NPASS Compound

Structure

CID125674 OpenBabel06191715482D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.1865 -3.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6496 -1.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8077 2.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5094 -2.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5575 -2.2740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1865 -3.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8077 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 -1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6496 -2.5278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2402 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8077 -2.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3219 1.5622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8077 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3219 -1.5622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2402 -1.2639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4858 -3.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7260 -1.7466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3219 2.5278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4858 -3.9760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5071 -2.3142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7260 -0.7811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3219 -2.5278 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 6 0 0 0 14 7 1 1 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 6 0 0 0 16 20 1 6 0 0 0 16 26 1 0 0 0 0 17 12 1 6 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 5 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	1.256
LogD:	1.056
LogS:	-2.291
# Rotatable Bonds:	3
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	5.208
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796
MDCK Permeability:	1.992655779758934e-05
Pgp-inhibitor:	0.369
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	79.056884765625%
Volume Distribution (VD):	1.597
Pgp-substrate:	13.575469017028809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.266
CYP2C19-inhibitor:	0.399
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.564
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.43

ADMET: Excretion

Clearance (CL):	8.104
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.622
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.658
Carcinogencity:	0.054
Eye Corrosion:	0.055
Eye Irritation:	0.04
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC125674

Natural Product ID:	NPC125674
*Common Name:**	Epoxynobilin
IUPAC Name:	n.a.
Synonyms:	Epoxynobilin
Standard InCHIKey:	DZTWAOVNNLDWNH-AUWKULLQSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6-,11-7-/t13-,14+,15+,16+,17-,20+/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@@H](/C(=C[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483867
PubChem CID:	9998730
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18662038]
NPO17248	Viguiera quinqueradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358640]
NPO1198	Viguiera eriophora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1198	Viguiera eriophora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26523	Alicyclobacillus acidocaldarius	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17285	Taraxacum udum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8147	Calea hispida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16661	Duboisia myoporoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15368	Trifolium medium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1198	Viguiera eriophora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17194	Linum capitatum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13648	Phialocephala fortinii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15676	Tricholoma scalpturatum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17248	Viguiera quinqueradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18310	Pecten jacobaeus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22725	Cirsium microspicatum	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
