NPASS Compound

Structure

NPC476351 OpenBabel07101719252D 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 3.9945 -1.6275 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 4.4945 0.9706 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 4.4945 2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9945 0.1045 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 1.4945 2.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4945 -0.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9945 -1.6275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5823 -0.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5334 -1.1275 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 7.5823 -2.4365 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 4.4945 -0.7615 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 6.9945 -1.6275 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 8.5334 -2.1275 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 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 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 20 1 0 0 0 0 12 13 1 0 0 0 0 12 19 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:	5.021
LogD:	4.583
LogS:	-4.725
# 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:	0.304
Synthetic Accessibility Score:	3.503
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:	-4.806
MDCK Permeability:	2.5903116693370976e-05
Pgp-inhibitor:	0.52
Pgp-substrate:	0.109
Human Intestinal Absorption (HIA):	0.38
20% Bioavailability (F20%):	0.608
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	100.18634796142578%
Volume Distribution (VD):	3.736
Pgp-substrate:	0.5959059596061707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	7.526
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.65
Skin Sensitization:	0.78
Carcinogencity:	0.866
Eye Corrosion:	0.004
Eye Irritation:	0.317
Respiratory Toxicity:	0.775

Download Data

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

Natural Product: NPC476351

Natural Product ID:	NPC476351
*Common Name:**	(5Z)-5-[(2R,5Z,10Z)-13-(Furan-3-Yl)-2,6,11-Trimethyltrideca-5,10-Dienylidene]-4-Hydroxy-3-Methylfuran-2-One
IUPAC Name:	(5Z)-5-[(2R,5Z,10Z)-13-(furan-3-yl)-2,6,11-trimethyltrideca-5,10-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:
Standard InCHIKey:	KLKIESMJEUHQLI-KLURGBKRSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-18(8-5-6-9-19(2)12-13-22-14-15-28-17-22)10-7-11-20(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/1OC(=O)C(=C1O)C)C)/CCC/C=C(CCc1cocc1)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574762
PubChem CID:	54736252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	7.3	ug.mL-1	PMID[480783]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	=	31.2	ug.mL-1	PMID[480783]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[480783]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug.mL-1	PMID[480783]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.12	ug.mL-1	PMID[480783]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6.25	ug.mL-1	PMID[480783]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	12.5	ug.mL-1	PMID[480783]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[480783]

