NPASS Compound

Structure

CID184136 OpenBabel06191715562D 22 24 0 0 0 0 0 0 0 0999 V2000 6.9282 3.0000 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 4.3301 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 5.1962 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 0.0000 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 5.1962 3.0000 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 -0.8660 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 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 -0.8660 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 1.7321 -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 -1.7321 0.0000 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 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 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 8 2 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	3.296
LogD:	2.329
LogS:	-3.576
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	2.275
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.965
MDCK Permeability:	1.1232133147132117e-05
Pgp-inhibitor:	0.384
Pgp-substrate:	0.737
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.576
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	96.9150161743164%
Volume Distribution (VD):	0.536
Pgp-substrate:	8.762252807617188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.316
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.614
CYP2D6-substrate:	0.697
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	4.547
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.559
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.249
Skin Sensitization:	0.939
Carcinogencity:	0.23
Eye Corrosion:	0.004
Eye Irritation:	0.908
Respiratory Toxicity:	0.298

Download Data

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

Natural Product: NPC184136

Natural Product ID:	NPC184136
*Common Name:**	4'-O-Methylscutellarein
IUPAC Name:	5,6,7-trihydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	XVMMEYCPXZYLAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-9-4-2-8(3-5-9)12-6-10(17)14-13(22-12)7-11(18)15(19)16(14)20/h2-7,18-20H,1H3
SMILES:	COc1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3741397
PubChem CID:	11174076
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4462	Tripterygium doianum	Species	Celastraceae	Eukaryota	n.a.	branch	n.a.	PMID[12165306]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711347]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18771240]
NPO8662	Lantana fucata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19634889]
NPO4462	Tripterygium doianum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7362	Thalictrum omeiense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4462	Tripterygium doianum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2004, 65, 2071]
NPO4462	Tripterygium doianum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7362	Thalictrum omeiense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7362	Thalictrum omeiense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8662	Lantana fucata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4462	Tripterygium doianum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	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	1
Others	10

Activity Type	# Activity
NON-MOLECULAR	2
Others	5
Tissue	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	6.4	s	PMID[524064]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	24.98	s	PMID[524064]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	31.53	s	PMID[524064]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	Activity	=	5.67	g/L	PMID[524064]
NPT35	Others	n.a.		IC50	=	25290.0	nM	PMID[524064]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	89.38	%	PMID[524064]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	63.27	%	PMID[524064]
NPT35	Others	n.a.		Solubility	=	6.31	ug.mL-1	PMID[524064]
NPT35	Others	n.a.		LogP	=	1.646	n.a.	PMID[524064]
NPT35	Others	n.a.		LogP	=	1.409	n.a.	PMID[524064]
NPT35	Others	n.a.		LogP	=	0.7846	n.a.	PMID[524064]

☑ 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 NPC184136 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	500
0.1-0.2	2089
0.2-0.3	5278
0.3-0.4	11699
0.4-0.5	5304
0.5-0.6	4004
0.6-0.7	5103
0.7-0.8	4704
0.8-0.85	2089
0.85-0.9	1158
0.9-0.95	570
0.95-1	199

