NPASS Compound

Structure

CID65005 OpenBabel06191715402D 25 26 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 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 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 0.8660 -1.5000 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 -3.4641 -1.0000 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 -6.9282 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 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 -5.1962 -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 -6.0622 -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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 19 2 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	357.586
LogP:	4.175
LogD:	3.085
LogS:	-3.568
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	2.666
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.023
MDCK Permeability:	1.438087838323554e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.622
30% Bioavailability (F30%):	0.601

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	100.12644958496094%
Volume Distribution (VD):	0.57
Pgp-substrate:	1.1684907674789429%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.698
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.667
CYP2D6-inhibitor:	0.866
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	16.117
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.478
AMES Toxicity:	0.728
Rat Oral Acute Toxicity:	0.553
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.962
Carcinogencity:	0.431
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.564

Download Data

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

Natural Product: NPC65005

Natural Product ID:	NPC65005
*Common Name:**	5'-Prenylbutein
IUPAC Name:	(E)-3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
Synonyms:	5'-Prenylbutein
Standard InCHIKey:	XHTOWVVXFDSBGH-XBXARRHUSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-12(2)3-5-14-9-13(10-19(24)20(14)25)4-8-17(22)16-7-6-15(21)11-18(16)23/h3-4,6-11,21,23-25H,5H2,1-2H3/b8-4+
SMILES:	CC(=CCc1cc(/C=C/C(=O)c2ccc(cc2O)O)cc(c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253677
PubChem CID:	11267805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[12828487]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17517504]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Barks	n.a.	n.a.	PMID[18302333]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20934335]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022281]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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	11
Ki	1

Activity Type	# Activity
Individual Protein	7
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	21.93	ug.mL-1	PMID[557960]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Ki	=	22.71	ug ml-1	PMID[557960]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	20.47	ug.mL-1	PMID[557960]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	3.15	ug.mL-1	PMID[557961]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	25.87	ug.mL-1	PMID[557961]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	32.78	ug.mL-1	PMID[557961]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	35.5	ug.mL-1	PMID[557961]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10300.0	nM	PMID[557957]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10300.0	nM	PMID[557958]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10300.0	nM	PMID[557959]

