NPASS Compound

Structure

CID68269 OpenBabel06191715402D 23 24 0 0 0 0 0 0 0 0999 V2000 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 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 -6.0622 -1.5000 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 -10.3923 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	328.864
LogP:	2.847
LogD:	2.917
LogS:	-3.427
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	2.301
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	1.5659381460864097e-05
Pgp-inhibitor:	0.174
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	99.2865219116211%
Volume Distribution (VD):	0.311
Pgp-substrate:	0.5844783782958984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.57
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.583
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	15.98
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.613
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.336
Skin Sensitization:	0.967
Carcinogencity:	0.457
Eye Corrosion:	0.01
Eye Irritation:	0.92
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC68269

Natural Product ID:	NPC68269
*Common Name:**	Bisdemethoxycurcumin
IUPAC Name:	(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Synonyms:	Bisdemethoxy Curcumin; Curcumin Lll
Standard InCHIKey:	PREBVFJICNPEKM-YDWXAUTNSA-N
Standard InCHI:	InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
SMILES:	c1cc(ccc1/C=C/C(=O)CC(=O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105350
PubChem CID:	5315472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO40808	Daucus Carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180819]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25160	Goniothalamus borneensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3532	Tridentata marginata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3251	Jacobaea maritima	Species	Asteraceae	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
NPO24124	NPC68269	Other	Rhizome	1403.35	6.7	2800	mg/100g	Database [DUKE]
NPO24124	NPC68269	Dried Or Powder	n.a.	1237.5	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO24124	NPC68269	n.a.	n.a.	1237.5	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

☑ 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	8
ED50	2
IC50	49
Ki	2
MIC	1
Others	66

Activity Type	# Activity
Cell Line	49
CELL-LINE	4
Individual Protein	18
NON-MOLECULAR	25
Organism	18
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	120000.0	nM	PMID[561350]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	80000.0	nM	PMID[561350]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	>	100000.0	nM	PMID[561351]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	13000.0	nM	PMID[561351]
NPT91	Cell Line	KB	Homo sapiens	CC50	=	8500.0	nM	PMID[561351]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	100000.0	nM	PMID[561352]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	36370.0	nM	PMID[561353]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	41.7	%	PMID[561353]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	33.2	%	PMID[561353]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	27300.0	nM	PMID[561356]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	19700.0	nM	PMID[561356]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	24300.0	nM	PMID[561356]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	21900.0	nM	PMID[561356]
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	3.1	ug ml-1	PMID[561357]
NPT3701	Individual Protein	CpG DNA methylase	Spiroplasma monobiae	IC50	=	30.0	nM	PMID[561360]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	2.0	ug ml-1	PMID[561361]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	3.5	ug ml-1	PMID[561361]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25120.0	nM	PMID[561362]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[561362]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	33780.0	nM	PMID[561362]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	30100.0	nM	PMID[561362]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	88100.0	nM	PMID[561362]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	=	200000.0	nM	PMID[561364]
