NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	264.953
LogP:	2.626
LogD:	2.514
LogS:	-2.834
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	2.1
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	1.2477497875806876e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	98.89435577392578%
Volume Distribution (VD):	0.549
Pgp-substrate:	1.1648470163345337%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.767
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.741
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	13.25
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.407
AMES Toxicity:	0.703
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.301
Skin Sensitization:	0.949
Carcinogencity:	0.654
Eye Corrosion:	0.085
Eye Irritation:	0.97
Respiratory Toxicity:	0.33

Download Data

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

Natural Product: NPC158222

Natural Product ID:	NPC158222
*Common Name:**	(E)-3-(2,4-Dihydroxyphenyl)-1-(4-Hydroxyphenyl)Prop-2-En-1-One
IUPAC Name:	(E)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	VDYSHUXENHRSOO-XBXARRHUSA-N
Standard InCHI:	InChI=1S/C15H12O4/c16-12-5-1-10(2-6-12)14(18)8-4-11-3-7-13(17)9-15(11)19/h1-9,16-17,19H/b8-4+
SMILES:	Oc1ccc(cc1)C(=O)/C=C/c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3335591
PubChem CID:	5322052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	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
EC50	1
IC50	2
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	EC50	=	38000.0	nM	PMID[570881]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	Ratio	=	8.1	n.a.	PMID[570881]
NPT4778	Organism	Streptococcus mutans UA159	Streptococcus mutans UA159	IC50	=	162000.0	nM	PMID[570882]
NPT4778	Organism	Streptococcus mutans UA159	Streptococcus mutans UA159	IC50	=	1063000.0	nM	PMID[570882]
NPT4778	Organism	Streptococcus mutans UA159	Streptococcus mutans UA159	Ratio IC50	=	6.6	n.a.	PMID[570882]

☑ 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 NPC158222 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	367
0.1-0.2	1834
0.2-0.3	4839
0.3-0.4	12741
0.4-0.5	5348
0.5-0.6	5571
0.6-0.7	7326
0.7-0.8	4022
0.8-0.85	453
0.85-0.9	152
0.9-0.95	30
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC159525
0.9737	High Similarity	NPC224273
0.9737	High Similarity	NPC73532
0.9737	High Similarity	NPC45438
0.9737	High Similarity	NPC267552
0.9737	High Similarity	NPC115159
0.9737	High Similarity	NPC19174
0.9737	High Similarity	NPC143427
0.9652	High Similarity	NPC133909
0.9652	High Similarity	NPC32032
0.9649	High Similarity	NPC297186
0.9565	High Similarity	NPC242895
0.9565	High Similarity	NPC156139
0.9487	High Similarity	NPC13238
0.9478	High Similarity	NPC248363
0.9328	High Similarity	NPC8745
0.9304	High Similarity	NPC161617
0.925	High Similarity	NPC103356
0.925	High Similarity	NPC105157
0.925	High Similarity	NPC23126
0.925	High Similarity	NPC169250
0.925	High Similarity	NPC30501
0.925	High Similarity	NPC162612
0.925	High Similarity	NPC100067
0.925	High Similarity	NPC190043
0.925	High Similarity	NPC266689
0.925	High Similarity	NPC98254
0.925	High Similarity	NPC72158
0.9244	High Similarity	NPC10926
0.9231	High Similarity	NPC196976
0.9217	High Similarity	NPC209486
0.9217	High Similarity	NPC40649
0.9174	High Similarity	NPC473017
0.9174	High Similarity	NPC21305
0.9174	High Similarity	NPC221777
0.9167	High Similarity	NPC62952
0.9167	High Similarity	NPC267846
0.9098	High Similarity	NPC474998
0.9098	High Similarity	NPC102829
0.9098	High Similarity	NPC120488
0.9091	High Similarity	NPC116513
0.906	High Similarity	NPC294037
0.9024	High Similarity	NPC26697
0.9024	High Similarity	NPC247779
0.9009	High Similarity	NPC17525
0.8992	High Similarity	NPC309765
0.8983	High Similarity	NPC149246
0.8983	High Similarity	NPC146642
0.8974	High Similarity	NPC195262
0.8974	High Similarity	NPC188814
0.8952	High Similarity	NPC475042
0.8952	High Similarity	NPC469526
0.8952	High Similarity	NPC34070
0.8943	High Similarity	NPC476119
0.8934	High Similarity	NPC107672
0.8919	High Similarity	NPC141523
0.8908	High Similarity	NPC215392
0.8908	High Similarity	NPC303737
0.8889	High Similarity	NPC241089
0.888	High Similarity	NPC112192