ED50	1
IC50	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.99	umol/L	PMID[525695]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	29648.31	nM	PMID[525696]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[525696]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	29660.0	nM	PMID[525696]

☑ 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 NPC125674 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	201
0.1-0.2	1263
0.2-0.3	4782
0.3-0.4	9938
0.4-0.5	13781
0.5-0.6	7176
0.6-0.7	3987
0.7-0.8	1276
0.8-0.85	186
0.85-0.9	69
0.9-0.95	29
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC228451
1.0	High Similarity	NPC475838
0.9885	High Similarity	NPC474247
0.9663	High Similarity	NPC230800
0.9663	High Similarity	NPC279621
0.954	High Similarity	NPC475855
0.9348	High Similarity	NPC288876
0.9318	High Similarity	NPC144133
0.9318	High Similarity	NPC179394
0.9302	High Similarity	NPC50637
0.9302	High Similarity	NPC475461
0.9302	High Similarity	NPC305475
0.9222	High Similarity	NPC303942
0.9222	High Similarity	NPC57405
0.9205	High Similarity	NPC166919
0.9186	High Similarity	NPC255307
0.9121	High Similarity	NPC14961
0.9121	High Similarity	NPC471141
0.9121	High Similarity	NPC270013
0.907	High Similarity	NPC191476
0.907	High Similarity	NPC114979
0.9032	High Similarity	NPC473326
0.9022	High Similarity	NPC476315
0.9022	High Similarity	NPC473859
0.9011	High Similarity	NPC81386
0.9011	High Similarity	NPC474035
0.8953	High Similarity	NPC473390
0.8953	High Similarity	NPC131669
0.8953	High Similarity	NPC40746
0.8953	High Similarity	NPC169575
0.8913	High Similarity	NPC475659
0.8913	High Similarity	NPC304886
0.8901	High Similarity	NPC212486
0.8901	High Similarity	NPC475912
0.8889	High Similarity	NPC469368
0.8864	High Similarity	NPC150755
0.8851	High Similarity	NPC141193
0.8851	High Similarity	NPC476804
0.8851	High Similarity	NPC96259
0.8842	High Similarity	NPC164598
0.8842	High Similarity	NPC474339
0.8837	High Similarity	NPC229825
0.883	High Similarity	NPC474213
0.8804	High Similarity	NPC474338
0.8804	High Similarity	NPC473316
0.8804	High Similarity	NPC473330
0.8804	High Similarity	NPC140543
0.8791	High Similarity	NPC473321
0.8778	High Similarity	NPC151770
0.8778	High Similarity	NPC474032
0.8778	High Similarity	NPC295312
0.8764	High Similarity	NPC160138
0.875	High Similarity	NPC471148
0.875	High Similarity	NPC470755
0.8736	High Similarity	NPC250315
0.8736	High Similarity	NPC116543
0.8721	High Similarity	NPC24417
0.8721	High Similarity	NPC141810
0.871	High Similarity	NPC471142
0.871	High Similarity	NPC36954
0.8696	High Similarity	NPC273579
0.8696	High Similarity	NPC288240
0.8696	High Similarity	NPC295204
0.8696	High Similarity	NPC162205
0.8681	High Similarity	NPC473619
0.8681	High Similarity	NPC312042
0.8667	High Similarity	NPC202672
0.8667	High Similarity	NPC476805
0.8667	High Similarity	NPC475819
0.8667	High Similarity	NPC473715
0.8646	High Similarity	NPC473332
0.8636	High Similarity	NPC158756
0.8632	High Similarity	NPC187268
0.8602	High Similarity	NPC476267
0.8602	High Similarity	NPC477131
0.8587	High Similarity	NPC30515
0.8587	High Similarity	NPC184463
0.8586	High Similarity	NPC477513
0.8556	High Similarity	NPC231889
0.8556	High Similarity	NPC475703
0.8539	High Similarity	NPC165162
0.8523	High Similarity	NPC272814
0.8523	High Similarity	NPC59097
0.8511	High Similarity	NPC477922
0.8506	High Similarity	NPC52861
0.8495	Intermediate Similarity	NPC179746
0.8495	Intermediate Similarity	NPC81419
0.8495	Intermediate Similarity	NPC476300
0.8488	Intermediate Similarity	NPC167881
0.8488	Intermediate Similarity	NPC98557
