NPASS Compound

Structure

CID328737 OpenBabel06191716202D 34 40 0 0 1 0 0 0 0 0999 V2000 2.4274 -3.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5654 -4.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7706 1.2999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 -1.2841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7349 -3.0661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 -2.1397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0830 -2.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4828 -1.7122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 0.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4475 -0.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7066 -0.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4828 0.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7404 0.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2923 -3.6335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7404 -0.4280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8842 -2.9765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9657 -1.7122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7066 -2.1397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1884 -1.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9134 -0.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 -0.4280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4475 -1.7122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9657 -0.8556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7414 0.4280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4828 -0.8556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7414 -0.4280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9645 -1.6444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1119 -0.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0296 -2.4984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4828 0.0000 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 16 2 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 17 29 1 1 0 0 0 18 16 1 1 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 25 1 6 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 27 1 0 0 0 0 24 26 1 1 0 0 0 25 21 1 6 0 0 0 26 13 1 1 0 0 0 27 29 1 6 0 0 0 27 34 1 0 0 0 0 28 24 1 6 0 0 0 28 33 1 0 0 0 0 29 28 1 1 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.29
Volume:	486.287
LogP:	5.325
LogD:	4.154
LogS:	-4.625
# Rotatable Bonds:	2
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	6.748
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.53
MDCK Permeability:	1.3894128642277792e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	77.48993682861328%
Volume Distribution (VD):	0.766
Pgp-substrate:	15.471388816833496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.503
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	5.83
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.842
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.804
Skin Sensitization:	0.056
Carcinogencity:	0.931
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC328737

Natural Product ID:	NPC328737
*Common Name:**	Breynceanothanolic Acid
IUPAC Name:	n.a.
Synonyms:	breynceanothanolic acid
Standard InCHIKey:	SNCMVKNGLNUISS-GCWSBASFSA-N
Standard InCHI:	InChI=1S/C29H40O5/c1-16(2)18-7-9-25(21(30)31)12-13-26-19(20(18)25)8-10-28(33-22(26)32)24(26,6)11-14-27-23(4,5)15-17(3)29(27,28)34-27/h17-20H,1,7-15H2,2-6H3,(H,30,31)/t17-,18-,19+,20+,24-,25-,26+,27+,28+,29-/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@]34[C@@]([C@@]1(CC2)C(=O)O3)(C)CC[C@@]12[C@@]4(O1)[C@@H](C)CC2(C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782589
PubChem CID:	53355687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	10200.0	nM	PMID[451954]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	14300.0	nM	PMID[451954]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14500.0	nM	PMID[451954]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12700.0	nM	PMID[451954]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	20000.0	nM	PMID[451954]

