NPASS Compound

Structure

NPC149011 OpenBabel07101718202D 42 45 0 0 1 0 0 0 0 0999 V2000 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 16 2 0 0 0 0 2 8 2 0 0 0 0 2 16 1 0 0 0 0 3 9 1 0 0 0 0 3 17 2 0 0 0 0 4 10 2 0 0 0 0 4 17 1 0 0 0 0 5 12 2 0 0 0 0 5 16 1 0 0 0 0 6 14 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 24 1 0 0 0 0 15 31 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 34 2 0 0 0 0 22 26 2 0 0 0 0 22 40 1 0 0 0 0 23 15 1 6 0 0 0 23 27 1 0 0 0 0 23 41 1 0 0 0 0 24 35 2 0 0 0 0 24 42 1 0 0 0 0 25 26 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 1 0 0 0 28 29 1 0 0 0 0 28 39 1 6 0 0 0 29 30 1 0 0 0 0 29 42 1 1 0 0 0 30 40 1 6 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.16
Volume:	564.419
LogP:	2.744
LogD:	1.857
LogS:	-3.243
# Rotatable Bonds:	10
TPSA:	203.44
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	4.128
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.437
MDCK Permeability:	9.986570148612373e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.338
20% Bioavailability (F20%):	0.548
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	101.7306900024414%
Volume Distribution (VD):	0.563
Pgp-substrate:	0.7776962518692017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.518
CYP2D6-inhibitor:	0.458
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	6.968
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.487
AMES Toxicity:	0.663
Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.962
Carcinogencity:	0.359
Eye Corrosion:	0.003
Eye Irritation:	0.238
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC149011

Natural Product ID:	NPC149011
*Common Name:**	4'-O-Beta-D-(2''-P-Coumaroyl)Glucopyranosyl-4,2',3'-Trihydroxychalcone
IUPAC Name:	[(2S,3R,4S,5S,6R)-2-[2,3-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	XKPBAPHWYIKWSN-SVQBVAIGSA-N
Standard InCHI:	InChI=1S/C30H28O12/c31-15-23-27(38)28(39)29(42-24(35)14-6-17-3-9-19(33)10-4-17)30(41-23)40-22-13-11-20(25(36)26(22)37)21(34)12-5-16-1-7-18(32)8-2-16/h1-14,23,27-33,36-39H,15H2/b12-5+,14-6+/t23-,27-,28+,29-,30-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(c(c2O)O)C(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504292
PubChem CID:	11827998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

*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
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.93	mM	PMID[544967]

☑ 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 NPC149011 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	399
0.1-0.2	1721
0.2-0.3	4145
0.3-0.4	8881
0.4-0.5	8955
0.5-0.6	4233
0.6-0.7	5002
0.7-0.8	5717
0.8-0.85	2176
0.85-0.9	1006
0.9-0.95	441
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC204937
0.9876	High Similarity	NPC88560
0.9876	High Similarity	NPC175230
0.9876	High Similarity	NPC172033
0.9755	High Similarity	NPC472991
0.9755	High Similarity	NPC472992
0.9753	High Similarity	NPC472993
0.975	High Similarity	NPC116745
0.9695	High Similarity	NPC476620
0.9695	High Similarity	NPC476621
0.9695	High Similarity	NPC476618
0.9695	High Similarity	NPC476623
0.9695	High Similarity	NPC476619
0.9695	High Similarity	NPC476622
0.9691	High Similarity	NPC47140
0.9691	High Similarity	NPC67134
0.9686	High Similarity	NPC88043
0.9634	High Similarity	NPC144097
0.9634	High Similarity	NPC61904
0.9627	High Similarity	NPC45400
0.9625	High Similarity	NPC165720
0.9576	High Similarity	NPC37668
0.9576	High Similarity	NPC217520
0.9576	High Similarity	NPC472387
0.9576	High Similarity	NPC139571
0.9576	High Similarity	NPC35167
0.9576	High Similarity	NPC113836
0.9576	High Similarity	NPC253521
0.9573	High Similarity	NPC223426
0.9573	High Similarity	NPC81042
0.9573	High Similarity	NPC34267
0.9573	High Similarity	NPC214621
0.9571	High Similarity	NPC172807
0.9571	High Similarity	NPC211594
0.9571	High Similarity	NPC254540
0.9568	High Similarity	NPC229687
0.9563	High Similarity	NPC270335
0.9563	High Similarity	NPC168822
0.9563	High Similarity	NPC191306