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC25270
0.9862	High Similarity	NPC275836
0.9862	High Similarity	NPC188203
0.9862	High Similarity	NPC212678
0.9862	High Similarity	NPC57030
0.9862	High Similarity	NPC120163
0.9862	High Similarity	NPC131624
0.9862	High Similarity	NPC198826
0.9862	High Similarity	NPC156222
0.9862	High Similarity	NPC241498
0.9862	High Similarity	NPC83508
0.9862	High Similarity	NPC71334
0.9862	High Similarity	NPC222830
0.9862	High Similarity	NPC301323
0.9862	High Similarity	NPC100887
0.9862	High Similarity	NPC239128
0.9862	High Similarity	NPC187498
0.9862	High Similarity	NPC162313
0.9862	High Similarity	NPC293183
0.9862	High Similarity	NPC256283
0.9862	High Similarity	NPC275722
0.9795	High Similarity	NPC47781
0.9795	High Similarity	NPC255350
0.9795	High Similarity	NPC22519
0.9795	High Similarity	NPC160951
0.9795	High Similarity	NPC69394
0.9795	High Similarity	NPC274327
0.9795	High Similarity	NPC183878
0.9795	High Similarity	NPC145379
0.9795	High Similarity	NPC231018
0.9795	High Similarity	NPC176775
0.979	High Similarity	NPC239312
0.979	High Similarity	NPC108406
0.979	High Similarity	NPC275772
0.979	High Similarity	NPC130230
0.9728	High Similarity	NPC213622
0.9728	High Similarity	NPC146165
0.9728	High Similarity	NPC20830
0.9728	High Similarity	NPC183597
0.9728	High Similarity	NPC4455
0.9728	High Similarity	NPC214138
0.9728	High Similarity	NPC196439
0.9728	High Similarity	NPC201136
0.9728	High Similarity	NPC167815
0.9728	High Similarity	NPC50715
0.9728	High Similarity	NPC2476
0.9728	High Similarity	NPC92659
0.9728	High Similarity	NPC138360
0.9728	High Similarity	NPC280339
0.9728	High Similarity	NPC128863
0.9728	High Similarity	NPC163780
0.9728	High Similarity	NPC201451
0.9728	High Similarity	NPC44079
0.9728	High Similarity	NPC256612
0.9728	High Similarity	NPC227325
0.9728	High Similarity	NPC26227
0.9726	High Similarity	NPC142540
0.9724	High Similarity	NPC62042
0.9724	High Similarity	NPC306821
0.9722	High Similarity	NPC12367
0.9722	High Similarity	NPC118726
0.9662	High Similarity	NPC247017
0.9662	High Similarity	NPC245546
0.9662	High Similarity	NPC49824
0.9662	High Similarity	NPC98661
0.9662	High Similarity	NPC43243
0.9662	High Similarity	NPC266960
0.966	High Similarity	NPC75279
0.966	High Similarity	NPC250822
0.966	High Similarity	NPC276409
0.9658	High Similarity	NPC226973
0.9658	High Similarity	NPC208043
0.9655	High Similarity	NPC17286
0.9655	High Similarity	NPC223579
0.9655	High Similarity	NPC259713
0.9655	High Similarity	NPC287101
0.9655	High Similarity	NPC216318
0.9655	High Similarity	NPC296197
0.9655	High Similarity	NPC183950
0.9655	High Similarity	NPC137062
0.9655	High Similarity	NPC87125
0.9655	High Similarity	NPC270465
0.9655	High Similarity	NPC52005
0.9655	High Similarity	NPC195351
0.9597	High Similarity	NPC101830
0.9597	High Similarity	NPC163524
0.9597	High Similarity	NPC176665
0.9597	High Similarity	NPC224137
0.9597	High Similarity	NPC287979
0.9597	High Similarity	NPC203891
0.9597	High Similarity	NPC189179
0.9597	High Similarity	NPC227192
0.9597	High Similarity	NPC470402
0.9597	High Similarity	NPC93376
0.9597	High Similarity	NPC110070
0.9597	High Similarity	NPC75215
0.9597	High Similarity	NPC305663
0.9595	High Similarity	NPC2928
0.9595	High Similarity	NPC208197