NPT3704	Individual Protein	Multidrug resistance protein CDR1	Candida albicans	IC50	=	40000.0	nM	PMID[561367]
NPT1566	Individual Protein	Glyoxalase I	Homo sapiens	Ki	=	18000.0	nM	PMID[561368]
NPT1566	Individual Protein	Glyoxalase I	Homo sapiens	Ki	=	18200.0	nM	PMID[561370]
NPT1674	Individual Protein	CaM kinase II alpha	Homo sapiens	IC50	=	37000.0	nM	PMID[561371]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	2.0	%	PMID[561372]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	38500.0	nM	PMID[561373]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	62900.0	nM	PMID[561373]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	38100.0	nM	PMID[561373]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	18270.0	nM	PMID[561374]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	24000.0	nM	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	MEC	=	13.0	uM	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	>	50.0	%	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	48.0	%	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	53.0	%	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	57.0	%	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	51.0	%	PMID[561375]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	MTC	=	82.0	uM	PMID[561375]
NPT2132	Cell Line	EOL1	Homo sapiens	Inhibition	=	26.0	%	PMID[561377]
NPT2132	Cell Line	EOL1	Homo sapiens	Inhibition	=	3.0	%	PMID[561377]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	21440.0	nM	PMID[561378]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	75500.0	nM	PMID[561383]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	100.1	%	PMID[561384]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	88.8	%	PMID[561384]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	88.8	%	PMID[561384]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	69.4	%	PMID[561384]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	101.1	%	PMID[561384]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	95.4	%	PMID[561384]
NPT1161	Cell Line	CHO	Cricetulus griseus	Activity	=	101.0	%	PMID[561385]
NPT1161	Cell Line	CHO	Cricetulus griseus	Activity	=	105.0	%	PMID[561385]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	98.0	%	PMID[561385]
NPT492	Cell Line	Caco-2	Homo sapiens	Activity	=	83.0	%	PMID[561385]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	75.0	%	PMID[561385]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	69.0	%	PMID[561385]
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	60.0	nM	PMID[561386]
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	5100.0	nM	PMID[561386]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	40000.0	nM	PMID[561388]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48900.0	nM	PMID[561388]
NPT1527	Cell Line	WRL68	Homo sapiens	IC50	=	45400.0	nM	PMID[561388]
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	100000.0	nM	PMID[561388]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Activity	=	79.7	%	PMID[561389]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	11000000.0	nM	PMID[561389]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	7000.0	nM	PMID[561389]
NPT27	Others	Unspecified		Fold increase	=	0.9	n.a.	PMID[561351]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[561355]
