NPASS Compound

Structure

CID295719 OpenBabel06191716102D 30 32 0 0 0 0 0 0 0 0999 V2000 -6.9282 1.0000 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 -2.5981 2.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -2.5981 -1.5000 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 1.5000 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 -0.8660 1.5000 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 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 6 1 0 0 0 0 5 15 2 0 0 0 0 6 17 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 21 2 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.18
Volume:	432.873
LogP:	5.761
LogD:	3.924
LogS:	-3.686
# Rotatable Bonds:	6
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	2.564
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.857
MDCK Permeability:	1.2655760656343773e-05
Pgp-inhibitor:	0.336
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.826
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.94934844970703%
Volume Distribution (VD):	0.743
Pgp-substrate:	1.403853178024292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.727
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.847
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.694
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	9.529
Half-life (T1/2):	0.496

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.65
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.572
Respiratory Toxicity:	0.199

Download Data

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

Natural Product: NPC295719

Natural Product ID:	NPC295719
*Common Name:**	Prenylterphenyllin
IUPAC Name:	2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-5-(4-hydroxyphenyl)-3,6-dimethoxyphenol
Synonyms:	Prenylterphenyllin
Standard InCHIKey:	YEVBMDOXFLFVJJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-15(2)5-6-17-13-18(9-12-21(17)27)23-22(29-3)14-20(25(30-4)24(23)28)16-7-10-19(26)11-8-16/h5,7-14,26-28H,6H2,1-4H3
SMILES:	CC(=CCc1cc(ccc1O)c1c(cc(c2ccc(cc2)O)c(c1O)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795464
PubChem CID:	23630784
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21486068]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	a root soil fungus isolated from the mangrove plant Acrostichum aureum	n.a.	n.a.	PMID[21486068]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	isolated from the root soil of the mangrove plant Acrostichum aureum	n.a.	n.a.	PMID[21486068]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21899268]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22906240]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13868	Gnaphalium oligandrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10556	Eria jarensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11828	Mucor hiemalis	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14357	Ixeris denticulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26896	Wulfenia orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12872	Taraxacum disseminatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22797	Fleroya stipulosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12686	Sideritis hirsuta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7010	Anthocleista procera	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14461	Vibrio fluvialis	Species	Vibrionaceae	Bacteria	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	5
Others	1

Activity Type	# Activity
Cell Line	4
Others	1
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2750.0	nM	PMID[572038]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1990.0	nM	PMID[572038]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3620.0	nM	PMID[572038]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2740.0	nM	PMID[572039]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	=	25700.0	nM	PMID[572039]
NPT2	Others	Unspecified		CC50	=	910.0	nM	PMID[572039]