0.9592	High Similarity	NPC39732
0.9592	High Similarity	NPC199100
0.9592	High Similarity	NPC120537
0.9592	High Similarity	NPC180234
0.9592	High Similarity	NPC301123
0.9592	High Similarity	NPC60972
0.9589	High Similarity	NPC149127
0.9589	High Similarity	NPC77858
0.9589	High Similarity	NPC45873
0.9589	High Similarity	NPC188871
0.9589	High Similarity	NPC10467
0.9589	High Similarity	NPC286342
0.9586	High Similarity	NPC119059
0.9586	High Similarity	NPC276930
0.9586	High Similarity	NPC120464
0.958	High Similarity	NPC279121
0.9533	High Similarity	NPC115798
0.9533	High Similarity	NPC288669
0.9533	High Similarity	NPC152166
0.9533	High Similarity	NPC18607
0.9533	High Similarity	NPC19687
0.9533	High Similarity	NPC18772
0.9533	High Similarity	NPC7846
0.9533	High Similarity	NPC9609
0.9533	High Similarity	NPC143828
0.9533	High Similarity	NPC191459
0.9533	High Similarity	NPC4481
0.9533	High Similarity	NPC25495
0.9533	High Similarity	NPC176300
0.9533	High Similarity	NPC253634
0.9533	High Similarity	NPC130894
0.9533	High Similarity	NPC261004
0.9533	High Similarity	NPC105242
0.9533	High Similarity	NPC300943
0.9533	High Similarity	NPC22472
0.9533	High Similarity	NPC204854
0.953	High Similarity	NPC255106
0.953	High Similarity	NPC472916
0.953	High Similarity	NPC235165
0.953	High Similarity	NPC474520
0.953	High Similarity	NPC292107
0.9527	High Similarity	NPC271779
0.9527	High Similarity	NPC86485
0.9527	High Similarity	NPC167091
0.9527	High Similarity	NPC206238
0.9527	High Similarity	NPC88645
0.9527	High Similarity	NPC292214
0.9524	High Similarity	NPC125062
0.9524	High Similarity	NPC225731
0.9524	High Similarity	NPC252933
0.9524	High Similarity	NPC204515
0.9524	High Similarity	NPC117579
0.9524	High Similarity	NPC200740
0.9524	High Similarity	NPC260895
0.9524	High Similarity	NPC308451
0.9524	High Similarity	NPC54394
0.9521	High Similarity	NPC328119
0.9521	High Similarity	NPC48479
0.9521	High Similarity	NPC177298
0.9517	High Similarity	NPC61871
0.9517	High Similarity	NPC12200
0.9517	High Similarity	NPC55557
0.9517	High Similarity	NPC30647
0.9514	High Similarity	NPC70136
0.951	High Similarity	NPC175013
0.947	High Similarity	NPC476980
0.9467	High Similarity	NPC99597
0.9467	High Similarity	NPC162869
0.9467	High Similarity	NPC78302
0.9467	High Similarity	NPC156057
0.9467	High Similarity	NPC245758
0.9467	High Similarity	NPC472913
0.9467	High Similarity	NPC472911
0.9467	High Similarity	NPC474208
0.9467	High Similarity	NPC472438
0.9467	High Similarity	NPC235215
0.9467	High Similarity	NPC210084
0.9467	High Similarity	NPC474836
0.9467	High Similarity	NPC29841
0.9467	High Similarity	NPC472910
0.9467	High Similarity	NPC78225
0.9467	High Similarity	NPC7973
0.9467	High Similarity	NPC475267
0.9467	High Similarity	NPC48208
0.9467	High Similarity	NPC222814
0.9467	High Similarity	NPC96167
0.9467	High Similarity	NPC472914
0.9463	High Similarity	NPC32557
0.9463	High Similarity	NPC189960
0.9463	High Similarity	NPC113906
0.9459	High Similarity	NPC216769
0.9459	High Similarity	NPC209487
0.9459	High Similarity	NPC101996
0.9459	High Similarity	NPC269451
0.9459	High Similarity	NPC279989
0.9459	High Similarity	NPC39007
0.9459	High Similarity	NPC35763
0.9459	High Similarity	NPC55205
0.9459	High Similarity	NPC181209
0.9459	High Similarity	NPC121522
0.9459	High Similarity	NPC82325

