NPASS Compound

Structure

CID276014 OpenBabel06191716082D 27 29 0 0 0 0 0 0 0 0999 V2000 8.6603 -3.0000 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 3.4641 0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 6.0622 -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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.15
Volume:	383.622
LogP:	3.441
LogD:	3.437
LogS:	-4.475
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.788
Synthetic Accessibility Score:	2.408
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.062
MDCK Permeability:	1.2664545465668198e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	99.62523651123047%
Volume Distribution (VD):	0.447
Pgp-substrate:	1.00130295753479%

ADMET: Metabolism

CYP1A2-inhibitor:	0.851
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.421
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	7.792
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.631
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.952
Carcinogencity:	0.78
Eye Corrosion:	0.004
Eye Irritation:	0.303
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC276014

Natural Product ID:	NPC276014
*Common Name:**	Cyclovalone
IUPAC Name:	(2E,6E)-2,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclohexan-1-one
Synonyms:	Cyclovalone; Divanilliden Cyclohexanone
Standard InCHIKey:	DHKKONBXGAAFTB-OTYYAQKOSA-N
Standard InCHI:	InChI=1S/C22H22O5/c1-26-20-12-14(6-8-18(20)23)10-16-4-3-5-17(22(16)25)11-15-7-9-19(24)21(13-15)27-2/h6-13,23-24H,3-5H2,1-2H3/b16-10+,17-11+
SMILES:	COc1cc(ccc1O)/C=C/1CCC/C(=Cc2ccc(c(c2)OC)O)/C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL17205
PubChem CID:	1550234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	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[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	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	4
GI50	69
IC50	23
Others	26
Potency	63

Activity Type	# Activity
Cell Line	92
Individual Protein	51
NON-MOLECULAR	6
Organism	8
Others	21
PROTEIN COMPLEX	3
Protein-Protein Interaction	4
SINGLE PROTEIN	1
Uncleic Acid	2

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	>	100000.0	nM	PMID[493815]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	2400.0	nM	PMID[493815]
NPT91	Cell Line	KB	Homo sapiens	CC50	=	6700.0	nM	PMID[493815]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	100000.0	nM	PMID[493816]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.9	uM	PMID[493817]
NPT1079	Individual Protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	111000.0	nM	PMID[493819]
NPT3887	Cell Line	CNE	Homo sapiens	IC50	=	17600.0	nM	PMID[493821]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10100.0	nM	PMID[493821]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	2600.0	nM	PMID[493824]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	63095.7	nM	PMID[493825]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	89125.1	nM	PMID[493825]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[493825]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[493825]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[493825]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	20000.0	nM	PMID[493825]
NPT5406	Individual Protein	Nucleotide-binding oligomerization domain-containing protein 2	Homo sapiens	EC50	=	9950.0	nM	PMID[493825]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[493825]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[493826]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	3749.0	nM	PMID[493825]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	IC50	>	100000.0	nM	PMID[493825]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[493825]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18348.9	nM	PMID[493825]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	=	4944.0	nM	PMID[493825]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	3596.5	nM	PMID[493825]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[493826]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[493825]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[493825]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[493827]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[493825]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[493827]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[493825]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	19011.5	