☑ 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 NPC328737 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	299
0.1-0.2	2268
0.2-0.3	7311
0.3-0.4	15343
0.4-0.5	6407
0.5-0.6	6093
0.6-0.7	4309
0.7-0.8	653
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8269	Intermediate Similarity	NPC124544
0.8252	Intermediate Similarity	NPC108371
0.8173	Intermediate Similarity	NPC121218
0.8173	Intermediate Similarity	NPC253886
0.8155	Intermediate Similarity	NPC472028
0.8148	Intermediate Similarity	NPC154906
0.8113	Intermediate Similarity	NPC301787
0.8113	Intermediate Similarity	NPC471293
0.8095	Intermediate Similarity	NPC170615
0.8077	Intermediate Similarity	NPC94906
0.8058	Intermediate Similarity	NPC469810
0.8058	Intermediate Similarity	NPC253586
0.8037	Intermediate Similarity	NPC222833
0.8037	Intermediate Similarity	NPC138908
0.8037	Intermediate Similarity	NPC200957
0.8	Intermediate Similarity	NPC295276
0.8	Intermediate Similarity	NPC252614
0.7981	Intermediate Similarity	NPC38471
0.7981	Intermediate Similarity	NPC98837
0.7981	Intermediate Similarity	NPC162459
0.7981	Intermediate Similarity	NPC28864
0.7981	Intermediate Similarity	NPC20479
0.7981	Intermediate Similarity	NPC38296
0.7963	Intermediate Similarity	NPC166993
0.7963	Intermediate Similarity	NPC59530
0.7961	Intermediate Similarity	NPC234564
0.7961	Intermediate Similarity	NPC256227
0.7944	Intermediate Similarity	NPC47281
0.7941	Intermediate Similarity	NPC477495
0.7931	Intermediate Similarity	NPC65858
0.7925	Intermediate Similarity	NPC304832
0.7925	Intermediate Similarity	NPC214946
0.7925	Intermediate Similarity	NPC88203
0.7925	Intermediate Similarity	NPC76866
0.7925	Intermediate Similarity	NPC148628
0.7925	Intermediate Similarity	NPC246736
0.7925	Intermediate Similarity	NPC286519
0.7905	Intermediate Similarity	NPC37047
0.7905	Intermediate Similarity	NPC477656
0.7905	Intermediate Similarity	NPC180733
0.7905	Intermediate Similarity	NPC293866
0.7905	Intermediate Similarity	NPC41971
0.789	Intermediate Similarity	NPC231278
0.789	Intermediate Similarity	NPC218123
0.789	Intermediate Similarity	NPC273155
0.789	Intermediate Similarity	NPC112895
0.7885	Intermediate Similarity	NPC190080
0.7885	Intermediate Similarity	NPC111187
0.7876	Intermediate Similarity	NPC298278
0.787	Intermediate Similarity	NPC37600
0.787	Intermediate Similarity	NPC28791
0.787	Intermediate Similarity	NPC50535
0.787	Intermediate Similarity	NPC295366
0.7864	Intermediate Similarity	NPC197158
0.7864	Intermediate Similarity	NPC471624
0.7864	Intermediate Similarity	NPC263135
0.7864	Intermediate Similarity	NPC288906
0.7863	Intermediate Similarity	NPC135038
0.7863	Intermediate Similarity	NPC43252
0.7863	Intermediate Similarity	NPC267822
0.785	Intermediate Similarity	NPC277074
0.785	Intermediate Similarity	NPC140723
0.785	Intermediate Similarity	NPC122811
0.785	Intermediate Similarity	NPC209298
0.7838	Intermediate Similarity	NPC94650
0.783	Intermediate Similarity	NPC52899
0.783	Intermediate Similarity	NPC75941
0.783	Intermediate Similarity	NPC46848
0.783	Intermediate Similarity	NPC163963
0.783	Intermediate Similarity	NPC39683
0.783	Intermediate Similarity	NPC289148
0.7822	Intermediate Similarity	NPC10274
0.7812	Intermediate Similarity	NPC232625
0.781	Intermediate Similarity	NPC119036
0.781	Intermediate Similarity	NPC89099
0.78	Intermediate Similarity	NPC250687
0.78	Intermediate Similarity	NPC254572
0.78	Intermediate Similarity	NPC48824
0.78	Intermediate Similarity	NPC229407
0.7798	Intermediate Similarity	NPC86852
0.7798	Intermediate Similarity	NPC251824
0.7797	Intermediate Similarity	NPC169818
0.7788	Intermediate Similarity	NPC29410
0.7788	Intermediate Similarity	NPC116683
0.7788	Intermediate Similarity	NPC200054
0.7778	Intermediate Similarity	NPC100078
0.7768	Intermediate Similarity	NPC280782
0.7757	Intermediate Similarity	NPC213528
0.7757	Intermediate Similarity	NPC244969