0.9521	High Similarity	NPC36138
0.9518	High Similarity	NPC471030
0.9515	High Similarity	NPC296018
0.9515	High Similarity	NPC154741
0.9512	High Similarity	NPC4390
0.9509	High Similarity	NPC20505
0.9509	High Similarity	NPC34287
0.9509	High Similarity	NPC235260
0.9509	High Similarity	NPC471416
0.9509	High Similarity	NPC155763
0.9506	High Similarity	NPC58716
0.9506	High Similarity	NPC229729
0.9506	High Similarity	NPC146792
0.9506	High Similarity	NPC45618
0.9503	High Similarity	NPC22832
0.9503	High Similarity	NPC311830
0.95	High Similarity	NPC77660
0.95	High Similarity	NPC189142
0.95	High Similarity	NPC285108
0.95	High Similarity	NPC33298
0.9497	High Similarity	NPC289346
0.9464	High Similarity	NPC470416
0.9458	High Similarity	NPC258044
0.9458	High Similarity	NPC267680
0.9458	High Similarity	NPC293626
0.9458	High Similarity	NPC477895
0.9458	High Similarity	NPC476773
0.9458	High Similarity	NPC217387
0.9458	High Similarity	NPC196127
0.9455	High Similarity	NPC135277
0.9455	High Similarity	NPC49344
0.9455	High Similarity	NPC43211
0.9455	High Similarity	NPC101191
0.9455	High Similarity	NPC210094
0.9455	High Similarity	NPC477848
0.9455	High Similarity	NPC237435
0.9455	High Similarity	NPC115760
0.9451	High Similarity	NPC307518
0.9451	High Similarity	NPC190003
0.9451	High Similarity	NPC175107
0.9451	High Similarity	NPC153755
0.9451	High Similarity	NPC48773
0.9451	High Similarity	NPC472386
0.9451	High Similarity	NPC205076
0.9448	High Similarity	NPC226294
0.9448	High Similarity	NPC112755
0.9448	High Similarity	NPC58053
0.9448	High Similarity	NPC138927
0.9448	High Similarity	NPC186807
0.9448	High Similarity	NPC475942
0.9448	High Similarity	NPC471457
0.9448	High Similarity	NPC105025
0.9448	High Similarity	NPC469931
0.9448	High Similarity	NPC201292
0.9448	High Similarity	NPC45638
0.9448	High Similarity	NPC170675
0.9448	High Similarity	NPC93337
0.9444	High Similarity	NPC197285
0.9444	High Similarity	NPC21100
0.9444	High Similarity	NPC236934
0.9444	High Similarity	NPC5778
0.9441	High Similarity	NPC222936
0.9441	High Similarity	NPC88023
0.9441	High Similarity	NPC29830
0.9441	High Similarity	NPC243930
0.9441	High Similarity	NPC284960
0.9441	High Similarity	NPC19709
0.9441	High Similarity	NPC309025
0.9405	High Similarity	NPC135831
0.9405	High Similarity	NPC199172
0.9405	High Similarity	NPC297503
0.9405	High Similarity	NPC35924
0.9405	High Similarity	NPC97119
0.9405	High Similarity	NPC470718
0.9398	High Similarity	NPC472385
0.9398	High Similarity	NPC198324
0.9398	High Similarity	NPC211532
0.9398	High Similarity	NPC268533
0.9398	High Similarity	NPC233994
0.939	High Similarity	NPC231194
0.939	High Similarity	NPC44558
0.939	High Similarity	NPC206123
0.939	High Similarity	NPC116864
0.939	High Similarity	NPC72249
0.939	High Similarity	NPC105511
0.939	High Similarity	NPC282987
0.939	High Similarity	NPC183357
0.939	High Similarity	NPC84265
0.939	High Similarity	NPC22195
0.939	High Similarity	NPC474434
0.939	High Similarity	NPC245014
0.939	High Similarity	NPC51326
0.939	High Similarity	NPC244776
0.939	High Similarity	NPC224462
0.939	High Similarity	NPC212748
0.939	High Similarity	NPC21190
0.9383	High Similarity	NPC277205
0.9379	High Similarity	NPC300537
0.9379	High Similarity	NPC90905
0.9379	High Similarity	NPC127782
0.9379	High Similarity	NPC4013
0.9379	High Similarity	NPC473043
0.9375	High Similarity	NPC203020
0.9375	High Similarity	NPC239966
0.9349	High Similarity	NPC25946
0.9349	High Similarity	NPC470720
0.9349	High Similarity	NPC21359
0.9349	High Similarity	NPC460984
0.9349	High Similarity	NPC470713
0.9349	High Similarity	NPC231254
0.9349	High Similarity	NPC470717
0.9345	High Similarity	NPC469371
0.9341	High Similarity	NPC267549
0.9337	High Similarity	NPC264735
0.9337	High Similarity	NPC253685
0.9333	High Similarity	NPC117260
0.9333	High Similarity	NPC235575
0.9333	High Similarity	NPC3583
0.9333	High Similarity	NPC259152
0.9333	High Similarity	NPC476405
0.9329	High Similarity	NPC120099
0.9329	High Similarity	NPC209296
