NPASS Compound

Structure

NPC219330 OpenBabel07101719242D 26 28 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 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 5.1962 -1.0000 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 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 -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 -1.7321 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 2.5981 -1.5000 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 -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 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 3.4641 -1.0000 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 -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 1.7321 2.0000 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 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	2.813
LogD:	2.442
LogS:	-3.632
# Rotatable Bonds:	4
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.468
Fsp3:	0.167
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:	-5.015
MDCK Permeability:	1.6137035345309414e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	89.6193618774414%
Volume Distribution (VD):	0.93
Pgp-substrate:	15.560153007507324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.829
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.567
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	5.997
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.433
Skin Sensitization:	0.42
Carcinogencity:	0.02
Eye Corrosion:	0.004
Eye Irritation:	0.68
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC219330

Natural Product ID:	NPC219330
*Common Name:**	3,5,7-Trihydroxy-3',4',5'-Trimethoxyflavone
IUPAC Name:	3,5,7-trihydroxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	LHNLHJJGLDWGFS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-23-12-4-8(5-13(24-2)18(12)25-3)17-16(22)15(21)14-10(20)6-9(19)7-11(14)26-17/h4-7,19-20,22H,1-3H3
SMILES:	COc1c(OC)cc(cc1OC)c1oc2cc(O)cc(c2c(=O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL75258
PubChem CID:	5481248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO16126	Vitex peduncularis	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25264585]
NPO16126	Vitex peduncularis	Species	Lamiaceae	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	3
MIC	10

Activity Type	# Activity
Individual Protein	1
Organism	11
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1567	Protein Complex	DNA gyrase	Escherichia coli K-12	IC50	>	500.0	ug.mL-1	PMID[521574]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	125.0	ug.mL-1	PMID[521574]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	125.0	ug.mL-1	PMID[521574]
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MIC	>	125.0	ug.mL-1	PMID[521574]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	125.0	ug.mL-1	PMID[521574]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	125.0	ug.mL-1	PMID[521574]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	3200.0	nM	PMID[521575]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30.0	ug.mL-1	PMID[521576]

☑ 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 NPC219330 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	455
0.1-0.2	2054
0.2-0.3	5050
0.3-0.4	11264
0.4-0.5	6005
0.5-0.6	3945
0.6-0.7	5032
0.7-0.8	4686
0.8-0.85	2103
0.85-0.9	1253
0.9-0.95	573
0.95-1	277