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 NPC184136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1011
0.2-0.3	1848
0.3-0.4	2668
0.4-0.5	1701
0.5-0.6	968
0.6-0.7	331
0.7-0.8	99
0.8-0.85	38
0.85-0.9	11
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9795	High Similarity	NPD2801	Approved
0.958	High Similarity	NPD1511	Approved
0.9448	High Similarity	NPD1512	Approved
0.9329	High Similarity	NPD1934	Approved
0.9267	High Similarity	NPD2393	Clinical (unspecified phase)
0.902	High Similarity	NPD3882	Suspended
0.8859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8831	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD3818	Discontinued
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD4338	Clinical (unspecified phase)
0.8696	High Similarity	NPD7054	Approved
0.8642	High Similarity	NPD7472	Approved
0.8639	High Similarity	NPD1550	Clinical (unspecified phase)
0.8639	High Similarity	NPD1552	Clinical (unspecified phase)
0.863	High Similarity	NPD1510	Phase 2
0.8589	High Similarity	NPD6797	Phase 2
0.8581	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8528	High Similarity	NPD7074	Phase 3
0.8491	Intermediate Similarity	NPD5494	Approved
0.8483	Intermediate Similarity	NPD1240	Approved
0.8483	Intermediate Similarity	NPD943	Approved
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8446	Intermediate Similarity	NPD2796	Approved
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8367	Intermediate Similarity	NPD1607	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD6799	Approved
0.8272	Intermediate Similarity	NPD6232	Discontinued
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.821	Intermediate Similarity	NPD1247	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD230	Phase 1
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.805	Intermediate Similarity	NPD7411	Suspended
0.8039	Intermediate Similarity	NPD2800	Approved
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7933	Intermediate Similarity	NPD447	Suspended
0.7914	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD5401	Approved
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD919	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD2344	Approved
0.7785	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD3748	Approved
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2313	Discontinued
0.7702	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD1243	Approved
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3027	Phase 3
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD9494	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD1653	Approved
0.7635	Intermediate Similarity	NPD1203	Approved
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD2309	Approved
0.7595	Intermediate Similarity	NPD6190	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7551	Intermediate Similarity	NPD9269	Phase 2
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD6651	Approved
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD6844	Discontinued
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7432	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3268	Approved
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD3225	Approved
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD1608	Approved
0.7312	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2654	Approved
0.7246	Intermediate Similarity	NPD37	Approved
0.7239	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4965	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2
0.7213	Intermediate Similarity	NPD4360	Phase 2
0.7213	Intermediate Similarity	NPD4363	Phase 3
0.7209	Intermediate Similarity	NPD5710	Approved
0.7209	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD1481	Phase 2
0.719	Intermediate Similarity	NPD2861	Phase 2
0.7171	Intermediate Similarity	NPD3266	Approved
0.7171	Intermediate Similarity	NPD1470	Approved
0.7171	Intermediate Similarity	NPD3267	Approved
0.7168	Intermediate Similarity	NPD5242	Approved
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1201	Approved
0.7126	Intermediate Similarity	NPD2403	Approved
0.7114	Intermediate Similarity	NPD17	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.711	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD9545	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6385	Approved
0.7081	Intermediate Similarity	NPD4361	Phase 2
0.7081	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3018	Phase 2
0.7075	Intermediate Similarity	NPD9493	Approved
0.7073	Intermediate Similarity	NPD4357	Discontinued
0.707	Intermediate Similarity	NPD4307	Phase 2
0.7059	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7051	Intermediate Similarity	NPD3764	Approved
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7027	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD1471	Phase 3
0.7013	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD7435	Discontinued
0.6995	Remote Similarity	NPD4287	Approved
0.6988	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1241	Discontinued
0.6979	Remote Similarity	NPD7584	Approved
0.6978	Remote Similarity	NPD8150	Discontinued
0.6977	Remote Similarity	NPD6971	Discontinued
0.6974	Remote Similarity	NPD3972	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