NPASS Compound

Structure

CID188646 OpenBabel06191715572D 21 22 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 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 5.1962 1.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -2.5981 1.5000 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 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.1
Volume:	299.545
LogP:	3.454
LogD:	3.38
LogS:	-4.992
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	2.004
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.851
MDCK Permeability:	1.3412893167696893e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	99.33106231689453%
Volume Distribution (VD):	0.501
Pgp-substrate:	1.1844139099121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	9.916
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.352
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.383
Skin Sensitization:	0.855
Carcinogencity:	0.697
Eye Corrosion:	0.053
Eye Irritation:	0.988
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC188646

Natural Product ID:	NPC188646
*Common Name:**	Flavokawain B
IUPAC Name:	(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	QKQLSQLKXBHUSO-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
SMILES:	COc1cc(O)c(c(c1)OC)C(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL104255
PubChem CID:	5356121
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
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[11325227]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444686]
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502333]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043420]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15193266]
NPO16772	Piper rusbyi	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17354169]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10407	Petromyzon marinus	Species	Petromyzontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25557	Alternaria porri	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24866	Smilax aspera	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24672	Helleborus purpurascens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5676	Annulohypoxylon multiforme	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25410	Manilkara bidentata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24549	Scutellaria cordifrons	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27620.1	Pteris cretica var. nervosa	Varieties	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16772	Piper rusbyi	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18762	Ilex microdonta	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24735	Cupania latifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28771	Clematis delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24821	Nidorella resedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16885	Phonus arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18259	Chaetanthera chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20691	Echinocereus merkeri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18529	Salvia broussoneti	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19082	Creolophus cirrhatus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25468	Tabernaemontana amygdalifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19721	Impatiens roylei	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24591	Trichosanthes dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19008	Mentha cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23489	Stachys anisochila	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8788	Renealmia nicolaioides	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22637	Kunzea ambigua	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17249	Lespedeza capitata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8943	Juniperus californica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25321	Acantholimon glumaceum	Species	Plumbaginaceae	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
EC50	1
GI50	58
IC50	27
Others	66
Potency	44

Activity Type	# Activity
Cell Line	116
Individual Protein	41
NON-MOLECULAR	2
Organism	10
Others	26
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20000.0	nM	PMID[568135]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	28.0	%	PMID[568136]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	1.7	ug ml-1	PMID[568137]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PMID[568140]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	17782.8	nM	PMID[568141]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	10000.0	nM	PMID[568141]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[568140]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	14125.4	nM	PMID[568140]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	11220.2	nM	PMID[568141]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[568140]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PMID[568140]
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	28183.8	nM	PMID[568141]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PMID[568140]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[568141]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[568141]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[568141]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	PMID[568141]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[568140]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[568141]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[568141]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[568141]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	10691.0	nM	PMID[568141]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[568140]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	3784.43	nM	PMID[568143]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	3288.52	nM	PMID[568143]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	5970.35	nM	PMID[568143]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	