0.7757	Intermediate Similarity	NPC193934
0.7757	Intermediate Similarity	NPC271980
0.7757	Intermediate Similarity	NPC275990
0.7748	Intermediate Similarity	NPC130302
0.7745	Intermediate Similarity	NPC219516
0.7736	Intermediate Similarity	NPC477655
0.7736	Intermediate Similarity	NPC287676
0.7723	Intermediate Similarity	NPC269267
0.7719	Intermediate Similarity	NPC266728
0.7719	Intermediate Similarity	NPC196931
0.7719	Intermediate Similarity	NPC49492
0.7714	Intermediate Similarity	NPC10864
0.7706	Intermediate Similarity	NPC166079
0.7706	Intermediate Similarity	NPC472655
0.7706	Intermediate Similarity	NPC306776
0.7699	Intermediate Similarity	NPC285086
0.7699	Intermediate Similarity	NPC317210
0.7699	Intermediate Similarity	NPC102619
0.7692	Intermediate Similarity	NPC241047
0.7692	Intermediate Similarity	NPC82633
0.7692	Intermediate Similarity	NPC98639
0.7692	Intermediate Similarity	NPC470229
0.7685	Intermediate Similarity	NPC87927
0.7685	Intermediate Similarity	NPC470310
0.7672	Intermediate Similarity	NPC42673
0.767	Intermediate Similarity	NPC224060
0.767	Intermediate Similarity	NPC244356
0.767	Intermediate Similarity	NPC294263
0.7664	Intermediate Similarity	NPC289670
0.7642	Intermediate Similarity	NPC471038
0.7642	Intermediate Similarity	NPC16911
0.7642	Intermediate Similarity	NPC78427
0.7632	Intermediate Similarity	NPC470116
0.7632	Intermediate Similarity	NPC470115
0.7632	Intermediate Similarity	NPC300051
0.7632	Intermediate Similarity	NPC326542
0.7627	Intermediate Similarity	NPC222688
0.7619	Intermediate Similarity	NPC235109
0.7619	Intermediate Similarity	NPC111834
0.7619	Intermediate Similarity	NPC169270
0.7619	Intermediate Similarity	NPC292718
0.7619	Intermediate Similarity	NPC329910
0.7619	Intermediate Similarity	NPC306797
0.7619	Intermediate Similarity	NPC163685
0.7615	Intermediate Similarity	NPC98603
0.7615	Intermediate Similarity	NPC84928
0.7615	Intermediate Similarity	NPC29705
0.7611	Intermediate Similarity	NPC476964
0.7611	Intermediate Similarity	NPC207251
0.7607	Intermediate Similarity	NPC143755
0.76	Intermediate Similarity	NPC80590
0.7596	Intermediate Similarity	NPC277399
0.7596	Intermediate Similarity	NPC475118
0.7593	Intermediate Similarity	NPC22388
0.7589	Intermediate Similarity	NPC98633
0.7589	Intermediate Similarity	NPC76084
0.7589	Intermediate Similarity	NPC471093
0.7589	Intermediate Similarity	NPC255655
0.7589	Intermediate Similarity	NPC124053
0.7573	Intermediate Similarity	NPC471747
0.757	Intermediate Similarity	NPC470388
0.7568	Intermediate Similarity	NPC473517
0.7568	Intermediate Similarity	NPC258323
0.7568	Intermediate Similarity	NPC63841
0.7568	Intermediate Similarity	NPC211224
0.7565	Intermediate Similarity	NPC469794
0.7565	Intermediate Similarity	NPC72772
0.7547	Intermediate Similarity	NPC170978
0.7547	Intermediate Similarity	NPC274793
0.7545	Intermediate Similarity	NPC278628
0.7545	Intermediate Similarity	NPC285927
0.7545	Intermediate Similarity	NPC231530
0.7545	Intermediate Similarity	NPC196528
0.7545	Intermediate Similarity	NPC470587
0.7544	Intermediate Similarity	NPC97002
0.7544	Intermediate Similarity	NPC962
0.7544	Intermediate Similarity	NPC250109
0.7544	Intermediate Similarity	NPC52634
0.7544	Intermediate Similarity	NPC471252
0.7542	Intermediate Similarity	NPC310511
0.7524	Intermediate Similarity	NPC279974
0.7524	Intermediate Similarity	NPC470232
0.7524	Intermediate Similarity	NPC205173
0.7523	Intermediate Similarity	NPC225238
0.7523	Intermediate Similarity	NPC471005
0.7523	Intermediate Similarity	NPC216114
0.7523	Intermediate Similarity	NPC469985
0.7522	Intermediate Similarity	NPC272242
0.7522	Intermediate Similarity	NPC471251
0.7522	Intermediate Similarity	NPC56025
0.7522	Intermediate Similarity	NPC469656
0.7522	Intermediate Similarity	NPC470311
0.7522	Intermediate Similarity	NPC29505
0.7522	Intermediate Similarity	NPC474846
0.7522	Intermediate Similarity	NPC469655
0.7522	Intermediate Similarity	NPC470281
0.7521	Intermediate Similarity	NPC472667
0.7521	Intermediate Similarity	NPC230513