nM	PMID[493825]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[493826]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	2376.84	nM	PMID[493828]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	2421.03	nM	PMID[493828]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	6745.28	nM	PMID[493828]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	2128.14	nM	PMID[493828]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	2055.89	nM	PMID[493828]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	1472.31	nM	PMID[493828]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	5199.96	nM	PMID[493828]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	2041.74	nM	PMID[493828]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	3467.37	nM	PMID[493828]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	2511.89	nM	PMID[493828]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	2172.7	nM	PMID[493828]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	3990.25	nM	PMID[493828]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	3221.07	nM	PMID[493828]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	2741.57	nM	PMID[493828]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	2831.39	nM	PMID[493828]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	2844.46	nM	PMID[493828]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	2084.49	nM	PMID[493828]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2910.72	nM	PMID[493828]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	1717.91	nM	PMID[493828]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	25099.9	nM	PMID[493826]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	9660.51	nM	PMID[493828]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	6151.77	nM	PMID[493828]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	5956.62	nM	PMID[493828]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	1513.56	nM	PMID[493828]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1282.33	nM	PMID[493828]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	5000.35	nM	PMID[493828]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2703.96	nM	PMID[493828]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	1857.8	nM	PMID[493828]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1573.98	nM	PMID[493828]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2870.78	nM	PMID[493828]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	2249.05	nM	PMID[493828]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	9074.3	nM	PMID[493826]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	5701.64	nM	PMID[493828]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	6095.37	nM	PMID[493828]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	1199.5	nM	PMID[493828]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	7345.14	nM	PMID[493828]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1671.09	nM	PMID[493828]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	3589.22	nM	PMID[493828]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	3564.51	nM	PMID[493828]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	2728.98	nM	PMID[493828]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	15170.5	nM	PMID[493828]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	2773.32	nM	PMID[493828]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	2999.16	nM	PMID[493828]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	2074.91	nM	PMID[493828]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	2338.84	nM	PMID[493828]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	2387.81	nM	PMID[493828]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	4325.14	nM	PMID[493828]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	6839.12	nM	PMID[493828]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	1845.02	nM	PMID[493828]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	1770.11	nM	PMID[493828]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	3655.95	nM	PMID[493828]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	2594.18	nM	PMID[493828]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	3288.52	nM	PMID[493828]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	3732.5	nM	PMID[493828]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1963.36	nM	PMID[493828]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	3126.08	nM	