NPASS Compound

Structure

CID82325 OpenBabel06191715422D 24 26 0 0 0 0 0 0 0 0999 V2000 4.3301 -2.5000 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 2.5981 0.5000 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 1.7321 -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 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 -2.5981 0.5000 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 2.0000 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 -0.8660 0.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 -3.4641 -0.0000 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 1.7321 2.0000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 12 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	2.804
LogD:	2.658
LogS:	-3.722
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	2.427
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.2011664694000501e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	94.02022552490234%
Volume Distribution (VD):	0.76
Pgp-substrate:	10.107172012329102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.387
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.7
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.637
CYP2D6-substrate:	0.696
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	7.373
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.622
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.558
Skin Sensitization:	0.515
Carcinogencity:	0.032
Eye Corrosion:	0.004
Eye Irritation:	0.91
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC82325

Natural Product ID:	NPC82325
*Common Name:**	5,7,3'-Trihydroxy-3,4'-Dimethoxyflavone
IUPAC Name:	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxychromen-4-one
Synonyms:	NSC-106970
Standard InCHIKey:	ZSPZNFOLWQEVQJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-22-12-4-3-8(5-10(12)19)16-17(23-2)15(21)14-11(20)6-9(18)7-13(14)24-16/h3-7,18-20H,1-2H3
SMILES:	COc1ccc(cc1O)c1c(c(=O)c2c(cc(cc2o1)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL309263
PubChem CID:	5380905
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-O-methylated flavonoids

*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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	bark and leaves	Koh Kong Province, Cambodia	2005-DEC	PMID[19053508]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO119	Cyperus alopecuroides	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO119	Cyperus alopecuroides	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO119	Cyperus alopecuroides	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4713	Eucalyptus cordata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO53	Nephelium mutabile	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3212	Bipolaris sorokiniana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5020	Jasonia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2839	Dovyalis abyssinica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3796	Pseudomonas viridiflava	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
GI50	1
IC50	1
Others	6

Activity Type	# Activity
Cell Line	4
Individual Protein	2
Protein Complex	1
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	1700.0	nM	PMID[457251]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[457252]
NPT3892	Individual Protein	Tumor necrosis factor receptor superfamily member 10B	Homo sapiens	FC	=	6.7	n.a.	PMID[457253]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	27.0	%	PMID[457253]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	24.0	%	PMID[457253]
NPT2715	Individual Protein	Receptor-type tyrosine-protein phosphatase S	Homo sapiens	Inhibition	=	-1.2	%	PMID[457254]
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	=	3000.0	nM	PMID[457251]
NPT782	Protein Family	Tubulin	Bos taurus	Inhibition	=	43.0	%	PMID[457251]
NPT782	Protein Family	Tubulin	Bos taurus	Inhibition	=	75.0	%	PMID[457251]

☑ 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 NPC82325 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	465
0.1-0.2	1989
0.2-0.3	5126
0.3-0.4	11261
0.4-0.5	5956
0.5-0.6	3911
0.6-0.7	5104
0.7-0.8	4720
0.8-0.85	2012
0.85-0.9	1274
0.9-0.95	597
0.95-1	282