NPT35	Others	n.a.		LogP	=	0.85	n.a.	PMID[561358]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	76.3	%	PMID[561359]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.4	%	PMID[561359]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	46.8	%	PMID[561359]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	38.3	%	PMID[561359]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	93.3	%	PMID[561362]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	7700.0	nM	PMID[561364]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	9500.0	nM	PMID[561364]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	4500.0	nM	PMID[561364]
NPT841	Organism	Leishmania major	Leishmania major	EC50	=	72000.0	nM	PMID[561364]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	EC50	=	63000.0	nM	PMID[561364]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	deltaA	=	0.37	n.a.	PMID[561365]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25.0	ug.mL-1	PMID[561366]
NPT1	Others	Radical scavenging activity		EC50	>	100000.0	nM	PMID[561369]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	7.13	%	PMID[561372]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	5.02	U/L	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	7.13	U/L	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	589.0	K/uL	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	485.0	K/uL	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	6.83	K/uL	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.69	K/uL	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	31.1	%	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	30.6	%	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.139	g	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.129	g	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.1	g	PMID[561375]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.987	g	PMID[561375]
NPT610	Others	Molecular identity unknown		Inhibition	=	100.3	%	PMID[561376]
NPT610	Others	Molecular identity unknown		Inhibition	=	69.1	%	PMID[561376]
NPT610	Others	Molecular identity unknown		Inhibition	=	77.7	%	PMID[561376]
NPT610	Others	Molecular identity unknown		Inhibition	=	72.5	%	PMID[561376]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22300.0	nM	PMID[561377]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	75.0	%	PMID[561379]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	logMIC	=	1.0	n.a.	PMID[561382]
NPT35	Others	n.a.		Solubility	=	3180.0	nM	PMID[561384]
NPT35	Others	n.a.		Solubility	=	4300.0	nM	PMID[561384]
NPT35	Others	n.a.		EC50	>	200000.0	nM	PMID[561384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[561384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	91400.0	nM	PMID[561384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54300.0	nM	PMID[561384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	104.6	%	PMID[561384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	107.9	%	PMID[561384]
NPT21728	CELL-LINE	EA.hy 926	Homo sapiens	Activity	=	95.8	%	PMID[561384]
NPT21728	CELL-LINE	EA.hy 926	Homo sapiens	Activity	=	104.6	%	PMID[561384]
NPT35	Others	n.a.		Solubility	=	25000.0	nM	PMID[561385]
NPT35	Others	n.a.		Inhibition	=	0.02	%	PMID[561385]
NPT35	Others	n.a.		Activity	=	0.28	uMequiv/uM	PMID[561385]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25000.0	nM	PMID[561385]
NPT21728	CELL-LINE	EA.hy 926	Homo sapiens	Activity	=	92.0	%	PMID[561385]
NPT21728	CELL-LINE	EA.hy 926	Homo sapiens	Activity	=	103.0	%	PMID[561385]

☑ 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 NPC68269 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	251
0.1-0.2	2033
0.2-0.3	5012
0.3-0.4	13132
0.4-0.5	5520
0.5-0.6	9285
0.6-0.7	6274
0.7-0.8	1054
0.8-0.85	98
0.85-0.9	26
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC130193
0.9579	High Similarity	NPC201967
0.9406	High Similarity	NPC88141
0.93	High Similarity	NPC70843
0.93	High Similarity	NPC95178
0.93	High Similarity	NPC29989
0.93	High Similarity	NPC69332
0.9135	High Similarity	NPC51698
0.9109	High Similarity	NPC188677
0.9	High Similarity	NPC135784
0.8958	High Similarity	NPC181709
0.8942	High Similarity	NPC222905
0.8942	High Similarity	NPC116842
0.8911	High Similarity	NPC120693
