NPASS Compound

Structure

CID3825 OpenBabel06191715322D 26 28 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 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 3.4641 -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 5.1962 -3.0000 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 4.3301 -3.5000 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 2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	357.82
LogP:	4.714
LogD:	2.447
LogS:	-3.141
# Rotatable Bonds:	3
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.77
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996
MDCK Permeability:	1.2339663953753188e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.915
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.01980590820312%
Volume Distribution (VD):	0.681
Pgp-substrate:	7.249461650848389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.72
CYP2D6-inhibitor:	0.699
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	7.865
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.373
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.947
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.215

Download Data

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

Natural Product: NPC3825

Natural Product ID:	NPC3825
*Common Name:**	3',4',5,7-Tetrahydroxy-6-(3,3-Dimethylallyl)-Flavone
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	AFJYQKPCJLMHCC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-10(2)3-5-12-14(22)8-18-19(20(12)25)16(24)9-17(26-18)11-4-6-13(21)15(23)7-11/h3-4,6-9,21-23,25H,5H2,1-2H3
SMILES:	CC(=CCc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915459
PubChem CID:	14604081
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-prenylated flavones

*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
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]
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]
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]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	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]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	8
Others	1

Activity Type	# Activity
Cell Line	8
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	14600.0	nM	PMID[528148]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	=	23800.0	nM	PMID[528148]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2500.0	nM	PMID[528148]
NPT381	Cell Line	OVCAR-8	Homo sapiens	Activity	=	40.19	%	PMID[528148]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	40000.0	nM	PMID[528149]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[528149]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[528149]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	40000.0	nM	PMID[528149]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	=	5400.0	nM	PMID[528148]

☑ 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 NPC3825 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	433
0.1-0.2	1911
0.2-0.3	4700
0.3-0.4	11411
0.4-0.5	6179
0.5-0.6	3721
0.6-0.7	4928
0.7-0.8	4800
0.8-0.85	2141
0.85-0.9	1588
0.9-0.95	809
0.95-1	76

