7612	Intermediate Similarity	NPC475092
0.7606	Intermediate Similarity	NPC34056
0.7603	Intermediate Similarity	NPC33938
0.7597	Intermediate Similarity	NPC272487
0.7591	Intermediate Similarity	NPC146872
0.7576	Intermediate Similarity	NPC474476
0.7574	Intermediate Similarity	NPC106247
0.7557	Intermediate Similarity	NPC221798
0.7554	Intermediate Similarity	NPC202260
0.754	Intermediate Similarity	NPC474987
0.754	Intermediate Similarity	NPC76844
0.7537	Intermediate Similarity	NPC238309
0.7537	Intermediate Similarity	NPC21460
0.7537	Intermediate Similarity	NPC476925
0.7536	Intermediate Similarity	NPC470742
0.7535	Intermediate Similarity	NPC137295
0.7519	Intermediate Similarity	NPC476917
0.7519	Intermediate Similarity	NPC327527
0.7518	Intermediate Similarity	NPC121158
0.7517	Intermediate Similarity	NPC69647
0.7517	Intermediate Similarity	NPC125182
0.75	Intermediate Similarity	NPC22678
0.75	Intermediate Similarity	NPC52035
0.75	Intermediate Similarity	NPC255414
0.75	Intermediate Similarity	NPC56197
0.7483	Intermediate Similarity	NPC474219
0.7483	Intermediate Similarity	NPC195920
0.7483	Intermediate Similarity	NPC474378
0.7483	Intermediate Similarity	NPC121615
0.7483	Intermediate Similarity	NPC294511
0.7482	Intermediate Similarity	NPC236532
0.7481	Intermediate Similarity	NPC130275
0.7481	Intermediate Similarity	NPC477645
0.7481	Intermediate Similarity	NPC61788
0.7466	Intermediate Similarity	NPC228842
0.7466	Intermediate Similarity	NPC470997
0.7465	Intermediate Similarity	NPC22248
0.7465	Intermediate Similarity	NPC476946
0.7465	Intermediate Similarity	NPC267632
0.7463	Intermediate Similarity	NPC223063
0.7463	Intermediate Similarity	NPC208389
0.7463	Intermediate Similarity	NPC120836
0.7462	Intermediate Similarity	NPC36255
0.746	Intermediate Similarity	NPC11821
0.7458	Intermediate Similarity	NPC156768
0.7448	Intermediate Similarity	NPC7388
0.7444	Intermediate Similarity	NPC475236
0.7444	Intermediate Similarity	NPC290955
0.744	Intermediate Similarity	NPC311987
0.7438	Intermediate Similarity	NPC42471
0.7432	Intermediate Similarity	NPC98206
0.7432	Intermediate Similarity	NPC34421
0.7432	Intermediate Similarity	NPC253201
0.7432	Intermediate Similarity	NPC237259
0.7432	Intermediate Similarity	NPC302054
0.7431	Intermediate Similarity	NPC346
0.7424	Intermediate Similarity	NPC473885
0.7424	Intermediate Similarity	NPC230979
0.7424	Intermediate Similarity	NPC471074
0.7419	Intermediate Similarity	NPC474314
0.7413	Intermediate Similarity	NPC476944
0.7413	Intermediate Similarity	NPC251865
0.741	Intermediate Similarity	NPC42400
0.741	Intermediate Similarity	NPC64157
0.741	Intermediate Similarity	NPC278832
0.741	Intermediate Similarity	NPC307401
0.741	Intermediate Similarity	NPC310830
0.7405	Intermediate Similarity	NPC69403
0.7405	Intermediate Similarity	NPC291189
0.74	Intermediate Similarity	NPC472778
0.74	Intermediate Similarity	NPC472776
0.74	Intermediate Similarity	NPC472777
0.7388	Intermediate Similarity	NPC329707
0.7388	Intermediate Similarity	NPC279877
0.7388	Intermediate Similarity	NPC26532
0.7383	Intermediate Similarity	NPC155939
0.7383	Intermediate Similarity	NPC141538
0.7383	Intermediate Similarity	NPC296807
0.7381	Intermediate Similarity	NPC252004
0.7379	Intermediate Similarity	NPC71821

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 NPC474136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	957
0.2-0.3	2136
0.3-0.4	2885
0.4-0.5	1850
0.5-0.6	905
0.6-0.7	205
0.7-0.8	10
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
0.7305	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9717	Approved
0.7236	Intermediate Similarity	NPD1358	Approved
0.7209	Intermediate Similarity	NPD9092	Discovery
0.7206	Intermediate Similarity	NPD6832	Phase 2
0.7185	Intermediate Similarity	NPD5647	Approved
