NPASS Compound

Structure

NPC471521 OpenBabel07101719122D 27 27 0 0 0 0 0 0 0 0999 V2000 -10.8475 -0.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0285 -2.5419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0841 1.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6437 -3.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8585 -1.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8913 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8749 -1.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4462 -1.8374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8968 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8639 -1.1329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4791 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2816 -0.4284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8804 -1.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 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 -10.4408 -1.7329 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 -7.2761 -0.3239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4736 -2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6829 0.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0614 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0951 1.3987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6547 -4.0826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6774 0.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0559 -3.0645 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	406.008
LogP:	5.325
LogD:	4.626
LogS:	-5.433
# Rotatable Bonds:	13
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	3.237
Fsp3:	0.455
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:	-4.652
MDCK Permeability:	2.238342131022364e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.777
30% Bioavailability (F30%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	95.55435943603516%
Volume Distribution (VD):	3.269
Pgp-substrate:	4.902620315551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.616
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.956
CYP2C9-substrate:	0.513
CYP2D6-inhibitor:	0.702
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	12.588
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.802
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.959
Carcinogencity:	0.622
Eye Corrosion:	0.019
Eye Irritation:	0.7
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC471521

Natural Product ID:	NPC471521
*Common Name:**	Dimethyl (E,6E)-6-[3-(Furan-3-Yl)Propylidene]-2-(4-Methylpent-3-Enyl)Hept-2-Enedioate
IUPAC Name:	dimethyl (E,6E)-6-[3-(furan-3-yl)propylidene]-2-(4-methylpent-3-enyl)hept-2-enedioate
Synonyms:
Standard InCHIKey:	RHYBSUZKHZEFTF-PFTXGBMHSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-17(2)8-5-10-19(21(23)25-3)12-7-13-20(22(24)26-4)11-6-9-18-14-15-27-16-18/h8,11-12,14-16H,5-7,9-10,13H2,1-4H3/b19-12+,20-11+
SMILES:	COC(=O)/C(=C/CCc1cocc1)/CC/C=C(/C(=O)OC)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254579
PubChem CID:	15840543
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12372	Baccharis thymifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232640]
NPO12372	Baccharis thymifolia	Species	Asteraceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	7.4	day	PMID[486050]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Inhibition	=	34.3	%	PMID[486050]

☑ 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 NPC471521 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	2023
0.2-0.3	5892
0.3-0.4	11903
0.4-0.5	9195
0.5-0.6	10739
0.6-0.7	2354
0.7-0.8	276
0.8-0.85	54
0.85-0.9	11
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473356
0.9615	High Similarity	NPC1811
0.9615	High Similarity	NPC26157
0.9519	High Similarity	NPC105249
0.9174	High Similarity	NPC131801
0.9143	High Similarity	NPC177331
0.9009	High Similarity	NPC473969
0.9009	High Similarity	NPC4898