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279989
0.9932	High Similarity	NPC236223
0.9932	High Similarity	NPC179126
0.9932	High Similarity	NPC78326
0.9932	High Similarity	NPC270620
0.9931	High Similarity	NPC125062
0.9931	High Similarity	NPC200740
0.9931	High Similarity	NPC54394
0.9931	High Similarity	NPC252933
0.9863	High Similarity	NPC123886
0.9863	High Similarity	NPC55205
0.9862	High Similarity	NPC149127
0.9862	High Similarity	NPC188871
0.9862	High Similarity	NPC286342
0.9797	High Similarity	NPC266960
0.9797	High Similarity	NPC43243
0.9797	High Similarity	NPC265511
0.9797	High Similarity	NPC245546
0.9796	High Similarity	NPC58382
0.9796	High Similarity	NPC162351
0.9795	High Similarity	NPC236769
0.9795	High Similarity	NPC133953
0.9795	High Similarity	NPC50403
0.9795	High Similarity	NPC28274
0.9795	High Similarity	NPC260895
0.9793	High Similarity	NPC137062
0.9793	High Similarity	NPC287101
0.9793	High Similarity	NPC223579
0.9793	High Similarity	NPC52005
0.9793	High Similarity	NPC183950
0.9793	High Similarity	NPC270465
0.9793	High Similarity	NPC159103
0.9793	High Similarity	NPC87125
0.9732	High Similarity	NPC305663
0.9732	High Similarity	NPC287979
0.9732	High Similarity	NPC203891
0.9732	High Similarity	NPC176665
0.9732	High Similarity	NPC163524
0.9732	High Similarity	NPC101830
0.9732	High Similarity	NPC110070
0.973	High Similarity	NPC44079
0.973	High Similarity	NPC201451
0.973	High Similarity	NPC26227
0.9726	High Similarity	NPC50728
0.9726	High Similarity	NPC166753
0.9724	High Similarity	NPC120464
0.9667	High Similarity	NPC143828
0.9667	High Similarity	NPC300943
0.9667	High Similarity	NPC191459
0.9667	High Similarity	NPC4481
0.9667	High Similarity	NPC204854
0.9667	High Similarity	NPC22472
0.9667	High Similarity	NPC19687
0.9667	High Similarity	NPC7846
0.9667	High Similarity	NPC152166
0.9667	High Similarity	NPC288669
0.9667	High Similarity	NPC18607
0.9667	High Similarity	NPC105242
0.9667	High Similarity	NPC176300
0.9667	High Similarity	NPC253634
0.9667	High Similarity	NPC25495
0.9667	High Similarity	NPC115798
0.9667	High Similarity	NPC9609
0.9667	High Similarity	NPC261004
0.9667	High Similarity	NPC18772
0.9667	High Similarity	NPC130894
0.9664	High Similarity	NPC100916
0.9664	High Similarity	NPC55619
0.9664	High Similarity	NPC247017
0.9664	High Similarity	NPC49824
0.9664	High Similarity	NPC200388
0.9664	High Similarity	NPC98661
0.9664	High Similarity	NPC292107
0.966	High Similarity	NPC76376
0.9658	High Similarity	NPC48479
0.9658	High Similarity	NPC177298
0.9655	High Similarity	NPC108406
0.9655	High Similarity	NPC12200
0.96	High Similarity	NPC78302
0.96	High Similarity	NPC224137
0.96	High Similarity	NPC472438
0.96	High Similarity	NPC7973
0.96	High Similarity	NPC189179
0.96	High Similarity	NPC75215
0.96	High Similarity	NPC29841
0.96	High Similarity	NPC471515
0.96	High Similarity	NPC174908
0.96	High Similarity	NPC227192
0.96	High Similarity	NPC235215
0.96	High Similarity	NPC471479
0.96	High Similarity	NPC93376
0.9597	High Similarity	NPC80534
0.9597	High Similarity	NPC133392
0.9597	High Similarity	NPC56786
0.9597	High Similarity	NPC32557
0.9597	High Similarity	NPC189960
0.9597	High Similarity	NPC214138
0.9595	High Similarity	NPC187498
0.9595	High Similarity	NPC83508
0.9595	High Similarity	NPC241498
0.9595	High Similarity	NPC198826
0.9595	High Similarity	NPC275722
0.9595	High Similarity	NPC301323
0.9595	High Similarity	NPC100887
0.9595	High Similarity	NPC212678
0.9595	High Similarity	NPC39732
0.9595	High Similarity	NPC222830
0.9595	High Similarity	NPC239128
0.9595	High Similarity	NPC131624
0.9595	High Similarity	NPC293183
0.9595	High Similarity	NPC304954
0.9595	High Similarity	NPC256283
0.9595	High Similarity	NPC57030
0.9595	High Similarity	NPC162313
0.9595	High Similarity	NPC120163
0.9595	High Similarity	NPC71334
0.9595	High Similarity	NPC156222
0.9595	High Similarity	NPC301123
0.9595	High Similarity	NPC275836
0.9595	High Similarity	NPC60972
0.9595	High Similarity	NPC188203
0.9595	High Similarity	NPC25270
0.9592	High Similarity	NPC219330
0.9589	High Similarity	NPC195202
0.9589	High Similarity	NPC261548
0.9586	High Similarity	NPC20791
0.9586	High Similarity	NPC179271
0.9536	High Similarity	NPC193842
0.9533	High Similarity	NPC326037
0.9533	High Similarity	NPC474520
0.9533	High Similarity	NPC13858
0.9533	High Similarity	NPC268161
0.9533	High Similarity	NPC320825
0.9533	High Similarity	NPC178854
0.9533	High Similarity	NPC471500
0.953	High Similarity	NPC246204
0.953	High Similarity	NPC274327
0.953	High Similarity	NPC145379
0.953	High Similarity	NPC69394
0.953	High Similarity	NPC176775
0.953	High Similarity	NPC255350
0.953	High Similarity	NPC183878
0.953	High Similarity	NPC47781
0.953	High Similarity	NPC160951
0.953	High Similarity	NPC22519
0.953	High Similarity	NPC86485
0.953	High Similarity	NPC231018
0.9527	High Similarity	NPC225731
0.9521	High Similarity	NPC74881
0.9521	High Similarity	NPC62536
0.9521	High Similarity	NPC33265
0.9521	High Similarity	NPC51443
0.9474	High Similarity	NPC246478
0.947	High Similarity	NPC67876
0.947	High Similarity	NPC52530
0.9467	High Similarity	NPC2476
0.9467	High Similarity	NPC213622
0.9467	High Similarity	NPC4455
0.9467	High Similarity	NPC227325
0.9467	High Similarity	NPC146165
0.9467	High Similarity	NPC138360
0.9467	High Similarity	NPC280339
0.9467	High Similarity	NPC92659
0.9467	High Similarity	NPC20830
0.9467	High Similarity	NPC183597
0.9467	High Similarity	NPC128863
0.9467	High Similarity	NPC163780
0.9467	High Similarity	NPC50715
0.9467	High Similarity	NPC201136
0.9467	High Similarity	NPC196439
0.9467	High Similarity	NPC167815
0.9467	High Similarity	NPC256612
0.9463	High Similarity	NPC37684
0.9463	High Similarity	NPC142540
0.9463	High Similarity	NPC219582
0.9463	High Similarity	NPC302950
0.9463	High Similarity	NPC27208
0.9463	High Similarity	NPC236637
0.9463	High Similarity	NPC63187
0.9463	High Similarity	NPC471982
0.9463	High Similarity	NPC157784
0.9459	High Similarity	NPC184136
0.9459	High Similarity	NPC306821
0.9456	High Similarity	NPC119059
0.9452	High Similarity	NPC169749
0.9452	High Similarity	NPC310259
0.9448	High Similarity	NPC279121
0.9408	High Similarity	NPC55738
0.9408	High Similarity	NPC280680
0.9408	High Similarity	NPC195832
0.9404	High Similarity	NPC474638
0.9404	High Similarity	NPC153512
0.9404	High Similarity	NPC250922
0.94	High Similarity	NPC75279
0.94	High Similarity	NPC18727
0.94	High Similarity	NPC276409
0.94	High Similarity	NPC141212
0.94	High Similarity	NPC250822
0.9396	High Similarity	NPC31363
0.9396	High Similarity	NPC59162