0.7154	Intermediate Similarity	NPD3134	Approved
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7071	Intermediate Similarity	NPD6355	Discontinued
0.7021	Intermediate Similarity	NPD6653	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.6985	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1203	Approved
0.695	Remote Similarity	NPD447	Suspended
0.6934	Remote Similarity	NPD1019	Discontinued
0.6899	Remote Similarity	NPD1241	Discontinued
0.6894	Remote Similarity	NPD9545	Approved
0.6892	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD1551	Phase 2
0.6866	Remote Similarity	NPD3496	Discontinued
0.6861	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD6798	Discontinued
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1933	Approved
0.6822	Remote Similarity	NPD7843	Approved
0.6818	Remote Similarity	NPD5760	Phase 2
0.6818	Remote Similarity	NPD5761	Phase 2
0.6809	Remote Similarity	NPD6233	Phase 2
0.6809	Remote Similarity	NPD4062	Phase 3
0.6806	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD2684	Approved
0.6755	Remote Similarity	NPD5403	Approved
0.6742	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD6362	Approved
0.6738	Remote Similarity	NPD411	Approved
0.6738	Remote Similarity	NPD3268	Approved
0.6716	Remote Similarity	NPD5585	Approved
0.6713	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7440	Discontinued
0.669	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2354	Approved
0.6644	Remote Similarity	NPD3887	Approved
0.6642	Remote Similarity	NPD1894	Discontinued
0.6623	Remote Similarity	NPD6599	Discontinued
0.6623	Remote Similarity	NPD5401	Approved
0.662	Remote Similarity	NPD2313	Discontinued
0.662	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8434	Phase 2
0.6603	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6005	Phase 3
0.6599	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6004	Phase 3
0.6599	Remote Similarity	NPD2344	Approved
0.6599	Remote Similarity	NPD6002	Phase 3
0.6594	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7075	Discontinued
0.6579	Remote Similarity	NPD6273	Approved
0.6571	Remote Similarity	NPD2798	Approved
0.6569	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD290	Approved
0.6558	Remote Similarity	NPD7458	Discontinued
0.6549	Remote Similarity	NPD7095	Approved
0.6547	Remote Similarity	NPD3225	Approved
0.6538	Remote Similarity	NPD6801	Discontinued
0.6536	Remote Similarity	NPD920	Approved
0.6535	Remote Similarity	NPD9697	Approved
0.6531	Remote Similarity	NPD2935	Discontinued
0.6531	Remote Similarity	NPD2240	Approved
0.6531	Remote Similarity	NPD2239	Approved
0.6528	Remote Similarity	NPD4307	Phase 2
0.6528	Remote Similarity	NPD4060	Phase 1
0.6522	Remote Similarity	NPD1481	Phase 2
0.6522	Remote Similarity	NPD1608	Approved
0.6512	Remote Similarity	NPD2182	Approved
0.6507	Remote Similarity	NPD7097	Phase 1
0.6506	Remote Similarity	NPD6765	Approved
0.6506	Remote Similarity	NPD6559	Discontinued
0.6506	Remote Similarity	NPD6764	Approved
0.65	Remote Similarity	NPD3266	Approved
0.65	Remote Similarity	NPD3267	Approved
0.6497	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.649	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2353	Approved
0.6486	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4340	Discontinued
0.6475	Remote Similarity	NPD4359	Approved
0.6471	Remote Similarity	NPD5049	Phase 3
0.6467	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4110	Phase 3
0.6463	Remote Similarity	NPD7033	Discontinued
0.6462	Remote Similarity	NPD2067	Discontinued
0.6456	Remote Similarity	NPD5402	Approved
0.6452	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1535	Discovery
0.6444	Remote Similarity	NPD5536	Phase 2
0.6443	Remote Similarity	NPD5958	Discontinued
0.6439	Remote Similarity	NPD5535	Approved