☑ 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 NPC476351 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	241
0.1-0.2	1257
0.2-0.3	4327
0.3-0.4	9769
0.4-0.5	10359
0.5-0.6	10370
0.6-0.7	5837
0.7-0.8	461
0.8-0.85	36
0.85-0.9	21
0.9-0.95	9
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC71274
0.9829	High Similarity	NPC75557
0.9826	High Similarity	NPC474136
0.9741	High Similarity	NPC289911
0.9741	High Similarity	NPC283284
0.9583	High Similarity	NPC474438
0.9583	High Similarity	NPC474279
0.958	High Similarity	NPC474260
0.958	High Similarity	NPC329694
0.958	High Similarity	NPC81912
0.958	High Similarity	NPC329922
0.9492	High Similarity	NPC475818
0.9402	High Similarity	NPC474817
0.9339	High Similarity	NPC476016
0.918	High Similarity	NPC474830
0.9153	High Similarity	NPC473969
0.9145	High Similarity	NPC131801
0.9055	High Similarity	NPC14650
0.9016	High Similarity	NPC474829
0.8983	High Similarity	NPC144745
0.8983	High Similarity	NPC208906
0.8957	High Similarity	NPC105249
0.8915	High Similarity	NPC215109
0.8915	High Similarity	NPC170604
0.8879	High Similarity	NPC1811
0.8879	High Similarity	NPC26157
0.8862	High Similarity	NPC471559
0.8828	High Similarity	NPC288209
0.8819	High Similarity	NPC97740
0.874	High Similarity	NPC17681
0.872	High Similarity	NPC471573
0.872	High Similarity	NPC471501
0.872	High Similarity	NPC473355
0.872	High Similarity	NPC471554
0.8696	High Similarity	NPC471521
0.8696	High Similarity	NPC473356
0.8672	High Similarity	NPC45358
0.8629	High Similarity	NPC243269
0.8605	High Similarity	NPC474426
0.8605	High Similarity	NPC474407
0.8605	High Similarity	NPC474425
0.8595	High Similarity	NPC187547
0.8595	High Similarity	NPC21831
0.8571	High Similarity	NPC137570
0.8525	High Similarity	NPC4898
0.8468	Intermediate Similarity	NPC471549
0.8468	Intermediate Similarity	NPC473379
0.8462	Intermediate Similarity	NPC177331
0.8409	Intermediate Similarity	NPC303217
0.8387	Intermediate Similarity	NPC1848
0.8347	Intermediate Similarity	NPC28054
0.8333	Intermediate Similarity	NPC65735
0.8333	Intermediate Similarity	NPC118853
0.8333	Intermediate Similarity	NPC188377
0.8321	Intermediate Similarity	NPC307346
0.8321	Intermediate Similarity	NPC261733
0.8321	Intermediate Similarity	NPC218712
0.8321	Intermediate Similarity	NPC267004
0.8222	Intermediate Similarity	NPC107571
0.8217	Intermediate Similarity	NPC207294
0.8217	Intermediate Similarity	NPC112706
0.8211	Intermediate Similarity	NPC312525
0.8211	Intermediate Similarity	NPC217180
0.8203	Intermediate Similarity	NPC46536
0.8203	Intermediate Similarity	NPC138139
0.8175	Intermediate Similarity	NPC477967
0.8175	Intermediate Similarity	NPC263870
0.8168	Intermediate Similarity	NPC89133
0.814	Intermediate Similarity	NPC83178
0.8125	Intermediate Similarity	NPC179354
0.811	Intermediate Similarity	NPC16922
0.8074	Intermediate Similarity	NPC473268
0.8065	Intermediate Similarity	NPC227660
0.806	Intermediate Similarity	NPC159786
0.8049	Intermediate Similarity	NPC205523
0.8047	Intermediate Similarity	NPC477038
0.8047	Intermediate Similarity	NPC477965
0.8031	Intermediate Similarity	NPC317217
0.8	Intermediate Similarity	NPC243704
0.8	Intermediate Similarity	NPC291619
0.8	Intermediate Similarity	NPC254958
0.7984	Intermediate Similarity	NPC476014
0.7984	Intermediate Similarity	NPC476031
0.7984	Intermediate Similarity	NPC45536
0.797	Intermediate Similarity	NPC471817
0.797	Intermediate Similarity	NPC471545
0.797	Intermediate Similarity	NPC471544
0.797	Intermediate Similarity	NPC473344
0.7956	Intermediate Similarity	NPC90953
0.7923	Intermediate Similarity	NPC74612
0.7923	Intermediate Similarity	NPC23086
0.791	Intermediate Similarity	NPC470740
0.7903	Intermediate Similarity	NPC150895
0.7895	Intermediate Similarity	NPC298190
0.7895	Intermediate Similarity	NPC136340
0.7863	Intermediate Similarity	NPC95567
0.7863	Intermediate Similarity	NPC319140
0.7857	Intermediate Similarity	NPC80635
0.7857	Intermediate Similarity	NPC293424
0.7857	Intermediate Similarity	NPC254198
0.7836	Intermediate Similarity	NPC473982