0.9	High Similarity	NPC144745
0.9	High Similarity	NPC208906
0.8929	High Similarity	NPC474817
0.8919	High Similarity	NPC21831
0.8919	High Similarity	NPC187547
0.885	High Similarity	NPC474136
0.885	High Similarity	NPC1848
0.8772	High Similarity	NPC283284
0.8772	High Similarity	NPC289911
0.8696	High Similarity	NPC475818
0.8696	High Similarity	NPC476351
0.8649	High Similarity	NPC28054
0.8547	High Similarity	NPC71274
0.8547	High Similarity	NPC474829
0.8547	High Similarity	NPC471559
0.8547	High Similarity	NPC179354
0.8547	High Similarity	NPC75557
0.8534	High Similarity	NPC16922
0.8475	Intermediate Similarity	NPC474260
0.8475	Intermediate Similarity	NPC329922
0.8475	Intermediate Similarity	NPC81912
0.8475	Intermediate Similarity	NPC329694
0.8462	Intermediate Similarity	NPC243269
0.8421	Intermediate Similarity	NPC243704
0.8403	Intermediate Similarity	NPC137570
0.8403	Intermediate Similarity	NPC471554
0.8403	Intermediate Similarity	NPC471501
0.8403	Intermediate Similarity	NPC473355
0.8403	Intermediate Similarity	NPC471573
0.8403	Intermediate Similarity	NPC474830
0.8403	Intermediate Similarity	NPC476016
0.8393	Intermediate Similarity	NPC292036
0.8333	Intermediate Similarity	NPC474438
0.8333	Intermediate Similarity	NPC312525
0.8333	Intermediate Similarity	NPC474279
0.8333	Intermediate Similarity	NPC227660
0.8333	Intermediate Similarity	NPC217180
0.8319	Intermediate Similarity	NPC150895
0.8319	Intermediate Similarity	NPC205523
0.8319	Intermediate Similarity	NPC138139
0.8319	Intermediate Similarity	NPC74612
0.8319	Intermediate Similarity	NPC46536
0.8305	Intermediate Similarity	NPC65735
0.8305	Intermediate Similarity	NPC188377
0.8291	Intermediate Similarity	NPC471549
0.8291	Intermediate Similarity	NPC317217
0.8291	Intermediate Similarity	NPC473379
0.8257	Intermediate Similarity	NPC140688
0.825	Intermediate Similarity	NPC83178
0.8246	Intermediate Similarity	NPC45536
0.819	Intermediate Similarity	NPC244862
0.819	Intermediate Similarity	NPC67345
0.8182	Intermediate Similarity	NPC207294
0.8182	Intermediate Similarity	NPC112706
0.8151	Intermediate Similarity	NPC477965
0.8151	Intermediate Similarity	NPC477038
0.8136	Intermediate Similarity	NPC477967
0.8136	Intermediate Similarity	NPC263870
0.813	Intermediate Similarity	NPC89133
0.813	Intermediate Similarity	NPC17681
0.8099	Intermediate Similarity	NPC95567
0.8099	Intermediate Similarity	NPC319140
0.8087	Intermediate Similarity	NPC476031
0.8087	Intermediate Similarity	NPC476014
0.8065	Intermediate Similarity	NPC97740
0.8065	Intermediate Similarity	NPC471817
0.8065	Intermediate Similarity	NPC45358
0.8037	Intermediate Similarity	NPC156768
0.8	Intermediate Similarity	NPC118853
0.8	Intermediate Similarity	NPC470740
0.8	Intermediate Similarity	NPC474426
0.8	Intermediate Similarity	NPC474425
0.8	Intermediate Similarity	NPC474407
0.7984	Intermediate Similarity	NPC298190
0.7937	Intermediate Similarity	NPC288209
0.7903	Intermediate Similarity	NPC21460
0.7899	Intermediate Similarity	NPC79557
0.7895	Intermediate Similarity	NPC22678
0.7886	Intermediate Similarity	NPC477039
0.7886	Intermediate Similarity	NPC477040
0.7886	Intermediate Similarity	NPC327527
0.7886	Intermediate Similarity	NPC477966
0.7886	Intermediate Similarity	NPC476917
0.7886	Intermediate Similarity	NPC477123
0.7881	Intermediate Similarity	NPC137710
0.7874	Intermediate Similarity	NPC92941
0.7874	Intermediate Similarity	NPC14650
0.7869	Intermediate Similarity	NPC23086
0.784	Intermediate Similarity	NPC475092
0.7838	Intermediate Similarity	NPC42471
0.7833	Intermediate Similarity	NPC36255
0.7833	Intermediate Similarity	NPC270807
0.7833	Intermediate Similarity	NPC174915
0.7812	Intermediate Similarity	NPC146872
0.7797	Intermediate Similarity	NPC254958
0.7797	Intermediate Similarity	NPC293424
0.7797	Intermediate Similarity	NPC291619
0.7787	Intermediate Similarity	NPC230979
0.776	Intermediate Similarity	NPC476925
0.7759	Intermediate Similarity	NPC252004