0.888	High Similarity	NPC189106
0.888	High Similarity	NPC66384
0.888	High Similarity	NPC128348
0.888	High Similarity	NPC309717
0.888	High Similarity	NPC164236
0.888	High Similarity	NPC135801
0.888	High Similarity	NPC262359
0.8871	High Similarity	NPC233056
0.887	High Similarity	NPC276111
0.887	High Similarity	NPC118288
0.885	High Similarity	NPC116842
0.8833	High Similarity	NPC91105
0.881	High Similarity	NPC213485
0.881	High Similarity	NPC87231
0.881	High Similarity	NPC129132
0.881	High Similarity	NPC40524
0.881	High Similarity	NPC257756
0.881	High Similarity	NPC139074
0.881	High Similarity	NPC212631
0.881	High Similarity	NPC205468
0.879	High Similarity	NPC92624
0.879	High Similarity	NPC109123
0.8772	High Similarity	NPC268388
0.876	High Similarity	NPC65761
0.876	High Similarity	NPC472029
0.875	High Similarity	NPC226699
0.875	High Similarity	NPC226275
0.874	High Similarity	NPC56031
0.874	High Similarity	NPC282780
0.874	High Similarity	NPC337373
0.874	High Similarity	NPC166480
0.874	High Similarity	NPC139813
0.874	High Similarity	NPC472365
0.874	High Similarity	NPC312318
0.874	High Similarity	NPC242294
0.874	High Similarity	NPC263670
0.874	High Similarity	NPC27643
0.874	High Similarity	NPC192304
0.874	High Similarity	NPC44437
0.874	High Similarity	NPC188646
0.874	High Similarity	NPC175098
0.873	High Similarity	NPC175738
0.873	High Similarity	NPC64359
0.873	High Similarity	NPC308037
0.873	High Similarity	NPC313618
0.8729	High Similarity	NPC283844
0.872	High Similarity	NPC259942
0.8672	High Similarity	NPC470210
0.8672	High Similarity	NPC61153
0.8672	High Similarity	NPC283590
0.8672	High Similarity	NPC130899
0.8672	High Similarity	NPC70859
0.8672	High Similarity	NPC286336
0.8672	High Similarity	NPC172262
0.8661	High Similarity	NPC6984
0.8651	High Similarity	NPC275504
0.8644	High Similarity	NPC230349
0.8644	High Similarity	NPC121259
0.8632	High Similarity	NPC322197
0.8621	High Similarity	NPC242136
0.8618	High Similarity	NPC475733
0.8605	High Similarity	NPC234560
0.8605	High Similarity	NPC65005
0.8605	High Similarity	NPC39426
0.8605	High Similarity	NPC264112
0.8605	High Similarity	NPC9985
0.8605	High Similarity	NPC131039
0.8605	High Similarity	NPC194764
0.8605	High Similarity	NPC239495
0.8596	High Similarity	NPC95172
0.8594	High Similarity	NPC204960
0.8594	High Similarity	NPC50898
0.8594	High Similarity	NPC20560
0.8594	High Similarity	NPC294593
0.8594	High Similarity	NPC57601
0.8594	High Similarity	NPC18877
0.8594	High Similarity	NPC159623
0.8594	High Similarity	NPC144051
0.8594	High Similarity	NPC78540
0.8594	High Similarity	NPC274121
0.8594	High Similarity	NPC28753
0.8594	High Similarity	NPC82225
0.8594	High Similarity	NPC213216
0.8571	High Similarity	NPC244441
0.8571	High Similarity	NPC147757
0.8571	High Similarity	NPC185497
0.856	High Similarity	NPC80694
0.856	High Similarity	NPC186098
0.856	High Similarity	NPC179898
0.8548	High Similarity	NPC95309
0.8538	High Similarity	NPC477244
0.8538	High Similarity	NPC66349
0.8538	High Similarity	NPC477243
0.8538	High Similarity	NPC213603
0.8538	High Similarity	NPC98115
0.8538	High Similarity	NPC41461
0.8538	High Similarity	NPC25287
0.8538	High Similarity	NPC472367
0.8538	High Similarity	NPC249606
0.8538	High Similarity	NPC12165
0.8538	High Similarity	NPC53414
0.8538	High Similarity	NPC235428
0.8538	High Similarity	NPC477242
0.8538	High Similarity	NPC290030
0.8538	High Similarity	NPC1486
0.8538	High Similarity	NPC186838
0.8538	High Similarity	NPC473391
0.8538	High Similarity	NPC44960
0.8538	High Similarity	NPC472364
0.8538	High Similarity	NPC53206
0.8538	High Similarity	NPC274109
0.8538	High Similarity	NPC87545
0.8538	High Similarity	NPC476333
0.8538	High Similarity	NPC168105
0.8538	High Similarity	NPC474110
0.8538	High Similarity	NPC150399
0.8538	High Similarity	NPC24394
0.8516	High Similarity	NPC267205
0.8512	High Similarity	NPC229649
0.8504	High Similarity	NPC198249
0.8496	Intermediate Similarity	NPC69332
0.8496	Intermediate Similarity	NPC70843
0.8496	Intermediate Similarity	NPC95178
0.8496	Intermediate Similarity	NPC29989
0.8492	Intermediate Similarity	NPC60558
0.848	Intermediate Similarity	NPC305518
0.848	Intermediate Similarity	NPC156539