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 NPC82325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	986
0.2-0.3	1860
0.3-0.4	2647
0.4-0.5	1729
0.5-0.6	961
0.6-0.7	359
0.7-0.8	106
0.8-0.85	35
0.85-0.9	12
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9586	High Similarity	NPD1512	Approved
0.953	High Similarity	NPD2801	Approved
0.9463	High Similarity	NPD1934	Approved
0.9448	High Similarity	NPD1511	Approved
0.9404	High Similarity	NPD3882	Suspended
0.9338	High Similarity	NPD3817	Phase 2
0.9145	High Similarity	NPD2393	Clinical (unspecified phase)
0.9108	High Similarity	NPD6168	Clinical (unspecified phase)
0.9108	High Similarity	NPD6166	Phase 2
0.9108	High Similarity	NPD6167	Clinical (unspecified phase)
0.8993	High Similarity	NPD4378	Clinical (unspecified phase)
0.8944	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD7251	Discontinued
0.8834	High Similarity	NPD4338	Clinical (unspecified phase)
0.8834	High Similarity	NPD7808	Phase 3
0.882	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7472	Approved
0.8758	High Similarity	NPD3818	Discontinued
0.8675	High Similarity	NPD6799	Approved
0.865	High Similarity	NPD7074	Phase 3
0.8608	High Similarity	NPD7075	Discontinued
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8471	Intermediate Similarity	NPD6801	Discontinued
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD5402	Approved
0.8364	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD919	Approved
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD5494	Approved
0.8269	Intermediate Similarity	NPD5403	Approved
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5401	Approved
0.8255	Intermediate Similarity	NPD1607	Approved
0.8243	Intermediate Similarity	NPD943	Approved
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1465	Phase 2
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8027	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1613	Approved
0.795	Intermediate Similarity	NPD7411	Suspended
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7947	Intermediate Similarity	NPD447	Suspended
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD6959	Discontinued
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7821	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2935	Discontinued
0.7722	Intermediate Similarity	NPD6190	Approved
0.7712	Intermediate Similarity	NPD1933	Approved
0.7711	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD9494	Approved
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7625	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1243	Approved
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD920	Approved
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD1653	Approved
0.7533	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD3226	Approved
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6651	Approved
0.7432	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD2309	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7355	Intermediate Similarity	NPD6233	Phase 2
0.7342	Intermediate Similarity	NPD2799	Discontinued
0.7341	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD9717	Approved
0.733	Intermediate Similarity	NPD5953	Discontinued
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.729	Intermediate Similarity	NPD3268	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7284	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD2798	Approved
0.7241	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3225	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.719	Intermediate Similarity	NPD2797	Approved
0.7184	Intermediate Similarity	NPD5242	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD411	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.716	Intermediate Similarity	NPD2654	Approved
0.7159	Intermediate Similarity	NPD2163	Approved
0.7159	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7115	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.7076	Intermediate Similarity	NPD5353	Approved
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7048	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3146	Approved
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4340	Discontinued
0.7039	Intermediate Similarity	NPD1201	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD2353	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6782	Approved
0.7029	Intermediate Similarity	NPD5710	Approved
0.7029	Intermediate Similarity	NPD5711	Approved
0.7025	Intermediate Similarity	NPD4062	Phase 3
0.702	Intermediate Similarity	NPD17	Approved
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7016	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7005	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4361	Phase 2
0.7	Intermediate Similarity	NPD9545	Approved
0.6995	Remote Similarity	NPD8150	Discontinued
0.6995	Remote Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD1558	Phase 1

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