NPASS Compound

Structure

CID253616 OpenBabel06191716052D 21 22 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 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 2.5981 1.5000 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 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 14 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	293.675
LogP:	2.293
LogD:	2.309
LogS:	-4.402
# Rotatable Bonds:	4
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	2.58
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	2.5149805878754705e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	74.96562957763672%
Volume Distribution (VD):	1.043
Pgp-substrate:	12.75308895111084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.571

ADMET: Excretion

Clearance (CL):	11.408
Half-life (T1/2):	0.678

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.747
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.531
Skin Sensitization:	0.518
Carcinogencity:	0.809
Eye Corrosion:	0.022
Eye Irritation:	0.543
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC253616

Natural Product ID:	NPC253616
*Common Name:**	5,7-Dimethoxy-8-(3-Methylbut-2-Enoyl)Chromen-2-One
IUPAC Name:	5,7-dimethoxy-8-(3-methylbut-2-enoyl)chromen-2-one
Synonyms:
Standard InCHIKey:	JEDBBFHVVHKMKS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-9(2)7-11(17)15-13(20-4)8-12(19-3)10-5-6-14(18)21-16(10)15/h5-8H,1-4H3
SMILES:	COc1cc(OC)c2c(c1C(=O)C=C(C)C)oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1399436
PubChem CID:	616303
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28681	Angelica glabra	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28681	Angelica glabra	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28681	Angelica glabra	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	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
Potency	17

Activity Type	# Activity
Cell Line	1
Individual Protein	10
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	11220.2	nM	PMID[465790]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	22387.2	nM	PMID[465790]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	63095.7	nM	PMID[465790]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[465790]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[465790]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[465790]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[465790]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[465790]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[465790]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[465790]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[465790]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	20786.5	nM	PMID[465790]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[465790]
NPT2	Others	Unspecified		Potency	n.a.	18356.4	nM	PMID[465790]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[465790]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[465790]