0.8911	High Similarity	NPC261573
0.8911	High Similarity	NPC8931
0.89	High Similarity	NPC472585
0.8785	High Similarity	NPC285350
0.8762	High Similarity	NPC21162
0.875	High Similarity	NPC17525
0.8704	High Similarity	NPC23402
0.8679	High Similarity	NPC297657
0.8673	High Similarity	NPC32977
0.8673	High Similarity	NPC81010
0.8673	High Similarity	NPC151715
0.8654	High Similarity	NPC260952
0.8624	High Similarity	NPC277394
0.8624	High Similarity	NPC299252
0.8624	High Similarity	NPC61062
0.8586	High Similarity	NPC26244
0.8586	High Similarity	NPC286006
0.8585	High Similarity	NPC183700
0.8532	High Similarity	NPC322197
0.8505	High Similarity	NPC177576
0.8505	High Similarity	NPC268388
0.85	High Similarity	NPC132271
0.85	High Similarity	NPC292730
0.85	High Similarity	NPC473388
0.85	High Similarity	NPC216520
0.85	High Similarity	NPC82664
0.8476	Intermediate Similarity	NPC141523
0.8469	Intermediate Similarity	NPC45040
0.8455	Intermediate Similarity	NPC19290
0.8416	Intermediate Similarity	NPC260000
0.8411	Intermediate Similarity	NPC321252
0.8411	Intermediate Similarity	NPC252544
0.8396	Intermediate Similarity	NPC206341
0.8381	Intermediate Similarity	NPC6984
0.835	Intermediate Similarity	NPC40258
0.835	Intermediate Similarity	NPC91461
0.835	Intermediate Similarity	NPC7686
0.8333	Intermediate Similarity	NPC51333
0.8333	Intermediate Similarity	NPC216468
0.8333	Intermediate Similarity	NPC78119
0.8333	Intermediate Similarity	NPC132078
0.8333	Intermediate Similarity	NPC280869
0.8333	Intermediate Similarity	NPC470355
0.8318	Intermediate Similarity	NPC95172
0.8318	Intermediate Similarity	NPC79543
0.8316	Intermediate Similarity	NPC265146
0.8304	Intermediate Similarity	NPC249435
0.8302	Intermediate Similarity	NPC226699
0.83	Intermediate Similarity	NPC128062
0.8283	Intermediate Similarity	NPC270547
0.8265	Intermediate Similarity	NPC280347
0.8265	Intermediate Similarity	NPC177420
0.8265	Intermediate Similarity	NPC98772
0.8257	Intermediate Similarity	NPC228988
0.8257	Intermediate Similarity	NPC286222
0.8252	Intermediate Similarity	NPC253746
0.8252	Intermediate Similarity	NPC213730
0.8247	Intermediate Similarity	NPC184169
0.8235	Intermediate Similarity	NPC140619
0.8229	Intermediate Similarity	NPC248817
0.8229	Intermediate Similarity	NPC175313
0.8218	Intermediate Similarity	NPC257182
0.8218	Intermediate Similarity	NPC246679
0.8218	Intermediate Similarity	NPC274678
0.819	Intermediate Similarity	NPC160900
0.819	Intermediate Similarity	NPC52087
0.819	Intermediate Similarity	NPC18984
0.819	Intermediate Similarity	NPC79672
0.819	Intermediate Similarity	NPC106659
0.819	Intermediate Similarity	NPC229084
0.8182	Intermediate Similarity	NPC55561
0.8163	Intermediate Similarity	NPC25493
0.8163	Intermediate Similarity	NPC113460
0.8163	Intermediate Similarity	NPC104216
0.8155	Intermediate Similarity	NPC245561
0.8155	Intermediate Similarity	NPC92730
0.8144	Intermediate Similarity	NPC197783
0.8137	Intermediate Similarity	NPC283711
0.8125	Intermediate Similarity	NPC124436
0.8125	Intermediate Similarity	NPC28951
0.8125	Intermediate Similarity	NPC128249
0.8125	Intermediate Similarity	NPC325646
0.8119	Intermediate Similarity	NPC76938
0.8113	Intermediate Similarity	NPC303141
0.8113	Intermediate Similarity	NPC243677
0.8113	Intermediate Similarity	NPC13495
0.8113	Intermediate Similarity	NPC127676
0.8103	Intermediate Similarity	NPC68167
0.8103	Intermediate Similarity	NPC86900
0.8095	Intermediate Similarity	NPC168829
0.8095	Intermediate Similarity	NPC470202
0.8095	Intermediate Similarity	NPC304638
0.8081	Intermediate Similarity	NPC123273
0.8081	Intermediate Similarity	NPC318325
0.8081	Intermediate Similarity	NPC242240
0.8077	Intermediate Similarity	NPC52472
0.8077	Intermediate Similarity	NPC223393
0.8073	Intermediate Similarity	NPC63345
0.807	Intermediate Similarity	NPC158222
0.8061	Intermediate Similarity	NPC23167
0.8058	Intermediate Similarity	NPC225464