☑ 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 NPC295719 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	487
0.1-0.2	1894
0.2-0.3	5383
0.3-0.4	12916
0.4-0.5	4579
0.5-0.6	3927
0.6-0.7	7088
0.7-0.8	5073
0.8-0.85	758
0.85-0.9	428
0.9-0.95	128
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC73505
1.0	High Similarity	NPC165026
1.0	High Similarity	NPC34431
0.9851	High Similarity	NPC175838
0.9848	High Similarity	NPC90615
0.9848	High Similarity	NPC272157
0.9848	High Similarity	NPC25111
0.9848	High Similarity	NPC201145
0.9848	High Similarity	NPC6262
0.9848	High Similarity	NPC73535
0.9773	High Similarity	NPC114155
0.9773	High Similarity	NPC476639
0.9773	High Similarity	NPC300846
0.9701	High Similarity	NPC12668
0.9701	High Similarity	NPC308768
0.9697	High Similarity	NPC261873
0.9697	High Similarity	NPC111655
0.9697	High Similarity	NPC283009
0.9627	High Similarity	NPC29868
0.9627	High Similarity	NPC105847
0.9627	High Similarity	NPC132804
0.9627	High Similarity	NPC220344
0.9627	High Similarity	NPC275061
0.9627	High Similarity	NPC212942
0.9627	High Similarity	NPC79622
0.9627	High Similarity	NPC243759
0.9627	High Similarity	NPC243996
0.9627	High Similarity	NPC218131
0.9621	High Similarity	NPC103967
0.9552	High Similarity	NPC242715
0.9552	High Similarity	NPC151656
0.9552	High Similarity	NPC266006
0.9552	High Similarity	NPC56329
0.9552	High Similarity	NPC230919
0.9552	High Similarity	NPC200935
0.9552	High Similarity	NPC266453
0.9552	High Similarity	NPC22902
0.9478	High Similarity	NPC205442
0.9478	High Similarity	NPC202846
0.9478	High Similarity	NPC30632
0.9478	High Similarity	NPC143139
0.947	High Similarity	NPC218884
0.9416	High Similarity	NPC183709
0.9403	High Similarity	NPC108198
0.9403	High Similarity	NPC10314
0.9403	High Similarity	NPC200557
0.9403	High Similarity	NPC241241
0.9403	High Similarity	NPC294884
0.9403	High Similarity	NPC158142
0.9403	High Similarity	NPC69029
0.9328	High Similarity	NPC125649
0.9328	High Similarity	NPC160697
0.9323	High Similarity	NPC6451
0.9318	High Similarity	NPC311680
0.9318	High Similarity	NPC234488
0.9318	High Similarity	NPC299221
0.9318	High Similarity	NPC51840
0.9259	High Similarity	NPC313081
0.9259	High Similarity	NPC256262
0.9248	High Similarity	NPC12275
0.9248	High Similarity	NPC45715
0.9248	High Similarity	NPC474356
0.9248	High Similarity	NPC232275
0.9242	High Similarity	NPC58164
0.9242	High Similarity	NPC10225
0.9197	High Similarity	NPC184613
0.9179	High Similarity	NPC228843
0.9173	High Similarity	NPC224157
0.9173	High Similarity	NPC192687
0.9167	High Similarity	NPC28765
0.9167	High Similarity	NPC154866
0.9167	High Similarity	NPC266691
0.9149	High Similarity	NPC126291
0.913	High Similarity	NPC259519
0.913	High Similarity	NPC20520
0.913	High Similarity	NPC61783
0.9104	High Similarity	NPC149337
0.9104	High Similarity	NPC471983
0.9098	High Similarity	NPC190144
0.9091	High Similarity	NPC324112
0.9091	High Similarity	NPC236791
0.9091	High Similarity	NPC124452
0.9091	High Similarity	NPC21563
0.9091	High Similarity	NPC252131
0.9091	High Similarity	NPC159968
0.9091	High Similarity	NPC74817
0.9091	High Similarity	NPC266555
0.9091	High Similarity	NPC236760
0.9091	High Similarity	NPC82679
0.9091	High Similarity	NPC293054
0.9091	High Similarity	NPC246620
0.9091	High Similarity	NPC282000
0.9091	High Similarity	NPC169474
0.9085	High Similarity	NPC275125
0.9085	High Similarity	NPC262297
0.9085	High Similarity	NPC170239