PMID[493828]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2811.9	nM	PMID[493828]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2766.94	nM	PMID[493828]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	2917.43	nM	PMID[493828]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	32196.8	nM	PMID[493826]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	4159.11	nM	PMID[493828]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	5011.87	nM	PMID[493828]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	2754.23	nM	PMID[493828]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	2065.38	nM	PMID[493828]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	1753.88	nM	PMID[493828]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	524.81	nM	PMID[493828]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[493825]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	6165.95	nM	PMID[493828]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	7603.26	nM	PMID[493828]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	3411.93	nM	PMID[493828]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	14223.29	nM	PMID[493828]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	2238.72	nM	PMID[493828]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	2741.57	nM	PMID[493828]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	5890.0	nM	PMID[493829]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	4430.0	nM	PMID[493829]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3730.0	nM	PMID[493829]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	13335.9	nM	PMID[493826]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[493825]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[493827]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[493825]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[493825]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[493825]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[493825]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[493825]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	31622.8	nM	PMID[493825]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[493825]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6680.0	nM	PMID[493830]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	32.0	%	PMID[493831]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	69.0	%	PMID[493831]
NPT1374	Cell Line	WI-38	Homo sapiens	Activity	=	58.0	%	PMID[493831]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	28.0	%	PMID[493831]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[493825]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[493827]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	651.3	nM	PMID[493825]
NPT1045	Cell Line	U2OS	Homo sapiens	Activity	=	57.6	%	PMID[493833]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[493825]
NPT2870	Cell Line	Sarcoma-180	Mus musculus	Activity	=	66.0	%	PMID[493834]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	=	4200.0	nM	PMID[493835]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	=	4400.0	nM	PMID[493835]
NPT27	Others	Unspecified		Fold increase	=	1.8	n.a.	PMID[493815]
NPT32	Organism	Mus musculus	Mus musculus	Free radical scavenging	=	30.0	%	PMID[493817]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	90.1	%	PMID[493818]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	96.0	%	PMID[493818]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4600.0	nM	PMID[493821]
NPT35	Others	n.a.		Activity	=	0.0	%	PMID[493821]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[493823]
NPT1	Others	Radical scavenging activity		IC50	=	316640.0	nM	PMID[493823]
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[493824]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[493825]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	=	5173.5	nM	PMID[493825]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	12589.3	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[493825]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[493825]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5358.2	nM	PMID[493826]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[493825]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[493827]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[493825]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	19952.6	nM	PMID[493825]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	50118.7	nM	PMID[493827]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[493827]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10691.0	nM	PMID[493826]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[493825]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	42561.5	nM	PMID[493825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	51850.0	nM	PMID[493830]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	66.8	%	PMID[493831]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	74.22	%	PMID[493831]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	>	200.0	nM	PMID[493832]