☑ 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 NPC65005 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	364
0.1-0.2	1577
0.2-0.3	4054
0.3-0.4	11563
0.4-0.5	7090
0.5-0.6	4523
0.6-0.7	5885
0.7-0.8	6025
0.8-0.85	1321
0.85-0.9	245
0.9-0.95	41
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC264112
1.0	High Similarity	NPC194764
0.9621	High Similarity	NPC290030
0.9538	High Similarity	NPC135801
0.9535	High Similarity	NPC244441
0.9535	High Similarity	NPC233056
0.9535	High Similarity	NPC26697
0.9478	High Similarity	NPC472903
0.9462	High Similarity	NPC34070
0.9462	High Similarity	NPC469526
0.9338	High Similarity	NPC472904
0.9308	High Similarity	NPC474998
0.9302	High Similarity	NPC103356
0.9302	High Similarity	NPC98254
0.9302	High Similarity	NPC169250
0.9302	High Similarity	NPC266689
0.9302	High Similarity	NPC162612
0.9302	High Similarity	NPC72158
0.9302	High Similarity	NPC190043
0.9302	High Similarity	NPC105157
0.9302	High Similarity	NPC30501
0.9302	High Similarity	NPC100067
0.9302	High Similarity	NPC23126
0.9248	High Similarity	NPC282780
0.9248	High Similarity	NPC166480
0.9231	High Similarity	NPC21305
0.9231	High Similarity	NPC473017
0.9231	High Similarity	NPC221777
0.9225	High Similarity	NPC267846
0.9225	High Similarity	NPC62952
0.9154	High Similarity	NPC107672
0.9154	High Similarity	NPC116513
0.9124	High Similarity	NPC203063
0.9118	High Similarity	NPC175552
0.9085	High Similarity	NPC171916
0.9085	High Similarity	NPC38545
0.9077	High Similarity	NPC8745
0.907	High Similarity	NPC13238
0.9065	High Similarity	NPC471417
0.903	High Similarity	NPC40524
0.903	High Similarity	NPC139074
0.903	High Similarity	NPC213485
0.9023	High Similarity	NPC475042
0.9021	High Similarity	NPC472279
0.9015	High Similarity	NPC109123
0.9015	High Similarity	NPC92624
0.9014	High Similarity	NPC166036
0.9014	High Similarity	NPC238279
0.9014	High Similarity	NPC203077
0.9	High Similarity	NPC10926
0.9	High Similarity	NPC105213
0.8993	High Similarity	NPC284556
0.8993	High Similarity	NPC301178
0.8971	High Similarity	NPC223836
0.8958	High Similarity	NPC154345
0.8958	High Similarity	NPC35
0.8958	High Similarity	NPC256406
0.8947	High Similarity	NPC259942
0.8936	High Similarity	NPC157133
0.8929	High Similarity	NPC287722
0.8929	High Similarity	NPC254659
0.8929	High Similarity	NPC238629
0.8915	High Similarity	NPC91105
0.8915	High Similarity	NPC32032
0.8915	High Similarity	NPC133909
0.8915	High Similarity	NPC309765
0.8913	High Similarity	NPC138099
0.8913	High Similarity	NPC242994
0.8905	High Similarity	NPC170742
0.8897	High Similarity	NPC237994
0.8897	High Similarity	NPC70859
0.8897	High Similarity	NPC283590
0.8897	High Similarity	NPC130899
0.8897	High Similarity	NPC323626
0.8897	High Similarity	NPC61153
0.8897	High Similarity	NPC324233
0.8889	High Similarity	NPC88804
0.8889	High Similarity	NPC3825
0.8872	High Similarity	NPC476119
0.8865	High Similarity	NPC142165
0.8857	High Similarity	NPC291078
0.8855	High Similarity	NPC475733
0.8849	High Similarity	NPC181560
0.8849	High Similarity	NPC169452
0.8846	High Similarity	NPC472029
0.8846	High Similarity	NPC65761
0.8841	High Similarity	NPC416
0.8841	High Similarity	NPC123714
0.8841	High Similarity	NPC61398
0.8837	High Similarity	NPC115159
0.8837	High Similarity	NPC242895
0.8837	High Similarity	NPC156139
0.8837	High Similarity	NPC196976
0.8837	High Similarity	NPC267552
0.8837	High Similarity	NPC45438
0.8837	High Similarity	NPC303737