0.848	Intermediate Similarity	NPC128428
0.8473	Intermediate Similarity	NPC303644
0.8473	Intermediate Similarity	NPC299379
0.8473	Intermediate Similarity	NPC266597
0.8473	Intermediate Similarity	NPC290291
0.8473	Intermediate Similarity	NPC188879
0.8473	Intermediate Similarity	NPC472419
0.8473	Intermediate Similarity	NPC20210
0.8473	Intermediate Similarity	NPC116632
0.8473	Intermediate Similarity	NPC153979
0.8473	Intermediate Similarity	NPC317119
0.8473	Intermediate Similarity	NPC7013
0.8473	Intermediate Similarity	NPC275055

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 NPC158222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	992
0.2-0.3	1401
0.3-0.4	2914
0.4-0.5	1946
0.5-0.6	1095
0.6-0.7	343
0.7-0.8	90
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.888	High Similarity	NPD943	Approved
0.873	High Similarity	NPD1240	Approved
0.8605	High Similarity	NPD1510	Phase 2
0.8594	High Similarity	NPD1607	Approved
0.8462	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD9269	Phase 2
0.8049	Intermediate Similarity	NPD9268	Approved
0.8034	Intermediate Similarity	NPD74	Approved
0.8034	Intermediate Similarity	NPD9266	Approved
0.8031	Intermediate Similarity	NPD1164	Approved
0.8031	Intermediate Similarity	NPD1470	Approved
0.8015	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1201	Approved
0.7982	Intermediate Similarity	NPD940	Approved
0.7982	Intermediate Similarity	NPD846	Approved
0.7971	Intermediate Similarity	NPD1511	Approved
0.7967	Intermediate Similarity	NPD9545	Approved
0.7949	Intermediate Similarity	NPD9267	Approved
0.7949	Intermediate Similarity	NPD9264	Approved
0.7949	Intermediate Similarity	NPD9263	Approved
0.7914	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1242	Phase 1
0.7857	Intermediate Similarity	NPD1512	Approved
0.7842	Intermediate Similarity	NPD7390	Discontinued
0.7805	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD9493	Approved
0.7762	Intermediate Similarity	NPD4380	Phase 2
0.7752	Intermediate Similarity	NPD1203	Approved
0.7737	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1551	Phase 2
0.7721	Intermediate Similarity	NPD2796	Approved
0.7714	Intermediate Similarity	NPD6799	Approved
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7647	Intermediate Similarity	NPD3748	Approved
0.7642	Intermediate Similarity	NPD9281	Approved
0.7607	Intermediate Similarity	NPD9261	Approved
0.7594	Intermediate Similarity	NPD3764	Approved
0.7591	Intermediate Similarity	NPD5408	Approved
0.7591	Intermediate Similarity	NPD5405	Approved
0.7591	Intermediate Similarity	NPD5404	Approved
0.7591	Intermediate Similarity	NPD5406	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7554	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1237	Approved
0.7534	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2935	Discontinued
0.7456	Intermediate Similarity	NPD2934	Approved
0.7456	Intermediate Similarity	NPD2933	Approved
0.745	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3749	Approved
0.745	Intermediate Similarity	NPD7075	Discontinued
0.7442	Intermediate Similarity	NPD422	Phase 1
0.7432	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2344	Approved
0.7402	Intermediate Similarity	NPD1548	Phase 1
0.7397	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD2859	Approved
0.7391	Intermediate Similarity	NPD2860	Approved
0.7385	Intermediate Similarity	NPD3972	Approved
0.7385	Intermediate Similarity	NPD9717	Approved
0.7372	Intermediate Similarity	NPD6651	Approved
0.7365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7819	Suspended
0.7305	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD2800	Approved
0.7297	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4750	Phase 3
0.7217	Intermediate Similarity	NPD1202	Approved
0.7206	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD2309	Approved
0.7203	Intermediate Similarity	NPD3020	Approved
0.7192	Intermediate Similarity	NPD5403	Approved
0.7176	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1610	Phase 2
0.7172	Intermediate Similarity	NPD5401	Approved
0.7164	Intermediate Similarity	NPD2798	Approved
0.7161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD520	Approved
