NPASS Compound

Structure

CID2928 OpenBabel06191715322D 23 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 4.3301 -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 -2.5981 -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 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 4.3301 -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 -2.5981 -0.5000 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 0.0000 -2.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 -3.4641 0.0000 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 1.0000 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 22 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 10 2 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.627
LogD:	2.651
LogS:	-3.364
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.719
Fsp3:	0.118
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:	-4.858
MDCK Permeability:	1.4680904314445797e-05
Pgp-inhibitor:	0.168
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	99.1429214477539%
Volume Distribution (VD):	0.482
Pgp-substrate:	1.806063175201416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.663
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	12.218
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.883
Rat Oral Acute Toxicity:	0.871
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.936
Carcinogencity:	0.718
Eye Corrosion:	0.004
Eye Irritation:	0.918
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC2928

Natural Product ID:	NPC2928
*Common Name:**	XUSPHMFWFNGRPP-UXBLZVDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUSPHMFWFNGRPP-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-22-16-13(20)7-12(19)14-15(21)10(8-23-17(14)16)6-9-2-4-11(18)5-3-9/h2-7,18-20H,8H2,1H3/b10-6+
SMILES:	COc1c(cc(c2C(=O)/C(=C/c3ccc(cc3)O)/COc12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594093
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids

*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
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163588]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[25282892]
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]
NPO29250	Coprinus comatus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26338495]
NPO40241	Hyacinthaceae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30951308]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29125	Ulex europaeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29125	Ulex europaeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29250	Coprinus comatus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29481	Streptomyces reticuli	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29499	Chionodoxa luciliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29125	Ulex europaeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18245	Coprinellus micaceus	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29213	Bulbine narcissifolia	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29278	Sicyos angulatus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29534	Sarcomelicope leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29396	Bidens bipinnata	Species	Asteraceae	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
GI50	4
IC50	2
MIC	5

Activity Type	# Activity
Cell Line	4
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[503865]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[503865]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	>	100000.0	nM	PMID[503866]
NPT5265	Cell Line	Y79	Homo sapiens	GI50	>	100000.0	nM	PMID[503866]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	48.0	ug.mL-1	PMID[503865]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	24.0	ug.mL-1	PMID[503865]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	48.0	ug.mL-1	PMID[503865]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	48.0	ug.mL-1	PMID[503865]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	48.0	ug.mL-1	PMID[503865]
NPT2	Others	Unspecified		GI50	=	40000.0	nM	PMID[503866]
NPT2	Others	Unspecified		GI50	>	100000.0	nM	PMID[503866]