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC88804
0.9862	High Similarity	NPC37684
0.9862	High Similarity	NPC63187
0.9862	High Similarity	NPC157784
0.9795	High Similarity	NPC170492
0.9793	High Similarity	NPC154345
0.9793	High Similarity	NPC304295
0.9793	High Similarity	NPC205046
0.9793	High Similarity	NPC59162
0.9728	High Similarity	NPC133392
0.9726	High Similarity	NPC471982
0.9726	High Similarity	NPC249570
0.9662	High Similarity	NPC276444
0.9662	High Similarity	NPC3980
0.9662	High Similarity	NPC471985
0.966	High Similarity	NPC213896
0.966	High Similarity	NPC476631
0.966	High Similarity	NPC192083
0.9653	High Similarity	NPC108406
0.9597	High Similarity	NPC476630
0.9597	High Similarity	NPC237418
0.9597	High Similarity	NPC218871
0.9597	High Similarity	NPC273843
0.9595	High Similarity	NPC321779
0.9595	High Similarity	NPC472280
0.9595	High Similarity	NPC234255
0.9592	High Similarity	NPC106976
0.9592	High Similarity	NPC237994
0.958	High Similarity	NPC279121
0.9533	High Similarity	NPC46736
0.9533	High Similarity	NPC197856
0.953	High Similarity	NPC291878
0.953	High Similarity	NPC475799
0.953	High Similarity	NPC68093
0.953	High Similarity	NPC35038
0.953	High Similarity	NPC195796
0.953	High Similarity	NPC282307
0.953	High Similarity	NPC191146
0.953	High Similarity	NPC278778
0.953	High Similarity	NPC13779
0.953	High Similarity	NPC170026
0.953	High Similarity	NPC472455
0.9527	High Similarity	NPC70433
0.9527	High Similarity	NPC273462
0.9527	High Similarity	NPC298692
0.9527	High Similarity	NPC227337
0.9527	High Similarity	NPC33051
0.9527	High Similarity	NPC74924
0.9527	High Similarity	NPC49402
0.9521	High Similarity	NPC270465
0.9521	High Similarity	NPC223579
0.9521	High Similarity	NPC38545
0.9521	High Similarity	NPC171916
0.9521	High Similarity	NPC183950
0.9521	High Similarity	NPC48479
0.9521	High Similarity	NPC177298
0.9521	High Similarity	NPC137062
0.9521	High Similarity	NPC52005
0.9521	High Similarity	NPC287101
0.9521	High Similarity	NPC87125
0.9514	High Similarity	NPC70136
0.951	High Similarity	NPC175013
0.947	High Similarity	NPC476283
0.947	High Similarity	NPC119209
0.947	High Similarity	NPC328102
0.947	High Similarity	NPC476280
0.947	High Similarity	NPC204290
0.947	High Similarity	NPC192686
0.947	High Similarity	NPC476980
0.947	High Similarity	NPC297212
0.947	High Similarity	NPC118256
0.9467	High Similarity	NPC474681
0.9467	High Similarity	NPC218313
0.9467	High Similarity	NPC472598
0.9467	High Similarity	NPC27337
0.9467	High Similarity	NPC474055
0.9467	High Similarity	NPC78225
0.9467	High Similarity	NPC291508
0.9467	High Similarity	NPC471209
0.9463	High Similarity	NPC45849
0.9463	High Similarity	NPC200761
0.9463	High Similarity	NPC152951
0.9463	High Similarity	NPC168247
0.9463	High Similarity	NPC57674
0.9463	High Similarity	NPC477503
0.9463	High Similarity	NPC470327
0.9463	High Similarity	NPC113906
0.9463	High Similarity	NPC117992
0.9463	High Similarity	NPC230149
0.9459	High Similarity	NPC323626
0.9459	High Similarity	NPC60972
0.9459	High Similarity	NPC39732
0.9459	High Similarity	NPC324233
0.9456	High Similarity	NPC184136
0.9456	High Similarity	NPC188871
0.9456	High Similarity	NPC149127
0.9456	High Similarity	NPC286342
0.9452	High Similarity	NPC203077
0.9452	High Similarity	NPC120464
0.9452	High Similarity	NPC166036
0.9452	High Similarity	NPC238279
0.9452	High Similarity	NPC195202
0.9452	High Similarity	NPC119059
0.9448	High Similarity	NPC179271
0.9448	High Similarity	NPC20791
0.9408	High Similarity	NPC167678
0.9408	High Similarity	NPC26326
0.9408	High Similarity	NPC198829
0.9408	High Similarity	NPC29876
0.9408	High Similarity	NPC474038
0.9408	High Similarity	NPC259456
0.9408	High Similarity	NPC258331
0.9404	High Similarity	NPC184755
0.9404	High Similarity	NPC469658
0.9404	High Similarity	NPC53545
0.9404	High Similarity	NPC74178
0.9404	High Similarity	NPC172770
0.9404	High Similarity	NPC117418
0.9404	High Similarity	NPC204879
0.9404	High Similarity	NPC210459
0.9404	High Similarity	NPC185258
0.9404	High Similarity	NPC22192
0.94	High Similarity	NPC6633
0.94	High Similarity	NPC5322
0.94	High Similarity	NPC470328
0.94	High Similarity	NPC142339
0.94	High Similarity	NPC209614
0.94	High Similarity	NPC138243
0.94	High Similarity	NPC472626
0.94	High Similarity	NPC133970
0.9396	High Similarity	NPC18727
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC270620
0.9396	High Similarity	NPC179126
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC78326
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC236223
0.9396	High Similarity	NPC189130
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC125062
0.9392	High Similarity	NPC252933
0.9392	High Similarity	NPC54394
0.9392	High Similarity	NPC256406
0.9392	High Similarity	NPC260895
0.9392	High Similarity	NPC200740
0.9384	High Similarity	NPC239312
0.9384	High Similarity	NPC33265
0.9384	High Similarity	NPC130230
0.9384	High Similarity	NPC12200
0.9384	High Similarity	NPC275772
0.9384	High Similarity	NPC62536
0.9384	High Similarity	NPC74881
0.9384	High Similarity	NPC51443
0.9346	High Similarity	NPC78332
0.9346	High Similarity	NPC329760
0.9346	High Similarity	NPC474150
0.9346	High Similarity	NPC194427
0.9346	High Similarity	NPC474162
0.9346	High Similarity	NPC472448
0.9346	High Similarity	NPC83922
0.9346	High Similarity	NPC206605
0.9342	High Similarity	NPC287328
0.9342	High Similarity	NPC235018
0.9342	High Similarity	NPC321399
0.9342	High Similarity	NPC36217
0.9342	High Similarity	NPC246478
0.9342	High Similarity	NPC28241
0.9342	High Similarity	NPC282009
0.9342	High Similarity	NPC471973
0.9342	High Similarity	NPC472624
0.9342	High Similarity	NPC45146
0.9342	High Similarity	NPC475784
0.9338	High Similarity	NPC136674
0.9338	High Similarity	NPC79053
0.9338	High Similarity	NPC36852
0.9338	High Similarity	NPC236796
0.9338	High Similarity	NPC473272
0.9338	High Similarity	NPC262286
0.9338	High Similarity	NPC476981
0.9338	High Similarity	NPC223787
0.9338	High Similarity	NPC52889
0.9338	High Similarity	NPC187745
0.9338	High Similarity	NPC161960
0.9338	High Similarity	NPC284820
0.9338	High Similarity	NPC304008
0.9333	High Similarity	NPC92659
0.9333	High Similarity	NPC167815
0.9333	High Similarity	NPC20830
0.9333	High Similarity	NPC163780
0.9333	High Similarity	NPC256612
0.9333	High Similarity	NPC128863
0.9333	High Similarity	NPC227325
0.9333	High Similarity	NPC80534