NPT2	Others	Unspecified		Potency	n.a.	5804.8	nM	PMID[493825]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[493825]
NPT610	Others	Molecular identity unknown		FC	=	7.9	n.a.	PMID[493833]
NPT610	Others	Molecular identity unknown		EC50	=	2600.0	nM	PMID[493833]
NPT610	Others	Molecular identity unknown		Inhibition	=	87.6	%	PMID[493833]
NPT610	Others	Molecular identity unknown		Inhibition	=	28.9	%	PMID[493833]
NPT610	Others	Molecular identity unknown		Inhibition	=	21.3	%	PMID[493833]
NPT610	Others	Molecular identity unknown		Inhibition	=	86.1	%	PMID[493833]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[493827]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[493825]
NPT2	Others	Unspecified		Potency	n.a.	19952.6	nM	PMID[493827]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[493825]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	7300.0	nM	PMID[493835]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.31	%	PMID[493837]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.231	n.a.	PMID[493838]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	5.467	%	PMID[493839]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.18	%	PMID[493840]

☑ 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 NPC276014 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	295
0.1-0.2	1455
0.2-0.3	4018
0.3-0.4	11401
0.4-0.5	6905
0.5-0.6	4334
0.6-0.7	9190
0.7-0.8	4717
0.8-0.85	283
0.85-0.9	62
0.9-0.95	36
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC151167
0.959	High Similarity	NPC276466
0.959	High Similarity	NPC123722
0.959	High Similarity	NPC5018
0.959	High Similarity	NPC123228
0.9583	High Similarity	NPC106659
0.9583	High Similarity	NPC160900
0.9583	High Similarity	NPC229084
0.9583	High Similarity	NPC18984
0.9508	High Similarity	NPC90128
0.9508	High Similarity	NPC84076
0.9508	High Similarity	NPC179777
0.9508	High Similarity	NPC303680
0.9496	High Similarity	NPC14007
0.9496	High Similarity	NPC189844
0.9496	High Similarity	NPC224814
0.9496	High Similarity	NPC158949
0.9496	High Similarity	NPC269843
0.9496	High Similarity	NPC109083
0.9496	High Similarity	NPC60962
0.9435	High Similarity	NPC304622
0.9339	High Similarity	NPC286573
0.9268	High Similarity	NPC257589
0.9268	High Similarity	NPC53305
0.9262	High Similarity	NPC4181
0.9262	High Similarity	NPC164778
0.9262	High Similarity	NPC257976
0.9262	High Similarity	NPC242372
0.9206	High Similarity	NPC66905
0.9194	High Similarity	NPC127937
0.9194	High Similarity	NPC92207
0.9187	High Similarity	NPC273686
0.9187	High Similarity	NPC312404
0.918	High Similarity	NPC114298
0.916	High Similarity	NPC280001
0.9055	High Similarity	NPC172673
0.9048	High Similarity	NPC226661
0.9032	High Similarity	NPC246704
0.9	High Similarity	NPC185738
0.896	High Similarity	NPC289459
0.8952	High Similarity	NPC163083
0.8943	High Similarity	NPC201777
0.8915	High Similarity	NPC239302
0.8906	High Similarity	NPC275724
0.8906	High Similarity	NPC319282
0.8906	High Similarity	NPC137427
0.8906	High Similarity	NPC215941
0.8906	High Similarity	NPC65935
0.8906	High Similarity	NPC244246
0.8906	High Similarity	NPC311419
0.8906	High Similarity	NPC123196
0.8898	High Similarity	NPC110313
0.8889	High Similarity	NPC213552
0.8889	High Similarity	NPC120225
0.8881	High Similarity	NPC472410
0.8852	High Similarity	NPC299406
0.8846	High Similarity	NPC327410
0.8815	High Similarity	NPC141817
0.8815	High Similarity	NPC192597
0.8815	High Similarity	NPC169214
0.8815	High Similarity	NPC176030
0.8815	High Similarity	NPC229218
0.881	High Similarity	NPC3221
0.8797	High Similarity	NPC284409
0.8788	High Similarity	NPC90431
0.877	High Similarity	NPC164706
0.877	High Similarity	NPC107588
0.877	High Similarity	NPC272471
0.877	High Similarity	NPC70744
0.877	High Similarity	NPC137537
0.877	High Similarity	NPC470626