0.7752	Intermediate Similarity	NPC170604
0.7752	Intermediate Similarity	NPC215109
0.7752	Intermediate Similarity	NPC470742
0.7752	Intermediate Similarity	NPC310830
0.7752	Intermediate Similarity	NPC42400
0.7724	Intermediate Similarity	NPC216810
0.7705	Intermediate Similarity	NPC130275
0.7705	Intermediate Similarity	NPC83115
0.7698	Intermediate Similarity	NPC136340
0.7692	Intermediate Similarity	NPC220094
0.7692	Intermediate Similarity	NPC476943
0.7692	Intermediate Similarity	NPC236532
0.768	Intermediate Similarity	NPC208389
0.7664	Intermediate Similarity	NPC146316
0.7647	Intermediate Similarity	NPC206007
0.7642	Intermediate Similarity	NPC471074
0.7642	Intermediate Similarity	NPC473885
0.7638	Intermediate Similarity	NPC471544
0.7638	Intermediate Similarity	NPC471545
0.7638	Intermediate Similarity	NPC473344
0.7634	Intermediate Similarity	NPC90953
0.7615	Intermediate Similarity	NPC307401
0.7615	Intermediate Similarity	NPC186626
0.7611	Intermediate Similarity	NPC157473
0.7611	Intermediate Similarity	NPC151530
0.7581	Intermediate Similarity	NPC52035
0.7576	Intermediate Similarity	NPC56197
0.7565	Intermediate Similarity	NPC229387
0.7563	Intermediate Similarity	NPC212918
0.7559	Intermediate Similarity	NPC61788
0.7559	Intermediate Similarity	NPC282230
0.7559	Intermediate Similarity	NPC183348
0.7542	Intermediate Similarity	NPC11821
0.754	Intermediate Similarity	NPC223063
0.754	Intermediate Similarity	NPC120836
0.754	Intermediate Similarity	NPC198904
0.7522	Intermediate Similarity	NPC176971
0.7521	Intermediate Similarity	NPC230951
0.752	Intermediate Similarity	NPC141059
0.75	Intermediate Similarity	NPC15083
0.75	Intermediate Similarity	NPC277525
0.75	Intermediate Similarity	NPC473982
0.75	Intermediate Similarity	NPC202260
0.75	Intermediate Similarity	NPC221798
0.75	Intermediate Similarity	NPC470977
0.75	Intermediate Similarity	NPC196979
0.75	Intermediate Similarity	NPC54626
0.75	Intermediate Similarity	NPC57879
0.75	Intermediate Similarity	NPC470976
0.75	Intermediate Similarity	NPC87466
0.748	Intermediate Similarity	NPC66246
0.748	Intermediate Similarity	NPC170546
0.7479	Intermediate Similarity	NPC470860
0.7479	Intermediate Similarity	NPC474987
0.7479	Intermediate Similarity	NPC316062
0.7479	Intermediate Similarity	NPC76844
0.7477	Intermediate Similarity	NPC233791
0.7463	Intermediate Similarity	NPC121158
0.7462	Intermediate Similarity	NPC159786
0.7459	Intermediate Similarity	NPC115859
0.7459	Intermediate Similarity	NPC97566
0.7456	Intermediate Similarity	NPC219969
0.7442	Intermediate Similarity	NPC293253
0.7442	Intermediate Similarity	NPC471006
0.7442	Intermediate Similarity	NPC218838
0.744	Intermediate Similarity	NPC83301
0.7434	Intermediate Similarity	NPC128730
0.7417	Intermediate Similarity	NPC217423
0.7417	Intermediate Similarity	NPC45104
0.7407	Intermediate Similarity	NPC223415
0.7407	Intermediate Similarity	NPC470741
0.7407	Intermediate Similarity	NPC80635
0.7407	Intermediate Similarity	NPC267632
0.7405	Intermediate Similarity	NPC303217
0.7402	Intermediate Similarity	NPC59502
0.7388	Intermediate Similarity	NPC20500
0.7385	Intermediate Similarity	NPC106247
0.7373	Intermediate Similarity	NPC53953
0.7368	Intermediate Similarity	NPC326447
0.7353	Intermediate Similarity	NPC261733
0.7353	Intermediate Similarity	NPC307346
0.7353	Intermediate Similarity	NPC142113
0.7353	Intermediate Similarity	NPC251865
0.7353	Intermediate Similarity	NPC199044
0.7353	Intermediate Similarity	NPC267004
0.7353	Intermediate Similarity	NPC218712
0.7353	Intermediate Similarity	NPC238843
0.7353	Intermediate Similarity	NPC476944
0.7348	Intermediate Similarity	NPC473268
0.7344	Intermediate Similarity	NPC238309
0.7339	Intermediate Similarity	NPC291189
0.7339	Intermediate Similarity	NPC272899

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 NPC471521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1118
0.2-0.3	2261
0.3-0.4	2968