0.8056	Intermediate Similarity	NPC317305
0.8039	Intermediate Similarity	NPC32714
0.8037	Intermediate Similarity	NPC1786
0.8037	Intermediate Similarity	NPC294902
0.8037	Intermediate Similarity	NPC1075
0.8019	Intermediate Similarity	NPC288411
0.8018	Intermediate Similarity	NPC242136
0.8017	Intermediate Similarity	NPC196976
0.8	Intermediate Similarity	NPC114682
0.8	Intermediate Similarity	NPC473136
0.8	Intermediate Similarity	NPC159525
0.8	Intermediate Similarity	NPC212718
0.8	Intermediate Similarity	NPC228609
0.8	Intermediate Similarity	NPC300017
0.7982	Intermediate Similarity	NPC471033
0.7982	Intermediate Similarity	NPC311091
0.7981	Intermediate Similarity	NPC275104
0.7963	Intermediate Similarity	NPC34715
0.7963	Intermediate Similarity	NPC228737
0.7944	Intermediate Similarity	NPC138942
0.7944	Intermediate Similarity	NPC233396
0.7944	Intermediate Similarity	NPC154899
0.7944	Intermediate Similarity	NPC219913
0.7944	Intermediate Similarity	NPC474839
0.7931	Intermediate Similarity	NPC60962
0.7931	Intermediate Similarity	NPC14007
0.7931	Intermediate Similarity	NPC269843
0.7931	Intermediate Similarity	NPC236520
0.7931	Intermediate Similarity	NPC109083
0.7931	Intermediate Similarity	NPC224814
0.7931	Intermediate Similarity	NPC294361
0.7931	Intermediate Similarity	NPC248363
0.7931	Intermediate Similarity	NPC189844
0.7928	Intermediate Similarity	NPC231717
0.7913	Intermediate Similarity	NPC141791
0.7913	Intermediate Similarity	NPC263386
0.7913	Intermediate Similarity	NPC182240
0.7913	Intermediate Similarity	NPC264976
0.7909	Intermediate Similarity	NPC208229
0.7909	Intermediate Similarity	NPC471535
0.7905	Intermediate Similarity	NPC248573
0.7905	Intermediate Similarity	NPC294741
0.7905	Intermediate Similarity	NPC275053
0.7905	Intermediate Similarity	NPC161571
0.79	Intermediate Similarity	NPC258219
0.7899	Intermediate Similarity	NPC197832
0.7895	Intermediate Similarity	NPC185738
0.7895	Intermediate Similarity	NPC280001
0.7895	Intermediate Similarity	NPC278652
0.789	Intermediate Similarity	NPC470039
0.789	Intermediate Similarity	NPC68260
0.789	Intermediate Similarity	NPC31274
0.789	Intermediate Similarity	NPC224584
0.789	Intermediate Similarity	NPC279887
0.7885	Intermediate Similarity	NPC32674
0.7881	Intermediate Similarity	NPC306100
0.7881	Intermediate Similarity	NPC285345
0.7876	Intermediate Similarity	NPC296526
0.787	Intermediate Similarity	NPC113457
0.787	Intermediate Similarity	NPC92623
0.787	Intermediate Similarity	NPC135464
0.787	Intermediate Similarity	NPC19149
0.7863	Intermediate Similarity	NPC115159
0.7863	Intermediate Similarity	NPC267552
0.7863	Intermediate Similarity	NPC45438
0.7863	Intermediate Similarity	NPC73532
0.7863	Intermediate Similarity	NPC19174
0.7863	Intermediate Similarity	NPC224273
0.7863	Intermediate Similarity	NPC143427
0.7857	Intermediate Similarity	NPC11824
0.7851	Intermediate Similarity	NPC221777
0.785	Intermediate Similarity	NPC93831
0.785	Intermediate Similarity	NPC119860
0.785	Intermediate Similarity	NPC323810
0.785	Intermediate Similarity	NPC471511
0.7845	Intermediate Similarity	NPC265454
0.7845	Intermediate Similarity	NPC34634
0.7843	Intermediate Similarity	NPC138117
0.7843	Intermediate Similarity	NPC325292
0.7843	Intermediate Similarity	NPC271440
0.7838	Intermediate Similarity	NPC139946
0.7833	Intermediate Similarity	NPC276014
0.783	Intermediate Similarity	NPC94343
0.7826	Intermediate Similarity	NPC184527
0.7826	Intermediate Similarity	NPC275519

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 NPC68269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	1023
0.2-0.3	1128
0.3-0.4	2942
0.4-0.5	2181
0.5-0.6	1187
0.6-0.7	395
0.7-0.8	55
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD2934	Approved
0.8673	High Similarity	NPD2933	Approved
0.8586	High Similarity	NPD2859	Approved
0.8586	High Similarity	NPD2860	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.819	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD111	Approved