0.7817	Intermediate Similarity	NPC104924
0.7812	Intermediate Similarity	NPC79557
0.781	Intermediate Similarity	NPC186626
0.7803	Intermediate Similarity	NPC477039
0.7803	Intermediate Similarity	NPC477040
0.7803	Intermediate Similarity	NPC477123
0.7803	Intermediate Similarity	NPC477966
0.7794	Intermediate Similarity	NPC476947
0.7794	Intermediate Similarity	NPC92941
0.7786	Intermediate Similarity	NPC216810
0.7786	Intermediate Similarity	NPC88403
0.7778	Intermediate Similarity	NPC218838
0.7778	Intermediate Similarity	NPC234494
0.7761	Intermediate Similarity	NPC475092
0.7746	Intermediate Similarity	NPC34056
0.774	Intermediate Similarity	NPC33938
0.7737	Intermediate Similarity	NPC146872
0.7727	Intermediate Similarity	NPC474476
0.7721	Intermediate Similarity	NPC106247
0.771	Intermediate Similarity	NPC221798
0.7698	Intermediate Similarity	NPC474987
0.7698	Intermediate Similarity	NPC202260
0.7698	Intermediate Similarity	NPC76844
0.7687	Intermediate Similarity	NPC238309
0.7687	Intermediate Similarity	NPC476925
0.7687	Intermediate Similarity	NPC21460
0.7681	Intermediate Similarity	NPC470742
0.768	Intermediate Similarity	NPC292036
0.7676	Intermediate Similarity	NPC137295
0.7669	Intermediate Similarity	NPC476917
0.7669	Intermediate Similarity	NPC327527
0.7661	Intermediate Similarity	NPC22678
0.766	Intermediate Similarity	NPC121158
0.7655	Intermediate Similarity	NPC125182
0.7655	Intermediate Similarity	NPC69647
0.7643	Intermediate Similarity	NPC56197
0.7639	Intermediate Similarity	NPC255414
0.7634	Intermediate Similarity	NPC130275
0.763	Intermediate Similarity	NPC61788
0.763	Intermediate Similarity	NPC477645
0.7626	Intermediate Similarity	NPC236532
0.7622	Intermediate Similarity	NPC195920
0.7619	Intermediate Similarity	NPC474378
0.7619	Intermediate Similarity	NPC474219
0.7619	Intermediate Similarity	NPC11821
0.7619	Intermediate Similarity	NPC121615
0.7619	Intermediate Similarity	NPC294511
0.7615	Intermediate Similarity	NPC36255
0.7615	Intermediate Similarity	NPC174915
0.7615	Intermediate Similarity	NPC270807
0.7612	Intermediate Similarity	NPC120836
0.7612	Intermediate Similarity	NPC208389
0.7612	Intermediate Similarity	NPC223063
0.7606	Intermediate Similarity	NPC267632
0.7606	Intermediate Similarity	NPC476946
0.7606	Intermediate Similarity	NPC22248
0.7603	Intermediate Similarity	NPC42471
0.7603	Intermediate Similarity	NPC470997
0.7603	Intermediate Similarity	NPC228842
0.7594	Intermediate Similarity	NPC475236
0.7594	Intermediate Similarity	NPC290955
0.7586	Intermediate Similarity	NPC7388
0.7581	Intermediate Similarity	NPC474314
0.7576	Intermediate Similarity	NPC471074
0.7576	Intermediate Similarity	NPC230979
0.7576	Intermediate Similarity	NPC473885
0.7569	Intermediate Similarity	NPC346
0.7568	Intermediate Similarity	NPC34421
0.7568	Intermediate Similarity	NPC98206
0.7568	Intermediate Similarity	NPC253201
0.7568	Intermediate Similarity	NPC237259
0.7568	Intermediate Similarity	NPC302054
0.7557	Intermediate Similarity	NPC69403
0.7557	Intermediate Similarity	NPC291189
0.7554	Intermediate Similarity	NPC310830
0.7554	Intermediate Similarity	NPC42400
0.7554	Intermediate Similarity	NPC278832
0.7554	Intermediate Similarity	NPC307401
0.7554	Intermediate Similarity	NPC64157
0.7552	Intermediate Similarity	NPC476944
0.7552	Intermediate Similarity	NPC251865
0.7541	Intermediate Similarity	NPC140688
0.7537	Intermediate Similarity	NPC26532
0.7537	Intermediate Similarity	NPC279877
0.7537	Intermediate Similarity	NPC329707
0.7533	Intermediate Similarity	NPC472778
0.7533	Intermediate Similarity	NPC472776
0.7533	Intermediate Similarity	NPC472777
0.7519	Intermediate Similarity	NPC137710
0.7519	Intermediate Similarity	NPC244862
0.7519	Intermediate Similarity	NPC67345
0.7518	Intermediate Similarity	NPC282973
0.7518	Intermediate Similarity	NPC148374
0.7517	Intermediate Similarity	NPC296807
0.7517	Intermediate Similarity	NPC250228
0.7517	Intermediate Similarity	NPC141538
0.7517	Intermediate Similarity	NPC71821
0.7517	Intermediate Similarity	NPC155939
0.7517	Intermediate Similarity	NPC471174