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 NPC3825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1000
0.2-0.3	1682
0.3-0.4	2733
0.4-0.5	1763
0.5-0.6	1028
0.6-0.7	363
0.7-0.8	103
0.8-0.85	52
0.85-0.9	11
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.966	High Similarity	NPD2393	Clinical (unspecified phase)
0.958	High Similarity	NPD1511	Approved
0.9448	High Similarity	NPD1512	Approved
0.9396	High Similarity	NPD2801	Approved
0.9329	High Similarity	NPD1934	Approved
0.9247	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD3882	Suspended
0.8861	High Similarity	NPD6168	Clinical (unspecified phase)
0.8861	High Similarity	NPD6166	Phase 2
0.8861	High Similarity	NPD6167	Clinical (unspecified phase)
0.8859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8831	High Similarity	NPD3817	Phase 2
0.8816	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD3818	Discontinued
0.8696	High Similarity	NPD7054	Approved
0.8642	High Similarity	NPD7472	Approved
0.8642	High Similarity	NPD7074	Phase 3
0.8639	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD1550	Clinical (unspecified phase)
0.863	High Similarity	NPD1510	Phase 2
0.8599	High Similarity	NPD7075	Discontinued
0.8589	High Similarity	NPD6797	Phase 2
0.8581	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD2796	Approved
0.8537	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8526	High Similarity	NPD7096	Clinical (unspecified phase)
0.8526	High Similarity	NPD7819	Suspended
0.85	High Similarity	NPD6232	Discontinued
0.8491	Intermediate Similarity	NPD5494	Approved
0.8483	Intermediate Similarity	NPD943	Approved
0.8483	Intermediate Similarity	NPD1240	Approved
0.8481	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6801	Discontinued
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8367	Intermediate Similarity	NPD1607	Approved
0.8354	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8301	Intermediate Similarity	NPD6799	Approved
0.8278	Intermediate Similarity	NPD2800	Approved
0.8224	Intermediate Similarity	NPD3750	Approved
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2935	Discontinued
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8138	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD1247	Approved
0.8095	Intermediate Similarity	NPD6559	Discontinued
0.8086	Intermediate Similarity	NPD919	Approved
0.8075	Intermediate Similarity	NPD7768	Phase 2
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1243	Approved
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8012	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2313	Discontinued
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7925	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD5403	Approved
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7895	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3748	Approved
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7881	Intermediate Similarity	NPD6651	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7843	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD6099	Approved
0.7836	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7815	Intermediate Similarity	NPD447	Suspended
0.7799	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2344	Approved
0.7792	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD3027	Phase 3
0.7785	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5953	Discontinued
0.7706	Intermediate Similarity	NPD7286	Phase 2
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4628	Phase 3
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1203	Approved
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3268	Approved
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2309	Approved
0.7584	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7199	Phase 2
0.755	Intermediate Similarity	NPD4625	Phase 3
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7517	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD4363	Phase 3
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1933	Approved
0.7453	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7436	Intermediate Similarity	NPD4308	Phase 3
0.7432	Intermediate Similarity	NPD9717	Approved
0.7432	Intermediate Similarity	NPD1608	Approved
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7423	Intermediate Similarity	NPD1653	Approved
0.7418	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD9494	Approved
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6190	Approved
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD1201	Approved
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7363	Intermediate Similarity	NPD4361	Phase 2
0.7363	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD37	Approved
0.7341	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD3225	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7285	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD1470	Approved
0.7285	Intermediate Similarity	NPD3267	Approved
0.7278	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD5404	Approved
0.7278	Intermediate Similarity	NPD5405	Approved
0.7278	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD4749	Approved
0.7262	Intermediate Similarity	NPD4288	Approved
0.725	Intermediate Similarity	NPD2654	Approved
0.7249	Intermediate Similarity	NPD7584	Approved
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD17	Approved
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD4307	Phase 2
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7169	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5242	Approved
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.7161	Intermediate Similarity	NPD1296	Phase 2
0.7159	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD2403	Approved
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7091	Intermediate Similarity	NPD5049	Phase 3
0.7086	Intermediate Similarity	NPD3972	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD3018	Phase 2
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD1164	Approved
0.7055	Intermediate Similarity	NPD2354	Approved
0.7051	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD5698	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