0.7905	Intermediate Similarity	NPD1242	Phase 1
0.7895	Intermediate Similarity	NPD5536	Phase 2
0.7818	Intermediate Similarity	NPD3021	Approved
0.7818	Intermediate Similarity	NPD3022	Approved
0.7798	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3028	Approved
0.7542	Intermediate Similarity	NPD3019	Approved
0.7542	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7458	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD74	Approved
0.7411	Intermediate Similarity	NPD9266	Approved
0.7387	Intermediate Similarity	NPD3134	Approved
0.7373	Intermediate Similarity	NPD9545	Approved
0.7364	Intermediate Similarity	NPD1237	Approved
0.7358	Intermediate Similarity	NPD844	Approved
0.7358	Intermediate Similarity	NPD1809	Phase 2
0.7355	Intermediate Similarity	NPD3972	Approved
0.735	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD845	Approved
0.7333	Intermediate Similarity	NPD3847	Discontinued
0.7321	Intermediate Similarity	NPD9264	Approved
0.7321	Intermediate Similarity	NPD9263	Approved
0.7321	Intermediate Similarity	NPD9267	Approved
0.7321	Intermediate Similarity	NPD1358	Approved
0.7317	Intermediate Similarity	NPD1164	Approved
0.7317	Intermediate Similarity	NPD1470	Approved
0.7302	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD1535	Discovery
0.7241	Intermediate Similarity	NPD2229	Approved
0.7241	Intermediate Similarity	NPD2234	Approved
0.7241	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD2228	Approved
0.7232	Intermediate Similarity	NPD968	Approved
0.7213	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD9493	Approved
0.7188	Intermediate Similarity	NPD943	Approved
0.7177	Intermediate Similarity	NPD1203	Approved
0.717	Intermediate Similarity	NPD1202	Approved
0.7158	Intermediate Similarity	NPD9087	Approved
0.7155	Intermediate Similarity	NPD5535	Approved
0.713	Intermediate Similarity	NPD288	Approved
0.7119	Intermediate Similarity	NPD255	Approved
0.7119	Intermediate Similarity	NPD256	Approved
0.7097	Intermediate Similarity	NPD1876	Approved
0.7097	Intermediate Similarity	NPD3225	Approved
0.7091	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1894	Discontinued
0.7059	Intermediate Similarity	NPD9568	Approved
0.7054	Intermediate Similarity	NPD1240	Approved
0.7054	Intermediate Similarity	NPD9610	Approved
0.7054	Intermediate Similarity	NPD9608	Approved
0.7049	Intermediate Similarity	NPD3023	Approved
0.7049	Intermediate Similarity	NPD3026	Approved
0.7048	Intermediate Similarity	NPD9256	Approved
0.7048	Intermediate Similarity	NPD9258	Approved
0.7045	Intermediate Similarity	NPD2935	Discontinued
0.7041	Intermediate Similarity	NPD9088	Approved
0.704	Intermediate Similarity	NPD2797	Approved
0.7034	Intermediate Similarity	NPD9281	Approved
0.7031	Intermediate Similarity	NPD3268	Approved
0.7025	Intermediate Similarity	NPD3024	Approved
0.7025	Intermediate Similarity	NPD3025	Approved
0.7018	Intermediate Similarity	NPD2342	Discontinued
0.7009	Intermediate Similarity	NPD7635	Approved
0.7	Intermediate Similarity	NPD2066	Phase 3
0.6992	Remote Similarity	NPD2344	Approved
0.6984	Remote Similarity	NPD2798	Approved
0.697	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD1510	Phase 2
0.6967	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD9261	Approved
0.6957	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1607	Approved
0.6942	Remote Similarity	NPD1759	Phase 1
0.6942	Remote Similarity	NPD5303	Approved
0.6942	Remote Similarity	NPD5304	Approved
0.6942	Remote Similarity	NPD3091	Approved
0.6929	Remote Similarity	NPD4208	Discontinued
0.6929	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5406	Approved
0.6917	Remote Similarity	NPD5408	Approved
0.6917	Remote Similarity	NPD5405	Approved
0.6917	Remote Similarity	NPD5404	Approved
0.6911	Remote Similarity	NPD3421	Phase 3
0.6909	Remote Similarity	NPD9273	Approved