0.4-0.5	1753
0.5-0.6	698
0.6-0.7	137
0.7-0.8	6
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
0.7402	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD3134	Approved
0.7304	Intermediate Similarity	NPD1358	Approved
0.7244	Intermediate Similarity	NPD1019	Discontinued
0.7239	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD9717	Approved
0.7165	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2182	Approved
0.6899	Remote Similarity	NPD1203	Approved
0.688	Remote Similarity	NPD5585	Approved
0.6866	Remote Similarity	NPD1933	Approved
0.6855	Remote Similarity	NPD9092	Discovery
0.685	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1238	Approved
0.6838	Remote Similarity	NPD9697	Approved
0.68	Remote Similarity	NPD9545	Approved
0.6791	Remote Similarity	NPD4307	Phase 2
0.6788	Remote Similarity	NPD1551	Phase 2
0.6783	Remote Similarity	NPD920	Approved
0.6772	Remote Similarity	NPD3496	Discontinued
0.6763	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5535	Approved
0.6715	Remote Similarity	NPD2799	Discontinued
0.6714	Remote Similarity	NPD4628	Phase 3
0.6693	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD3887	Approved
0.6643	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD411	Approved
0.6642	Remote Similarity	NPD2313	Discontinued
0.6641	Remote Similarity	NPD2797	Approved
0.6641	Remote Similarity	NPD3266	Approved
0.6641	Remote Similarity	NPD3267	Approved
0.664	Remote Similarity	NPD9493	Approved
0.6618	Remote Similarity	NPD447	Suspended
0.6615	Remote Similarity	NPD4359	Approved
0.661	Remote Similarity	NPD164	Approved
0.6594	Remote Similarity	NPD4308	Phase 3
0.6591	Remote Similarity	NPD5647	Approved
0.6573	Remote Similarity	NPD6799	Approved
0.6565	Remote Similarity	NPD1876	Approved
0.6562	Remote Similarity	NPD17	Approved
0.6541	Remote Similarity	NPD9494	Approved
0.6525	Remote Similarity	NPD1243	Approved
0.6519	Remote Similarity	NPD3268	Approved
0.6519	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6798	Discontinued
0.6515	Remote Similarity	NPD6362	Approved
0.651	Remote Similarity	NPD5761	Phase 2
0.651	Remote Similarity	NPD5760	Phase 2
0.6503	Remote Similarity	NPD7440	Discontinued
0.65	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2353	Approved
0.65	Remote Similarity	NPD2344	Approved
0.65	Remote Similarity	NPD1471	Phase 3
0.6496	Remote Similarity	NPD6355	Discontinued
0.6484	Remote Similarity	NPD5691	Approved
0.6483	Remote Similarity	NPD6273	Approved
0.6483	Remote Similarity	NPD2186	Approved
0.6475	Remote Similarity	NPD3748	Approved
0.6471	Remote Similarity	NPD4062	Phase 3
0.6471	Remote Similarity	NPD6233	Phase 2
0.6466	Remote Similarity	NPD2798	Approved
0.6457	Remote Similarity	NPD5536	Phase 2
0.6447	Remote Similarity	NPD919	Approved
0.6439	Remote Similarity	NPD3225	Approved
0.6429	Remote Similarity	NPD2796	Approved
0.6429	Remote Similarity	NPD2935	Discontinued
0.6412	Remote Similarity	NPD1481	Phase 2
0.6412	Remote Similarity	NPD1608	Approved
0.6393	Remote Similarity	NPD2684	Approved
0.6385	Remote Similarity	NPD3847	Discontinued
0.6383	Remote Similarity	NPD2346	Discontinued
0.6377	Remote Similarity	NPD4618	Approved
0.6377	Remote Similarity	NPD4622	Approved
0.6358	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7033	Discontinued
0.6341	Remote Similarity	NPD2067	Discontinued
0.6336	Remote Similarity	NPD1535	Discovery
0.6331	Remote Similarity	NPD6653	Approved
0.6327	Remote Similarity	NPD5403	Approved
0.6327	Remote Similarity	NPD3873	Phase 3
0.6327	Remote Similarity	NPD3869	Phase 3
0.6323	Remote Similarity	NPD6808	Phase 2
0.632	Remote Similarity	NPD7843	Approved
0.6319	Remote Similarity	NPD2309	Approved
0.6319	Remote Similarity	NPD2354	Approved
0.6309	Remote Similarity	NPD6599	Discontinued
0.6304	Remote Similarity	NPD2979	Phase 3
0.6301	Remote Similarity	NPD5401	Approved
0.6296	Remote Similarity	NPD454	Approved
0.6286	Remote Similarity	NPD5688	Approved
0.6286	Remote Similarity	NPD5689	Approved