0.9329	High Similarity	NPC203050
0.9329	High Similarity	NPC472383
0.9329	High Similarity	NPC95855
0.9329	High Similarity	NPC223747
0.9329	High Similarity	NPC219904
0.9329	High Similarity	NPC183036
0.9329	High Similarity	NPC472381
0.9329	High Similarity	NPC225434
0.9329	High Similarity	NPC86008
0.9329	High Similarity	NPC195257
0.9329	High Similarity	NPC210042
0.9325	High Similarity	NPC115674
0.9325	High Similarity	NPC179950
0.9325	High Similarity	NPC274618
0.9325	High Similarity	NPC281131
0.9325	High Similarity	NPC56077
0.9325	High Similarity	NPC210073
0.9325	High Similarity	NPC308404
0.9325	High Similarity	NPC145038
0.9325	High Similarity	NPC253662
0.9325	High Similarity	NPC88789
0.9325	High Similarity	NPC8856
0.9325	High Similarity	NPC276222
0.9325	High Similarity	NPC118284
0.9321	High Similarity	NPC121290
0.9317	High Similarity	NPC270675
0.9317	High Similarity	NPC477628
0.9317	High Similarity	NPC472994
0.9317	High Similarity	NPC210961
0.9317	High Similarity	NPC477629
0.9317	High Similarity	NPC182045
0.9317	High Similarity	NPC195685
0.9313	High Similarity	NPC160780
0.9313	High Similarity	NPC289811
0.9294	High Similarity	NPC104910
0.9294	High Similarity	NPC474093
0.9294	High Similarity	NPC473554
0.9294	High Similarity	NPC470719
0.9294	High Similarity	NPC295625

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 NPC149011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	930
0.2-0.3	1951
0.3-0.4	2614
0.4-0.5	1809
0.5-0.6	927
0.6-0.7	363
0.7-0.8	139
0.8-0.85	32
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9455	High Similarity	NPD4338	Clinical (unspecified phase)
0.9387	High Similarity	NPD3818	Discontinued
0.9329	High Similarity	NPD7054	Approved
0.9273	High Similarity	NPD7472	Approved
0.9273	High Similarity	NPD7074	Phase 3
0.9187	High Similarity	NPD4868	Clinical (unspecified phase)
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.9102	High Similarity	NPD6797	Phase 2
0.9048	High Similarity	NPD7251	Discontinued
0.903	High Similarity	NPD6167	Clinical (unspecified phase)
0.903	High Similarity	NPD6166	Phase 2
0.903	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD7808	Phase 3
0.8882	High Similarity	NPD1934	Approved
0.8765	High Similarity	NPD7993	Clinical (unspecified phase)
0.8712	High Similarity	NPD2801	Approved
0.8712	High Similarity	NPD2393	Clinical (unspecified phase)
0.8659	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD3882	Suspended
0.8605	High Similarity	NPD6559	Discontinued
0.8538	High Similarity	NPD7804	Clinical (unspecified phase)
0.8528	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD1511	Approved
0.8443	Intermediate Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD5402	Approved
0.843	Intermediate Similarity	NPD5844	Phase 1
0.8405	Intermediate Similarity	NPD1653	Approved
0.8395	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD1465	Phase 2
0.8364	Intermediate Similarity	NPD7411	Suspended
0.8353	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7473	Discontinued
0.8295	Intermediate Similarity	NPD8312	Approved
0.8295	Intermediate Similarity	NPD8313	Approved
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5494	Approved
0.8232	Intermediate Similarity	NPD5403	Approved
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD7199	Phase 2
0.8182	Intermediate Similarity	NPD7685	Pre-registration
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7228	Approved
0.816	Intermediate Similarity	NPD6799	Approved
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5401	Approved
0.8107	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6234	Discontinued
0.8057	Intermediate Similarity	NPD3751	Discontinued
0.8046	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD37	Approved
0.7977	Intermediate Similarity	NPD6959	Discontinued
0.7953	Intermediate Similarity	NPD4967	Phase 2
0.7953	Intermediate Similarity	NPD4966	Approved
0.7953	Intermediate Similarity	NPD4965	Approved
0.7939	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3787	Discontinued
0.7927	Intermediate Similarity	NPD6190	Approved