8729.71	nM	PMID[568143]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	5834.45	nM	PMID[568143]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	3723.92	nM	PMID[568143]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	7726.81	nM	PMID[568143]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	1207.81	nM	PMID[568143]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	3784.43	nM	PMID[568143]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	9268.3	nM	PMID[568143]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	4613.18	nM	PMID[568143]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	4425.88	nM	PMID[568143]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	7095.78	nM	PMID[568143]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	5370.32	nM	PMID[568143]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	12022.64	nM	PMID[568143]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	3801.89	nM	PMID[568143]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	4602.57	nM	PMID[568143]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	3639.15	nM	PMID[568143]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	23878.11	nM	PMID[568143]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	7638.36	nM	PMID[568143]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	3467.37	nM	PMID[568143]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1849.27	nM	PMID[568143]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	6546.36	nM	PMID[568143]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	3845.92	nM	PMID[568143]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	2421.03	nM	PMID[568143]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	3515.6	nM	PMID[568143]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	7943.28	nM	PMID[568143]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	5164.16	nM	PMID[568143]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	3854.78	nM	PMID[568143]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	7998.34	nM	PMID[568143]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	2290.87	nM	PMID[568143]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	4466.84	nM	PMID[568143]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	4623.81	nM	PMID[568143]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	2971.67	nM	PMID[568143]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	10327.61	nM	PMID[568143]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	4508.17	nM	PMID[568143]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	5636.38	nM	PMID[568143]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	4977.37	nM	PMID[568143]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	10399.2	nM	PMID[568143]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	6095.37	nM	PMID[568143]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	7798.3	nM	PMID[568143]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	11614.49	nM	PMID[568143]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	6823.39	nM	PMID[568143]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	3539.97	nM	PMID[568143]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	5284.45	nM	PMID[568143]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	4140.0	nM	PMID[568143]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	4709.77	nM	PMID[568143]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	13031.67	nM	PMID[568143]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	4528.98	nM	PMID[568143]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	3198.9	nM	PMID[568143]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	4623.81	nM	PMID[568143]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	10789.47	nM	PMID[568143]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	2269.86	nM	PMID[568143]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	4149.54	nM	PMID[568143]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	7655.97	nM	PMID[568143]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	3341.95	nM	PMID[568143]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	12502.59	nM	PMID[568143]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	14521.12	nM	PMID[568143]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	101.0	%	PMID[568144]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	191.0	%	PMID[568144]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	67.9	%	PMID[568145]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Inhibition	=	60.4	%	PMID[568145]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[568141]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[568141]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[568141]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	27.15	%	PMID[568146]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[568141]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[568140]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[568141]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[568140]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[568141]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[568141]
NPT1229	Cell Line	Huh-7	Homo sapiens	Survival	=	10.0	%	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	Survival	=	1.0	%	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Survival	=	19.0	%	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	Survival	=	0.0	%	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	Survival	=	27.0	%	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Survival	=	2.0	%	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	Survival	=	7.0	%	PMID[568151]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	15900.0	nM	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	9900.0	nM	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	16300.0	nM	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	7500.0	nM	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	9100.0	nM	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	IC50	=	11300.0	nM	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	13600.0	nM	PMID[568151]
