NPASS Compound

Structure

NPC168822 OpenBabel07101718182D 31 34 0 0 1 0 0 0 0 0999 V2000 -6.0622 0.5000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -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 -6.0622 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -7.7942 1.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 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 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 4 2 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 22 1 0 0 0 0 9 15 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 30 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 29 1 6 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	404.357
LogP:	0.987
LogD:	0.439
LogS:	-3.956
# Rotatable Bonds:	4
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	3.765
Fsp3:	0.286
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:	-6.085
MDCK Permeability:	1.1375167559890542e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.872
Human Intestinal Absorption (HIA):	0.599
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	91.71699523925781%
Volume Distribution (VD):	0.645
Pgp-substrate:	9.526726722717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.433
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.205
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.421
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	3.952
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.741
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.919
Carcinogencity:	0.727
Eye Corrosion:	0.003
Eye Irritation:	0.242
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC168822

Natural Product ID:	NPC168822
*Common Name:**	7-O-Beta-D-Glucopyranosyl-7,3',4'-Trihydroxyflavone
IUPAC Name:	2-(3,4-dihydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	IVCZEZUJCMWBBR-YMQHIKHWSA-N
Standard InCHI:	InChI=1S/C21H20O10/c22-8-17-18(26)19(27)20(28)21(31-17)29-10-2-3-11-13(24)7-15(30-16(11)6-10)9-1-4-12(23)14(25)5-9/h1-7,17-23,25-28H,8H2/t17-,18-,19+,20-,21-/m1/s1
SMILES:	c1cc(c(cc1c1cc(=O)c2ccc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1084924
PubChem CID:	14656729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO11069	Fadogia ancylantha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20058934]
NPO11069	Fadogia ancylantha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
IC50	1
MIC	6
Others	5

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2219	Cell Line	C2C12	Mus musculus	IC10	=	10.07	ug ml-1	PMID[465887]
NPT2219	Cell Line	C2C12	Mus musculus	IC50	=	40.02	ug.mL-1	PMID[465887]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	68.88	%	PMID[465887]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	500.0	ug.mL-1	PMID[465886]
NPT22	Organism	Bacillus subtilis subsp. spizizenii	Bacillus subtilis subsp. spizizenii	MIC	=	1000.0	ug.mL-1	PMID[465886]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	1000.0	ug.mL-1	PMID[465886]
NPT22	Organism	Bacillus subtilis subsp. spizizenii	Bacillus subtilis subsp. spizizenii	MBC	=	1.0	mg/ml	PMID[465886]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2000.0	ug.mL-1	PMID[465886]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	4000.0	ug.mL-1	PMID[465886]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	4000.0	ug.mL-1	PMID[465886]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	4.0	mg/ml	PMID[465886]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	4.0	mg/ml	PMID[465886]
NPT1	Others	Radical scavenging activity		EC50	=	28.4	ug.mL-1	PMID[465886]

☑ 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 NPC168822 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	445
0.1-0.2	1835
0.2-0.3	4139
0.3-0.4	9743
0.4-0.5	8335
0.5-0.6	4113
0.6-0.7	5112
0.7-0.8	5204
0.8-0.85	1975
0.85-0.9	1251
0.9-0.95	404
0.95-1	141

