NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.08
Volume:	247.372
LogP:	3.303
LogD:	3.188
LogS:	-3.487
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	1.727
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.752
MDCK Permeability:	1.924633397720754e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.528
Plasma Protein Binding (PPB):	99.8326187133789%
Volume Distribution (VD):	0.642
Pgp-substrate:	1.0645203590393066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.33
CYP2C19-inhibitor:	0.935
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.342
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	6.428
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.552
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.931
Carcinogencity:	0.612
Eye Corrosion:	0.264
Eye Irritation:	0.991
Respiratory Toxicity:	0.685

Download Data

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

Natural Product: NPC141523

Natural Product ID:	NPC141523
*Common Name:**	(E)-3-(2-Hydroxyphenyl)-1-Phenylprop-2-En-1-One
IUPAC Name:	(E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	UDOOPSJCRMKSGL-ZHACJKMWSA-N
Standard InCHI:	InChI=1S/C15H12O2/c16-14-9-5-4-8-13(14)10-11-15(17)12-6-2-1-3-7-12/h1-11,16H/b11-10+
SMILES:	O=C(c1ccccc1)/C=C/c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL147067
PubChem CID:	5367146
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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	Species	Fabaceae	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	4
IC50	5
MIC	5
Others	21
Potency	12

Activity Type	# Activity
Cell Line	3
Individual Protein	14
NON-MOLECULAR	1
Organism	17
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	12.0	uM	PMID[515343]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[515348]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[515348]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[515348]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[515348]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[515348]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[515348]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[515348]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	44668.4	nM	PMID[515348]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[515348]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[515348]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	105000.0	nM	PMID[515352]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	145000.0	nM	PMID[515355]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	32.1	%	PMID[515356]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	71.9	%	PMID[515356]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31.25	ug.mL-1	PMID[515345]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	21.0	mm	PMID[515345]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	62.5	ug.mL-1	PMID[515345]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	22.0	mm	PMID[515346]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	62.5	ug.mL-1	PMID[515346]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[515347]
NPT27	Others	Unspecified		Activity	<	5.0	%	PMID[515347]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[515348]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[515349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[515349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[515349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.31	n.a.	PMID[515349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.15	n.a.	PMID[515349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.75	n.a.	PMID[515349]
NPT1328	Organism	Culex quinquefasciatus	Culex quinquefasciatus	mortality	=	100.0	%	PMID[515350]
NPT1328	Organism	Culex quinquefasciatus	Culex quinquefasciatus	LC50	=	104.0	umol/dm3	PMID[515350]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[515348]
NPT35	Others	n.a.		Rf	=	0.49	n.a.	PMID[515351]
NPT2	Others	Unspecified		Ratio EC50	=	0.43	n.a.	PMID[515353]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	EC50	=	333700.0	nM	PMID[515353]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	EC50	=	91740.0	nM	PMID[515353]