☑ 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 NPC2928 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	412
0.1-0.2	1765
0.2-0.3	4833
0.3-0.4	10904
0.4-0.5	6533
0.5-0.6	3484
0.6-0.7	4774
0.7-0.8	5366
0.8-0.85	2468
0.85-0.9	1424
0.9-0.95	643
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC472916
0.9866	High Similarity	NPC99597
0.9866	High Similarity	NPC210084
0.9799	High Similarity	NPC235165
0.9799	High Similarity	NPC255106
0.9797	High Similarity	NPC167091
0.9797	High Similarity	NPC206238
0.9797	High Similarity	NPC271779
0.9797	High Similarity	NPC472915
0.9797	High Similarity	NPC88645
0.9797	High Similarity	NPC292214
0.9796	High Similarity	NPC31363
0.9733	High Similarity	NPC472910
0.9733	High Similarity	NPC48208
0.9733	High Similarity	NPC474836
0.9733	High Similarity	NPC472914
0.9733	High Similarity	NPC474208
0.9733	High Similarity	NPC162869
0.9733	High Similarity	NPC222814
0.9733	High Similarity	NPC156057
0.9733	High Similarity	NPC96167
0.9733	High Similarity	NPC472911
0.9733	High Similarity	NPC475267
0.9733	High Similarity	NPC472913
0.9733	High Similarity	NPC245758
0.9732	High Similarity	NPC256612
0.9732	High Similarity	NPC213622
0.9732	High Similarity	NPC20830
0.973	High Similarity	NPC25270
0.973	High Similarity	NPC239128
0.973	High Similarity	NPC198826
0.973	High Similarity	NPC83508
0.973	High Similarity	NPC100887
0.973	High Similarity	NPC120163
0.973	High Similarity	NPC187498
0.973	High Similarity	NPC101996
0.973	High Similarity	NPC257648
0.973	High Similarity	NPC71334
0.973	High Similarity	NPC39007
0.973	High Similarity	NPC212678
0.973	High Similarity	NPC199100
0.973	High Similarity	NPC222830
0.973	High Similarity	NPC57030
0.973	High Similarity	NPC188203
0.973	High Similarity	NPC156222
0.973	High Similarity	NPC180234
0.973	High Similarity	NPC120537
0.973	High Similarity	NPC275722
0.973	High Similarity	NPC301323
0.973	High Similarity	NPC293183
0.973	High Similarity	NPC161277
0.973	High Similarity	NPC162313
0.973	High Similarity	NPC275836
0.973	High Similarity	NPC477231
0.973	High Similarity	NPC256283
0.973	High Similarity	NPC131624
0.973	High Similarity	NPC241498
0.9671	High Similarity	NPC308992
0.9664	High Similarity	NPC69394
0.9664	High Similarity	NPC183878
0.9664	High Similarity	NPC22519
0.9664	High Similarity	NPC255350
0.9664	High Similarity	NPC145379
0.9664	High Similarity	NPC176775
0.9664	High Similarity	NPC274327
0.9664	High Similarity	NPC231018
0.9664	High Similarity	NPC47781
0.9664	High Similarity	NPC160951
0.9662	High Similarity	NPC149614
0.9662	High Similarity	NPC171010
0.9662	High Similarity	NPC117579
0.9662	High Similarity	NPC251110
0.9605	High Similarity	NPC263449
0.9603	High Similarity	NPC36852
0.9603	High Similarity	NPC469584
0.9603	High Similarity	NPC470402
0.9603	High Similarity	NPC262286
0.9603	High Similarity	NPC299520
0.9603	High Similarity	NPC181960
0.9603	High Similarity	NPC129684
0.9603	High Similarity	NPC78225
0.96	High Similarity	NPC146165
0.96	High Similarity	NPC196439
0.96	High Similarity	NPC138360
0.96	High Similarity	NPC183597
0.96	High Similarity	NPC208197
0.96	High Similarity	NPC37392
0.96	High Similarity	NPC92659
0.96	High Similarity	NPC50715
0.96	High Similarity	NPC4455
0.96	High Similarity	NPC2476
0.96	High Similarity	NPC44079
0.96	High Similarity	NPC472909
0.96	High Similarity	NPC280339
0.96	High Similarity	NPC167815
0.96	High Similarity	NPC201136
0.96	High Similarity	NPC163780
0.96	High Similarity	NPC26227
0.96	High Similarity	NPC128863
0.96	High Similarity	NPC201451
0.96	High Similarity	NPC227325
0.9597	High Similarity	NPC209487
0.9597	High Similarity	NPC39732
0.9597	High Similarity	NPC269451
0.9597	High Similarity	NPC181209
0.9597	High Similarity	NPC216769
0.9597	High Similarity	NPC131266
0.9597	High Similarity	NPC236637
0.9597	High Similarity	NPC100971
0.9597	High Similarity	NPC35763
0.9597	High Similarity	NPC245382
0.9597	High Similarity	NPC219582
0.9597	High Similarity	NPC142540
0.9597	High Similarity	NPC60972
0.9597	High Similarity	NPC121522
0.9597	High Similarity	NPC100263
0.9597	High Similarity	NPC291802
0.9597	High Similarity	NPC302950
0.9595	High Similarity	NPC179183
0.9595	High Similarity	NPC61620
0.9595	High Similarity	NPC62042
0.9595	High Similarity	NPC184136
0.9595	High Similarity	NPC306821
0.9595	High Similarity	NPC248102
0.9595	High Similarity	NPC29231
0.9595	High Similarity	NPC45873
0.9542	High Similarity	NPC266314
0.9539	High Similarity	NPC55738
0.9539	High Similarity	NPC95936
0.9539	High Similarity	NPC152904
0.9539	High Similarity	NPC250214
0.9536	High Similarity	NPC138243
0.9536	High Similarity	NPC43243
0.9536	High Similarity	NPC245546
0.9536	High Similarity	NPC191146
0.9536	High Similarity	NPC49824
0.9536	High Similarity	NPC98661
0.9536	High Similarity	NPC266960
0.9536	High Similarity	NPC247017
0.9536	High Similarity	NPC68093
0.9536	High Similarity	NPC474638
0.9533	High Similarity	NPC124714
0.9533	High Similarity	NPC280937
0.9533	High Similarity	NPC250822
0.9533	High Similarity	NPC469550
0.9533	High Similarity	NPC276409
0.9533	High Similarity	NPC75279
0.9533	High Similarity	NPC18727
0.953	High Similarity	NPC208043
0.953	High Similarity	NPC204515
0.953	High Similarity	NPC45291
0.953	High Similarity	NPC19980
0.953	High Similarity	NPC308451
0.953	High Similarity	NPC226973
0.9527	High Similarity	NPC296197
0.9527	High Similarity	NPC92722
0.9527	High Similarity	NPC287101
0.9527	High Similarity	NPC17286
0.9527	High Similarity	NPC259713
0.9527	High Similarity	NPC52005
0.9527	High Similarity	NPC102003
0.9527	High Similarity	NPC137062
0.9527	High Similarity	NPC216318
0.9527	High Similarity	NPC200221
0.9527	High Similarity	NPC294502
0.9527	High Similarity	NPC223579
0.9527	High Similarity	NPC183950
0.9524	High Similarity	NPC95864
0.9481	High Similarity	NPC472448
0.9481	High Similarity	NPC83922
0.9477	High Similarity	NPC476980
0.9474	High Similarity	NPC67876
0.9474	High Similarity	NPC305663
0.9474	High Similarity	NPC52530
0.9474	High Similarity	NPC241904
0.9474	High Similarity	NPC287979
0.9474	High Similarity	NPC291508
0.9474	High Similarity	NPC227192
0.9474	High Similarity	NPC203891
0.9474	High Similarity	NPC223787
0.9474	High Similarity	NPC176665
0.9474	High Similarity	NPC101830
0.9474	High Similarity	NPC93376
0.9474	High Similarity	NPC75215
0.9474	High Similarity	NPC163524
0.9474	High Similarity	NPC300727
0.9474	High Similarity	NPC224137
0.9474	High Similarity	NPC189179
0.9474	High Similarity	NPC110070
0.947	High Similarity	NPC117992
0.947	High Similarity	NPC39184
0.947	High Similarity	NPC152951
0.947	High Similarity	NPC255807
0.947	High Similarity	NPC113906
0.947	High Similarity	NPC168247
0.947	High Similarity	NPC31018
0.947	High Similarity	NPC230149
0.947	High Similarity	NPC57674
0.9467	High Similarity	NPC301123
0.9467	High Similarity	NPC472912