0.6277	Remote Similarity	NPD3764	Approved
0.6268	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6005	Phase 3
0.6268	Remote Similarity	NPD6004	Phase 3
0.6268	Remote Similarity	NPD6002	Phase 3
0.6268	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7411	Suspended
0.6261	Remote Similarity	NPD1202	Approved
0.625	Remote Similarity	NPD2614	Approved
0.625	Remote Similarity	NPD9261	Approved
0.625	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3750	Approved
0.6242	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD4870	Approved
0.6232	Remote Similarity	NPD8032	Phase 2
0.6225	Remote Similarity	NPD6280	Approved
0.6225	Remote Similarity	NPD6279	Approved
0.622	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD9257	Approved
0.6216	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD9259	Approved
0.6212	Remote Similarity	NPD1281	Approved
0.6204	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD2240	Approved
0.6197	Remote Similarity	NPD4477	Approved
0.6197	Remote Similarity	NPD4476	Approved
0.6197	Remote Similarity	NPD2239	Approved
0.6184	Remote Similarity	NPD7819	Suspended
0.6184	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4626	Approved
0.6179	Remote Similarity	NPD290	Approved
0.6174	Remote Similarity	NPD957	Approved
0.6172	Remote Similarity	NPD7157	Approved
0.6164	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD5890	Approved
0.6159	Remote Similarity	NPD1296	Phase 2
0.6159	Remote Similarity	NPD5889	Approved
0.6154	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5049	Phase 3
0.6138	Remote Similarity	NPD7003	Approved
0.6138	Remote Similarity	NPD4110	Phase 3
0.6138	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6801	Discontinued
0.6111	Remote Similarity	NPD6765	Approved
0.6111	Remote Similarity	NPD2897	Discontinued
0.6111	Remote Similarity	NPD6764	Approved
0.6111	Remote Similarity	NPD6559	Discontinued
0.6111	Remote Similarity	NPD1549	Phase 2
0.6107	Remote Similarity	NPD1670	Discontinued
0.6104	Remote Similarity	NPD7768	Phase 2
0.6098	Remote Similarity	NPD968	Approved
0.609	Remote Similarity	NPD6287	Discontinued
0.609	Remote Similarity	NPD422	Phase 1
0.6087	Remote Similarity	NPD7095	Approved
0.6087	Remote Similarity	NPD5163	Phase 2
0.6087	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5746	Approved
0.6084	Remote Similarity	NPD2438	Suspended
0.6084	Remote Similarity	NPD2531	Phase 2
0.6081	Remote Similarity	NPD4661	Approved
0.6081	Remote Similarity	NPD4662	Approved
0.6074	Remote Similarity	NPD1283	Approved
0.6069	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD7075	Discontinued
0.6065	Remote Similarity	NPD3749	Approved
0.6063	Remote Similarity	NPD769	Approved
0.6063	Remote Similarity	NPD821	Approved
0.6056	Remote Similarity	NPD743	Approved
0.6056	Remote Similarity	NPD7097	Phase 1
0.6053	Remote Similarity	NPD6385	Approved
0.6053	Remote Similarity	NPD958	Approved
0.6053	Remote Similarity	NPD6386	Approved
0.6051	Remote Similarity	NPD1247	Approved
0.6051	Remote Similarity	NPD5262	Discontinued
0.6048	Remote Similarity	NPD9264	Approved
0.6048	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD9267	Approved
0.6048	Remote Similarity	NPD9263	Approved
0.6042	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD3817	Phase 2
0.6039	Remote Similarity	NPD5402	Approved
0.6028	Remote Similarity	NPD230	Phase 1
0.6028	Remote Similarity	NPD4340	Discontinued
0.6027	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3226	Approved
0.6026	Remote Similarity	NPD7458	Discontinued
0.6024	Remote Similarity	NPD8434	Phase 2
0.6016	Remote Similarity	NPD9069	Phase 1
0.6014	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD7317	Phase 3
0.6	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6	Remote Similarity	NPD74	Approved
0.6	Remote Similarity	NPD5958	Discontinued
0.6	Remote Similarity	NPD9258	Approved
0.6	Remote Similarity	NPD4534	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