NPT2	Others	Unspecified		Ratio EC50	=	1.56	n.a.	PMID[515353]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	EC50	=	75890.0	nM	PMID[515353]
NPT2	Others	Unspecified		Ratio EC50	=	1.88	n.a.	PMID[515353]
NPT27	Others	Unspecified		EC50	=	143000.0	nM	PMID[515353]
NPT35	Others	n.a.		Activity	=	-0.6	%	PMID[515354]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.0	%	PMID[515354]
NPT35	Others	n.a.		Activity	<	0.1	mmolequiv/mmol	PMID[515355]
NPT35	Others	n.a.		Inhibition	=	10.8	%	PMID[515355]
NPT2	Others	Unspecified		IC50	=	6700.0	nM	PMID[515357]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[515357]

☑ 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 NPC141523 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	314
0.1-0.2	2049
0.2-0.3	4718
0.3-0.4	12394
0.4-0.5	5982
0.5-0.6	7878
0.6-0.7	7291
0.7-0.8	1853
0.8-0.85	154
0.85-0.9	54
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC17525
0.932	High Similarity	NPC224584
0.9143	High Similarity	NPC116842
0.9126	High Similarity	NPC95178
0.9126	High Similarity	NPC69332
0.9126	High Similarity	NPC29989
0.9057	High Similarity	NPC268388
0.9038	High Similarity	NPC226699
0.9038	High Similarity	NPC34715
0.8942	High Similarity	NPC70843
0.8942	High Similarity	NPC6984
0.8919	High Similarity	NPC158222
0.8899	High Similarity	NPC322197
0.8889	High Similarity	NPC242136
0.8868	High Similarity	NPC88141
0.8868	High Similarity	NPC95172
0.8839	High Similarity	NPC159525
0.8829	High Similarity	NPC184527
0.8785	High Similarity	NPC21162
0.8761	High Similarity	NPC297186
0.875	High Similarity	NPC188814
0.875	High Similarity	NPC120693
0.875	High Similarity	NPC261573
0.875	High Similarity	NPC8931
0.875	High Similarity	NPC195262
0.8727	High Similarity	NPC161304
0.8727	High Similarity	NPC240163
0.8725	High Similarity	NPC280869
0.8704	High Similarity	NPC212718
0.8704	High Similarity	NPC114682
0.8684	High Similarity	NPC73532
0.8684	High Similarity	NPC45438
0.8684	High Similarity	NPC267552
0.8684	High Similarity	NPC115159
0.8684	High Similarity	NPC19174
0.8684	High Similarity	NPC224273
0.8684	High Similarity	NPC156139
0.8684	High Similarity	NPC143427
0.8679	High Similarity	NPC303264
0.8661	High Similarity	NPC249435
0.8654	High Similarity	NPC13426
0.8649	High Similarity	NPC108288
0.8636	High Similarity	NPC276111
0.8636	High Similarity	NPC118288
0.8627	High Similarity	NPC260000
0.8609	High Similarity	NPC133909
0.8609	High Similarity	NPC300274
0.8609	High Similarity	NPC32032
0.8598	High Similarity	NPC100551
0.8596	High Similarity	NPC216216
0.8585	High Similarity	NPC188677
0.8571	High Similarity	NPC269414
0.8545	High Similarity	NPC11824
0.8534	High Similarity	NPC375356
0.8522	High Similarity	NPC295034
0.8522	High Similarity	NPC242895
0.8522	High Similarity	NPC196976
0.8509	High Similarity	NPC233282
0.8509	High Similarity	NPC216297
0.8509	High Similarity	NPC7151
0.8509	High Similarity	NPC473662
0.8509	High Similarity	NPC285829
0.8509	High Similarity	NPC206778
0.8496	Intermediate Similarity	NPC41567
0.8482	Intermediate Similarity	NPC477453
0.8476	Intermediate Similarity	NPC68269
0.8476	Intermediate Similarity	NPC135784
0.8468	Intermediate Similarity	NPC285350
0.8462	Intermediate Similarity	NPC13238
0.8462	Intermediate Similarity	NPC52472
0.8462	Intermediate Similarity	NPC193805
0.8455	Intermediate Similarity	NPC231717
0.8455	Intermediate Similarity	NPC286222
0.8448	Intermediate Similarity	NPC217756
0.8447	Intermediate Similarity	NPC201967
0.8435	Intermediate Similarity	NPC248363
0.8431	Intermediate Similarity	NPC246679
0.8421	Intermediate Similarity	NPC473767
0.8421	Intermediate Similarity	NPC161617
0.8411	Intermediate Similarity	NPC187913
0.8407	Intermediate Similarity	NPC160199
0.8407	Intermediate Similarity	NPC121259
0.8396	Intermediate Similarity	NPC249067
0.8393	Intermediate Similarity	NPC23402
0.839	Intermediate Similarity	NPC103540
0.8378	Intermediate Similarity	NPC211421
0.8365	Intermediate Similarity	NPC245561
0.8365	Intermediate Similarity	NPC130193
0.8362	Intermediate Similarity	NPC198336
0.8362	Intermediate Similarity	NPC120545
0.835	Intermediate Similarity	NPC283711
0.8333	Intermediate Similarity	NPC29883
0.8333	Intermediate Similarity	NPC474890
0.8333	Intermediate Similarity	NPC228737
0.8333	Intermediate Similarity	NPC128062
0.8333	Intermediate Similarity	NPC273282