0.8488	Intermediate Similarity	NPC617
0.8485	Intermediate Similarity	NPC243998
0.8478	Intermediate Similarity	NPC475748
0.8478	Intermediate Similarity	NPC476004
0.8478	Intermediate Similarity	NPC51004
0.8478	Intermediate Similarity	NPC474761
0.8478	Intermediate Similarity	NPC473448
0.8462	Intermediate Similarity	NPC476803
0.8454	Intermediate Similarity	NPC201718
0.8454	Intermediate Similarity	NPC476270
0.8454	Intermediate Similarity	NPC150923
0.8444	Intermediate Similarity	NPC122502
0.8444	Intermediate Similarity	NPC469910
0.8438	Intermediate Similarity	NPC221615
0.8438	Intermediate Similarity	NPC471144
0.8421	Intermediate Similarity	NPC477921
0.8404	Intermediate Similarity	NPC471147
0.8404	Intermediate Similarity	NPC323008
0.8404	Intermediate Similarity	NPC198853
0.8404	Intermediate Similarity	NPC470010
0.8404	Intermediate Similarity	NPC470013
0.8404	Intermediate Similarity	NPC262133
0.8387	Intermediate Similarity	NPC475925
0.8387	Intermediate Similarity	NPC158061
0.8387	Intermediate Similarity	NPC131209
0.8387	Intermediate Similarity	NPC208886
0.8387	Intermediate Similarity	NPC133698
0.8387	Intermediate Similarity	NPC12172
0.8372	Intermediate Similarity	NPC471465
0.8372	Intermediate Similarity	NPC93763
0.8372	Intermediate Similarity	NPC108816
0.8372	Intermediate Similarity	NPC196653
0.837	Intermediate Similarity	NPC307411
0.8367	Intermediate Similarity	NPC140591
0.8367	Intermediate Similarity	NPC197835
0.8367	Intermediate Similarity	NPC149371
0.8367	Intermediate Similarity	NPC303653
0.8367	Intermediate Similarity	NPC86077
0.8367	Intermediate Similarity	NPC291500
0.8367	Intermediate Similarity	NPC189609
0.8351	Intermediate Similarity	NPC475949
0.8333	Intermediate Similarity	NPC319795
0.8333	Intermediate Similarity	NPC215364
0.8333	Intermediate Similarity	NPC38468
0.8333	Intermediate Similarity	NPC261380
0.8333	Intermediate Similarity	NPC161493
0.8333	Intermediate Similarity	NPC471462
0.8333	Intermediate Similarity	NPC471140
0.8333	Intermediate Similarity	NPC50362
0.8316	Intermediate Similarity	NPC170120
0.8316	Intermediate Similarity	NPC67584
0.8316	Intermediate Similarity	NPC52044
0.8316	Intermediate Similarity	NPC213698
0.83	Intermediate Similarity	NPC223450
0.8298	Intermediate Similarity	NPC475302
0.828	Intermediate Similarity	NPC251385
0.828	Intermediate Similarity	NPC62815
0.828	Intermediate Similarity	NPC49342
0.828	Intermediate Similarity	NPC129419
0.828	Intermediate Similarity	NPC474232
0.8276	Intermediate Similarity	NPC89128
0.8276	Intermediate Similarity	NPC270126
0.8265	Intermediate Similarity	NPC264477
0.8265	Intermediate Similarity	NPC47880
0.8265	Intermediate Similarity	NPC477511
0.8256	Intermediate Similarity	NPC141789
0.8256	Intermediate Similarity	NPC171204
0.8256	Intermediate Similarity	NPC7563
0.8256	Intermediate Similarity	NPC320630
0.8256	Intermediate Similarity	NPC116177
0.8256	Intermediate Similarity	NPC476028
0.8247	Intermediate Similarity	NPC279561
0.8247	Intermediate Similarity	NPC208233
0.8242	Intermediate Similarity	NPC470242
0.8242	Intermediate Similarity	NPC284902
0.8229	Intermediate Similarity	NPC17585
0.8229	Intermediate Similarity	NPC35498
0.8229	Intermediate Similarity	NPC213078
0.8211	Intermediate Similarity	NPC127019
0.8202	Intermediate Similarity	NPC89555
0.82	Intermediate Similarity	NPC100487
0.82	Intermediate Similarity	NPC474741
0.8191	Intermediate Similarity	NPC476705
0.8191	Intermediate Similarity	NPC475881
0.8191	Intermediate Similarity	NPC20713
0.8191	Intermediate Similarity	NPC70251
0.8182	Intermediate Similarity	NPC281132
0.8172	Intermediate Similarity	NPC206001
0.8172	Intermediate Similarity	NPC218927
0.8172	Intermediate Similarity	NPC268298
0.8163	Intermediate Similarity	NPC475053
0.8161	Intermediate Similarity	NPC267231
0.8152	Intermediate Similarity	NPC72513
0.8152	Intermediate Similarity	NPC5130
0.814	Intermediate Similarity	NPC235906
