NPASS Compound

Structure

CID191104 OpenBabel06191715572D 25 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 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 -1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 -2.5981 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 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 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.15
Volume:	360.172
LogP:	5.912
LogD:	4.502
LogS:	-6.232
# Rotatable Bonds:	6
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	2.858
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	1.9385202904231846e-05
Pgp-inhibitor:	0.732
Pgp-substrate:	0.128
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.134
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.64766693115234%
Volume Distribution (VD):	1.028
Pgp-substrate:	8.808755874633789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.747
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.717
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	10.8
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.394
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.719
Respiratory Toxicity:	0.612

Download Data

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

Natural Product: NPC191104

Natural Product ID:	NPC191104
*Common Name:**	Bergamottin
IUPAC Name:	4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
Synonyms:	Bergomottin
Standard InCHIKey:	DBMJZOMNXBSRED-OQLLNIDSSA-N
Standard InCHI:	InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
SMILES:	CC(=CCC/C(=C/COc1c2ccc(=O)oc2cc2c1cco2)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078442
PubChem CID:	5471349
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO30686	Citrus hystrix	Species	Rutaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[20964319]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7279	Ferulago capillaries	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7279	Ferulago capillaries	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	57
IC50	2
Ki	9
Others	18
Potency	10

Activity Type	# Activity
Cell Line	63
Individual Protein	33

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	2420.0	nM	PMID[489233]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	12589.3	nM	PMID[489234]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	50118.7	nM	PMID[489235]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	10.0	nM	PMID[489234]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	25118.9	nM	PMID[489234]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	63.1	nM	PMID[489234]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	31.6	nM	PMID[489234]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[489235]
NPT627	Individual Protein	Cytochrome P450 2B6	Homo sapiens	Ki	=	5200.0	nM	PMID[489237]
NPT627	Individual Protein	Cytochrome P450 2B6	Homo sapiens	Kinact	=	0.087	min-1	PMID[489237]
NPT241	Individual Protein	Cytochrome P450 2E1	Homo sapiens	Ki	=	40000.0	nM	PMID[489237]
NPT241	Individual Protein	Cytochrome P450 2E1	Homo sapiens	Kinact	=	0.08	min-1	PMID[489237]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	7700.0	nM	PMID[489237]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.3	min-1	PMID[489237]
NPT4023	Individual Protein	Cytochrome P450 3A5	Homo sapiens	Ki	=	20000.0	nM	PMID[489237]
NPT4023	Individual Protein	Cytochrome P450 3A5	Homo sapiens	Kinact	=	0.045	min-1	PMID[489237]
NPT5073	Individual Protein	Cytochrome P450 2B4	Oryctolagus cuniculus	Ki	=	2800.0	nM	PMID[489237]
NPT5073	Individual Protein	Cytochrome P450 2B4	Oryctolagus cuniculus	Kinact	=	0.068	min-1	PMID[489237]
NPT1775	Individual Protein	Cytochrome P450 2B1	Rattus norvegicus	Ki	=	2400.0	nM	PMID[489237]
NPT1775	Individual Protein	Cytochrome P450 2B1	Rattus norvegicus	Kinact	=	0.049	min-1	PMID[489237]
NPT627	Individual Protein	Cytochrome P450 2B6	Homo sapiens	Partition ratio	=	2.0	n.a.	PMID[489237]
NPT4023	Individual Protein	Cytochrome P450 3A5	Homo sapiens	Partition ratio	=	20.0	n.a.	PMID[489237]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[489235]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	38282.47	nM	PMID[489239]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	34673.69	nM	PMID[489239]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	27352.69	nM	PMID[489239]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	22803.42	nM	PMID[489239]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	21478.3	nM	PMID[489239]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	50234.26	nM	PMID[489239]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	16368.17	nM	PMID[489239]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	37153.52	nM	PMID[489239]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	14893.61	nM	PMID[489239]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	33496.54	nM	PMID[489239]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	22438.82	nM	PMID[489239]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	23067.47	nM	PMID[489239]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	25409.73	nM	PMID[489239]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	15381.55	nM	PMID[489239]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	43351.09	nM	PMID[489239]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	20606.3	nM	PMID[489239]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	34994.52	nM	PMID[489239]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	23768.4	nM	PMID[489239]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	43651.58	nM	PMID[489239]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	32284.94	nM	PMID[489239]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	15170.5	nM	PMID[489239]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	24434.31	nM	PMID[489239]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	42169.65	nM	PMID[489239]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	37757.22	nM	PMID[489239]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	32658.78	nM	PMID[489239]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	18967.06	nM	PMID[489239]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	27669.42	nM	PMID[489239]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	33806.48	nM	PMID[489239]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	17139.57	nM	PMID[489239]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	41399.97	nM	PMID[489239]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	44258.84	nM	PMID[489239]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	21037.78	nM	PMID[489239]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	16032.45	nM	PMID[489239]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	24945.95	nM	PMID[489239]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	28248.8	nM	PMID[489239]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	30408.85	nM	PMID[489239]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	54075.43	nM	PMID[489239]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	23768.4	nM	PMID[489239]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[489239]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	22233.1	nM	PMID[489239]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	29853.83	nM	PMID[489239]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	19275.25	nM	PMID[489239]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	27542.29	nM	PMID[489239]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	29853.83	nM	PMID[489239]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	10715.19	nM	PMID[489239]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	43954.16	nM	PMID[489239]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	34593.94	nM	PMID[489239]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	25409.73	nM	PMID[489239]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	39536.66	nM	PMID[489239]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	48083.93	nM	PMID[489239]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[489239]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	32359.37	nM	PMID[489239]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[489239]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	30060.76	nM	PMID[489239]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[489239]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	59156.16	nM	PMID[489239]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[489239]
NPT1631	Individual Protein	Solute carrier organic anion transporter family member 1A5	Rattus norvegicus	Activity	=	22.0	%	PMID[489240]
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	Activity	=	40.0	%	PMID[489241]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ratio	=	0.04	/uM/min	PMID[489245]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	Ki	=	587000.0	nM	PMID[489247]
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	=	9.4	uM	PMID[489249]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	=	2.2	uM	PMID[489249]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	4.6	uM	PMID[489249]
NPT461	Cell Line	PANC-1	Homo sapiens	Activity	=	100.0	%	PMID[489249]
NPT461	Cell Line	PANC-1	Homo sapiens	Activity	=	30.0	%	PMID[489249]
NPT461	Cell Line	PANC-1	Homo sapiens	Inhibition	=	100.0	%	PMID[489249]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	32200.0	nM	PMID[489238]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	34800.0	nM	PMID[489238]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	700.0	nM	PMID[489238]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	EC200	=	0.035	uM	PMID[489242]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[489235]