0.8333	Intermediate Similarity	NPC161943
0.8319	Intermediate Similarity	NPC61062
0.8319	Intermediate Similarity	NPC277394
0.8319	Intermediate Similarity	NPC299252
0.8319	Intermediate Similarity	NPC96915
0.8319	Intermediate Similarity	NPC8745
0.8319	Intermediate Similarity	NPC128825
0.8319	Intermediate Similarity	NPC62952
0.8319	Intermediate Similarity	NPC19290
0.8318	Intermediate Similarity	NPC13495
0.8318	Intermediate Similarity	NPC219913
0.8318	Intermediate Similarity	NPC163734
0.8305	Intermediate Similarity	NPC173978
0.8305	Intermediate Similarity	NPC142956
0.8291	Intermediate Similarity	NPC283514
0.8291	Intermediate Similarity	NPC244351
0.8291	Intermediate Similarity	NPC68167
0.8291	Intermediate Similarity	NPC307174
0.8291	Intermediate Similarity	NPC91478
0.8273	Intermediate Similarity	NPC252544
0.8273	Intermediate Similarity	NPC321252
0.8261	Intermediate Similarity	NPC232178
0.825	Intermediate Similarity	NPC105157
0.825	Intermediate Similarity	NPC100067
0.825	Intermediate Similarity	NPC30501
0.825	Intermediate Similarity	NPC266689
0.825	Intermediate Similarity	NPC103356
0.825	Intermediate Similarity	NPC169250
0.825	Intermediate Similarity	NPC72158
0.825	Intermediate Similarity	NPC98254
0.825	Intermediate Similarity	NPC162612
0.825	Intermediate Similarity	NPC23126
0.825	Intermediate Similarity	NPC190043
0.825	Intermediate Similarity	NPC22783
0.8246	Intermediate Similarity	NPC150919
0.8246	Intermediate Similarity	NPC125252
0.8241	Intermediate Similarity	NPC184658
0.8235	Intermediate Similarity	NPC10926
0.8235	Intermediate Similarity	NPC181709
0.8235	Intermediate Similarity	NPC271440
0.822	Intermediate Similarity	NPC93730
0.8198	Intermediate Similarity	NPC177576
0.8182	Intermediate Similarity	NPC282923
0.8182	Intermediate Similarity	NPC48248
0.8182	Intermediate Similarity	NPC155393
0.8182	Intermediate Similarity	NPC21305
0.8182	Intermediate Similarity	NPC473017
0.8182	Intermediate Similarity	NPC96024
0.8182	Intermediate Similarity	NPC95537
0.8182	Intermediate Similarity	NPC221777
0.8174	Intermediate Similarity	NPC40649
0.8174	Intermediate Similarity	NPC94637
0.8174	Intermediate Similarity	NPC32298
0.8174	Intermediate Similarity	NPC209486
0.8167	Intermediate Similarity	NPC267846
0.8167	Intermediate Similarity	NPC3224
0.8167	Intermediate Similarity	NPC160499
0.8165	Intermediate Similarity	NPC211439
0.8158	Intermediate Similarity	NPC128249
0.8158	Intermediate Similarity	NPC83718
0.8151	Intermediate Similarity	NPC234890
0.8151	Intermediate Similarity	NPC164014
0.8151	Intermediate Similarity	NPC236189
0.8151	Intermediate Similarity	NPC310540
0.8151	Intermediate Similarity	NPC74507
0.8142	Intermediate Similarity	NPC163154
0.8142	Intermediate Similarity	NPC81808
0.8137	Intermediate Similarity	NPC45040
0.8136	Intermediate Similarity	NPC282577
0.8136	Intermediate Similarity	NPC309765
0.8136	Intermediate Similarity	NPC46634
0.8131	Intermediate Similarity	NPC255676
0.8131	Intermediate Similarity	NPC470202
0.812	Intermediate Similarity	NPC190971
0.812	Intermediate Similarity	NPC165197
0.8115	Intermediate Similarity	NPC109123
0.8115	Intermediate Similarity	NPC99731
0.8115	Intermediate Similarity	NPC102829
0.8115	Intermediate Similarity	NPC120488
0.8115	Intermediate Similarity	NPC34414
0.8115	Intermediate Similarity	NPC474998
0.8115	Intermediate Similarity	NPC146647
0.8108	Intermediate Similarity	NPC222905
0.8103	Intermediate Similarity	NPC184579
0.8103	Intermediate Similarity	NPC90522
0.8103	Intermediate Similarity	NPC328459
0.8103	Intermediate Similarity	NPC35744
0.8103	Intermediate Similarity	NPC201284
0.8103	Intermediate Similarity	NPC233165
0.8103	Intermediate Similarity	NPC54243
0.81	Intermediate Similarity	NPC407
0.81	Intermediate Similarity	NPC307235
0.8099	Intermediate Similarity	NPC116513
0.8087	Intermediate Similarity	NPC174087
0.8083	Intermediate Similarity	NPC4164
0.8073	Intermediate Similarity	NPC317592
0.8067	Intermediate Similarity	NPC174991
0.8067	Intermediate Similarity	NPC477153
0.8067	Intermediate Similarity	NPC275145
0.8053	Intermediate Similarity	NPC223004
0.8053	Intermediate Similarity	NPC279916
0.8051	Intermediate Similarity	NPC303737
0.8051	Intermediate Similarity	NPC25168
0.8049	Intermediate Similarity	NPC7569