0.814	Intermediate Similarity	NPC68819
0.8137	Intermediate Similarity	NPC14862
0.8137	Intermediate Similarity	NPC474664
0.8137	Intermediate Similarity	NPC233379
0.8132	Intermediate Similarity	NPC474547
0.8132	Intermediate Similarity	NPC137033
0.8132	Intermediate Similarity	NPC21469
0.8125	Intermediate Similarity	NPC474947
0.8125	Intermediate Similarity	NPC107476
0.8119	Intermediate Similarity	NPC166115
0.8119	Intermediate Similarity	NPC475802
0.8111	Intermediate Similarity	NPC231601
0.8105	Intermediate Similarity	NPC469645
0.8105	Intermediate Similarity	NPC476049
0.8105	Intermediate Similarity	NPC469692

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 NPC125674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1822
0.2-0.3	3691
0.3-0.4	2341
0.4-0.5	688
0.5-0.6	325
0.6-0.7	74
0.7-0.8	14
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6698	Approved
0.828	Intermediate Similarity	NPD46	Approved
0.7979	Intermediate Similarity	NPD1695	Approved
0.7895	Intermediate Similarity	NPD7838	Discovery
0.781	Intermediate Similarity	NPD6371	Approved
0.7692	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5344	Discontinued
0.7353	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5785	Approved
0.734	Intermediate Similarity	NPD7154	Phase 3
0.7292	Intermediate Similarity	NPD4249	Approved
0.7273	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4251	Approved
0.7216	Intermediate Similarity	NPD4250	Approved
0.7188	Intermediate Similarity	NPD5363	Approved
0.7184	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD6686	Approved
0.7129	Intermediate Similarity	NPD5282	Discontinued
0.7115	Intermediate Similarity	NPD6648	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.7027	Intermediate Similarity	NPD6053	Discontinued
0.7021	Intermediate Similarity	NPD4819	Approved
0.7021	Intermediate Similarity	NPD4820	Approved
0.7021	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4822	Approved
0.7021	Intermediate Similarity	NPD4821	Approved
0.6979	Remote Similarity	NPD5362	Discontinued
0.6977	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.693	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD4269	Approved
0.6857	Remote Similarity	NPD7638	Approved
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1694	Approved
0.6837	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4268	Approved
0.6809	Remote Similarity	NPD4271	Approved
0.6771	Remote Similarity	NPD5369	Approved
0.6768	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6636	Remote Similarity	NPD6008	Approved
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8517	Approved
0.6555	Remote Similarity	NPD8513	Phase 3
0.6555	Remote Similarity	NPD8515	Approved
0.6555	Remote Similarity	NPD8516	Approved
0.6531	Remote Similarity	NPD5209	Approved
0.6495	Remote Similarity	NPD5368	Approved
0.6465	Remote Similarity	NPD5331	Approved
0.6465	Remote Similarity	NPD5332	Approved
0.6446	Remote Similarity	NPD7642	Approved
0.6442	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD4790	Discontinued
0.6408	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7632	Discontinued
0.6354	Remote Similarity	NPD4756	Discovery
0.6341	Remote Similarity	NPD8273	Phase 1
0.6311	Remote Similarity	NPD7829	Approved
0.6311	Remote Similarity	NPD7830	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.629	Remote Similarity	NPD8074	Phase 3
0.6286	Remote Similarity	NPD6411	Approved
0.6283	Remote Similarity	NPD5697	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5370	Suspended
0.6239	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD6881	Approved
0.621	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD6650	Approved
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.6174	Remote Similarity	NPD6013	Approved
0.6174	Remote Similarity	NPD6012	Approved
0.6174	Remote Similarity	NPD6014	Approved
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.6146	Remote Similarity	NPD8039	Approved