0.9085	High Similarity	NPC97937
0.9065	High Similarity	NPC472089
0.9058	High Similarity	NPC260741
0.9058	High Similarity	NPC319647
0.9058	High Similarity	NPC114171
0.9058	High Similarity	NPC25966
0.9058	High Similarity	NPC230124
0.9058	High Similarity	NPC127218
0.9058	High Similarity	NPC70682
0.9058	High Similarity	NPC6300
0.9058	High Similarity	NPC245207
0.9044	High Similarity	NPC209199
0.9037	High Similarity	NPC14224
0.9037	High Similarity	NPC161958
0.903	High Similarity	NPC126836
0.9015	High Similarity	NPC223136
0.9015	High Similarity	NPC78974
0.9015	High Similarity	NPC223953
0.9015	High Similarity	NPC28730
0.9015	High Similarity	NPC18924
0.9015	High Similarity	NPC103823
0.9015	High Similarity	NPC214406
0.9015	High Similarity	NPC44748
0.9007	High Similarity	NPC280092
0.9007	High Similarity	NPC45257
0.9007	High Similarity	NPC50250
0.9007	High Similarity	NPC12641
0.9007	High Similarity	NPC93323
0.9	High Similarity	NPC472088
0.9	High Similarity	NPC472087
0.9	High Similarity	NPC470917
0.8993	High Similarity	NPC266650
0.8986	High Similarity	NPC474282
0.8986	High Similarity	NPC326797
0.8986	High Similarity	NPC102904
0.8986	High Similarity	NPC176051
0.8986	High Similarity	NPC107551
0.8986	High Similarity	NPC276490
0.8986	High Similarity	NPC103976
0.8978	High Similarity	NPC281521
0.8978	High Similarity	NPC201357
0.8978	High Similarity	NPC255147
0.8971	High Similarity	NPC32778
0.8963	High Similarity	NPC15543
0.8958	High Similarity	NPC113790
0.8947	High Similarity	NPC127587
0.8944	High Similarity	NPC125617
0.8939	High Similarity	NPC221077
0.8939	High Similarity	NPC17943
0.8939	High Similarity	NPC208950
0.8939	High Similarity	NPC299584
0.8939	High Similarity	NPC475169
0.8939	High Similarity	NPC82483
0.8939	High Similarity	NPC116907
0.8939	High Similarity	NPC234400
0.8939	High Similarity	NPC60885
0.8939	High Similarity	NPC105925
0.8939	High Similarity	NPC193544
0.8939	High Similarity	NPC233410
0.8939	High Similarity	NPC298757
0.8939	High Similarity	NPC57490
0.8939	High Similarity	NPC117214
0.8939	High Similarity	NPC251855
0.8939	High Similarity	NPC203133
0.8939	High Similarity	NPC265483
0.8939	High Similarity	NPC472093
0.8936	High Similarity	NPC85264
0.8936	High Similarity	NPC102044
0.8936	High Similarity	NPC47633
0.8936	High Similarity	NPC477616
0.8936	High Similarity	NPC469630
0.8929	High Similarity	NPC35216
0.8929	High Similarity	NPC19158
0.8929	High Similarity	NPC471389
0.8929	High Similarity	NPC265075
0.8921	High Similarity	NPC22517
0.8913	High Similarity	NPC162659
0.8913	High Similarity	NPC173660
0.8913	High Similarity	NPC472336
0.8913	High Similarity	NPC270456
0.8913	High Similarity	NPC265433
0.8913	High Similarity	NPC248727
0.8913	High Similarity	NPC472334
0.8905	High Similarity	NPC206737
0.8905	High Similarity	NPC56764
0.8905	High Similarity	NPC469659
0.8905	High Similarity	NPC106215
0.8905	High Similarity	NPC289258
0.8905	High Similarity	NPC276026
0.8905	High Similarity	NPC188378
0.8905	High Similarity	NPC7515
0.8905	High Similarity	NPC555
0.8897	High Similarity	NPC127624
0.8897	High Similarity	NPC86655
0.8897	High Similarity	NPC202762
0.8889	High Similarity	NPC143483
0.8889	High Similarity	NPC214860
0.8881	High Similarity	NPC23012
0.8881	High Similarity	NPC38017
0.8881	High Similarity	NPC112251
0.8881	High Similarity	NPC260397
0.8881	High Similarity	NPC215300
0.8881	High Similarity	NPC233980
0.8881	High Similarity	NPC472968