☑ 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 NPC253616 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	421
0.1-0.2	1926
0.2-0.3	5232
0.3-0.4	11256
0.4-0.5	6330
0.5-0.6	4761
0.6-0.7	5932
0.7-0.8	4537
0.8-0.85	1423
0.85-0.9	654
0.9-0.95	199
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC268081
0.9774	High Similarity	NPC36414
0.9701	High Similarity	NPC472515
0.9552	High Similarity	NPC38153
0.9478	High Similarity	NPC472516
0.947	High Similarity	NPC229646
0.9412	High Similarity	NPC473209
0.9412	High Similarity	NPC136095
0.9407	High Similarity	NPC103001
0.9403	High Similarity	NPC46869
0.9343	High Similarity	NPC470856
0.9333	High Similarity	NPC161196
0.9265	High Similarity	NPC332594
0.9237	High Similarity	NPC473907
0.9214	High Similarity	NPC171656
0.9214	High Similarity	NPC469953
0.9209	High Similarity	NPC36181
0.9197	High Similarity	NPC17848
0.9191	High Similarity	NPC174999
0.9191	High Similarity	NPC254741
0.9185	High Similarity	NPC66705
0.9179	High Similarity	NPC101294
0.9179	High Similarity	NPC55147
0.9179	High Similarity	NPC54503
0.9179	High Similarity	NPC473655
0.9167	High Similarity	NPC473894
0.9161	High Similarity	NPC191104
0.916	High Similarity	NPC475496
0.916	High Similarity	NPC49852
0.9149	High Similarity	NPC470322
0.9149	High Similarity	NPC154217
0.9143	High Similarity	NPC112791
0.9143	High Similarity	NPC94794
0.9143	High Similarity	NPC196459
0.9143	High Similarity	NPC188632
0.9143	High Similarity	NPC470296
0.9143	High Similarity	NPC87609
0.9137	High Similarity	NPC201820
0.9137	High Similarity	NPC254010
0.9137	High Similarity	NPC103362
0.9137	High Similarity	NPC110969
0.913	High Similarity	NPC11566
0.913	High Similarity	NPC262635
0.913	High Similarity	NPC23257
0.9124	High Similarity	NPC131782
0.9124	High Similarity	NPC157855
0.9124	High Similarity	NPC474624
0.9124	High Similarity	NPC259685
0.9124	High Similarity	NPC138047
0.9111	High Similarity	NPC292998
0.9104	High Similarity	NPC278556
0.9104	High Similarity	NPC284424
0.9091	High Similarity	NPC88445
0.9085	High Similarity	NPC282335
0.9085	High Similarity	NPC180477
0.9085	High Similarity	NPC218300
0.9078	High Similarity	NPC196137
0.9078	High Similarity	NPC294365
0.9078	High Similarity	NPC469935
0.9078	High Similarity	NPC1886
0.9078	High Similarity	NPC178627
0.9071	High Similarity	NPC313036
0.9071	High Similarity	NPC11561
0.9071	High Similarity	NPC226636
0.9065	High Similarity	NPC474037
0.9065	High Similarity	NPC159275
0.9065	High Similarity	NPC221173
0.9065	High Similarity	NPC172986
0.9065	High Similarity	NPC472409
0.9065	High Similarity	NPC471587
0.9065	High Similarity	NPC241100
0.9065	High Similarity	NPC270883
0.9065	High Similarity	NPC261227
0.9065	High Similarity	NPC150522
0.9065	High Similarity	NPC307990
0.9065	High Similarity	NPC16455
0.9058	High Similarity	NPC219584
0.9058	High Similarity	NPC183639
0.9058	High Similarity	NPC470669
0.9058	High Similarity	NPC131130
0.9058	High Similarity	NPC199458
0.9058	High Similarity	NPC470668
0.9058	High Similarity	NPC470083
0.9044	High Similarity	NPC125920
0.9044	High Similarity	NPC61499
0.9044	High Similarity	NPC229128
0.9044	High Similarity	NPC125269
0.9023	High Similarity	NPC211120
0.9021	High Similarity	NPC266743
0.9015	High Similarity	NPC37512
0.9014	High Similarity	NPC57470
0.9014	High Similarity	NPC473927
0.9014	High Similarity	NPC181388
0.9008	High Similarity	NPC65041
0.9007	High Similarity	NPC59522