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 NPC141523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	1001
0.2-0.3	1137
0.3-0.4	2695
0.4-0.5	2228
0.5-0.6	1236
0.6-0.7	412
0.7-0.8	91
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD405	Clinical (unspecified phase)
0.8598	High Similarity	NPD74	Approved
0.8598	High Similarity	NPD9266	Approved
0.8522	High Similarity	NPD1201	Approved
0.8505	High Similarity	NPD9264	Approved
0.8505	High Similarity	NPD9263	Approved
0.8505	High Similarity	NPD9267	Approved
0.8396	Intermediate Similarity	NPD1237	Approved
0.839	Intermediate Similarity	NPD1470	Approved
0.8333	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8319	Intermediate Similarity	NPD9493	Approved
0.8235	Intermediate Similarity	NPD1164	Approved
0.8131	Intermediate Similarity	NPD9261	Approved
0.8103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD1203	Approved
0.7982	Intermediate Similarity	NPD9281	Approved
0.7981	Intermediate Similarity	NPD2934	Approved
0.7981	Intermediate Similarity	NPD2933	Approved
0.7941	Intermediate Similarity	NPD9256	Approved
0.7941	Intermediate Similarity	NPD9258	Approved
0.792	Intermediate Similarity	NPD943	Approved
0.792	Intermediate Similarity	NPD1240	Approved
0.7905	Intermediate Similarity	NPD2859	Approved
0.7905	Intermediate Similarity	NPD2860	Approved
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1202	Approved
0.7869	Intermediate Similarity	NPD2798	Approved
0.7863	Intermediate Similarity	NPD9545	Approved
0.7795	Intermediate Similarity	NPD1607	Approved
0.7686	Intermediate Similarity	NPD9717	Approved
0.7685	Intermediate Similarity	NPD3020	Approved
0.7674	Intermediate Similarity	NPD1510	Phase 2
0.7636	Intermediate Similarity	NPD1930	Approved
0.7636	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1929	Approved
0.7619	Intermediate Similarity	NPD3764	Approved
0.7619	Intermediate Similarity	NPD2313	Discontinued
0.7586	Intermediate Similarity	NPD1241	Discontinued
0.757	Intermediate Similarity	NPD844	Approved
0.7557	Intermediate Similarity	NPD2344	Approved
0.7549	Intermediate Similarity	NPD9259	Approved
0.7549	Intermediate Similarity	NPD9257	Approved
0.7547	Intermediate Similarity	NPD845	Approved
0.7541	Intermediate Similarity	NPD3972	Approved
0.7538	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD288	Approved
0.7481	Intermediate Similarity	NPD2935	Discontinued
0.7456	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD111	Approved
0.7438	Intermediate Similarity	NPD3019	Approved
0.7438	Intermediate Similarity	NPD2932	Approved
0.7424	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD520	Approved
0.7419	Intermediate Similarity	NPD1876	Approved
0.7417	Intermediate Similarity	NPD1759	Phase 1
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD4308	Phase 3
0.74	Intermediate Similarity	NPD942	Approved
0.7398	Intermediate Similarity	NPD1481	Phase 2
0.7388	Intermediate Similarity	NPD3750	Approved
0.7387	Intermediate Similarity	NPD1932	Approved
0.7387	Intermediate Similarity	NPD846	Approved
0.7387	Intermediate Similarity	NPD940	Approved
0.7373	Intermediate Similarity	NPD5951	Approved
0.7364	Intermediate Similarity	NPD2066	Phase 3
0.7348	Intermediate Similarity	NPD5404	Approved
0.7348	Intermediate Similarity	NPD5405	Approved
0.7348	Intermediate Similarity	NPD5406	Approved
0.7348	Intermediate Similarity	NPD1551	Phase 2
0.7348	Intermediate Similarity	NPD5408	Approved
0.7344	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD1758	Phase 1
0.7323	Intermediate Similarity	NPD6832	Phase 2
0.7317	Intermediate Similarity	NPD1535	Discovery
0.7315	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD256	Approved
0.7311	Intermediate Similarity	NPD255	Approved
0.7297	Intermediate Similarity	NPD1242	Phase 1
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9495	Approved
0.7258	Intermediate Similarity	NPD4878	Approved
0.7255	Intermediate Similarity	NPD9491	Approved
0.725	Intermediate Similarity	NPD9568	Approved
0.7248	Intermediate Similarity	NPD1809	Phase 2
0.7217	Intermediate Similarity	NPD2342	Discontinued
0.72	Intermediate Similarity	NPD1755	Approved
0.7196	Intermediate Similarity	NPD1239	Approved
0.7164	Intermediate Similarity	NPD2346	Discontinued