NPT2186	Cell Line	RL	Homo sapiens	IC50	=	8200.0	nM	PMID[568151]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15500.0	nM	PMID[568151]
NPT1229	Cell Line	Huh-7	Homo sapiens	Activity_index	=	2.2	n.a.	PMID[568151]
NPT1229	Cell Line	Huh-7	Homo sapiens	Activity	=	55.0	%	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity_index	=	9.7	n.a.	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	42.0	%	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity_index	=	5.2	n.a.	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	54.0	%	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity_index	=	1.1	n.a.	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	37.0	%	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	Activity_index	=	4.2	n.a.	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	35.0	%	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Activity_index	=	0.8	n.a.	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Activity	=	39.0	%	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity_index	=	3.4	n.a.	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	50.0	%	PMID[568151]
NPT1229	Cell Line	Huh-7	Homo sapiens	Activity_index	=	1.7	n.a.	PMID[568151]
NPT1229	Cell Line	Huh-7	Homo sapiens	Activity	=	30.0	%	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity_index	=	19.3	n.a.	PMID[568151]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	40.0	%	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity_index	=	6.8	n.a.	PMID[568151]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	40.0	%	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity_index	=	0.6	n.a.	PMID[568151]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	28.0	%	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	Activity_index	=	2.0	n.a.	PMID[568151]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	20.0	%	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Activity_index	=	0.2	n.a.	PMID[568151]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Activity	=	7.0	%	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity_index	=	0.9	n.a.	PMID[568151]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	21.0	%	PMID[568151]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	20000.0	nM	PMID[568154]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	20000.0	nM	PMID[568154]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	19700.0	nM	PMID[568154]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	18200.0	nM	PMID[568154]
NPT2142	Cell Line	REH	Homo sapiens	IC50	>	20000.0	nM	PMID[568154]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	20000.0	nM	PMID[568154]
NPT3213	Individual Protein	MAP kinase signal-integrating kinase 2	Homo sapiens	Inhibition	>	50.0	%	PMID[568155]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	80.6	%	PMID[568156]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4200.0	nM	PMID[568156]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	26500.0	nM	PMID[568156]
NPT27	Others	Unspecified		IC50	=	7.2	ug.mL-1	PMID[568137]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[568138]
NPT2	Others	Unspecified		IC50	=	8.0	ug.mL-1	PMID[568139]
NPT27	Others	Unspecified		IC50	=	6.6	ug.mL-1	PMID[568139]
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PMID[568141]
NPT2	Others	Unspecified		IC50	=	3300.0	nM	PMID[568142]
NPT27	Others	Unspecified		Activity	<	5.0	%	PMID[568142]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[568141]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[568141]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[568141]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[568140]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[568141]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	4.56	%	PMID[568146]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[568141]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[568141]
NPT22906	PROTEIN COMPLEX	Urease subunit alpha/Urease subunit beta	Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)	IC50	=	1220000.0	nM	PMID[568147]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	141.41	%	PMID[568148]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	125.2	%	PMID[568148]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[568141]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[568140]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[568141]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.9	ug.mL-1	PMID[568149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7700.0	nM	PMID[568150]
NPT2	Others	Unspecified		Survival	=	32.0	%	PMID[568151]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	1.7	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	2.7	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	1.6	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	3.5	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	2.9	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	2.3	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	1.9	n.a.	PMID[568151]
NPT2	Others	Unspecified		Ratio IC50	=	3.2	n.a.	PMID[568151]
NPT35	Others	n.a.		LogP	=	3.9	n.a.	PMID[568152]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	EC50	=	6200.0	nM	PMID[568152]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	2.45	%	PMID[568153]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	12.32	%	PMID[568153]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	10.96	%	PMID[568153]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	9.23	%	PMID[568153]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	7.33	%	PMID[568153]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	6.59	%	PMID[568153]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-7.74	%	PMID[568153]

☑ 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 NPC188646 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	336
0.1-0.2	1675
0.2-0.3	4572
0.3-0.4	11265
0.4-0.5	6395
0.5-0.6	3924
0.6-0.7	5937
0.7-0.8	5369
0.8-0.85	1949
0.85-0.9	870
0.9-0.95	314