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 NPC295719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	975
0.2-0.3	1799
0.3-0.4	2818
0.4-0.5	1578
0.5-0.6	881
0.6-0.7	569
0.7-0.8	102
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD3027	Phase 3
0.8603	High Similarity	NPD1529	Clinical (unspecified phase)
0.8529	High Similarity	NPD1530	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD4625	Phase 3
0.8201	Intermediate Similarity	NPD4908	Phase 1
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD2801	Approved
0.7848	Intermediate Similarity	NPD6234	Discontinued
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.7842	Intermediate Similarity	NPD4749	Approved
0.7826	Intermediate Similarity	NPD1610	Phase 2
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7803	Intermediate Similarity	NPD228	Approved
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7756	Intermediate Similarity	NPD37	Approved
0.7756	Intermediate Similarity	NPD1934	Approved
0.7746	Intermediate Similarity	NPD2861	Phase 2
0.7724	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3620	Phase 2
0.7708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6674	Discontinued
0.7667	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1548	Phase 1
0.7613	Intermediate Similarity	NPD1653	Approved
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4965	Approved
0.761	Intermediate Similarity	NPD4966	Approved
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7589	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7515	Intermediate Similarity	NPD7228	Approved
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7468	Intermediate Similarity	NPD1511	Approved
0.7423	Intermediate Similarity	NPD7199	Phase 2
0.7417	Intermediate Similarity	NPD3540	Phase 1
0.7413	Intermediate Similarity	NPD6696	Suspended
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7388	Intermediate Similarity	NPD4750	Phase 3
0.7383	Intermediate Similarity	NPD4097	Suspended
0.7372	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5494	Approved
0.7353	Intermediate Similarity	NPD7635	Approved
0.7351	Intermediate Similarity	NPD2935	Discontinued
0.7351	Intermediate Similarity	NPD3539	Phase 1
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6671	Approved
0.7317	Intermediate Similarity	NPD6959	Discontinued
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4626	Approved
0.7296	Intermediate Similarity	NPD4380	Phase 2
0.7294	Intermediate Similarity	NPD7549	Discontinued
0.7292	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7248	Intermediate Similarity	NPD1558	Phase 1
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2342	Discontinued
0.7237	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7233	Intermediate Similarity	NPD4005	Discontinued
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8053	Approved
0.7209	Intermediate Similarity	NPD8054	Approved
0.7203	Intermediate Similarity	NPD3705	Approved
0.7203	Intermediate Similarity	NPD1611	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD7447	Phase 1
0.719	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD1607	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7134	Intermediate Similarity	NPD7213	Phase 3
0.7134	Intermediate Similarity	NPD7212	Phase 2
0.7134	Intermediate Similarity	NPD4055	Discovery
0.7134	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7118	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1651	Approved
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4538	Approved
0.7097	Intermediate Similarity	NPD5177	Phase 3
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7081	Intermediate Similarity	NPD4678	Approved
0.7081	Intermediate Similarity	NPD4675	Approved
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6584	Phase 3
0.7069	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6233	Phase 2
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD5929	Approved
0.705	Intermediate Similarity	NPD1398	Phase 1
0.7048	Intermediate Similarity	NPD6746	Phase 2
0.7047	Intermediate Similarity	NPD7095	Approved
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7035	Intermediate Similarity	NPD7240	Approved
0.703	Intermediate Similarity	NPD7075	Discontinued
0.7025	Intermediate Similarity	NPD7041	Phase 2
0.7025	Intermediate Similarity	NPD7390	Discontinued
0.7025	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7340	Approved
0.702	Intermediate Similarity	NPD1240	Approved
0.7019	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.7007	Intermediate Similarity	NPD5451	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD5691	Approved
0.6993	Remote Similarity	NPD6111	Discontinued
0.6989	Remote Similarity	NPD7906	Approved
0.6987	Remote Similarity	NPD3060	Approved
0.6981	Remote Similarity	NPD2532	Approved
0.6981	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2533	Approved
0.6981	Remote Similarity	NPD2534	Approved
0.6977	Remote Similarity	NPD6797	Phase 2
0.6974	Remote Similarity	NPD5735	Approved
0.6974	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3657	Discovery
0.6974	Remote Similarity	NPD5124	Phase 1
0.697	Remote Similarity	NPD6788	Approved
0.6966	Remote Similarity	NPD1091	Approved
0.6959	Remote Similarity	NPD4624	Approved
0.6954	Remote Similarity	NPD2674	Phase 3
0.6951	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8455	Phase 2
0.6951	Remote Similarity	NPD7819	Suspended
0.695	Remote Similarity	NPD7157	Approved
0.6948	Remote Similarity	NPD5588	Approved
0.6948	Remote Similarity	NPD5960	Phase 3
0.6944	Remote Similarity	NPD5846	Approved
0.6944	Remote Similarity	NPD6516	Phase 2
0.6943	Remote Similarity	NPD6331	Phase 2
0.6943	Remote Similarity	NPD3750	Approved
0.6943	Remote Similarity	NPD7003	Approved
0.6936	Remote Similarity	NPD7251	Discontinued
0.6934	Remote Similarity	NPD2684	Approved
0.6933	Remote Similarity	NPD7411	Suspended
0.6932	Remote Similarity	NPD4663	Approved
0.6912	Remote Similarity	NPD968	Approved
0.6908	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD943	Approved
0.6908	Remote Similarity	NPD2238	Phase 2
0.6905	Remote Similarity	NPD1247	Approved
0.6897	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7808	Phase 3
0.6887	Remote Similarity	NPD5110	Phase 2
0.6887	Remote Similarity	NPD5109	Approved
0.6887	Remote Similarity	NPD5111	Phase 2
0.6882	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1652	Phase 2
0.6879	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1357	Approved
0.6871	Remote Similarity	NPD6582	Phase 2
0.6871	Remote Similarity	NPD6599	Discontinued
0.6871	Remote Similarity	NPD6583	Phase 3
0.6871	Remote Similarity	NPD1669	Approved
0.6867	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3787	Discontinued
0.6863	Remote Similarity	NPD230	Phase 1
0.6859	Remote Similarity	NPD5762	Approved
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5763	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