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC189142
0.9935	High Similarity	NPC77660
0.9871	High Similarity	NPC270335
0.9871	High Similarity	NPC19709
0.9871	High Similarity	NPC191306
0.9809	High Similarity	NPC229729
0.9808	High Similarity	NPC277205
0.9808	High Similarity	NPC22832
0.9808	High Similarity	NPC311830
0.9806	High Similarity	NPC473043
0.9745	High Similarity	NPC210073
0.9745	High Similarity	NPC115674
0.9745	High Similarity	NPC276222
0.9745	High Similarity	NPC281131
0.9745	High Similarity	NPC197285
0.9745	High Similarity	NPC88789
0.9745	High Similarity	NPC145038
0.9745	High Similarity	NPC8856
0.9745	High Similarity	NPC21100
0.9745	High Similarity	NPC274618
0.9745	High Similarity	NPC179950
0.9745	High Similarity	NPC253662
0.9745	High Similarity	NPC56077
0.9745	High Similarity	NPC308404
0.9745	High Similarity	NPC118284
0.9744	High Similarity	NPC222936
0.9744	High Similarity	NPC243930
0.9744	High Similarity	NPC309025
0.9744	High Similarity	NPC29830
0.9744	High Similarity	NPC88023
0.9744	High Similarity	NPC284960
0.9744	High Similarity	NPC88043
0.9686	High Similarity	NPC51326
0.9686	High Similarity	NPC206123
0.9686	High Similarity	NPC231194
0.9684	High Similarity	NPC127546
0.9684	High Similarity	NPC84362
0.9684	High Similarity	NPC45400
0.9684	High Similarity	NPC58716
0.9684	High Similarity	NPC52550
0.9684	High Similarity	NPC173637
0.9684	High Similarity	NPC146792
0.9684	High Similarity	NPC45618
0.9684	High Similarity	NPC223424
0.9684	High Similarity	NPC317489
0.9682	High Similarity	NPC240431
0.9682	High Similarity	NPC55786
0.9682	High Similarity	NPC19388
0.9682	High Similarity	NPC165720
0.9679	High Similarity	NPC300537
0.9679	High Similarity	NPC127782
0.9625	High Similarity	NPC48773
0.9625	High Similarity	NPC205076
0.9625	High Similarity	NPC235575
0.9625	High Similarity	NPC307518
0.9623	High Similarity	NPC195257
0.9623	High Similarity	NPC219904
0.9623	High Similarity	NPC229687
0.9623	High Similarity	NPC226294
0.9623	High Similarity	NPC86008
0.9623	High Similarity	NPC201292
0.9623	High Similarity	NPC120099
0.9623	High Similarity	NPC58053
0.9623	High Similarity	NPC469931
0.9623	High Similarity	NPC209296
0.9623	High Similarity	NPC223747
0.9623	High Similarity	NPC475942
0.9623	High Similarity	NPC186807
0.9623	High Similarity	NPC93337
0.9623	High Similarity	NPC225434
0.9623	High Similarity	NPC45638
0.9623	High Similarity	NPC203050
0.9623	High Similarity	NPC105025
0.962	High Similarity	NPC73855
0.962	High Similarity	NPC277174
0.962	High Similarity	NPC135599
0.962	High Similarity	NPC113968
0.962	High Similarity	NPC5778
0.962	High Similarity	NPC236934
0.962	High Similarity	NPC328940
0.9615	High Similarity	NPC182045
0.961	High Similarity	NPC261866
0.9565	High Similarity	NPC472993
0.9563	High Similarity	NPC149011
0.9563	High Similarity	NPC150767
0.9563	High Similarity	NPC34287
0.9563	High Similarity	NPC255157
0.9563	High Similarity	NPC20505
0.9563	High Similarity	NPC67105
0.9563	High Similarity	NPC224462
0.9563	High Similarity	NPC155763
0.9563	High Similarity	NPC471416
0.9563	High Similarity	NPC235260
0.9563	High Similarity	NPC245014
0.9563	High Similarity	NPC204937
0.9563	High Similarity	NPC285197
0.9563	High Similarity	NPC254855
0.9563	High Similarity	NPC67326
0.9563	High Similarity	NPC84265