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263670
1.0	High Similarity	NPC56031
1.0	High Similarity	NPC175098
1.0	High Similarity	NPC242294
1.0	High Similarity	NPC337373
1.0	High Similarity	NPC139813
1.0	High Similarity	NPC312318
1.0	High Similarity	NPC472365
1.0	High Similarity	NPC192304
0.9922	High Similarity	NPC286336
0.9921	High Similarity	NPC257756
0.9921	High Similarity	NPC212631
0.9921	High Similarity	NPC205468
0.9921	High Similarity	NPC87231
0.9921	High Similarity	NPC129132
0.9844	High Similarity	NPC18877
0.9844	High Similarity	NPC20560
0.9844	High Similarity	NPC159623
0.9844	High Similarity	NPC144051
0.9844	High Similarity	NPC28753
0.9844	High Similarity	NPC294593
0.9844	High Similarity	NPC204960
0.9844	High Similarity	NPC82225
0.9843	High Similarity	NPC64359
0.9843	High Similarity	NPC308037
0.9843	High Similarity	NPC262359
0.9769	High Similarity	NPC168105
0.9769	High Similarity	NPC477242
0.9769	High Similarity	NPC66349
0.9769	High Similarity	NPC472367
0.9769	High Similarity	NPC476333
0.9769	High Similarity	NPC473391
0.9769	High Similarity	NPC98115
0.9769	High Similarity	NPC472364
0.9769	High Similarity	NPC150399
0.9769	High Similarity	NPC249606
0.9769	High Similarity	NPC12165
0.9769	High Similarity	NPC186838
0.9769	High Similarity	NPC41461
0.9769	High Similarity	NPC25287
0.9769	High Similarity	NPC477243
0.9769	High Similarity	NPC1486
0.9769	High Similarity	NPC274109
0.9769	High Similarity	NPC477244
0.9695	High Similarity	NPC472419
0.9695	High Similarity	NPC153979
0.9695	High Similarity	NPC188879
0.9695	High Similarity	NPC317119
0.9692	High Similarity	NPC131039
0.9692	High Similarity	NPC13575
0.9692	High Similarity	NPC156092
0.9688	High Similarity	NPC475008
0.9688	High Similarity	NPC309717
0.9688	High Similarity	NPC186097
0.9688	High Similarity	NPC128348
0.9688	High Similarity	NPC313618
0.9688	High Similarity	NPC66384
0.9688	High Similarity	NPC112192
0.9688	High Similarity	NPC164236
0.9688	High Similarity	NPC189106
0.9688	High Similarity	NPC475009
0.9685	High Similarity	NPC247779
0.9621	High Similarity	NPC21350
0.9621	High Similarity	NPC124269
0.9621	High Similarity	NPC472368
0.9618	High Similarity	NPC240593
0.9618	High Similarity	NPC213603
0.9615	High Similarity	NPC103842
0.9606	High Similarity	NPC211120
0.9549	High Similarity	NPC470211
0.9549	High Similarity	NPC472366
0.9549	High Similarity	NPC477956
0.9545	High Similarity	NPC266597
0.9545	High Similarity	NPC116632
0.9545	High Similarity	NPC303644
0.9545	High Similarity	NPC162680
0.9545	High Similarity	NPC7013
0.9545	High Similarity	NPC209560
0.9545	High Similarity	NPC250266
0.9545	High Similarity	NPC181124
0.9545	High Similarity	NPC294409
0.9538	High Similarity	NPC27643
0.9528	High Similarity	NPC80694
0.9528	High Similarity	NPC186098
0.9478	High Similarity	NPC172250
0.9478	High Similarity	NPC215311
0.9478	High Similarity	NPC213659
0.9478	High Similarity	NPC48624
0.9478	High Similarity	NPC11056
0.9478	High Similarity	NPC259166
0.9478	High Similarity	NPC219917
0.9478	High Similarity	NPC326109
0.9478	High Similarity	NPC204985
0.9478	High Similarity	NPC144118
0.9478	High Similarity	NPC80962
0.9474	High Similarity	NPC471620
0.9474	High Similarity	NPC90665
0.9474	High Similarity	NPC251681
0.9474	High Similarity	NPC279668
0.9474	High Similarity	NPC278323
0.9474	High Similarity	NPC99333
0.9474	High Similarity	NPC309154
0.9474	High Similarity	NPC243528
0.9474	High Similarity	NPC55162
0.9474	High Similarity	NPC12175
0.9474	High Similarity	NPC188947
0.9474	High Similarity	NPC280284
0.947	High Similarity	NPC473887
0.947	High Similarity	NPC231772
0.947	High Similarity	NPC29353
0.947	High Similarity	NPC124784
0.947	High Similarity	NPC127447
0.947	High Similarity	NPC13408
0.947	High Similarity	NPC194281
0.947	High Similarity	NPC234133
0.947	High Similarity	NPC47815
0.9449	High Similarity	NPC305518
0.9449	High Similarity	NPC128428
0.9407	High Similarity	NPC55832
0.9407	High Similarity	NPC26051
0.9407	High Similarity	NPC268204
0.9407	High Similarity	NPC469404
0.9407	High Similarity	NPC470087
0.9407	High Similarity	NPC470089
0.9407	High Similarity	NPC321980
0.9407	High Similarity	NPC52789
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC49108
0.9403	High Similarity	NPC109232
0.9403	High Similarity	NPC283429
0.9403	High Similarity	NPC295384
0.9398	High Similarity	NPC290291
0.9398	High Similarity	NPC275055
0.9394	High Similarity	NPC39426
0.9394	High Similarity	NPC234560
0.938	High Similarity	NPC185497
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC471417
0.9338	High Similarity	NPC119663
0.9338	High Similarity	NPC226636
0.9333	High Similarity	NPC129853
0.9333	High Similarity	NPC253822
0.9333	High Similarity	NPC188243
0.9333	High Similarity	NPC110228
0.9333	High Similarity	NPC6407
0.9333	High Similarity	NPC76445
0.9333	High Similarity	NPC159275
0.9333	High Similarity	NPC69769
0.9333	High Similarity	NPC269652
0.9333	High Similarity	NPC172986
0.9333	High Similarity	NPC270883
0.9333	High Similarity	NPC241100
0.9333	High Similarity	NPC101366
0.9333	High Similarity	NPC265178
0.9333	High Similarity	NPC284550
0.9333	High Similarity	NPC281207
0.9333	High Similarity	NPC261227
0.9323	High Similarity	NPC24394
0.9323	High Similarity	NPC87545
0.9323	High Similarity	NPC235428
0.9318	High Similarity	NPC172262
0.9318	High Similarity	NPC164136
0.9313	High Similarity	NPC15834
0.9313	High Similarity	NPC203817
0.9313	High Similarity	NPC215875
0.9313	High Similarity	NPC10971
0.9302	High Similarity	NPC69235
0.9302	High Similarity	NPC212379
0.9302	High Similarity	NPC60558
0.9291	High Similarity	NPC65041
0.927	High Similarity	NPC149026
0.927	High Similarity	NPC18585
0.927	High Similarity	NPC475705
0.927	High Similarity	NPC117836
0.927	High Similarity	NPC301751
0.927	High Similarity	NPC166138
0.927	High Similarity	NPC175504
0.927	High Similarity	NPC91560
0.927	High Similarity	NPC39329
0.927	High Similarity	NPC75049
0.927	High Similarity	NPC106985
0.927	High Similarity	NPC143896
0.927	High Similarity	NPC257097
0.927	High Similarity	NPC245482
0.927	High Similarity	NPC169591