0.6897	Remote Similarity	NPD5451	Approved
0.6897	Remote Similarity	NPD1792	Phase 2
0.6897	Remote Similarity	NPD4750	Phase 3
0.6897	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4093	Discontinued
0.6885	Remote Similarity	NPD1651	Approved
0.688	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1758	Phase 1
0.6855	Remote Similarity	NPD422	Phase 1
0.6852	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9697	Approved
0.6838	Remote Similarity	NPD3750	Approved
0.6838	Remote Similarity	NPD8166	Discontinued
0.6829	Remote Similarity	NPD4589	Approved
0.6829	Remote Similarity	NPD2286	Discontinued
0.6829	Remote Similarity	NPD4059	Approved
0.6829	Remote Similarity	NPD4626	Approved
0.6822	Remote Similarity	NPD7095	Approved
0.6815	Remote Similarity	NPD1549	Phase 2
0.6814	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD1930	Approved
0.6814	Remote Similarity	NPD6647	Phase 2
0.6814	Remote Similarity	NPD1929	Approved
0.681	Remote Similarity	NPD2684	Approved
0.6807	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5283	Phase 1
0.6803	Remote Similarity	NPD1548	Phase 1
0.68	Remote Similarity	NPD2562	Approved
0.68	Remote Similarity	NPD9717	Approved
0.68	Remote Similarity	NPD2561	Approved
0.68	Remote Similarity	NPD9269	Phase 2
0.6797	Remote Similarity	NPD9494	Approved
0.6788	Remote Similarity	NPD2309	Approved
0.6788	Remote Similarity	NPD6190	Approved
0.6783	Remote Similarity	NPD1444	Approved
0.6783	Remote Similarity	NPD1445	Approved
0.678	Remote Similarity	NPD228	Approved
0.6772	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6798	Discontinued
0.6769	Remote Similarity	NPD2313	Discontinued
0.6768	Remote Similarity	NPD9294	Approved
0.6765	Remote Similarity	NPD9089	Approved
0.6754	Remote Similarity	NPD5909	Discontinued
0.675	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5951	Approved
0.6748	Remote Similarity	NPD9268	Approved
0.6746	Remote Similarity	NPD6583	Phase 3
0.6746	Remote Similarity	NPD1755	Approved
0.6746	Remote Similarity	NPD4659	Approved
0.6746	Remote Similarity	NPD6582	Phase 2
0.6744	Remote Similarity	NPD2614	Approved
0.6744	Remote Similarity	NPD4207	Discontinued
0.6741	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7266	Discontinued
0.6741	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD9716	Approved
0.6723	Remote Similarity	NPD9377	Approved
0.6723	Remote Similarity	NPD9379	Approved
0.6723	Remote Similarity	NPD7843	Approved
0.672	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3092	Approved
0.6719	Remote Similarity	NPD7451	Discontinued
0.6718	Remote Similarity	NPD4062	Phase 3
0.6718	Remote Similarity	NPD6233	Phase 2
0.6718	Remote Similarity	NPD6663	Approved
0.6716	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4628	Phase 3
0.6699	Remote Similarity	NPD3971	Phase 1
0.6696	Remote Similarity	NPD1238	Approved
0.6695	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6671	Approved
0.6694	Remote Similarity	NPD3095	Discontinued
0.6693	Remote Similarity	NPD5311	Approved
0.6693	Remote Similarity	NPD5310	Approved
0.6693	Remote Similarity	NPD1283	Approved
0.6692	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD9257	Approved
0.6667	Remote Similarity	NPD9500	Approved
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD9259	Approved
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9093	Approved
0.6643	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3267	Approved
0.6641	Remote Similarity	NPD4103	Phase 2
0.6641	Remote Similarity	NPD3055	Approved
0.6641	Remote Similarity	NPD3266	Approved
0.6641	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3094	Phase 2
0.6641	Remote Similarity	NPD3053	Approved
0.664	Remote Similarity	NPD3496	Discontinued
0.6639	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD7440	Discontinued
0.6617	Remote Similarity	NPD6355	Discontinued
0.6617	Remote Similarity	NPD4340	Discontinued

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