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC76376
0.9861	High Similarity	NPC166753
0.9861	High Similarity	NPC50728
0.9795	High Similarity	NPC58382
0.9795	High Similarity	NPC246204
0.9795	High Similarity	NPC162351
0.9793	High Similarity	NPC236769
0.9793	High Similarity	NPC133953
0.9793	High Similarity	NPC50403
0.9793	High Similarity	NPC28274
0.9792	High Similarity	NPC159103
0.979	High Similarity	NPC62536
0.979	High Similarity	NPC33265
0.9726	High Similarity	NPC123886
0.9722	High Similarity	NPC261548
0.9722	High Similarity	NPC195202
0.9662	High Similarity	NPC100916
0.9662	High Similarity	NPC55619
0.9662	High Similarity	NPC178854
0.9662	High Similarity	NPC200388
0.9662	High Similarity	NPC474520
0.966	High Similarity	NPC86485
0.966	High Similarity	NPC78326
0.966	High Similarity	NPC236223
0.966	High Similarity	NPC270620
0.966	High Similarity	NPC179126
0.9658	High Similarity	NPC252933
0.9658	High Similarity	NPC54394
0.9658	High Similarity	NPC200740
0.9658	High Similarity	NPC125062
0.9655	High Similarity	NPC328119
0.9655	High Similarity	NPC48479
0.9655	High Similarity	NPC177298
0.9653	High Similarity	NPC12200
0.9597	High Similarity	NPC29841
0.9597	High Similarity	NPC235215
0.9597	High Similarity	NPC472438
0.9597	High Similarity	NPC7973
0.9597	High Similarity	NPC227192
0.9597	High Similarity	NPC189179
0.9597	High Similarity	NPC93376
0.9597	High Similarity	NPC75215
0.9597	High Similarity	NPC224137
0.9597	High Similarity	NPC78302
0.9595	High Similarity	NPC189960
0.9595	High Similarity	NPC32557
0.9592	High Similarity	NPC55205
0.9592	High Similarity	NPC279989
0.9592	High Similarity	NPC134677
0.9592	High Similarity	NPC82325
0.9592	High Similarity	NPC301123
0.9586	High Similarity	NPC120464
0.9533	High Similarity	NPC9609
0.9533	High Similarity	NPC18607
0.9533	High Similarity	NPC152166
0.9533	High Similarity	NPC261004
0.9533	High Similarity	NPC19687
0.9533	High Similarity	NPC18772
0.9533	High Similarity	NPC115798
0.9533	High Similarity	NPC7846
0.9533	High Similarity	NPC143828
0.9533	High Similarity	NPC253634
0.9533	High Similarity	NPC191459
0.9533	High Similarity	NPC288669
0.9533	High Similarity	NPC4481
0.9533	High Similarity	NPC25495
0.9533	High Similarity	NPC176300
0.9533	High Similarity	NPC130894
0.9533	High Similarity	NPC105242
0.9533	High Similarity	NPC300943
0.9533	High Similarity	NPC22472
0.9533	High Similarity	NPC204854
0.953	High Similarity	NPC265511
0.953	High Similarity	NPC247017
0.953	High Similarity	NPC268161
0.953	High Similarity	NPC49824
0.953	High Similarity	NPC98661
0.9527	High Similarity	NPC75279
0.9527	High Similarity	NPC250822
0.9527	High Similarity	NPC276409
0.9524	High Similarity	NPC308451
0.9524	High Similarity	NPC226973
0.9524	High Similarity	NPC208043
0.9521	High Similarity	NPC270465
0.9521	High Similarity	NPC223579
0.9521	High Similarity	NPC52005
0.9521	High Similarity	NPC183950
0.9521	High Similarity	NPC137062
0.9521	High Similarity	NPC287101
0.9521	High Similarity	NPC87125
0.9467	High Similarity	NPC101830
0.9467	High Similarity	NPC174908
0.9467	High Similarity	NPC305663
0.9467	High Similarity	NPC110070
0.9467	High Similarity	NPC163524
0.9467	High Similarity	NPC287979
0.9467	High Similarity	NPC203891
0.9467	High Similarity	NPC176665
0.9463	High Similarity	NPC201451
0.9463	High Similarity	NPC128863
0.9463	High Similarity	NPC92659
0.9463	High Similarity	NPC4455
0.9463	High Similarity	NPC2476
0.9463	High Similarity	NPC146165
0.9463	High Similarity	NPC138360
0.9463	High Similarity	NPC280339
0.9463	High Similarity	NPC208197
0.9463	High Similarity	NPC227325
0.9463	High Similarity	NPC183597
0.9463	High Similarity	NPC44079
0.9463	High Similarity	NPC26227
0.9463	High Similarity	NPC196439
0.9463	High Similarity	NPC163780
0.9463	High Similarity	NPC50715
0.9463	High Similarity	NPC167815
0.9463	High Similarity	NPC201136
0.9459	High Similarity	NPC471982
0.9459	High Similarity	NPC60972
0.9459	High Similarity	NPC39732
0.9456	High Similarity	NPC188871
0.9456	High Similarity	NPC149127
0.9456	High Similarity	NPC306821
0.9456	High Similarity	NPC286342
0.9456	High Similarity	NPC338131
0.9448	High Similarity	NPC310259
0.9448	High Similarity	NPC169749
0.9441	High Similarity	NPC29536
0.9404	High Similarity	NPC193842
0.94	High Similarity	NPC266960
0.94	High Similarity	NPC292107
0.94	High Similarity	NPC245546
0.94	High Similarity	NPC43243
0.94	High Similarity	NPC250922
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC280937
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC59162
0.9392	High Similarity	NPC304295
0.9392	High Similarity	NPC260895
0.9392	High Similarity	NPC205046
0.9388	High Similarity	NPC181250
0.9384	High Similarity	NPC299923
0.9384	High Similarity	NPC108406
0.9375	High Similarity	NPC70853
0.9375	High Similarity	NPC9966
0.9342	High Similarity	NPC246478
0.9342	High Similarity	NPC470326
0.9338	High Similarity	NPC63454
0.9338	High Similarity	NPC183
0.9338	High Similarity	NPC471479
0.9338	High Similarity	NPC471515
0.9338	High Similarity	NPC183851
0.9338	High Similarity	NPC67876
0.9333	High Similarity	NPC20830
0.9333	High Similarity	NPC133392
0.9333	High Similarity	NPC214138
0.9333	High Similarity	NPC256612
0.9333	High Similarity	NPC80534
0.9333	High Similarity	NPC56786
0.9333	High Similarity	NPC213622
0.9329	High Similarity	NPC241498
0.9329	High Similarity	NPC162313
0.9329	High Similarity	NPC120163
0.9329	High Similarity	NPC293183
0.9329	High Similarity	NPC27208
0.9329	High Similarity	NPC71334
0.9329	High Similarity	NPC222830
0.9329	High Similarity	NPC188203
0.9329	High Similarity	NPC157784
0.9329	High Similarity	NPC275836
0.9329	High Similarity	NPC239128
0.9329	High Similarity	NPC275722
0.9329	High Similarity	NPC187498
0.9329	High Similarity	NPC142540
0.9329	High Similarity	NPC63187
0.9329	High Similarity	NPC57030
0.9329	High Similarity	NPC198826
0.9329	High Similarity	NPC83508
0.9329	High Similarity	NPC100887
0.9329	High Similarity	NPC301323
0.9329	High Similarity	NPC212678
0.9329	High Similarity	NPC131624
0.9329	High Similarity	NPC37684
0.9329	High Similarity	NPC25270
0.9329	High Similarity	NPC156222
0.9329	High Similarity	NPC256283
0.9324	High Similarity	NPC259058
0.9324	High Similarity	NPC201547
0.9315	High Similarity	NPC179271
0.9315	High Similarity	NPC20791
0.9315	High Similarity	NPC302408
0.9315	High Similarity	NPC283002

