NPASS Compound

Structure

CID209364 OpenBabel06191716002D 35 40 0 0 1 0 0 0 0 0999 V2000 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -1.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9237 -1.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4816 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4359 -2.1487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 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 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.18
Volume:	397.204
LogP:	5.072
LogD:	3.588
LogS:	-4.391
# Rotatable Bonds:	2
TPSA:	81.95
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	3.675
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.783
MDCK Permeability:	8.915206308302004e-06
Pgp-inhibitor:	0.276
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.673

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.13152313232422%
Volume Distribution (VD):	0.719
Pgp-substrate:	3.930422782897949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.48
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.436
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	2.715
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.725
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.867
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.861

Download Data

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

Natural Product: NPC209364

Natural Product ID:	NPC209364
*Common Name:**	Gedunin
IUPAC Name:	n.a.
Synonyms:	Gedunin
Standard InCHIKey:	YJXDGWUNRYLINJ-BHAPSIHVSA-N
Standard InCHI:	InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465226
PubChem CID:	12004512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO32938	cedrela spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820113]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	cortex	n.a.	PMID[16989525]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989525]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO4899	Streptomyces fungicidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20353165]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO13287	Cedrela odorata	Species	Meliaceae	Eukaryota	n.a.	xylem	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7417	Pieris melete	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4899	Streptomyces fungicidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10266	Alaria nana	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13287	Cedrela odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9736	Artemisia arctica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1469	Cyperus compressus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8937	Ferreirea spectabilis	n.a.	n.a.	n.a.	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
AC50	2
EC50	3
IC50	22
LD50	1
Others	144
Potency	28

Activity Type	# Activity
Cell Line	13
Individual Protein	21
NON-MOLECULAR	2
Organism	151
Others	8
PROTEIN COMPLEX	4
SINGLE PROTEIN	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	32.0	%	PMID[479885]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.3	ug.mL-1	PMID[479885]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8840.0	nM	PMID[479886]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	3220.0	nM	PMID[479886]
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.3	ug.mL-1	PMID[479888]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	EC50	=	38.95	nM	PMID[479889]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	28183.8	nM	PMID[479891]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[479891]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	22230.0	nM	PMID[479891]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	12589.3	nM	PMID[479891]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[479891]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[479891]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[479891]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5900.0	nM	PMID[479893]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	8300.0	nM	PMID[479893]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[479893]
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	4566.0	nM	PMID[479891]
NPT2867	Individual Protein	Protein RecA	Mycobacterium tuberculosis	EC50	=	16100.0	nM	PMID[479891]
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	44530.0	nM	PMID[479891]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	251.2	nM	PMID[479891]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[479891]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[479894]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[479891]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[479891]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[479891]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[479891]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[479891]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[479891]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10900.0	nM	PMID[479902]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.8	ug.mL-1	PMID[479885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.72	ug.mL-1	PMID[479885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.039	ug.mL-1	PMID[479885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.02	ug.mL-1	PMID[479885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1000.0	nM	PMID[479887]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	300.0	nM	PMID[479887]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1660.0	nM	PMID[479890]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1310.0	nM	PMID[479890]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PMID[479891]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000.0	nM	PMID[479891]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16900.0	nM	PMID[479893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[479893]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3294.4	nM	PMID[479891]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[479891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1651.1	nM	PMID[479891]
NPT2	Others	Unspecified		Potency	n.a.	2059.6	nM	PMID[479891]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	760.0	nM	PMID[479894]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[479891]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	43.16	%	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	ECI	=	20.07	%	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	46.46	%	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	1.007	mg/mg/day	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	0.4707	mg/mg/day	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	2.357	mg/mg/day	PMID[479895]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	FDI	=	18.8	%	PMID[479895]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	PC95	=	218.4	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	5.0	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	6.8	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	10.5	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	11.0	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	9.0	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	8.5	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	PC50	=	49.0	ug	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	13.3	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	23.3	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	49.3	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	39.3	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	51.3	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	82.0	%	PMID[479896]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Activity	=	80.0	%	PMID[479896]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.11	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.55	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Ratio	=	0.71	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.1	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.51	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.77	n.a.	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	8.4	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	100.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	11.6	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	13.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	15.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	41.7	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	54.2	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.35	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.05	%	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LC50	=	11.93	ug.mL-1	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	100.0	%	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	87.1	%	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	AFI	=	81.0	%	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	AFI	=	98.0	%	PMID[479897]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	AFI	=	100.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	68.8	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	74.5	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	85.6	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	89.9	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	100.0	%	PMID[479897]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	30.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.55	n.a.	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.51	n.a.	PMID[479898]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LC50	=	11.93	ug.mL-1	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.11	n.a.	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.71	n.a.	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.1	n.a.	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Growth_index	=	0.77	n.a.	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Inhibition	=	0.0	%	PMID[479898]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	11.0	%	PMID[479898]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	100.0	%	PMID[479898]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	87.1	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LD50	=	10.78	ug ml-1	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	14.1	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	54.7	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	100.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	98.7	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	11.6	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.05	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	38.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	70.8	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	33.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	20.0	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.7	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	32.5	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.3	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.9	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	7.1	%	PMID[479898]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.17	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.7	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	17.9	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	864.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	840.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	792.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	20.8	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	52.0	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	122.4	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	147.9	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	576.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	552.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	TIME	=	528.0	hr	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.1	mm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.0	mm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.6	mm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.9	mm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.2	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.8	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.45	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.61	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.95	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	16.12	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LC50	=	39.0	ppm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	70.8	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	48.3	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	38.3	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	33.3	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	mortality	=	25.0	%	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.2	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.25	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.3	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.35	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.4	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	0.5	cm	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	1.9	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	2.3	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.4	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	3.6	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	4.9	mg	PMID[479899]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	6.12	mg	PMID[479899]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	AFI	=	37.3	%	PMID[479900]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[479891]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	10322.5	nM	PMID[479891]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	65.45	%	PMID[479901]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	105.39	%	PMID[479901]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[479891]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[479891]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[479891]
NPT2	Others	Unspecified		EC50	=	895.0	nM	PMID[479891]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.39	%	PMID[479903]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	83.0	%	PMID[479904]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	65.0	%	PMID[479904]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	2.391	%	PMID[479905]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.95	%	PMID[479906]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[479907]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[479907]