0.876	High Similarity	NPC268317
0.875	High Similarity	NPC478215
0.8731	High Similarity	NPC474784
0.8712	High Similarity	NPC477301
0.871	High Similarity	NPC204466
0.8689	High Similarity	NPC293619
0.8689	High Similarity	NPC39793
0.8682	High Similarity	NPC83062
0.8682	High Similarity	NPC241354
0.8672	High Similarity	NPC16651
0.8672	High Similarity	NPC20287
0.8672	High Similarity	NPC12022
0.8672	High Similarity	NPC293641
0.8672	High Similarity	NPC32163
0.8672	High Similarity	NPC20404
0.8667	High Similarity	NPC78987
0.8667	High Similarity	NPC82336
0.8661	High Similarity	NPC197832
0.8661	High Similarity	NPC280767
0.8661	High Similarity	NPC87113
0.864	High Similarity	NPC177291
0.864	High Similarity	NPC194416
0.864	High Similarity	NPC70752
0.8636	High Similarity	NPC471110
0.8629	High Similarity	NPC242885
0.8629	High Similarity	NPC165133
0.8629	High Similarity	NPC95614
0.8629	High Similarity	NPC2058
0.8629	High Similarity	NPC232316
0.8629	High Similarity	NPC56214
0.8629	High Similarity	NPC117780
0.8629	High Similarity	NPC202474
0.8629	High Similarity	NPC227217
0.8607	High Similarity	NPC277394
0.8607	High Similarity	NPC299252
0.8607	High Similarity	NPC19290
0.8607	High Similarity	NPC61062
0.8605	High Similarity	NPC278308
0.8593	High Similarity	NPC288452
0.8593	High Similarity	NPC289690
0.8583	High Similarity	NPC20443
0.8583	High Similarity	NPC146886
0.8583	High Similarity	NPC60517
0.8583	High Similarity	NPC51698
0.8571	High Similarity	NPC204592
0.8571	High Similarity	NPC152209
0.8561	High Similarity	NPC475468
0.856	High Similarity	NPC207613
0.856	High Similarity	NPC471877
0.8551	High Similarity	NPC300603
0.8551	High Similarity	NPC91694
0.8548	High Similarity	NPC281298
0.8548	High Similarity	NPC310338
0.8527	High Similarity	NPC117237
0.8527	High Similarity	NPC203719
0.8516	High Similarity	NPC29008
0.8516	High Similarity	NPC67951
0.8516	High Similarity	NPC266705
0.8516	High Similarity	NPC228771
0.8507	High Similarity	NPC120852
0.8504	High Similarity	NPC238810
0.8504	High Similarity	NPC306100
0.8496	Intermediate Similarity	NPC4982
0.8496	Intermediate Similarity	NPC144662
0.8496	Intermediate Similarity	NPC5310
0.8496	Intermediate Similarity	NPC300776
0.8496	Intermediate Similarity	NPC176814
0.8496	Intermediate Similarity	NPC68779
0.8492	Intermediate Similarity	NPC113865
0.8492	Intermediate Similarity	NPC324571
0.8492	Intermediate Similarity	NPC473853
0.8492	Intermediate Similarity	NPC54872
0.8492	Intermediate Similarity	NPC343720
0.8492	Intermediate Similarity	NPC470212
0.8492	Intermediate Similarity	NPC312675
0.8492	Intermediate Similarity	NPC262156
0.8492	Intermediate Similarity	NPC184651
0.8492	Intermediate Similarity	NPC38996
0.8492	Intermediate Similarity	NPC160380
0.8487	Intermediate Similarity	NPC36108
0.8487	Intermediate Similarity	NPC233731
0.8487	Intermediate Similarity	NPC246358
0.8487	Intermediate Similarity	NPC7097
0.8485	Intermediate Similarity	NPC50763
0.8478	Intermediate Similarity	NPC160378
0.8478	Intermediate Similarity	NPC46880
0.8478	Intermediate Similarity	NPC16353
0.8478	Intermediate Similarity	NPC239608
0.8478	Intermediate Similarity	NPC224884
0.8478	Intermediate Similarity	NPC209085
0.8478	Intermediate Similarity	NPC46161
0.8468	Intermediate Similarity	NPC277460
0.8467	Intermediate Similarity	NPC110419
0.8456	Intermediate Similarity	NPC322021
0.845	Intermediate Similarity	NPC304630
0.845	Intermediate Similarity	NPC17837
0.845	Intermediate Similarity	NPC118584
0.8443	Intermediate Similarity	NPC294941
0.8433	Intermediate Similarity	NPC113295
0.8433	Intermediate Similarity	NPC252343
0.8429	Intermediate Similarity	NPC39361
0.8425	Intermediate Similarity	NPC85488
0.8425	Intermediate Similarity	NPC262253
0.8425	Intermediate Similarity	NPC71579
0.8425	Intermediate Similarity	NPC473411
0.8417	Intermediate Similarity	NPC207732
0.8406	Intermediate Similarity	NPC312256
0.8394	Intermediate Similarity	NPC29599
0.8394	Intermediate Similarity	NPC28398
0.8394	Intermediate Similarity	NPC326065
0.8387	Intermediate Similarity	NPC86947
0.8372	Intermediate Similarity	NPC9067
0.837	Intermediate Similarity	NPC324929
0.8359	Intermediate Similarity	NPC31344
0.8359	Intermediate Similarity	NPC317769
0.8359	Intermediate Similarity	NPC280704
0.8359	Intermediate Similarity	NPC285345
0.8359	Intermediate Similarity	NPC471693
0.8359	Intermediate Similarity	NPC244876
0.8358	Intermediate Similarity	NPC237594
0.8358	Intermediate Similarity	NPC119060