0.75	Intermediate Similarity	NPC475958
0.75	Intermediate Similarity	NPC475061
0.75	Intermediate Similarity	NPC473570
0.75	Intermediate Similarity	NPC477053
0.75	Intermediate Similarity	NPC477051
0.75	Intermediate Similarity	NPC469790
0.75	Intermediate Similarity	NPC204652
0.75	Intermediate Similarity	NPC274827
0.75	Intermediate Similarity	NPC49532
0.75	Intermediate Similarity	NPC291373
0.75	Intermediate Similarity	NPC471790
0.75	Intermediate Similarity	NPC477052
0.75	Intermediate Similarity	NPC471250

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 NPC328737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2601
0.2-0.3	4120
0.3-0.4	1439
0.4-0.5	334
0.5-0.6	201
0.6-0.7	163
0.7-0.8	7
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
0.7706	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD1700	Approved
0.7411	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD8035	Phase 2
0.7404	Intermediate Similarity	NPD8034	Phase 2
0.7377	Intermediate Similarity	NPD7078	Approved
0.7358	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5739	Approved
0.7232	Intermediate Similarity	NPD6402	Approved
0.7232	Intermediate Similarity	NPD7128	Approved
0.7232	Intermediate Similarity	NPD6675	Approved
0.7213	Intermediate Similarity	NPD7492	Approved
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD6373	Approved
0.7177	Intermediate Similarity	NPD7736	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7167	Intermediate Similarity	NPD6054	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD6616	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7105	Intermediate Similarity	NPD6881	Approved
0.7105	Intermediate Similarity	NPD6899	Approved
0.7105	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6001	Approved
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7094	Intermediate Similarity	NPD4632	Approved
0.7069	Intermediate Similarity	NPD6650	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD6370	Approved
0.7025	Intermediate Similarity	NPD6319	Approved
0.7018	Intermediate Similarity	NPD5701	Approved
0.7018	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.6992	Remote Similarity	NPD7604	Phase 2
0.6983	Remote Similarity	NPD7290	Approved
0.6983	Remote Similarity	NPD6883	Approved
0.6983	Remote Similarity	NPD7102	Approved
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD8133	Approved
0.6937	Remote Similarity	NPD7640	Approved
0.6937	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6617	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD6869	Approved
0.6917	Remote Similarity	NPD6009	Approved
0.6911	Remote Similarity	NPD5988	Approved
0.6909	Remote Similarity	NPD6083	Phase 2
0.6909	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD6013	Approved
0.6897	Remote Similarity	NPD6012	Approved
0.6897	Remote Similarity	NPD6014	Approved
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD6399	Phase 3
0.6847	Remote Similarity	NPD5696	Approved
0.6829	Remote Similarity	NPD5983	Phase 2
0.681	Remote Similarity	NPD6011	Approved
0.6803	Remote Similarity	NPD7516	Approved
0.68	Remote Similarity	NPD6697	Approved
0.68	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD6118	Approved
0.6796	Remote Similarity	NPD4788	Approved
0.678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7115	Discovery
0.6762	Remote Similarity	NPD6098	Approved
0.6757	Remote Similarity	NPD4755	Approved
0.6746	Remote Similarity	NPD6336	Discontinued
0.6729	Remote Similarity	NPD6673	Approved
0.6729	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD6904	Approved
0.6727	Remote Similarity	NPD5695	Phase 3
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7327	Approved
0.6721	Remote Similarity	NPD7328	Approved
0.6696	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.6637	Remote Similarity	NPD4696	Approved
0.6637	Remote Similarity	NPD5286	Approved
0.6637	Remote Similarity	NPD4700	Approved
0.6637	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD5284	Approved
0.6606	Remote Similarity	NPD5281	Approved