0.9	High Similarity	NPC156590
0.9	High Similarity	NPC282300
0.9	High Similarity	NPC147688
0.9	High Similarity	NPC205006
0.9	High Similarity	NPC24075
0.9	High Similarity	NPC470555
0.9	High Similarity	NPC118840
0.9	High Similarity	NPC64908
0.8993	High Similarity	NPC18260
0.8993	High Similarity	NPC303633
0.8993	High Similarity	NPC53181
0.8993	High Similarity	NPC139554
0.8993	High Similarity	NPC96565
0.8993	High Similarity	NPC301217
0.8993	High Similarity	NPC220062
0.8993	High Similarity	NPC217186
0.8993	High Similarity	NPC241975
0.8993	High Similarity	NPC216978
0.8993	High Similarity	NPC55018
0.8993	High Similarity	NPC78913
0.8993	High Similarity	NPC19476
0.8978	High Similarity	NPC101752
0.8978	High Similarity	NPC151113
0.8978	High Similarity	NPC60667
0.8978	High Similarity	NPC99854
0.8971	High Similarity	NPC223354
0.8971	High Similarity	NPC93756
0.8971	High Similarity	NPC247743
0.8971	High Similarity	NPC108113
0.8963	High Similarity	NPC175159
0.8958	High Similarity	NPC164299
0.8958	High Similarity	NPC19238
0.8951	High Similarity	NPC249942
0.8951	High Similarity	NPC74539
0.8951	High Similarity	NPC304443
0.8951	High Similarity	NPC129650
0.8951	High Similarity	NPC297886
0.8951	High Similarity	NPC140120
0.8944	High Similarity	NPC311741
0.8944	High Similarity	NPC234629
0.8944	High Similarity	NPC179970
0.8936	High Similarity	NPC166858
0.8936	High Similarity	NPC112829
0.8936	High Similarity	NPC294432
0.8936	High Similarity	NPC470556
0.8936	High Similarity	NPC51146
0.8936	High Similarity	NPC147145
0.8931	High Similarity	NPC73413
0.8931	High Similarity	NPC201667
0.8929	High Similarity	NPC235239
0.8929	High Similarity	NPC475680
0.8929	High Similarity	NPC69769
0.8929	High Similarity	NPC305355
0.8921	High Similarity	NPC201395
0.8921	High Similarity	NPC124269
0.8913	High Similarity	NPC1486
0.8913	High Similarity	NPC12165
0.8913	High Similarity	NPC98115
0.8913	High Similarity	NPC477243
0.8913	High Similarity	NPC66349
0.8913	High Similarity	NPC156910
0.8913	High Similarity	NPC186838
0.8913	High Similarity	NPC72452
0.8913	High Similarity	NPC150399
0.8913	High Similarity	NPC274109
0.8913	High Similarity	NPC61546
0.8913	High Similarity	NPC41461
0.8913	High Similarity	NPC477242
0.8913	High Similarity	NPC168105
0.8913	High Similarity	NPC477244
0.8913	High Similarity	NPC249606
0.8913	High Similarity	NPC25287
0.8897	High Similarity	NPC182428
0.8897	High Similarity	NPC10971
0.8897	High Similarity	NPC474735
0.8897	High Similarity	NPC180351
0.8897	High Similarity	NPC474660
0.8897	High Similarity	NPC151973
0.8889	High Similarity	NPC208303
0.8889	High Similarity	NPC211811
0.8889	High Similarity	NPC161864
0.8889	High Similarity	NPC472517
0.8889	High Similarity	NPC469933
0.8873	High Similarity	NPC33653
0.8873	High Similarity	NPC310130
0.8873	High Similarity	NPC169591
0.8873	High Similarity	NPC38219
0.8873	High Similarity	NPC68104
0.8873	High Similarity	NPC150408
0.8873	High Similarity	NPC257097
0.8873	High Similarity	NPC184738
0.8873	High Similarity	NPC75049
0.8873	High Similarity	NPC307895
0.8873	High Similarity	NPC221432
0.8873	High Similarity	NPC474939
0.8873	High Similarity	NPC164980
0.8873	High Similarity	NPC106985
0.8873	High Similarity	NPC175504
0.8873	High Similarity	NPC470909
0.8873	High Similarity	NPC470553
0.8873	High Similarity	NPC91560
0.8873	High Similarity	NPC96216
0.8873	High Similarity	NPC39329
0.8873	High Similarity	NPC17262
0.8873	High Similarity	NPC149026