0.8837	High Similarity	NPC224273
0.8837	High Similarity	NPC73532
0.8837	High Similarity	NPC143427
0.8837	High Similarity	NPC19174
0.8837	High Similarity	NPC215392
0.8836	High Similarity	NPC70433
0.8836	High Similarity	NPC49402
0.8836	High Similarity	NPC273462
0.8836	High Similarity	NPC189130
0.8836	High Similarity	NPC33051
0.8836	High Similarity	NPC227337
0.8832	High Similarity	NPC118919
0.8832	High Similarity	NPC191976
0.8828	High Similarity	NPC227485
0.8815	High Similarity	NPC175738
0.8794	High Similarity	NPC119663
0.8776	High Similarity	NPC472280
0.8776	High Similarity	NPC57674
0.8776	High Similarity	NPC234255
0.8776	High Similarity	NPC152951
0.8776	High Similarity	NPC230149
0.8776	High Similarity	NPC117992
0.8776	High Similarity	NPC168247
0.8768	High Similarity	NPC53414
0.8768	High Similarity	NPC471905
0.8768	High Similarity	NPC53206
0.8767	High Similarity	NPC37684
0.8767	High Similarity	NPC63187
0.8767	High Similarity	NPC157784
0.876	High Similarity	NPC297186
0.876	High Similarity	NPC248363
0.876	High Similarity	NPC149246
0.8759	High Similarity	NPC85131
0.8759	High Similarity	NPC470210
0.875	High Similarity	NPC80710
0.875	High Similarity	NPC203747
0.875	High Similarity	NPC254702
0.875	High Similarity	NPC194653
0.875	High Similarity	NPC139364
0.875	High Similarity	NPC267205
0.8741	High Similarity	NPC275504
0.8732	High Similarity	NPC242893
0.8732	High Similarity	NPC207732
0.8732	High Similarity	NPC38065
0.8723	High Similarity	NPC193555
0.8722	High Similarity	NPC156539
0.8716	High Similarity	NPC282307
0.8716	High Similarity	NPC170026
0.8716	High Similarity	NPC472455
0.8712	High Similarity	NPC477454
0.8707	High Similarity	NPC213896
0.8707	High Similarity	NPC192083
0.8707	High Similarity	NPC170492
0.8707	High Similarity	NPC93552
0.8699	High Similarity	NPC304295
0.8699	High Similarity	NPC205046
0.8699	High Similarity	NPC59162
0.8696	High Similarity	NPC131039
0.8696	High Similarity	NPC254847
0.869	High Similarity	NPC102003
0.869	High Similarity	NPC264289
0.869	High Similarity	NPC92722
0.869	High Similarity	NPC333691
0.869	High Similarity	NPC200060
0.869	High Similarity	NPC69430
0.869	High Similarity	NPC195763
0.869	High Similarity	NPC264550
0.869	High Similarity	NPC40290
0.869	High Similarity	NPC139293
0.869	High Similarity	NPC142876
0.8686	High Similarity	NPC475088
0.8686	High Similarity	NPC44437
0.8682	High Similarity	NPC159525
0.8658	High Similarity	NPC218313
0.8658	High Similarity	NPC161960
0.8658	High Similarity	NPC222689
0.8658	High Similarity	NPC474681
0.8658	High Similarity	NPC304008
0.8658	High Similarity	NPC291508
0.8658	High Similarity	NPC187745
0.8658	High Similarity	NPC35598
0.8652	High Similarity	NPC110419
0.8649	High Similarity	NPC39184
0.8649	High Similarity	NPC321779
0.8649	High Similarity	NPC133392
0.8649	High Similarity	NPC113906
0.8649	High Similarity	NPC134287
0.8649	High Similarity	NPC256925
0.8649	High Similarity	NPC130589
0.8647	High Similarity	NPC473691
0.8643	High Similarity	NPC21350
0.8639	High Similarity	NPC471982
0.8639	High Similarity	NPC249570
0.8639	High Similarity	NPC106976
0.8633	High Similarity	NPC44960
0.8633	High Similarity	NPC472364
0.8633	High Similarity	NPC1486
0.8633	High Similarity	NPC168105
0.8633	High Similarity	NPC150399
0.8633	High Similarity	NPC474110
0.8633	High Similarity	NPC186838
0.8633	High Similarity	NPC41461
0.8633	High Similarity	NPC25287
0.8633	High Similarity	NPC477244