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 NPC219330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	438
0.1-0.2	1007
0.2-0.3	1917
0.3-0.4	2657
0.4-0.5	1678
0.5-0.6	957
0.6-0.7	332
0.7-0.8	106
0.8-0.85	37
0.85-0.9	9
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD2801	Approved
0.9333	High Similarity	NPD3817	Phase 2
0.9315	High Similarity	NPD1512	Approved
0.92	High Similarity	NPD1934	Approved
0.9178	High Similarity	NPD1511	Approved
0.9145	High Similarity	NPD3882	Suspended
0.9116	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD6168	Clinical (unspecified phase)
0.9103	High Similarity	NPD6166	Phase 2
0.9103	High Similarity	NPD6167	Clinical (unspecified phase)
0.9013	High Similarity	NPD2393	Clinical (unspecified phase)
0.8827	High Similarity	NPD7808	Phase 3
0.882	High Similarity	NPD6797	Phase 2
0.8812	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7251	Discontinued
0.8758	High Similarity	NPD7472	Approved
0.875	High Similarity	NPD3818	Discontinued
0.8712	High Similarity	NPD4338	Clinical (unspecified phase)
0.8642	High Similarity	NPD7074	Phase 3
0.8599	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD4380	Phase 2
0.8543	High Similarity	NPD6799	Approved
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1510	Phase 2
0.85	High Similarity	NPD6232	Discontinued
0.8487	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6801	Discontinued
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8456	Intermediate Similarity	NPD1549	Phase 2
0.8446	Intermediate Similarity	NPD2796	Approved
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5494	Approved
0.8356	Intermediate Similarity	NPD1240	Approved
0.8354	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3926	Phase 2
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD5403	Approved
0.8253	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1607	Approved
0.8239	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6599	Discontinued
0.821	Intermediate Similarity	NPD1247	Approved
0.821	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD919	Approved
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8165	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD943	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD447	Suspended
0.7922	Intermediate Similarity	NPD2800	Approved
0.7891	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6559	Discontinued
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.7838	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD230	Phase 1
0.7785	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD2533	Approved
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6651	Approved
0.7748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1613	Approved
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1933	Approved
0.7697	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD1243	Approved
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3027	Phase 3
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD3748	Approved
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7595	Intermediate Similarity	NPD6190	Approved
0.7593	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD920	Approved
0.7564	Intermediate Similarity	NPD2344	Approved
0.7561	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1653	Approved
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7453	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7438	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7427	Intermediate Similarity	NPD2403	Approved
0.7421	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD9494	Approved
0.7417	Intermediate Similarity	NPD3018	Phase 2
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7286	Phase 2
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3268	Approved
0.7375	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7358	Intermediate Similarity	NPD2654	Approved
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2798	Approved
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.7326	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD2982	Phase 2
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD5353	Approved
0.726	Intermediate Similarity	NPD5536	Phase 2
0.7248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD7228	Approved
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD3225	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7213	Intermediate Similarity	NPD4363	Phase 3
0.7213	Intermediate Similarity	NPD4360	Phase 2
0.7209	Intermediate Similarity	NPD5710	Approved
0.7209	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD2981	Phase 2
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7186	Intermediate Similarity	NPD6385	Approved
0.7186	Intermediate Similarity	NPD6386	Approved
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7081	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.707	Intermediate Similarity	NPD4060	Phase 1
0.7068	Intermediate Similarity	NPD7584	Approved
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7055	Intermediate Similarity	NPD2354	Approved
0.7045	Intermediate Similarity	NPD2163	Approved
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD3146	Approved
0.703	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1201	Approved
0.7019	Intermediate Similarity	NPD1471	Phase 3
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD8151	Discontinued
0.6987	Remote Similarity	NPD7095	Approved
0.6983	Remote Similarity	NPD7039	Approved
0.6983	Remote Similarity	NPD7038	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data