☑ 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 NPC209364 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	428
0.1-0.2	1547
0.2-0.3	3341
0.3-0.4	6112
0.4-0.5	10293
0.5-0.6	10215
0.6-0.7	9024
0.7-0.8	1342
0.8-0.85	243
0.85-0.9	83
0.9-0.95	54
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC286722
0.9866	High Similarity	NPC473473
0.9866	High Similarity	NPC475295
0.9865	High Similarity	NPC107646
0.9735	High Similarity	NPC5079
0.9732	High Similarity	NPC60973
0.9671	High Similarity	NPC234660
0.9671	High Similarity	NPC51568
0.9669	High Similarity	NPC475381
0.9605	High Similarity	NPC470939
0.96	High Similarity	NPC126723
0.9539	High Similarity	NPC335761
0.9536	High Similarity	NPC472283
0.9484	High Similarity	NPC473766
0.9484	High Similarity	NPC473753
0.9474	High Similarity	NPC237155
0.947	High Similarity	NPC263265
0.9416	High Similarity	NPC39986
0.9416	High Similarity	NPC469846
0.9416	High Similarity	NPC134254
0.9416	High Similarity	NPC302369
0.9412	High Similarity	NPC25255
0.9412	High Similarity	NPC305016
0.9412	High Similarity	NPC472653
0.9404	High Similarity	NPC469850
0.9363	High Similarity	NPC302392
0.9359	High Similarity	NPC173516
0.9355	High Similarity	NPC476856
0.9355	High Similarity	NPC476857
0.9355	High Similarity	NPC476858
0.9351	High Similarity	NPC290400
0.9351	High Similarity	NPC193798
0.9351	High Similarity	NPC96443
0.9299	High Similarity	NPC471397
0.929	High Similarity	NPC292389
0.929	High Similarity	NPC469338
0.9272	High Similarity	NPC476201
0.9267	High Similarity	NPC196864
0.9267	High Similarity	NPC159927
0.9267	High Similarity	NPC469335
0.9267	High Similarity	NPC477404
0.9252	High Similarity	NPC86935
0.9236	High Similarity	NPC472282
0.9236	High Similarity	NPC476853
0.9236	High Similarity	NPC476850
0.9236	High Similarity	NPC476861
0.9231	High Similarity	NPC476860
0.9231	High Similarity	NPC469849
0.9231	High Similarity	NPC123088
0.9231	High Similarity	NPC276551
0.9231	High Similarity	NPC470940
0.9226	High Similarity	NPC117986
0.9226	High Similarity	NPC82851
0.9226	High Similarity	NPC69028
0.9226	High Similarity	NPC149896
0.9221	High Similarity	NPC477403
0.9221	High Similarity	NPC473368
0.9205	High Similarity	NPC18135
0.9177	High Similarity	NPC271235
0.9177	High Similarity	NPC160651
0.9172	High Similarity	NPC470875
0.9172	High Similarity	NPC23387
0.9167	High Similarity	NPC476197
0.9167	High Similarity	NPC477405
0.9156	High Similarity	NPC249021
0.9156	High Similarity	NPC187149
0.915	High Similarity	NPC44675
0.915	High Similarity	NPC214541
0.915	High Similarity	NPC476262
0.9139	High Similarity	NPC476122
0.9139	High Similarity	NPC46551
0.9114	High Similarity	NPC472651
0.9103	High Similarity	NPC18347
0.9103	High Similarity	NPC197596
0.9085	High Similarity	NPC178932
0.9067	High Similarity	NPC221809
0.9057	High Similarity	NPC472652
0.9038	High Similarity	NPC477402
0.9038	High Similarity	NPC191828
0.9032	High Similarity	NPC167142
0.9032	High Similarity	NPC261597
0.9032	High Similarity	NPC299038
0.9026	High Similarity	NPC469336
0.902	High Similarity	NPC469503
0.9	High Similarity	NPC262198
0.8987	High Similarity	NPC271657
0.8981	High Similarity	NPC329938
0.8981	High Similarity	NPC263432
0.8974	High Similarity	NPC307383
0.8974	High Similarity	NPC475967
0.8961	High Similarity	NPC282445
0.8961	High Similarity	NPC30222
0.8961	High Similarity	NPC57998
0.894	High Similarity	NPC470941
0.891	High Similarity	NPC45101
0.891	High Similarity	NPC36655
0.8903	High Similarity	NPC264943
0.8903	High Similarity	NPC35000