0.6438	Remote Similarity	NPD919	Approved
0.6434	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1876	Approved
0.6424	Remote Similarity	NPD2309	Approved
0.6423	Remote Similarity	NPD17	Approved
0.6415	Remote Similarity	NPD3882	Suspended
0.6414	Remote Similarity	NPD3142	Approved
0.6414	Remote Similarity	NPD3140	Approved
0.6405	Remote Similarity	NPD4661	Approved
0.6405	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4662	Approved
0.6403	Remote Similarity	NPD3972	Approved
0.64	Remote Similarity	NPD1238	Approved
0.6389	Remote Similarity	NPD3764	Approved
0.6377	Remote Similarity	NPD3847	Discontinued
0.6376	Remote Similarity	NPD2346	Discontinued
0.6376	Remote Similarity	NPD5763	Approved
0.6376	Remote Similarity	NPD5762	Approved
0.637	Remote Similarity	NPD230	Phase 1
0.6369	Remote Similarity	NPD7411	Suspended
0.6369	Remote Similarity	NPD958	Approved
0.6364	Remote Similarity	NPD2614	Approved
0.6364	Remote Similarity	NPD969	Suspended
0.6358	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7003	Approved
0.6358	Remote Similarity	NPD3750	Approved
0.6358	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6785	Approved
0.6353	Remote Similarity	NPD6784	Approved
0.6352	Remote Similarity	NPD3817	Phase 2
0.6338	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4534	Discontinued
0.6312	Remote Similarity	NPD7768	Phase 2
0.6312	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD5712	Approved
0.6304	Remote Similarity	NPD4626	Approved
0.6294	Remote Similarity	NPD454	Approved
0.6291	Remote Similarity	NPD1243	Approved
0.6289	Remote Similarity	NPD7819	Suspended
0.6276	Remote Similarity	NPD1048	Approved
0.6268	Remote Similarity	NPD987	Approved
0.6267	Remote Similarity	NPD1471	Phase 3
0.6266	Remote Similarity	NPD6677	Suspended
0.6259	Remote Similarity	NPD4622	Approved
0.6259	Remote Similarity	NPD4618	Approved
0.6258	Remote Similarity	NPD2186	Approved
0.625	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6647	Phase 2
0.6242	Remote Similarity	NPD3748	Approved
0.6242	Remote Similarity	NPD2649	Approved
0.6242	Remote Similarity	NPD2651	Approved
0.6242	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8032	Phase 2
0.6232	Remote Similarity	NPD5691	Approved
0.6231	Remote Similarity	NPD968	Approved
0.623	Remote Similarity	NPD9365	Approved
0.6225	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1549	Phase 2
0.6225	Remote Similarity	NPD2424	Discontinued
0.6218	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD422	Phase 1
0.6214	Remote Similarity	NPD1091	Approved
0.6207	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD164	Approved
0.62	Remote Similarity	NPD4477	Approved
0.62	Remote Similarity	NPD4476	Approved
0.62	Remote Similarity	NPD2438	Suspended
0.62	Remote Similarity	NPD6032	Approved
0.62	Remote Similarity	NPD2796	Approved
0.62	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD1283	Approved
0.6194	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2979	Phase 3
0.6184	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD9264	Approved
0.6183	Remote Similarity	NPD9267	Approved
0.6183	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD9263	Approved
0.6178	Remote Similarity	NPD957	Approved
0.6174	Remote Similarity	NPD5689	Approved
0.6174	Remote Similarity	NPD5688	Approved
0.6173	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD3749	Approved
0.6173	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2163	Approved
0.6164	Remote Similarity	NPD6385	Approved
0.6164	Remote Similarity	NPD6386	Approved
0.6159	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8127	Discontinued
0.6144	Remote Similarity	NPD8166	Discontinued
0.6139	Remote Similarity	NPD3455	Phase 2
0.6139	Remote Similarity	NPD3226	Approved
0.6136	Remote Similarity	NPD74	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