0.7164	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3225	Approved
0.7132	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7003	Approved
0.7132	Intermediate Similarity	NPD1196	Approved
0.7131	Intermediate Similarity	NPD1894	Discontinued
0.713	Intermediate Similarity	NPD968	Approved
0.712	Intermediate Similarity	NPD9269	Phase 2
0.712	Intermediate Similarity	NPD1608	Approved
0.7119	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9273	Approved
0.7109	Intermediate Similarity	NPD9494	Approved
0.7101	Intermediate Similarity	NPD1543	Discontinued
0.7101	Intermediate Similarity	NPD1511	Approved
0.7099	Intermediate Similarity	NPD4307	Phase 2
0.7094	Intermediate Similarity	NPD3021	Approved
0.7094	Intermediate Similarity	NPD3022	Approved
0.7087	Intermediate Similarity	NPD3266	Approved
0.7087	Intermediate Similarity	NPD3267	Approved
0.7083	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD411	Approved
0.7073	Intermediate Similarity	NPD9268	Approved
0.7063	Intermediate Similarity	NPD5157	Phase 1
0.7063	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5159	Phase 2
0.7059	Intermediate Similarity	NPD1195	Approved
0.7059	Intermediate Similarity	NPD7635	Approved
0.705	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD447	Suspended
0.7043	Intermediate Similarity	NPD9697	Approved
0.7029	Intermediate Similarity	NPD3300	Phase 2
0.7016	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3748	Approved
0.7009	Intermediate Similarity	NPD2329	Discontinued
0.7008	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9260	Approved
0.7	Intermediate Similarity	NPD1512	Approved
0.6991	Remote Similarity	NPD3028	Approved
0.6978	Remote Similarity	NPD7390	Discontinued
0.6975	Remote Similarity	NPD9508	Approved
0.6963	Remote Similarity	NPD2796	Approved
0.6961	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5909	Discontinued
0.6957	Remote Similarity	NPD164	Approved
0.6949	Remote Similarity	NPD4750	Phase 3
0.6942	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1651	Approved
0.6923	Remote Similarity	NPD4380	Phase 2
0.6917	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1933	Approved
0.6917	Remote Similarity	NPD5277	Phase 2
0.6909	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD422	Phase 1
0.6899	Remote Similarity	NPD4980	Approved
0.6899	Remote Similarity	NPD1019	Discontinued
0.6893	Remote Similarity	NPD226	Approved
0.6884	Remote Similarity	NPD4628	Phase 3
0.688	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD1565	Approved
0.6875	Remote Similarity	NPD1564	Approved
0.6875	Remote Similarity	NPD1566	Phase 3
0.6869	Remote Similarity	NPD9087	Approved
0.6863	Remote Similarity	NPD9490	Approved
0.6861	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6799	Approved
0.6855	Remote Similarity	NPD1548	Phase 1
0.6853	Remote Similarity	NPD3226	Approved
0.6853	Remote Similarity	NPD7458	Discontinued
0.6852	Remote Similarity	NPD800	Approved
0.6847	Remote Similarity	NPD1693	Approved
0.6835	Remote Similarity	NPD2354	Approved
0.6831	Remote Similarity	NPD5403	Approved
0.6825	Remote Similarity	NPD3026	Approved
0.6825	Remote Similarity	NPD3023	Approved
0.6825	Remote Similarity	NPD3847	Discontinued
0.6822	Remote Similarity	NPD650	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.6818	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1508	Approved
0.6815	Remote Similarity	NPD9279	Approved
0.681	Remote Similarity	NPD9610	Approved
0.681	Remote Similarity	NPD9608	Approved
0.6809	Remote Similarity	NPD4662	Approved
0.6809	Remote Similarity	NPD5401	Approved
0.6809	Remote Similarity	NPD4661	Approved
0.6807	Remote Similarity	NPD1792	Phase 2
0.68	Remote Similarity	NPD3025	Approved
0.68	Remote Similarity	NPD3024	Approved
0.6791	Remote Similarity	NPD1184	Approved
0.6791	Remote Similarity	NPD230	Phase 1
0.6789	Remote Similarity	NPD1090	Approved
0.6789	Remote Similarity	NPD1089	Approved
0.6789	Remote Similarity	NPD1086	Approved
0.6786	Remote Similarity	NPD7440	Discontinued
0.6774	Remote Similarity	NPD5536	Phase 2
0.6772	Remote Similarity	NPD1281	Approved
0.6769	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9088	Approved
0.6761	Remote Similarity	NPD5049	Phase 3
0.6759	Remote Similarity	NPD7411	Suspended

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