NPASS Compound

Structure

CID208197 OpenBabel06191716002D 27 29 0 0 0 0 0 0 0 0999 V2000 3.4641 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 -3.4641 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 1.7321 1.0000 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 -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 -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 3.4641 -0.0000 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 -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 -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 -2.5981 -0.5000 0.0000 C 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 -0.5000 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -3.4641 -0.0000 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 20 2 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.836
LogD:	3.39
LogS:	-3.297
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.236
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.434
MDCK Permeability:	1.9119750504614785e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.79
Plasma Protein Binding (PPB):	60.48897171020508%
Volume Distribution (VD):	0.941
Pgp-substrate:	29.185407638549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.205
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.434
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	10.57
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.2
Carcinogencity:	0.073
Eye Corrosion:	0.237
Eye Irritation:	0.603
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC208197

Natural Product ID:	NPC208197
*Common Name:**	3',8-Dihydroxy-4',5',6,7-Tetramethoxyflavone
IUPAC Name:	8-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	ATPIHJKFWBNCAS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O8/c1-23-14-6-9(5-12(21)18(14)25-3)13-8-11(20)10-7-15(24-2)19(26-4)16(22)17(10)27-13/h5-8,21-22H,1-4H3
SMILES:	COc1cc(cc(c1OC)O)c1cc(=O)c2cc(c(c(c2o1)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409235
PubChem CID:	72204300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-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
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075761]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11524	Macrotomia ugamensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28808	Piptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28939	Piptanthus nepalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29157	Reichardia gaditana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28829	Pelvetia wrightii	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28974	Smilax ornata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26540	Echinopsis spachiana	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29402	Launaea arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29194	Harziella entomophila	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29013	Annulohypoxylon cohaerens	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25969	Aspergillus nomius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28870	Clausena lenis	Species	Rutaceae	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	4
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	30000.0	nM	PMID[572098]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	85000.0	nM	PMID[572098]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	105000.0	nM	PMID[572098]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	25000.0	nM	PMID[572098]
NPT885	Cell Line	PBL		Activity	=	35.0	%	PMID[572098]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	56.8	%	PMID[572098]

☑ 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 NPC208197 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	439
0.1-0.2	1946
0.2-0.3	5069
0.3-0.4	11237
0.4-0.5	6132
0.5-0.6	3949
0.6-0.7	5045
0.7-0.8	4770
0.8-0.85	2026
0.85-0.9	1169
0.9-0.95	646
0.95-1	269