0.8358	Intermediate Similarity	NPC249791
0.8358	Intermediate Similarity	NPC476387
0.8358	Intermediate Similarity	NPC135127
0.8358	Intermediate Similarity	NPC111635
0.8357	Intermediate Similarity	NPC157133
0.8357	Intermediate Similarity	NPC73416
0.8357	Intermediate Similarity	NPC160777
0.8347	Intermediate Similarity	NPC297657

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 NPC276014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	868
0.2-0.3	1381
0.3-0.4	2719
0.4-0.5	1999
0.5-0.6	1171
0.6-0.7	649
0.7-0.8	93
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD4379	Clinical (unspecified phase)
0.9	High Similarity	NPD5536	Phase 2
0.8527	High Similarity	NPD9494	Approved
0.8347	Intermediate Similarity	NPD228	Approved
0.8065	Intermediate Similarity	NPD5283	Phase 1
0.8028	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD3027	Phase 3
0.7905	Intermediate Similarity	NPD2801	Approved
0.7838	Intermediate Similarity	NPD1934	Approved
0.7817	Intermediate Similarity	NPD8166	Discontinued
0.78	Intermediate Similarity	NPD3882	Suspended
0.7762	Intermediate Similarity	NPD6190	Approved
0.7742	Intermediate Similarity	NPD3022	Approved
0.7742	Intermediate Similarity	NPD3021	Approved
0.7721	Intermediate Similarity	NPD7095	Approved
0.7681	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3620	Phase 2
0.7667	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6798	Discontinued
0.766	Intermediate Similarity	NPD2935	Discontinued
0.7655	Intermediate Similarity	NPD1511	Approved
0.7655	Intermediate Similarity	NPD4357	Discontinued
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6233	Phase 2
0.7581	Intermediate Similarity	NPD1358	Approved
0.7566	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6166	Phase 2
0.7557	Intermediate Similarity	NPD1357	Approved
0.7557	Intermediate Similarity	NPD1651	Approved
0.7551	Intermediate Similarity	NPD1512	Approved
0.7537	Intermediate Similarity	NPD2982	Phase 2
0.7537	Intermediate Similarity	NPD2983	Phase 2
0.7518	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1241	Discontinued
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7467	Intermediate Similarity	NPD7028	Phase 2
0.7463	Intermediate Similarity	NPD2981	Phase 2
0.7463	Intermediate Similarity	NPD3972	Approved
0.7448	Intermediate Similarity	NPD4628	Phase 3
0.7448	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4110	Phase 3
0.7445	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3847	Discontinued
0.7429	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD1613	Approved
0.7429	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3145	Approved
0.741	Intermediate Similarity	NPD3144	Approved
0.74	Intermediate Similarity	NPD3455	Phase 2
0.74	Intermediate Similarity	NPD824	Approved
0.7395	Intermediate Similarity	NPD9296	Approved
0.7386	Intermediate Similarity	NPD3817	Phase 2
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1933	Approved
0.7376	Intermediate Similarity	NPD230	Phase 1
0.7376	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD2798	Approved
0.736	Intermediate Similarity	NPD3134	Approved
0.7358	Intermediate Similarity	NPD3818	Discontinued
0.7357	Intermediate Similarity	NPD2674	Phase 3
0.7357	Intermediate Similarity	NPD4062	Phase 3
0.7355	Intermediate Similarity	NPD6234	Discontinued
0.7353	Intermediate Similarity	NPD1876	Approved
0.7353	Intermediate Similarity	NPD1283	Approved
0.7343	Intermediate Similarity	NPD1510	Phase 2
0.7325	Intermediate Similarity	NPD6232	Discontinued
0.7319	Intermediate Similarity	NPD3018	Phase 2
0.7312	Intermediate Similarity	NPD7054	Approved
0.7305	Intermediate Similarity	NPD1240	Approved
0.7305	Intermediate Similarity	NPD1558	Phase 1
0.7305	Intermediate Similarity	NPD943	Approved
0.7299	Intermediate Similarity	NPD2797	Approved
0.7296	Intermediate Similarity	NPD7473	Discontinued
0.7287	Intermediate Similarity	NPD5535	Approved
0.7286	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD7458	Discontinued
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD7472	Approved
0.7259	Intermediate Similarity	NPD1535	Discovery
0.7255	Intermediate Similarity	NPD37	Approved
0.7246	Intermediate Similarity	NPD6584	Phase 3
0.7244	Intermediate Similarity	NPD2684	Approved
0.7239	Intermediate Similarity	NPD3019	Approved
0.7239	Intermediate Similarity	NPD4626	Approved
0.7237	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7219	Intermediate Similarity	NPD1653	Approved