0.8896	High Similarity	NPC44577
0.8882	High Similarity	NPC470995
0.8875	High Similarity	NPC472775
0.8875	High Similarity	NPC472774
0.8868	High Similarity	NPC470182
0.8867	High Similarity	NPC142113
0.8861	High Similarity	NPC472771
0.8861	High Similarity	NPC200782
0.8846	High Similarity	NPC469485
0.8844	High Similarity	NPC476943
0.8827	High Similarity	NPC160818
0.8827	High Similarity	NPC169299
0.882	High Similarity	NPC327922
0.8812	High Similarity	NPC478178
0.8812	High Similarity	NPC475779
0.8805	High Similarity	NPC472773
0.8805	High Similarity	NPC224394
0.8805	High Similarity	NPC663
0.879	High Similarity	NPC472772
0.879	High Similarity	NPC173544
0.8782	High Similarity	NPC281258
0.878	High Similarity	NPC262386
0.8776	High Similarity	NPC310830
0.8774	High Similarity	NPC75906
0.8773	High Similarity	NPC469848
0.8766	High Similarity	NPC156189
0.8765	High Similarity	NPC82602
0.8758	High Similarity	NPC19747
0.8742	High Similarity	NPC211777
0.8742	High Similarity	NPC472668
0.8742	High Similarity	NPC207978
0.8734	High Similarity	NPC474932
0.872	High Similarity	NPC236004
0.8716	High Similarity	NPC220094
0.8712	High Similarity	NPC159232
0.8701	High Similarity	NPC471001
0.8693	High Similarity	NPC255414
0.8688	High Similarity	NPC472669
0.8688	High Similarity	NPC198047
0.8675	High Similarity	NPC223415
0.8667	High Similarity	NPC167340
0.8654	High Similarity	NPC268905
0.8642	High Similarity	NPC476224
0.8642	High Similarity	NPC478179
0.8627	High Similarity	NPC346
0.8625	High Similarity	NPC188649
0.8625	High Similarity	NPC471167
0.8625	High Similarity	NPC6326
0.8625	High Similarity	NPC471166
0.8618	High Similarity	NPC476944
0.8616	High Similarity	NPC474611
0.8616	High Similarity	NPC262872
0.8614	High Similarity	NPC478177
0.8609	High Similarity	NPC121158
0.8606	High Similarity	NPC94763
0.8589	High Similarity	NPC296558
0.8581	High Similarity	NPC125182
0.8581	High Similarity	NPC195325
0.8581	High Similarity	NPC470790
0.8581	High Similarity	NPC69647
0.8581	High Similarity	NPC472654
0.8581	High Similarity	NPC470791
0.858	High Similarity	NPC93172
0.858	High Similarity	NPC97574
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC419
0.8571	High Similarity	NPC250228
0.8571	High Similarity	NPC71821
0.8571	High Similarity	NPC165218
0.8571	High Similarity	NPC288602
0.8571	High Similarity	NPC471168
0.8562	High Similarity	NPC470789
0.8562	High Similarity	NPC41182
0.8553	High Similarity	NPC472776
0.8553	High Similarity	NPC243577
0.8553	High Similarity	NPC472777
0.8553	High Similarity	NPC472778
0.8553	High Similarity	NPC470741
0.8535	High Similarity	NPC246164
0.8528	High Similarity	NPC100333
0.8523	High Similarity	NPC310043
0.8519	High Similarity	NPC146991
0.8506	High Similarity	NPC470999
0.8506	High Similarity	NPC62799
0.8497	Intermediate Similarity	NPC251865
0.8497	Intermediate Similarity	NPC137295
0.8491	Intermediate Similarity	NPC204663
0.8487	Intermediate Similarity	NPC473152
0.8481	Intermediate Similarity	NPC114880
0.8477	Intermediate Similarity	NPC90296
0.8477	Intermediate Similarity	NPC56197
0.8471	Intermediate Similarity	NPC247563
0.8471	Intermediate Similarity	NPC116717
0.8471	Intermediate Similarity	NPC272590
0.8471	Intermediate Similarity	NPC242068
0.8466	Intermediate Similarity	NPC472141
0.8462	Intermediate Similarity	NPC211625
0.8457	Intermediate Similarity	NPC475039
0.8457	Intermediate Similarity	NPC476035
0.8457	Intermediate Similarity	NPC472139
0.8457	Intermediate Similarity	NPC14499
0.8456	Intermediate Similarity	NPC214572