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC250822
0.9932	High Similarity	NPC276409
0.9932	High Similarity	NPC75279
0.9865	High Similarity	NPC146165
0.9865	High Similarity	NPC227325
0.9865	High Similarity	NPC163780
0.9865	High Similarity	NPC201136
0.9865	High Similarity	NPC167815
0.9865	High Similarity	NPC128863
0.9865	High Similarity	NPC256612
0.9865	High Similarity	NPC50715
0.9865	High Similarity	NPC2476
0.9865	High Similarity	NPC280339
0.9865	High Similarity	NPC4455
0.9865	High Similarity	NPC138360
0.9865	High Similarity	NPC92659
0.9865	High Similarity	NPC20830
0.9865	High Similarity	NPC183597
0.9865	High Similarity	NPC196439
0.9799	High Similarity	NPC474520
0.9797	High Similarity	NPC231018
0.9797	High Similarity	NPC47781
0.9797	High Similarity	NPC255350
0.9797	High Similarity	NPC22519
0.9797	High Similarity	NPC160951
0.9797	High Similarity	NPC69394
0.9797	High Similarity	NPC274327
0.9797	High Similarity	NPC183878
0.9797	High Similarity	NPC145379
0.9797	High Similarity	NPC176775
0.9733	High Similarity	NPC472438
0.9733	High Similarity	NPC93376
0.9733	High Similarity	NPC7973
0.9733	High Similarity	NPC78302
0.9733	High Similarity	NPC75215
0.9733	High Similarity	NPC235215
0.9733	High Similarity	NPC189179
0.9733	High Similarity	NPC29841
0.9733	High Similarity	NPC227192
0.9733	High Similarity	NPC224137
0.9732	High Similarity	NPC213622
0.973	High Similarity	NPC39732
0.973	High Similarity	NPC25270
0.973	High Similarity	NPC241498
0.973	High Similarity	NPC239128
0.973	High Similarity	NPC198826
0.973	High Similarity	NPC187498
0.973	High Similarity	NPC83508
0.973	High Similarity	NPC100887
0.973	High Similarity	NPC120163
0.973	High Similarity	NPC71334
0.973	High Similarity	NPC142540
0.973	High Similarity	NPC212678
0.973	High Similarity	NPC222830
0.973	High Similarity	NPC57030
0.973	High Similarity	NPC156222
0.973	High Similarity	NPC275722
0.973	High Similarity	NPC301323
0.973	High Similarity	NPC293183
0.973	High Similarity	NPC188203
0.973	High Similarity	NPC162313
0.973	High Similarity	NPC275836
0.973	High Similarity	NPC256283
0.973	High Similarity	NPC60972
0.973	High Similarity	NPC131624
0.9669	High Similarity	NPC143828
0.9669	High Similarity	NPC191459
0.9669	High Similarity	NPC4481
0.9669	High Similarity	NPC204854
0.9669	High Similarity	NPC288669
0.9669	High Similarity	NPC115798
0.9669	High Similarity	NPC22472
0.9669	High Similarity	NPC152166
0.9669	High Similarity	NPC19687
0.9669	High Similarity	NPC300943
0.9669	High Similarity	NPC7846
0.9669	High Similarity	NPC176300
0.9669	High Similarity	NPC253634
0.9669	High Similarity	NPC18772
0.9669	High Similarity	NPC193842
0.9669	High Similarity	NPC25495
0.9669	High Similarity	NPC9609
0.9669	High Similarity	NPC18607
0.9669	High Similarity	NPC261004
0.9669	High Similarity	NPC105242
0.9669	High Similarity	NPC130894
0.9667	High Similarity	NPC55619
0.9667	High Similarity	NPC247017
0.9667	High Similarity	NPC49824
0.9667	High Similarity	NPC200388
0.9667	High Similarity	NPC472916
0.9667	High Similarity	NPC268161
0.9667	High Similarity	NPC100916
0.9667	High Similarity	NPC98661
0.9664	High Similarity	NPC250557
0.9664	High Similarity	NPC280937
0.9662	High Similarity	NPC226973
0.9662	High Similarity	NPC208043
0.9662	High Similarity	NPC308451
0.966	High Similarity	NPC328119
0.966	High Similarity	NPC177298
0.966	High Similarity	NPC48479
0.9605	High Similarity	NPC476980
0.9603	High Similarity	NPC36852
0.9603	High Similarity	NPC470402
0.9603	High Similarity	NPC262286
0.9603	High Similarity	NPC176665
0.9603	High Similarity	NPC101830
0.9603	High Similarity	NPC305663
0.9603	High Similarity	NPC110070
0.9603	High Similarity	NPC163524
0.9603	High Similarity	NPC287979
0.9603	High Similarity	NPC203891
0.96	High Similarity	NPC44079
0.96	High Similarity	NPC26227
0.96	High Similarity	NPC201451
0.96	High Similarity	NPC2928
0.9597	High Similarity	NPC101996
0.9595	High Similarity	NPC306821
0.9595	High Similarity	NPC184136
0.9595	High Similarity	NPC45873
0.9592	High Similarity	NPC120464
0.9542	High Similarity	NPC258331
0.9536	High Similarity	NPC43243
0.9536	High Similarity	NPC245546
0.9536	High Similarity	NPC265511
0.9536	High Similarity	NPC292107
0.9536	High Similarity	NPC266960
0.9536	High Similarity	NPC178854
0.9536	High Similarity	NPC138243
0.9533	High Similarity	NPC86485
0.9533	High Similarity	NPC167091
0.9533	High Similarity	NPC124714
0.9533	High Similarity	NPC246204
0.9533	High Similarity	NPC472915
0.9533	High Similarity	NPC88645
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC292214
0.9533	High Similarity	NPC162351
0.9533	High Similarity	NPC206238
0.9533	High Similarity	NPC271779
0.953	High Similarity	NPC45291
0.953	High Similarity	NPC133953
0.953	High Similarity	NPC19980
0.953	High Similarity	NPC50403
0.953	High Similarity	NPC171010
0.953	High Similarity	NPC28274
0.9527	High Similarity	NPC296197
0.9527	High Similarity	NPC259713
0.9527	High Similarity	NPC216318
0.9527	High Similarity	NPC92722
0.9527	High Similarity	NPC287101
0.9527	High Similarity	NPC223579
0.9527	High Similarity	NPC17286
0.9527	High Similarity	NPC52005
0.9527	High Similarity	NPC102003
0.9527	High Similarity	NPC137062
0.9527	High Similarity	NPC183950
0.9524	High Similarity	NPC30647
0.9524	High Similarity	NPC62536
0.9524	High Similarity	NPC61871
0.9524	High Similarity	NPC55557
0.9524	High Similarity	NPC33265
0.9481	High Similarity	NPC472448
0.9481	High Similarity	NPC83922
0.9481	High Similarity	NPC81679
0.9477	High Similarity	NPC246478
0.9474	High Similarity	NPC472910
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC78103
0.9474	High Similarity	NPC469584
0.9474	High Similarity	NPC472913
0.9474	High Similarity	NPC241904
0.9474	High Similarity	NPC222814
0.9474	High Similarity	NPC48208
0.9474	High Similarity	NPC96167
0.9474	High Similarity	NPC472914
0.9474	High Similarity	NPC476981
0.9474	High Similarity	NPC99597
0.9474	High Similarity	NPC162869
0.9474	High Similarity	NPC156057
0.9474	High Similarity	NPC245758
0.9474	High Similarity	NPC78225
0.9474	High Similarity	NPC474208
0.9474	High Similarity	NPC300727
0.9474	High Similarity	NPC472911
0.9474	High Similarity	NPC210084
0.9474	High Similarity	NPC475267
0.947	High Similarity	NPC32557
0.947	High Similarity	NPC113906
0.947	High Similarity	NPC189960
0.947	High Similarity	NPC134287
0.947	High Similarity	NPC214138
0.947	High Similarity	NPC130589
0.9467	High Similarity	NPC245382
0.9467	High Similarity	NPC100263
0.9467	High Similarity	NPC301123
0.9467	High Similarity	NPC289968
0.9467	High Similarity	NPC161277
0.9467	High Similarity	NPC100971