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 NPC253616 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	996
0.2-0.3	1741
0.3-0.4	2690
0.4-0.5	1829
0.5-0.6	1027
0.6-0.7	335
0.7-0.8	104
0.8-0.85	31
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD1243	Approved
0.9051	High Similarity	NPD2796	Approved
0.8951	High Similarity	NPD920	Approved
0.8936	High Similarity	NPD643	Clinical (unspecified phase)
0.8873	High Similarity	NPD6799	Approved
0.8836	High Similarity	NPD7411	Suspended
0.8811	High Similarity	NPD642	Clinical (unspecified phase)
0.8811	High Similarity	NPD4378	Clinical (unspecified phase)
0.8776	High Similarity	NPD6801	Discontinued
0.8716	High Similarity	NPD7096	Clinical (unspecified phase)
0.8716	High Similarity	NPD7819	Suspended
0.8681	High Similarity	NPD7410	Clinical (unspecified phase)
0.8639	High Similarity	NPD6599	Discontinued
0.8571	High Similarity	NPD3748	Approved
0.8551	High Similarity	NPD1240	Approved
0.8543	High Similarity	NPD7075	Discontinued
0.8529	High Similarity	NPD6832	Phase 2
0.8521	High Similarity	NPD1549	Phase 2
0.8487	Intermediate Similarity	NPD919	Approved
0.8462	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1510	Phase 2
0.8429	Intermediate Similarity	NPD1607	Approved
0.8406	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2799	Discontinued
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8276	Intermediate Similarity	NPD3750	Approved
0.8273	Intermediate Similarity	NPD1296	Phase 2
0.8267	Intermediate Similarity	NPD4380	Phase 2
0.8235	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD9717	Approved
0.8217	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD5401	Approved
0.817	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD2313	Discontinued
0.8125	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD1551	Phase 2
0.8116	Intermediate Similarity	NPD1019	Discontinued
0.8082	Intermediate Similarity	NPD2800	Approved
0.8077	Intermediate Similarity	NPD5494	Approved
0.8065	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3749	Approved
0.8054	Intermediate Similarity	NPD2532	Approved
0.8054	Intermediate Similarity	NPD2534	Approved
0.8054	Intermediate Similarity	NPD2533	Approved
0.8043	Intermediate Similarity	NPD3267	Approved
0.8043	Intermediate Similarity	NPD3266	Approved
0.8043	Intermediate Similarity	NPD1203	Approved
0.8042	Intermediate Similarity	NPD6651	Approved
0.8015	Intermediate Similarity	NPD422	Phase 1
0.7987	Intermediate Similarity	NPD1511	Approved
0.7987	Intermediate Similarity	NPD2801	Approved
0.7972	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.7959	Intermediate Similarity	NPD2654	Approved
0.795	Intermediate Similarity	NPD7286	Phase 2
0.7922	Intermediate Similarity	NPD1934	Approved
0.7911	Intermediate Similarity	NPD1247	Approved
0.7902	Intermediate Similarity	NPD4307	Phase 2
0.7887	Intermediate Similarity	NPD3268	Approved
0.7885	Intermediate Similarity	NPD3882	Suspended
0.7883	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1512	Approved
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5124	Phase 1
0.7847	Intermediate Similarity	NPD1933	Approved
0.7847	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3226	Approved
0.784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5402	Approved
0.7786	Intermediate Similarity	NPD2797	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD1241	Discontinued
0.7742	Intermediate Similarity	NPD5890	Approved
0.7742	Intermediate Similarity	NPD5889	Approved
0.773	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD2798	Approved
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD3926	Phase 2
0.7698	Intermediate Similarity	NPD3972	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD7033	Discontinued
0.7687	Intermediate Similarity	NPD4308	Phase 3
0.7677	Intermediate Similarity	NPD6585	Discontinued
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD411	Approved
0.7609	Intermediate Similarity	NPD17	Approved
0.7603	Intermediate Similarity	NPD447	Suspended
0.7591	Intermediate Similarity	NPD9545	Approved
0.759	Intermediate Similarity	NPD6559	Discontinued
0.7589	Intermediate Similarity	NPD3225	Approved
0.7584	Intermediate Similarity	NPD2344	Approved
0.7574	Intermediate Similarity	NPD9493	Approved
0.7561	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7545	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.7484	Intermediate Similarity	NPD4288	Approved
0.747	Intermediate Similarity	NPD7074	Phase 3
0.747	Intermediate Similarity	NPD7472	Approved
0.7467	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2353	Approved
0.7447	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD5710	Approved
0.7415	Intermediate Similarity	NPD3140	Approved
0.7415	Intermediate Similarity	NPD3142	Approved
0.7407	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9697	Approved
0.7386	Intermediate Similarity	NPD2309	Approved
0.7381	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD1652	Phase 2
0.7365	Intermediate Similarity	NPD230	Phase 1
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1471	Phase 3
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2403	Approved
0.7317	Intermediate Similarity	NPD6808	Phase 2
0.7312	Intermediate Similarity	NPD1465	Phase 2
0.7308	Intermediate Similarity	NPD5049	Phase 3
0.7308	Intermediate Similarity	NPD2186	Approved
0.7297	Intermediate Similarity	NPD943	Approved
0.7286	Intermediate Similarity	NPD5691	Approved
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD6100	Approved
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD6104	Discontinued
0.7273	Intermediate Similarity	NPD2354	Approved
0.7262	Intermediate Similarity	NPD1729	Discontinued
0.7252	Intermediate Similarity	NPD9261	Approved
0.7222	Intermediate Similarity	NPD1876	Approved
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3134	Approved
0.7214	Intermediate Similarity	NPD1548	Phase 1
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD7003	Approved
0.7172	Intermediate Similarity	NPD1164	Approved
0.7171	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5242	Approved
0.7164	Intermediate Similarity	NPD1358	Approved
0.716	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7133	Intermediate Similarity	NPD1281	Approved
0.7124	Intermediate Similarity	NPD6004	Phase 3
0.7124	Intermediate Similarity	NPD6005	Phase 3
0.7124	Intermediate Similarity	NPD6002	Phase 3
0.7124	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4360	Phase 2
0.7119	Intermediate Similarity	NPD4363	Phase 3
0.7115	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.7113	Intermediate Similarity	NPD1778	Approved
0.7113	Intermediate Similarity	NPD4626	Approved
0.7092	Intermediate Similarity	NPD1894	Discontinued
0.7089	Intermediate Similarity	NPD6273	Approved
0.7086	Intermediate Similarity	NPD4287	Approved
0.7079	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4361	Phase 2
0.7073	Intermediate Similarity	NPD6971	Discontinued
0.707	Intermediate Similarity	NPD7390	Discontinued
0.707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7051	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3764	Approved
0.7042	Intermediate Similarity	NPD1651	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