0.9563	High Similarity	NPC29958
0.9563	High Similarity	NPC282987
0.9563	High Similarity	NPC78734
0.9563	High Similarity	NPC105511
0.9563	High Similarity	NPC156869
0.9563	High Similarity	NPC259896
0.9563	High Similarity	NPC244776
0.9563	High Similarity	NPC218488
0.9563	High Similarity	NPC95866
0.9563	High Similarity	NPC116864
0.9563	High Similarity	NPC136042
0.956	High Similarity	NPC275454
0.956	High Similarity	NPC149244
0.956	High Similarity	NPC92565
0.956	High Similarity	NPC265530
0.956	High Similarity	NPC160156
0.956	High Similarity	NPC48640
0.956	High Similarity	NPC226304
0.956	High Similarity	NPC116745
0.956	High Similarity	NPC325555
0.9551	High Similarity	NPC110349
0.9548	High Similarity	NPC156457
0.9548	High Similarity	NPC313163
0.9548	High Similarity	NPC161749
0.9548	High Similarity	NPC258035
0.9548	High Similarity	NPC197896
0.9506	High Similarity	NPC34267
0.9506	High Similarity	NPC214621
0.9506	High Similarity	NPC223426
0.9506	High Similarity	NPC81042
0.9503	High Similarity	NPC26230
0.9503	High Similarity	NPC259152
0.9503	High Similarity	NPC245452
0.9503	High Similarity	NPC117260
0.9503	High Similarity	NPC471748
0.9503	High Similarity	NPC175107
0.9503	High Similarity	NPC256760
0.9503	High Similarity	NPC67134
0.9503	High Similarity	NPC176740
0.9503	High Similarity	NPC476405
0.9503	High Similarity	NPC254540
0.9503	High Similarity	NPC134532
0.9503	High Similarity	NPC153755
0.9503	High Similarity	NPC203259
0.9503	High Similarity	NPC33054
0.9503	High Similarity	NPC172807
0.9503	High Similarity	NPC180918
0.9503	High Similarity	NPC47140
0.9503	High Similarity	NPC155877
0.9503	High Similarity	NPC211594
0.9503	High Similarity	NPC190003
0.9503	High Similarity	NPC471725
0.9503	High Similarity	NPC60735
0.9503	High Similarity	NPC3583
0.95	High Similarity	NPC43587
0.95	High Similarity	NPC52382
0.95	High Similarity	NPC227508
0.95	High Similarity	NPC170675
0.95	High Similarity	NPC105283
0.95	High Similarity	NPC471457
0.95	High Similarity	NPC112755
0.95	High Similarity	NPC138927
0.95	High Similarity	NPC270578
0.9497	High Similarity	NPC255615
0.9497	High Similarity	NPC67037
0.9497	High Similarity	NPC254306
0.9487	High Similarity	NPC73511
0.9481	High Similarity	NPC143851
0.9481	High Similarity	NPC29763
0.9481	High Similarity	NPC210003
0.9481	High Similarity	NPC83283
0.9481	High Similarity	NPC39360
0.9448	High Similarity	NPC472992
0.9448	High Similarity	NPC61904
0.9448	High Similarity	NPC472991
0.9448	High Similarity	NPC144097
0.9444	High Similarity	NPC88560
0.9444	High Similarity	NPC24043
0.9444	High Similarity	NPC204693
0.9444	High Similarity	NPC169977
0.9444	High Similarity	NPC208668
0.9444	High Similarity	NPC172033
0.9444	High Similarity	NPC4390
0.9444	High Similarity	NPC101026
0.9444	High Similarity	NPC42773
0.9444	High Similarity	NPC45522
0.9444	High Similarity	NPC21666
0.9444	High Similarity	NPC175230
0.9441	High Similarity	NPC474434
0.9441	High Similarity	NPC177731
0.9441	High Similarity	NPC44328
0.9441	High Similarity	NPC44558
0.9441	High Similarity	NPC22195
0.9441	High Similarity	NPC212748
0.9441	High Similarity	NPC105095
0.9441	High Similarity	NPC79056
0.9441	High Similarity	NPC183357
0.9441	High Similarity	NPC72249
0.9441	High Similarity	NPC21190
0.9437	High Similarity	NPC135345
0.9437	High Similarity	NPC477502