0.927	High Similarity	NPC51887
0.927	High Similarity	NPC68104
0.927	High Similarity	NPC150408
0.927	High Similarity	NPC310130
0.927	High Similarity	NPC164980
0.927	High Similarity	NPC476178
0.927	High Similarity	NPC221432
0.9265	High Similarity	NPC126534
0.9265	High Similarity	NPC90582
0.9265	High Similarity	NPC3188
0.9265	High Similarity	NPC262094
0.9265	High Similarity	NPC147688
0.9265	High Similarity	NPC232021
0.9265	High Similarity	NPC64908
0.9265	High Similarity	NPC26238

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 NPC188646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	986
0.2-0.3	1483
0.3-0.4	2635
0.4-0.5	1904
0.5-0.6	1217
0.6-0.7	415
0.7-0.8	141
0.8-0.85	40
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD1240	Approved
0.9538	High Similarity	NPD1607	Approved
0.9394	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1549	Phase 2
0.9111	High Similarity	NPD1550	Clinical (unspecified phase)
0.9111	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD2796	Approved
0.8857	High Similarity	NPD6799	Approved
0.875	High Similarity	NPD4380	Phase 2
0.869	High Similarity	NPD7411	Suspended
0.8633	High Similarity	NPD970	Clinical (unspecified phase)
0.8592	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.854	High Similarity	NPD6651	Approved
0.8523	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD8443	Clinical (unspecified phase)
0.8511	High Similarity	NPD1878	Clinical (unspecified phase)
0.8503	High Similarity	NPD1934	Approved
0.8493	Intermediate Similarity	NPD6599	Discontinued
0.8489	Intermediate Similarity	NPD1551	Phase 2
0.8489	Intermediate Similarity	NPD2935	Discontinued
0.8472	Intermediate Similarity	NPD1512	Approved
0.8446	Intermediate Similarity	NPD7819	Suspended
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD3750	Approved
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.831	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1203	Approved
0.8261	Intermediate Similarity	NPD943	Approved
0.8212	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD2654	Approved
0.8169	Intermediate Similarity	NPD2344	Approved
0.8163	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD3749	Approved
0.8146	Intermediate Similarity	NPD3817	Phase 2
0.8102	Intermediate Similarity	NPD6832	Phase 2
0.8088	Intermediate Similarity	NPD2798	Approved
0.8077	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6166	Phase 2
0.8077	Intermediate Similarity	NPD9493	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.806	Intermediate Similarity	NPD3972	Approved
0.806	Intermediate Similarity	NPD9717	Approved
0.8056	Intermediate Similarity	NPD1243	Approved
0.8028	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3748	Approved
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.8027	Intermediate Similarity	NPD5401	Approved
0.8027	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD2534	Approved
0.8027	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7955	Intermediate Similarity	NPD9545	Approved
0.7945	Intermediate Similarity	NPD2309	Approved
0.7937	Intermediate Similarity	NPD5953	Discontinued
0.7925	Intermediate Similarity	NPD7286	Phase 2
0.7925	Intermediate Similarity	NPD7054	Approved
0.7925	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD920	Approved
0.7891	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7875	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7821	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD3268	Approved
0.773	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2313	Discontinued
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7673	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7655	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1610	Phase 2
0.7582	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD1933	Approved
0.7569	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3225	Approved
0.7554	Intermediate Similarity	NPD1876	Approved
0.7534	Intermediate Similarity	NPD4308	Phase 3
0.7532	Intermediate Similarity	NPD919	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7464	Intermediate Similarity	NPD1201	Approved
0.7462	Intermediate Similarity	NPD9266	Approved
0.7462	Intermediate Similarity	NPD74	Approved
0.7448	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD1019	Discontinued
0.7439	Intermediate Similarity	NPD1729	Discontinued
0.7438	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9494	Approved
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD9263	Approved
0.7385	Intermediate Similarity	NPD9264	Approved
0.7385	Intermediate Similarity	NPD9267	Approved
0.7376	Intermediate Similarity	NPD3267	Approved
0.7376	Intermediate Similarity	NPD3266	Approved
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7361	Intermediate Similarity	NPD1296	Phase 2
0.7349	Intermediate Similarity	NPD6104	Discontinued
0.7342	Intermediate Similarity	NPD4288	Approved
0.7342	Intermediate Similarity	NPD2296	Approved
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.7261	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3140	Approved
0.726	Intermediate Similarity	NPD4307	Phase 2
0.726	Intermediate Similarity	NPD3142	Approved
0.7241	Intermediate Similarity	NPD4361	Phase 2
0.7241	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6798	Discontinued
0.7237	Intermediate Similarity	NPD2354	Approved
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4662	Approved
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7153	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7132	Intermediate Similarity	NPD9281	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD9268	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7113	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD3751	Discontinued
0.7107	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD6280	Approved
0.7107	Intermediate Similarity	NPD6279	Approved
0.7103	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7091	Intermediate Similarity	NPD2403	Approved
0.7086	Intermediate Similarity	NPD2355	Clinical (unspecified phase)

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