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 NPC65005 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	968
0.2-0.3	1539
0.3-0.4	2866
0.4-0.5	1940
0.5-0.6	1035
0.6-0.7	352
0.7-0.8	104
0.8-0.85	13
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9538	High Similarity	NPD943	Approved
0.8707	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD651	Clinical (unspecified phase)
0.8696	High Similarity	NPD1509	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1511	Approved
0.8389	Intermediate Similarity	NPD1934	Approved
0.8356	Intermediate Similarity	NPD1512	Approved
0.8345	Intermediate Similarity	NPD7390	Discontinued
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD2801	Approved
0.8273	Intermediate Similarity	NPD1240	Approved
0.8209	Intermediate Similarity	NPD9269	Phase 2
0.8169	Intermediate Similarity	NPD1510	Phase 2
0.8163	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8041	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1470	Approved
0.8	Intermediate Similarity	NPD1201	Approved
0.7986	Intermediate Similarity	NPD5404	Approved
0.7986	Intermediate Similarity	NPD5408	Approved
0.7986	Intermediate Similarity	NPD5405	Approved
0.7986	Intermediate Similarity	NPD5406	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6232	Discontinued
0.7958	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD7075	Discontinued
0.7925	Intermediate Similarity	NPD7473	Discontinued
0.7919	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD9268	Approved
0.7899	Intermediate Similarity	NPD1164	Approved
0.7877	Intermediate Similarity	NPD1549	Phase 2
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7808	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2796	Approved
0.7733	Intermediate Similarity	NPD6799	Approved
0.7727	Intermediate Similarity	NPD7411	Suspended
0.7722	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6801	Discontinued
0.7669	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7595	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7251	Discontinued
0.7557	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD3021	Approved
0.7556	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6599	Discontinued
0.7534	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2800	Approved
0.7453	Intermediate Similarity	NPD6959	Discontinued
0.7451	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD2532	Approved
0.7438	Intermediate Similarity	NPD919	Approved
0.7434	Intermediate Similarity	NPD3300	Phase 2
0.7432	Intermediate Similarity	NPD2799	Discontinued
0.7425	Intermediate Similarity	NPD7808	Phase 3
0.7425	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7768	Phase 2
0.7417	Intermediate Similarity	NPD3750	Approved
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6190	Approved
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7362	Intermediate Similarity	NPD3926	Phase 2
0.7351	Intermediate Similarity	NPD1243	Approved
0.7351	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD74	Approved
0.7348	Intermediate Similarity	NPD9266	Approved
0.7346	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD2344	Approved
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9493	Approved
0.7292	Intermediate Similarity	NPD9494	Approved
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7273	Intermediate Similarity	NPD9263	Approved
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9264	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD3749	Approved
0.7241	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD447	Suspended
0.7222	Intermediate Similarity	NPD2798	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7202	Intermediate Similarity	NPD5953	Discontinued
0.719	Intermediate Similarity	NPD8166	Discontinued
0.7172	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4750	Phase 3
0.7153	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD920	Approved
0.7134	Intermediate Similarity	NPD5403	Approved
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2932	Approved
0.7092	Intermediate Similarity	NPD3019	Approved
0.7086	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD7286	Phase 2
0.7083	Intermediate Similarity	NPD6020	Phase 2
0.7078	Intermediate Similarity	NPD4628	Phase 3
0.7071	Intermediate Similarity	NPD9545	Approved
0.7069	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1613	Approved
0.7047	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6099	Approved
0.7039	Intermediate Similarity	NPD6100	Approved
0.7029	Intermediate Similarity	NPD9281	Approved
0.7027	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5401	Approved
0.697	Remote Similarity	NPD9261	Approved
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8150	Discontinued
0.6944	Remote Similarity	NPD9717	Approved
0.6944	Remote Similarity	NPD3972	Approved
0.6937	Remote Similarity	NPD3455	Phase 2
0.6937	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD6234	Discontinued
0.6903	Remote Similarity	NPD2654	Approved
0.6899	Remote Similarity	NPD2860	Approved
0.6899	Remote Similarity	NPD2859	Approved
0.6893	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6832	Phase 2
0.6887	Remote Similarity	NPD1933	Approved
0.6886	Remote Similarity	NPD5710	Approved
0.6886	Remote Similarity	NPD5711	Approved
0.6883	Remote Similarity	NPD7266	Discontinued
0.6879	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD257	Approved
0.6871	Remote Similarity	NPD258	Approved
0.687	Remote Similarity	NPD3020	Approved
0.6863	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7199	Phase 2
0.6822	Remote Similarity	NPD2934	Approved
0.6822	Remote Similarity	NPD2933	Approved
0.681	Remote Similarity	NPD37	Approved
0.68	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.68	Remote Similarity	NPD411	Approved
0.68	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4308	Phase 3
0.6752	Remote Similarity	NPD7003	Approved
0.6752	Remote Similarity	NPD3400	Discontinued
0.6746	Remote Similarity	NPD5242	Approved
0.6746	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.674	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4625	Phase 3
0.673	Remote Similarity	NPD4357	Discontinued
0.6722	Remote Similarity	NPD6534	Approved
0.6722	Remote Similarity	NPD6535	Approved
0.6716	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1929	Approved
0.6716	Remote Similarity	NPD1930	Approved
0.6715	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1608	Approved
0.6711	Remote Similarity	NPD826	Approved
0.6711	Remote Similarity	NPD825	Approved
0.6711	Remote Similarity	NPD3018	Phase 2
0.671	Remote Similarity	NPD9570	Approved
0.669	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD3026	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD3024	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