0.66	Remote Similarity	NPD6117	Approved
0.6583	Remote Similarity	NPD6053	Discontinued
0.6581	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5328	Approved
0.656	Remote Similarity	NPD8379	Approved
0.656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8296	Approved
0.656	Remote Similarity	NPD8380	Approved
0.656	Remote Similarity	NPD8335	Approved
0.656	Remote Similarity	NPD8378	Approved
0.6557	Remote Similarity	NPD6274	Approved
0.6555	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD4223	Phase 3
0.6538	Remote Similarity	NPD4221	Approved
0.6535	Remote Similarity	NPD6116	Phase 1
0.6532	Remote Similarity	NPD7100	Approved
0.6532	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD7632	Discontinued
0.6522	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD5226	Approved
0.6509	Remote Similarity	NPD5329	Approved
0.6486	Remote Similarity	NPD7748	Approved
0.6481	Remote Similarity	NPD5208	Approved
0.6481	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8377	Approved
0.648	Remote Similarity	NPD8294	Approved
0.6471	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD6052	Approved
0.6466	Remote Similarity	NPD5174	Approved
0.646	Remote Similarity	NPD7902	Approved
0.6455	Remote Similarity	NPD6050	Approved
0.6455	Remote Similarity	NPD5693	Phase 1
0.6455	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD6335	Approved
0.6449	Remote Similarity	NPD7334	Approved
0.6449	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5330	Approved
0.6449	Remote Similarity	NPD6409	Approved
0.6449	Remote Similarity	NPD6684	Approved
0.6449	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD6921	Approved
0.6429	Remote Similarity	NPD6908	Approved
0.6429	Remote Similarity	NPD6909	Approved
0.6429	Remote Similarity	NPD8033	Approved
0.6422	Remote Similarity	NPD4753	Phase 2
0.6415	Remote Similarity	NPD4197	Approved
0.641	Remote Similarity	NPD5141	Approved
0.64	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4202	Approved
0.6392	Remote Similarity	NPD5360	Phase 3
0.6392	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3573	Approved
0.6372	Remote Similarity	NPD4697	Phase 3
0.6371	Remote Similarity	NPD6317	Approved
0.6371	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5692	Phase 3
0.6364	Remote Similarity	NPD6081	Approved
0.6356	Remote Similarity	NPD4768	Approved
0.6356	Remote Similarity	NPD4767	Approved
0.6337	Remote Similarity	NPD3703	Phase 2
0.633	Remote Similarity	NPD6672	Approved
0.633	Remote Similarity	NPD5737	Approved
0.6328	Remote Similarity	NPD6067	Discontinued
0.6328	Remote Similarity	NPD8328	Phase 3
0.6325	Remote Similarity	NPD4754	Approved
0.632	Remote Similarity	NPD6314	Approved
0.632	Remote Similarity	NPD6313	Approved
0.6306	Remote Similarity	NPD7515	Phase 2
0.6306	Remote Similarity	NPD5694	Approved
0.6296	Remote Similarity	NPD5205	Approved
0.6296	Remote Similarity	NPD4138	Approved
0.6296	Remote Similarity	NPD4689	Approved
0.6296	Remote Similarity	NPD4688	Approved
0.6296	Remote Similarity	NPD3618	Phase 1
0.6296	Remote Similarity	NPD4690	Approved
0.6296	Remote Similarity	NPD4693	Phase 3
0.6283	Remote Similarity	NPD5210	Approved
0.6283	Remote Similarity	NPD4629	Approved
0.6262	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5222	Approved
0.62	Remote Similarity	NPD5777	Approved
0.6195	Remote Similarity	NPD7900	Approved
0.6195	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD4224	Phase 2
0.6174	Remote Similarity	NPD5173	Approved
0.616	Remote Similarity	NPD6868	Approved
0.6148	Remote Similarity	NPD5251	Approved
0.6148	Remote Similarity	NPD5247	Approved
0.6148	Remote Similarity	NPD5249	Phase 3
0.6148	Remote Similarity	NPD5248	Approved
0.6148	Remote Similarity	NPD5250	Approved
0.6147	Remote Similarity	NPD4694	Approved
0.6147	Remote Similarity	NPD5280	Approved
0.6147	Remote Similarity	NPD5690	Phase 2
0.6132	Remote Similarity	NPD4692	Approved
0.6132	Remote Similarity	NPD4139	Approved
0.6121	Remote Similarity	NPD4225	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