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 NPC208197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	1003
0.2-0.3	1920
0.3-0.4	2688
0.4-0.5	1674
0.5-0.6	963
0.6-0.7	334
0.7-0.8	108
0.8-0.85	32
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD2801	Approved
0.9211	High Similarity	NPD1934	Approved
0.9189	High Similarity	NPD1511	Approved
0.9156	High Similarity	NPD3882	Suspended
0.9067	High Similarity	NPD1512	Approved
0.9026	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD3818	Discontinued
0.8968	High Similarity	NPD3817	Phase 2
0.8875	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6167	Clinical (unspecified phase)
0.8841	High Similarity	NPD4338	Clinical (unspecified phase)
0.8827	High Similarity	NPD7054	Approved
0.879	High Similarity	NPD4868	Clinical (unspecified phase)
0.8773	High Similarity	NPD7472	Approved
0.8659	High Similarity	NPD7074	Phase 3
0.8627	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD5494	Approved
0.8606	High Similarity	NPD6797	Phase 2
0.859	High Similarity	NPD4380	Phase 2
0.8554	High Similarity	NPD7251	Discontinued
0.8503	High Similarity	NPD7808	Phase 3
0.85	High Similarity	NPD4381	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5402	Approved
0.8428	Intermediate Similarity	NPD1465	Phase 2
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8387	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD6799	Approved
0.8289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD943	Approved
0.8255	Intermediate Similarity	NPD1240	Approved
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD1247	Approved
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD230	Phase 1
0.8075	Intermediate Similarity	NPD7411	Suspended
0.805	Intermediate Similarity	NPD5403	Approved
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7961	Intermediate Similarity	NPD447	Suspended
0.7937	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5401	Approved
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD3750	Approved
0.7892	Intermediate Similarity	NPD919	Approved
0.7888	Intermediate Similarity	NPD1653	Approved
0.7867	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2800	Approved
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD6190	Approved
0.7725	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7682	Intermediate Similarity	NPD9494	Approved
0.7679	Intermediate Similarity	NPD6234	Discontinued
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7613	Intermediate Similarity	NPD1933	Approved
0.761	Intermediate Similarity	NPD1243	Approved
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD920	Approved
0.7595	Intermediate Similarity	NPD2344	Approved
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.758	Intermediate Similarity	NPD3748	Approved
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7564	Intermediate Similarity	NPD6651	Approved
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD6099	Approved
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD9269	Phase 2
0.7456	Intermediate Similarity	NPD4967	Phase 2
0.7456	Intermediate Similarity	NPD4966	Approved
0.7456	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.7429	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7371	Intermediate Similarity	NPD7228	Approved
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5242	Approved
0.7294	Intermediate Similarity	NPD5353	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7237	Intermediate Similarity	NPD9717	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7212	Intermediate Similarity	NPD4357	Discontinued
0.72	Intermediate Similarity	NPD9268	Approved
0.7197	Intermediate Similarity	NPD3268	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7179	Intermediate Similarity	NPD4908	Phase 1
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7159	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7098	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2983	Phase 2
0.7078	Intermediate Similarity	NPD2982	Phase 2
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4363	Phase 3
0.7059	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD1610	Phase 2
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.705	Intermediate Similarity	NPD2899	Discontinued
0.7032	Intermediate Similarity	NPD3225	Approved
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7698	Approved
0.7031	Intermediate Similarity	NPD7697	Approved
0.7013	Intermediate Similarity	NPD1608	Approved
0.7013	Intermediate Similarity	NPD2981	Phase 2
0.7006	Intermediate Similarity	NPD2861	Phase 2
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD4288	Approved
0.6987	Remote Similarity	NPD1470	Approved
0.6981	Remote Similarity	NPD6798	Discontinued
0.6979	Remote Similarity	NPD6823	Phase 2
0.6974	Remote Similarity	NPD7701	Phase 2
0.697	Remote Similarity	NPD1652	Phase 2
0.6968	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD6535	Approved
0.6968	Remote Similarity	NPD4749	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7229	Phase 3
0.6931	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4361	Phase 2
0.6923	Remote Similarity	NPD7039	Approved
0.6923	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