0.614	Remote Similarity	NPD6412	Phase 2
0.614	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD6695	Phase 3
0.6139	Remote Similarity	NPD6110	Phase 1
0.6132	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD7290	Approved
0.6107	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4632	Approved
0.6087	Remote Similarity	NPD6011	Approved
0.6087	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7320	Approved
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6617	Approved
0.6068	Remote Similarity	NPD6869	Approved
0.6066	Remote Similarity	NPD6319	Approved
0.6063	Remote Similarity	NPD7319	Approved
0.6033	Remote Similarity	NPD7641	Discontinued
0.6019	Remote Similarity	NPD7748	Approved
0.6017	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD7492	Approved
0.5981	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD5284	Approved
0.5981	Remote Similarity	NPD5693	Phase 1
0.5981	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD7331	Phase 2
0.5969	Remote Similarity	NPD7260	Phase 2
0.5965	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD7334	Approved
0.5962	Remote Similarity	NPD3618	Phase 1
0.5962	Remote Similarity	NPD7521	Approved
0.5962	Remote Similarity	NPD6684	Approved
0.5962	Remote Similarity	NPD7146	Approved
0.5962	Remote Similarity	NPD6409	Approved
0.5962	Remote Similarity	NPD5330	Approved
0.5952	Remote Similarity	NPD6616	Approved
0.5952	Remote Similarity	NPD8451	Approved
0.595	Remote Similarity	NPD6009	Approved
0.595	Remote Similarity	NPD7500	Approved
0.5948	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4753	Phase 2
0.5935	Remote Similarity	NPD6054	Approved
0.5922	Remote Similarity	NPD3666	Approved
0.5922	Remote Similarity	NPD3133	Approved
0.5922	Remote Similarity	NPD3665	Phase 1
0.592	Remote Similarity	NPD7604	Phase 2
0.5906	Remote Similarity	NPD7078	Approved
0.5906	Remote Similarity	NPD8448	Approved
0.5905	Remote Similarity	NPD7524	Approved
0.5905	Remote Similarity	NPD7750	Discontinued
0.5902	Remote Similarity	NPD7327	Approved
0.5902	Remote Similarity	NPD7328	Approved
0.5893	Remote Similarity	NPD5285	Approved
0.5893	Remote Similarity	NPD4696	Approved
0.5893	Remote Similarity	NPD5286	Approved
0.5891	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6016	Approved
0.5887	Remote Similarity	NPD5983	Phase 2
0.5887	Remote Similarity	NPD6015	Approved
0.5887	Remote Similarity	NPD7503	Approved
0.5887	Remote Similarity	NPD8033	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5877	Remote Similarity	NPD6647	Phase 2
0.5873	Remote Similarity	NPD8340	Approved
0.5873	Remote Similarity	NPD8341	Approved
0.5873	Remote Similarity	NPD8342	Approved
0.5873	Remote Similarity	NPD8299	Approved
0.5872	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7900	Approved
0.587	Remote Similarity	NPD7341	Phase 2
0.5868	Remote Similarity	NPD6274	Approved
0.5865	Remote Similarity	NPD1696	Phase 3
0.5859	Remote Similarity	NPD7736	Approved
0.5856	Remote Similarity	NPD4755	Approved
0.5854	Remote Similarity	NPD7516	Approved
0.5849	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6903	Approved
0.5849	Remote Similarity	NPD5737	Approved
0.5849	Remote Similarity	NPD6672	Approved
0.5847	Remote Similarity	NPD6421	Discontinued
0.5842	Remote Similarity	NPD6930	Phase 2
0.5842	Remote Similarity	NPD6931	Approved
0.5842	Remote Similarity	NPD4695	Discontinued
0.584	Remote Similarity	NPD6370	Approved
0.584	Remote Similarity	NPD5988	Approved
0.5833	Remote Similarity	NPD8133	Approved
0.581	Remote Similarity	NPD6422	Discontinued
0.581	Remote Similarity	NPD5279	Phase 3
0.581	Remote Similarity	NPD4519	Discontinued
0.581	Remote Similarity	NPD4623	Approved
0.5806	Remote Similarity	NPD6059	Approved
0.5806	Remote Similarity	NPD8294	Approved
0.5806	Remote Similarity	NPD8377	Approved
0.5802	Remote Similarity	NPD6845	Suspended
0.5798	Remote Similarity	NPD7116	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data