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 NPC168822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	929
0.2-0.3	1905
0.3-0.4	2694
0.4-0.5	1797
0.5-0.6	934
0.6-0.7	295
0.7-0.8	135
0.8-0.85	20
0.85-0.9	17
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9623	High Similarity	NPD7054	Approved
0.9563	High Similarity	NPD7472	Approved
0.956	High Similarity	NPD3818	Discontinued
0.9548	High Similarity	NPD4381	Clinical (unspecified phase)
0.9503	High Similarity	NPD6797	Phase 2
0.9444	High Similarity	NPD7251	Discontinued
0.9441	High Similarity	NPD7074	Phase 3
0.9387	High Similarity	NPD4338	Clinical (unspecified phase)
0.9268	High Similarity	NPD7808	Phase 3
0.9045	High Similarity	NPD1934	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8957	High Similarity	NPD6166	Phase 2
0.8957	High Similarity	NPD6168	Clinical (unspecified phase)
0.8957	High Similarity	NPD6167	Clinical (unspecified phase)
0.8917	High Similarity	NPD4380	Phase 2
0.8909	High Similarity	NPD7804	Clinical (unspecified phase)
0.8896	High Similarity	NPD1511	Approved
0.8875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8868	High Similarity	NPD2801	Approved
0.8782	High Similarity	NPD1512	Approved
0.8696	High Similarity	NPD3817	Phase 2
0.8642	High Similarity	NPD3882	Suspended
0.8639	High Similarity	NPD6559	Discontinued
0.8476	Intermediate Similarity	NPD7075	Discontinued
0.8471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD5402	Approved
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8438	Intermediate Similarity	NPD1653	Approved
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5403	Approved
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD5494	Approved
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5401	Approved
0.8205	Intermediate Similarity	NPD2796	Approved
0.8187	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD7411	Suspended
0.814	Intermediate Similarity	NPD5844	Phase 1
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7685	Pre-registration
0.8081	Intermediate Similarity	NPD3751	Discontinued
0.8037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8312	Approved
0.8011	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7953	Intermediate Similarity	NPD6232	Discontinued
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7925	Intermediate Similarity	NPD7266	Discontinued
0.7919	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7888	Intermediate Similarity	NPD3750	Approved
0.7888	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7874	Intermediate Similarity	NPD7228	Approved
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7584	Approved
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1551	Phase 2
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6190	Approved
0.7722	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7719	Intermediate Similarity	NPD3749	Approved
0.7701	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD6779	Approved
0.7701	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD6776	Approved
0.7701	Intermediate Similarity	NPD6781	Approved
0.7701	Intermediate Similarity	NPD6782	Approved
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD37	Approved
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD919	Approved
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7661	Intermediate Similarity	NPD4965	Approved
0.7661	Intermediate Similarity	NPD4966	Approved
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.7647	Intermediate Similarity	NPD8455	Phase 2
0.7636	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7586	Intermediate Similarity	NPD1247	Approved
0.758	Intermediate Similarity	NPD3027	Phase 3
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD3748	Approved
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7698	Approved
0.7469	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.7447	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.7433	Intermediate Similarity	NPD6534	Approved
0.7433	Intermediate Similarity	NPD6535	Approved
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD7585	Approved
0.7403	Intermediate Similarity	NPD1091	Approved
0.7403	Intermediate Similarity	NPD7240	Approved
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD920	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD2532	Approved
0.7371	Intermediate Similarity	NPD7583	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1203	Approved
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD3226	Approved
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2800	Approved
0.7289	Intermediate Similarity	NPD1243	Approved
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD2798	Approved
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7233	Intermediate Similarity	NPD9494	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7204	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6213	Phase 3
0.7196	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6212	Phase 3
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD6674	Discontinued
0.7186	Intermediate Similarity	NPD1652	Phase 2
0.7179	Intermediate Similarity	NPD8319	Approved
0.7179	Intermediate Similarity	NPD8320	Phase 1
0.7178	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2344	Approved
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7167	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7134	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5124	Phase 1
0.707	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3225	Approved
0.7041	Intermediate Similarity	NPD7680	Approved
0.7025	Intermediate Similarity	NPD9717	Approved
0.7017	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD2309	Approved
0.6994	Remote Similarity	NPD3268	Approved
0.6994	Remote Similarity	NPD6798	Discontinued
0.699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6842	Approved
0.6984	Remote Similarity	NPD6841	Approved
0.6984	Remote Similarity	NPD6843	Phase 3
0.6977	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD422	Phase 1
0.6961	Remote Similarity	NPD5710	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