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 NPC2928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	973
0.2-0.3	1845
0.3-0.4	2643
0.4-0.5	1690
0.5-0.6	993
0.6-0.7	443
0.7-0.8	132
0.8-0.85	34
0.85-0.9	11
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD2801	Approved
0.9597	High Similarity	NPD1934	Approved
0.9281	High Similarity	NPD3882	Suspended
0.9276	High Similarity	NPD2393	Clinical (unspecified phase)
0.9189	High Similarity	NPD1511	Approved
0.9067	High Similarity	NPD1512	Approved
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8882	High Similarity	NPD3818	Discontinued
0.8861	High Similarity	NPD5494	Approved
0.8846	High Similarity	NPD3817	Phase 2
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	NPD7074	Phase 3
0.8773	High Similarity	NPD7472	Approved
0.8725	High Similarity	NPD1549	Phase 2
0.8658	High Similarity	NPD1550	Clinical (unspecified phase)
0.8658	High Similarity	NPD1552	Clinical (unspecified phase)
0.8606	High Similarity	NPD6797	Phase 2
0.859	High Similarity	NPD4380	Phase 2
0.8554	High Similarity	NPD7251	Discontinued
0.8523	High Similarity	NPD1510	Phase 2
0.8506	High Similarity	NPD4378	Clinical (unspecified phase)
0.8503	High Similarity	NPD7808	Phase 3
0.85	High Similarity	NPD7075	Discontinued
0.85	High Similarity	NPD4381	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD1465	Phase 2
0.8378	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD943	Approved
0.8375	Intermediate Similarity	NPD5402	Approved
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD1247	Approved
0.8344	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD230	Phase 1
0.8187	Intermediate Similarity	NPD7411	Suspended
0.8153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6801	Discontinued
0.8133	Intermediate Similarity	NPD1613	Approved
0.8133	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8108	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD447	Suspended
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3926	Phase 2
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7939	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD5403	Approved
0.7925	Intermediate Similarity	NPD5401	Approved
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD9494	Approved
0.7898	Intermediate Similarity	NPD3750	Approved
0.7888	Intermediate Similarity	NPD1653	Approved
0.7882	Intermediate Similarity	NPD3751	Discontinued
0.787	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1933	Approved
0.7834	Intermediate Similarity	NPD2800	Approved
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3027	Phase 3
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6190	Approved
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD920	Approved
0.7707	Intermediate Similarity	NPD2344	Approved
0.7705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3748	Approved
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.755	Intermediate Similarity	NPD1203	Approved
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD6844	Discontinued
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD9269	Phase 2
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD1610	Phase 2
0.7399	Intermediate Similarity	NPD5242	Approved
0.7396	Intermediate Similarity	NPD5353	Approved
0.7381	Intermediate Similarity	NPD37	Approved
0.7371	Intermediate Similarity	NPD7228	Approved
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.736	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4965	Approved
0.7351	Intermediate Similarity	NPD9717	Approved
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6651	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7321	Intermediate Similarity	NPD6386	Approved
0.7321	Intermediate Similarity	NPD6385	Approved
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7261	Intermediate Similarity	NPD6233	Phase 2
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD5710	Approved
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7212	Intermediate Similarity	NPD4357	Discontinued
0.7212	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.72	Intermediate Similarity	NPD9268	Approved
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7197	Intermediate Similarity	NPD411	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7549	Discontinued
0.7166	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD7266	Discontinued
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7136	Intermediate Similarity	NPD2899	Discontinued
0.7133	Intermediate Similarity	NPD9545	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.7098	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7073	Intermediate Similarity	NPD2654	Approved
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD6535	Approved
0.7059	Intermediate Similarity	NPD6534	Approved
0.7052	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3225	Approved
0.7027	Intermediate Similarity	NPD1241	Discontinued
0.7027	Intermediate Similarity	NPD4287	Approved
0.7025	Intermediate Similarity	NPD4625	Phase 3
0.7024	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7038	Approved
0.7017	Intermediate Similarity	NPD7039	Approved
0.7013	Intermediate Similarity	NPD1481	Phase 2

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