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 NPC476351 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	975
0.2-0.3	2051
0.3-0.4	2822
0.4-0.5	1861
0.5-0.6	974
0.6-0.7	240
0.7-0.8	15
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
0.7447	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD9717	Approved
0.7353	Intermediate Similarity	NPD6832	Phase 2
0.7292	Intermediate Similarity	NPD4628	Phase 3
0.7214	Intermediate Similarity	NPD6355	Discontinued
0.7206	Intermediate Similarity	NPD5647	Approved
0.7132	Intermediate Similarity	NPD1203	Approved
0.712	Intermediate Similarity	NPD1358	Approved
0.7099	Intermediate Similarity	NPD9092	Discovery
0.7092	Intermediate Similarity	NPD447	Suspended
0.708	Intermediate Similarity	NPD1019	Discontinued
0.7054	Intermediate Similarity	NPD1241	Discontinued
0.7045	Intermediate Similarity	NPD9545	Approved
0.7042	Intermediate Similarity	NPD6653	Approved
0.704	Intermediate Similarity	NPD3134	Approved
0.7029	Intermediate Similarity	NPD9494	Approved
0.7027	Intermediate Similarity	NPD6799	Approved
0.7014	Intermediate Similarity	NPD1551	Phase 2
0.7007	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1933	Approved
0.695	Remote Similarity	NPD4062	Phase 3
0.695	Remote Similarity	NPD6233	Phase 2
0.6948	Remote Similarity	NPD5761	Phase 2
0.6948	Remote Similarity	NPD5760	Phase 2
0.6944	Remote Similarity	NPD2799	Discontinued
0.6894	Remote Similarity	NPD9493	Approved
0.6889	Remote Similarity	NPD3496	Discontinued
0.6887	Remote Similarity	NPD5403	Approved
0.6884	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD411	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6853	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7440	Discontinued
0.6846	Remote Similarity	NPD7843	Approved
0.6828	Remote Similarity	NPD4308	Phase 3
0.6822	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2684	Approved
0.6791	Remote Similarity	NPD1894	Discontinued
0.6779	Remote Similarity	NPD2354	Approved
0.6779	Remote Similarity	NPD3887	Approved
0.6763	Remote Similarity	NPD6362	Approved
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD5401	Approved
0.6753	Remote Similarity	NPD6599	Discontinued
0.6741	Remote Similarity	NPD5585	Approved
0.6735	Remote Similarity	NPD6005	Phase 3
0.6735	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6004	Phase 3
0.6735	Remote Similarity	NPD6002	Phase 3
0.6735	Remote Similarity	NPD2344	Approved
0.6731	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8434	Phase 2
0.6715	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2798	Approved
0.6711	Remote Similarity	NPD6273	Approved
0.6709	Remote Similarity	NPD7075	Discontinued
0.6692	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD1778	Approved
0.6688	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2239	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1481	Phase 2
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6627	Remote Similarity	NPD6559	Discontinued
0.6627	Remote Similarity	NPD6764	Approved
0.6627	Remote Similarity	NPD6765	Approved
0.6624	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2353	Approved
0.6622	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2067	Discontinued
0.6601	Remote Similarity	NPD5049	Phase 3
0.66	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4110	Phase 3
0.6594	Remote Similarity	NPD1535	Discovery
0.6589	Remote Similarity	NPD290	Approved
0.6582	Remote Similarity	NPD5402	Approved
0.6581	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5958	Discontinued
0.6573	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7095	Approved
0.6571	Remote Similarity	NPD3225	Approved
0.6571	Remote Similarity	NPD1876	Approved
0.6569	Remote Similarity	NPD17	Approved
0.6562	Remote Similarity	NPD9697	Approved
0.6562	Remote Similarity	NPD919	Approved
0.656	Remote Similarity	NPD1238	Approved