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 NPC209364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1045
0.2-0.3	2210
0.3-0.4	2665
0.4-0.5	1805
0.5-0.6	784
0.6-0.7	262
0.7-0.8	19
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5760	Phase 2
0.8313	Intermediate Similarity	NPD5761	Phase 2
0.8198	Intermediate Similarity	NPD8434	Phase 2
0.7803	Intermediate Similarity	NPD6764	Approved
0.7803	Intermediate Similarity	NPD6765	Approved
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6785	Approved
0.7627	Intermediate Similarity	NPD6784	Approved
0.7576	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD5494	Approved
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD920	Approved
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7317	Intermediate Similarity	NPD6799	Approved
0.7283	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7228	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3749	Approved
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD5402	Approved
0.7193	Intermediate Similarity	NPD3817	Phase 2
0.7175	Intermediate Similarity	NPD3751	Discontinued
0.7152	Intermediate Similarity	NPD7236	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8404	Phase 2
0.7099	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.7066	Intermediate Similarity	NPD5401	Approved
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4107	Approved
0.7052	Intermediate Similarity	NPD3882	Suspended
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD3748	Approved
0.703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1243	Approved
0.6964	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2346	Discontinued
0.6941	Remote Similarity	NPD7239	Suspended
0.694	Remote Similarity	NPD8313	Approved
0.694	Remote Similarity	NPD8312	Approved
0.6936	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4482	Phase 3
0.6927	Remote Similarity	NPD7473	Discontinued
0.6923	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8285	Discontinued
0.6901	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD3226	Approved
0.6893	Remote Similarity	NPD8127	Discontinued
0.6886	Remote Similarity	NPD3887	Approved
0.6885	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1934	Approved
0.6872	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6166	Phase 2
0.6872	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6856	Remote Similarity	NPD7435	Discontinued
0.6855	Remote Similarity	NPD6832	Phase 2
0.6852	Remote Similarity	NPD6355	Discontinued
0.6831	Remote Similarity	NPD7251	Discontinued
0.6829	Remote Similarity	NPD2799	Discontinued
0.6826	Remote Similarity	NPD3750	Approved
0.6811	Remote Similarity	NPD8407	Phase 2
0.6807	Remote Similarity	NPD1549	Phase 2
0.6802	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6959	Discontinued
0.6796	Remote Similarity	NPD3818	Discontinued
0.6793	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6784	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2403	Approved
0.6778	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6797	Phase 2
0.6776	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2800	Approved
0.6761	Remote Similarity	NPD7768	Phase 2
0.676	Remote Similarity	NPD6232	Discontinued
0.6747	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7685	Pre-registration
0.6739	Remote Similarity	NPD8368	Discontinued
0.6732	Remote Similarity	NPD7907	Approved
0.6728	Remote Similarity	NPD8032	Phase 2
0.6725	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7074	Phase 3