0.7152	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD1465	Phase 2
0.7132	Intermediate Similarity	NPD1759	Phase 1
0.7121	Intermediate Similarity	NPD1481	Phase 2
0.7105	Intermediate Similarity	NPD9258	Approved
0.7105	Intermediate Similarity	NPD9256	Approved
0.7092	Intermediate Similarity	NPD6100	Approved
0.7092	Intermediate Similarity	NPD6099	Approved
0.709	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD3817	Phase 2
0.708	Intermediate Similarity	NPD1296	Phase 2
0.708	Intermediate Similarity	NPD2313	Discontinued
0.7075	Intermediate Similarity	NPD920	Approved
0.7075	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3818	Discontinued
0.7063	Intermediate Similarity	NPD2654	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7055	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1758	Phase 1
0.7051	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6166	Phase 2
0.7051	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1535	Discovery
0.7032	Intermediate Similarity	NPD6232	Discontinued
0.7023	Intermediate Similarity	NPD2932	Approved
0.7023	Intermediate Similarity	NPD3019	Approved
0.7015	Intermediate Similarity	NPD1876	Approved
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.6992	Remote Similarity	NPD1608	Approved
0.6985	Remote Similarity	NPD9494	Approved
0.6974	Remote Similarity	NPD4288	Approved
0.6968	Remote Similarity	NPD6959	Discontinued
0.6966	Remote Similarity	NPD6190	Approved
0.6964	Remote Similarity	NPD111	Approved
0.6963	Remote Similarity	NPD3267	Approved
0.6963	Remote Similarity	NPD3266	Approved
0.6939	Remote Similarity	NPD2532	Approved
0.6939	Remote Similarity	NPD2534	Approved
0.6939	Remote Similarity	NPD2533	Approved
0.6937	Remote Similarity	NPD5953	Discontinued
0.6934	Remote Similarity	NPD4908	Phase 1
0.6934	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7286	Phase 2
0.6918	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7054	Approved
0.6901	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD255	Approved
0.6899	Remote Similarity	NPD256	Approved
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1196	Approved
0.6885	Remote Similarity	NPD1930	Approved
0.6885	Remote Similarity	NPD1929	Approved
0.6885	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7074	Phase 3
0.6875	Remote Similarity	NPD7472	Approved
0.6871	Remote Similarity	NPD1543	Discontinued
0.6867	Remote Similarity	NPD7458	Discontinued
0.6864	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5402	Approved
0.6861	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4307	Phase 2
0.6849	Remote Similarity	NPD2354	Approved
0.6847	Remote Similarity	NPD9089	Approved
0.6846	Remote Similarity	NPD9568	Approved
0.6835	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD411	Approved
0.6832	Remote Similarity	NPD6797	Phase 2
0.6832	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1195	Approved
0.6825	Remote Similarity	NPD3022	Approved
0.6825	Remote Similarity	NPD3021	Approved
0.6815	Remote Similarity	NPD1755	Approved
0.6815	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6020	Phase 2
0.6813	Remote Similarity	NPD5844	Phase 1
0.6809	Remote Similarity	NPD447	Suspended
0.6807	Remote Similarity	NPD1809	Phase 2
0.6807	Remote Similarity	NPD844	Approved
0.6803	Remote Similarity	NPD3300	Phase 2
0.6795	Remote Similarity	NPD5494	Approved
0.679	Remote Similarity	NPD7251	Discontinued
0.6781	Remote Similarity	NPD7003	Approved
0.678	Remote Similarity	NPD845	Approved
0.6777	Remote Similarity	NPD1238	Approved
0.6767	Remote Similarity	NPD17	Approved
0.6757	Remote Similarity	NPD9093	Approved
0.6755	Remote Similarity	NPD3226	Approved
0.6754	Remote Similarity	NPD9257	Approved
0.6754	Remote Similarity	NPD9259	Approved
0.675	Remote Similarity	NPD288	Approved
0.6748	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7808	Phase 3
0.6748	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1894	Discontinued
0.6741	Remote Similarity	NPD4878	Approved
0.6738	Remote Similarity	NPD1613	Approved
0.6738	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD919	Approved
0.6721	Remote Similarity	NPD3028	Approved
0.6721	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7422	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