0.6556	Remote Similarity	NPD2309	Approved
0.6552	Remote Similarity	NPD4060	Phase 1
0.6552	Remote Similarity	NPD3142	Approved
0.6552	Remote Similarity	NPD3140	Approved
0.6547	Remote Similarity	NPD3972	Approved
0.6541	Remote Similarity	NPD3882	Suspended
0.6536	Remote Similarity	NPD4661	Approved
0.6536	Remote Similarity	NPD4662	Approved
0.6536	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7097	Phase 1
0.6528	Remote Similarity	NPD3764	Approved
0.651	Remote Similarity	NPD2346	Discontinued
0.6507	Remote Similarity	NPD4340	Discontinued
0.6507	Remote Similarity	NPD230	Phase 1
0.6503	Remote Similarity	NPD2614	Approved
0.65	Remote Similarity	NPD4359	Approved
0.65	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD958	Approved
0.6497	Remote Similarity	NPD7411	Suspended
0.649	Remote Similarity	NPD3750	Approved
0.649	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7003	Approved
0.649	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7033	Discontinued
0.6479	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3817	Phase 2
0.6471	Remote Similarity	NPD6785	Approved
0.6471	Remote Similarity	NPD6784	Approved
0.6467	Remote Similarity	NPD4534	Discontinued
0.6466	Remote Similarity	NPD5535	Approved
0.646	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7768	Phase 2
0.6434	Remote Similarity	NPD454	Approved
0.6424	Remote Similarity	NPD1243	Approved
0.6415	Remote Similarity	NPD7819	Suspended
0.6403	Remote Similarity	NPD3847	Discontinued
0.64	Remote Similarity	NPD5763	Approved
0.64	Remote Similarity	NPD5762	Approved
0.64	Remote Similarity	NPD1471	Phase 3
0.6395	Remote Similarity	NPD4622	Approved
0.6395	Remote Similarity	NPD4618	Approved
0.6392	Remote Similarity	NPD6677	Suspended
0.6391	Remote Similarity	NPD969	Suspended
0.6387	Remote Similarity	NPD2186	Approved
0.6376	Remote Similarity	NPD3748	Approved
0.6375	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.637	Remote Similarity	NPD8032	Phase 2
0.6369	Remote Similarity	NPD2649	Approved
0.6369	Remote Similarity	NPD2651	Approved
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1549	Phase 2
0.6357	Remote Similarity	NPD164	Approved
0.635	Remote Similarity	NPD5536	Phase 2
0.6346	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1283	Approved
0.6336	Remote Similarity	NPD9267	Approved
0.6336	Remote Similarity	NPD9263	Approved
0.6336	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD9264	Approved
0.6333	Remote Similarity	NPD2438	Suspended
0.6333	Remote Similarity	NPD2796	Approved
0.6333	Remote Similarity	NPD4477	Approved
0.6333	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5712	Approved
0.6333	Remote Similarity	NPD4476	Approved
0.6331	Remote Similarity	NPD4626	Approved
0.6327	Remote Similarity	NPD2979	Phase 3
0.6323	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD5688	Approved
0.6309	Remote Similarity	NPD5689	Approved
0.6306	Remote Similarity	NPD957	Approved
0.6301	Remote Similarity	NPD1048	Approved
0.6299	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3749	Approved
0.6296	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD987	Approved
0.6291	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6386	Approved
0.6289	Remote Similarity	NPD6385	Approved
0.6288	Remote Similarity	NPD74	Approved
0.6288	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD9266	Approved
0.6287	Remote Similarity	NPD2163	Approved
0.628	Remote Similarity	NPD8127	Discontinued
0.6279	Remote Similarity	NPD6647	Phase 2
0.6275	Remote Similarity	NPD8166	Discontinued
0.6266	Remote Similarity	NPD3455	Phase 2
0.6266	Remote Similarity	NPD3226	Approved
0.626	Remote Similarity	NPD968	Approved
0.6259	Remote Similarity	NPD5691	Approved
0.625	Remote Similarity	NPD2629	Approved
0.625	Remote Similarity	NPD7577	Discontinued
0.625	Remote Similarity	NPD2424	Discontinued

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