0.7218	Intermediate Similarity	NPD1894	Discontinued
0.7212	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7003	Approved
0.7206	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD1607	Approved
0.7188	Intermediate Similarity	NPD5451	Approved
0.7178	Intermediate Similarity	NPD7685	Pre-registration
0.7174	Intermediate Similarity	NPD1203	Approved
0.7171	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5585	Approved
0.7163	Intermediate Similarity	NPD3764	Approved
0.7154	Intermediate Similarity	NPD7843	Approved
0.7152	Intermediate Similarity	NPD2821	Approved
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD3060	Approved
0.7133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1281	Approved
0.7123	Intermediate Similarity	NPD2344	Approved
0.7121	Intermediate Similarity	NPD7157	Approved
0.7117	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.7115	Intermediate Similarity	NPD4966	Approved
0.7115	Intermediate Similarity	NPD4967	Phase 2
0.7115	Intermediate Similarity	NPD4965	Approved
0.7111	Intermediate Similarity	NPD2932	Approved
0.7111	Intermediate Similarity	NPD6516	Phase 2
0.7111	Intermediate Similarity	NPD5846	Approved
0.7107	Intermediate Similarity	NPD2933	Approved
0.7107	Intermediate Similarity	NPD2934	Approved
0.7101	Intermediate Similarity	NPD2922	Phase 1
0.7101	Intermediate Similarity	NPD3225	Approved
0.7099	Intermediate Similarity	NPD5844	Phase 1
0.7097	Intermediate Similarity	NPD1465	Phase 2
0.7095	Intermediate Similarity	NPD3750	Approved
0.7091	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9545	Approved
0.7087	Intermediate Similarity	NPD968	Approved
0.7086	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1608	Approved
0.7078	Intermediate Similarity	NPD6386	Approved
0.7078	Intermediate Similarity	NPD6873	Phase 2
0.7078	Intermediate Similarity	NPD6385	Approved
0.7075	Intermediate Similarity	NPD1549	Phase 2
0.7073	Intermediate Similarity	NPD7251	Discontinued
0.707	Intermediate Similarity	NPD7075	Discontinued
0.7067	Intermediate Similarity	NPD6799	Approved
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7051	Intermediate Similarity	NPD5977	Approved
0.7051	Intermediate Similarity	NPD5978	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD2860	Approved
0.7047	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD5241	Discontinued
0.7044	Intermediate Similarity	NPD7199	Phase 2
0.7042	Intermediate Similarity	NPD5110	Phase 2
0.7042	Intermediate Similarity	NPD5109	Approved
0.7042	Intermediate Similarity	NPD5111	Phase 2
0.7042	Intermediate Similarity	NPD2313	Discontinued
0.7042	Intermediate Similarity	NPD5718	Phase 2
0.7042	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7228	Approved
0.703	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7808	Phase 3
0.7029	Intermediate Similarity	NPD6582	Phase 2
0.7029	Intermediate Similarity	NPD6583	Phase 3
0.7021	Intermediate Similarity	NPD4908	Phase 1
0.7021	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3020	Approved
0.7014	Intermediate Similarity	NPD4340	Discontinued
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7007	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3705	Approved
0.7	Intermediate Similarity	NPD7440	Discontinued
0.7	Intermediate Similarity	NPD5647	Approved
0.6993	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD6671	Approved
0.6987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD1778	Approved
0.6981	Remote Similarity	NPD5494	Approved
0.697	Remote Similarity	NPD7038	Approved
0.697	Remote Similarity	NPD7039	Approved
0.6966	Remote Similarity	NPD2492	Phase 1
0.6966	Remote Similarity	NPD6653	Approved
0.6962	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4534	Discontinued
0.6959	Remote Similarity	NPD2424	Discontinued
0.6957	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9717	Approved
0.695	Remote Similarity	NPD2861	Phase 2
0.6944	Remote Similarity	NPD825	Approved
0.6944	Remote Similarity	NPD826	Approved
0.6944	Remote Similarity	NPD2979	Phase 3
0.694	Remote Similarity	NPD9493	Approved
0.6939	Remote Similarity	NPD2796	Approved
0.6939	Remote Similarity	NPD2438	Suspended
0.6933	Remote Similarity	NPD2309	Approved
0.6929	Remote Similarity	NPD3267	Approved
0.6929	Remote Similarity	NPD3266	Approved
0.6929	Remote Similarity	NPD1470	Approved
0.6928	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7097	Phase 1
0.6913	Remote Similarity	NPD4162	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