0.6716	Remote Similarity	NPD4111	Phase 1
0.6687	Remote Similarity	NPD1551	Phase 2
0.6685	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6808	Phase 2
0.665	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7874	Approved
0.6648	Remote Similarity	NPD2801	Approved
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD2344	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2353	Approved
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1933	Approved
0.6634	Remote Similarity	NPD4665	Approved
0.6633	Remote Similarity	NPD3057	Approved
0.663	Remote Similarity	NPD7472	Approved
0.663	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7033	Discontinued
0.6624	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5980	Discovery
0.6615	Remote Similarity	NPD6778	Approved
0.6615	Remote Similarity	NPD6780	Approved
0.6615	Remote Similarity	NPD6776	Approved
0.6615	Remote Similarity	NPD6782	Approved
0.6615	Remote Similarity	NPD6781	Approved
0.6615	Remote Similarity	NPD6777	Approved
0.6615	Remote Similarity	NPD6779	Approved
0.6607	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7095	Approved
0.6603	Remote Similarity	NPD17	Approved
0.6599	Remote Similarity	NPD7696	Phase 3
0.6599	Remote Similarity	NPD7697	Approved
0.6599	Remote Similarity	NPD7698	Approved
0.6591	Remote Similarity	NPD37	Approved
0.6587	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD4307	Phase 2
0.6582	Remote Similarity	NPD3972	Approved
0.6579	Remote Similarity	NPD8435	Approved
0.6575	Remote Similarity	NPD7229	Phase 3
0.6573	Remote Similarity	NPD7058	Phase 2
0.6573	Remote Similarity	NPD7057	Phase 3
0.6573	Remote Similarity	NPD4967	Phase 2
0.6573	Remote Similarity	NPD4966	Approved
0.6573	Remote Similarity	NPD4965	Approved
0.6566	Remote Similarity	NPD8320	Phase 1
0.6566	Remote Similarity	NPD7097	Phase 1
0.6566	Remote Similarity	NPD8319	Approved
0.6566	Remote Similarity	NPD7870	Phase 2
0.6566	Remote Similarity	NPD7871	Phase 2
0.6564	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6798	Discontinued
0.6562	Remote Similarity	NPD3266	Approved
0.6562	Remote Similarity	NPD3267	Approved
0.6561	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1465	Phase 2
0.6548	Remote Similarity	NPD3533	Approved
0.6548	Remote Similarity	NPD2972	Approved
0.6532	Remote Similarity	NPD1512	Approved
0.6531	Remote Similarity	NPD4580	Approved
0.6529	Remote Similarity	NPD7003	Approved
0.6527	Remote Similarity	NPD1510	Phase 2
0.6524	Remote Similarity	NPD6233	Phase 2
0.6522	Remote Similarity	NPD7228	Approved
0.6517	Remote Similarity	NPD5353	Approved
0.6517	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7497	Discontinued
0.6509	Remote Similarity	NPD2897	Discontinued
0.65	Remote Similarity	NPD6234	Discontinued
0.6497	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8361	Approved
0.6492	Remote Similarity	NPD8360	Approved
0.6491	Remote Similarity	NPD2354	Approved
0.6491	Remote Similarity	NPD2309	Approved
0.6489	Remote Similarity	NPD2968	Approved
0.6489	Remote Similarity	NPD2971	Approved
0.6488	Remote Similarity	NPD2438	Suspended
0.6485	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD5711	Approved
0.6478	Remote Similarity	NPD1608	Approved
0.6468	Remote Similarity	NPD7701	Phase 2
0.6463	Remote Similarity	NPD3268	Approved
0.6463	Remote Similarity	NPD3764	Approved
0.6462	Remote Similarity	NPD2974	Approved
0.6462	Remote Similarity	NPD2973	Approved
0.6462	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2975	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