0.7917	Intermediate Similarity	NPD8151	Discontinued
0.7901	Intermediate Similarity	NPD7266	Discontinued
0.7892	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7866	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7768	Phase 2
0.784	Intermediate Similarity	NPD2796	Approved
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7812	Intermediate Similarity	NPD1933	Approved
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7758	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD943	Approved
0.775	Intermediate Similarity	NPD1613	Approved
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD447	Suspended
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6776	Approved
0.7684	Intermediate Similarity	NPD6782	Approved
0.7684	Intermediate Similarity	NPD6779	Approved
0.7684	Intermediate Similarity	NPD6777	Approved
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7684	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD6778	Approved
0.7684	Intermediate Similarity	NPD6780	Approved
0.768	Intermediate Similarity	NPD7240	Approved
0.7657	Intermediate Similarity	NPD919	Approved
0.7653	Intermediate Similarity	NPD7783	Phase 2
0.7653	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD1240	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1607	Approved
0.7538	Intermediate Similarity	NPD7584	Approved
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7526	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2935	Discontinued
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7698	Approved
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7472	Intermediate Similarity	NPD1247	Approved
0.7471	Intermediate Similarity	NPD2533	Approved
0.7471	Intermediate Similarity	NPD2532	Approved
0.7471	Intermediate Similarity	NPD2534	Approved
0.7455	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD3027	Phase 3
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5953	Discontinued
0.7423	Intermediate Similarity	NPD6823	Phase 2
0.7421	Intermediate Similarity	NPD6534	Approved
0.7421	Intermediate Similarity	NPD6535	Approved
0.7411	Intermediate Similarity	NPD7701	Phase 2
0.7399	Intermediate Similarity	NPD7458	Discontinued
0.7399	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7680	Approved
0.7384	Intermediate Similarity	NPD920	Approved
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7323	Intermediate Similarity	NPD7585	Approved
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1203	Approved
0.7306	Intermediate Similarity	NPD7700	Phase 2
0.7306	Intermediate Similarity	NPD7699	Phase 2
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.73	Intermediate Similarity	NPD7801	Approved
0.7288	Intermediate Similarity	NPD5353	Approved
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7233	Intermediate Similarity	NPD9269	Phase 2
0.7233	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9494	Approved
0.7204	Intermediate Similarity	NPD7038	Approved
0.7204	Intermediate Similarity	NPD7039	Approved
0.7198	Intermediate Similarity	NPD5242	Approved
0.7195	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD6212	Phase 3
0.7188	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6213	Phase 3
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7176	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD1243	Approved
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4287	Approved
0.7119	Intermediate Similarity	NPD6385	Approved
0.7119	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6844	Discontinued
0.7076	Intermediate Similarity	NPD1652	Phase 2
0.7074	Intermediate Similarity	NPD7549	Discontinued
0.7071	Intermediate Similarity	NPD5005	Approved
0.7071	Intermediate Similarity	NPD5006	Approved
0.7069	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5710	Approved
0.7049	Intermediate Similarity	NPD5711	Approved
0.7049	Intermediate Similarity	NPD7229	Phase 3
0.7041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD6100	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