☑ 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 NPC191104 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	418
0.1-0.2	1759
0.2-0.3	4470
0.3-0.4	10540
0.4-0.5	8111
0.5-0.6	4559
0.6-0.7	5767
0.7-0.8	5263
0.8-0.85	1199
0.85-0.9	478
0.9-0.95	121
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC88445
0.979	High Similarity	NPC304443
0.979	High Similarity	NPC74539
0.965	High Similarity	NPC246903
0.9597	High Similarity	NPC269495
0.9586	High Similarity	NPC266743
0.9514	High Similarity	NPC208584
0.951	High Similarity	NPC51146
0.951	High Similarity	NPC313036
0.951	High Similarity	NPC166858
0.947	High Similarity	NPC49009
0.9463	High Similarity	NPC295608
0.9463	High Similarity	NPC250769
0.9463	High Similarity	NPC278010
0.9448	High Similarity	NPC190572
0.9408	High Similarity	NPC14822
0.9396	High Similarity	NPC131725
0.9342	High Similarity	NPC95472
0.9342	High Similarity	NPC169
0.9342	High Similarity	NPC239270
0.9342	High Similarity	NPC303210
0.9338	High Similarity	NPC270044
0.9324	High Similarity	NPC148423
0.9324	High Similarity	NPC135303
0.9324	High Similarity	NPC155882
0.9306	High Similarity	NPC254010
0.9301	High Similarity	NPC262635
0.9252	High Similarity	NPC198427
0.9236	High Similarity	NPC470856
0.92	High Similarity	NPC130015
0.92	High Similarity	NPC38361
0.9195	High Similarity	NPC472406
0.9189	High Similarity	NPC306788
0.9167	High Similarity	NPC472515
0.9167	High Similarity	NPC155264
0.9167	High Similarity	NPC67450
0.9167	High Similarity	NPC210460
0.9167	High Similarity	NPC193881
0.9161	High Similarity	NPC253616
0.9156	High Similarity	NPC216092
0.9139	High Similarity	NPC41719
0.9133	High Similarity	NPC472407
0.9097	High Similarity	NPC36414
0.9091	High Similarity	NPC243509
0.9091	High Similarity	NPC268081
0.9079	High Similarity	NPC233776
0.9073	High Similarity	NPC263676
0.9048	High Similarity	NPC17262
0.9038	High Similarity	NPC179464
0.9034	High Similarity	NPC136095
0.9026	High Similarity	NPC33320
0.902	High Similarity	NPC160015
0.902	High Similarity	NPC247677
0.9007	High Similarity	NPC98028
0.9	High Similarity	NPC37226
0.9	High Similarity	NPC226644
0.8974	High Similarity	NPC78612
0.8974	High Similarity	NPC234536
0.8968	High Similarity	NPC115432
0.8968	High Similarity	NPC260296
0.8961	High Similarity	NPC260902
0.8961	High Similarity	NPC296957
0.8958	High Similarity	NPC472516
0.8904	High Similarity	NPC473209
0.8903	High Similarity	NPC244750
0.8903	High Similarity	NPC476350
0.8903	High Similarity	NPC476349
0.8897	High Similarity	NPC103001
0.8896	High Similarity	NPC470625
0.8889	High Similarity	NPC1477
0.8889	High Similarity	NPC213608
0.8889	High Similarity	NPC122365
0.8882	High Similarity	NPC290671
0.8882	High Similarity	NPC170169
0.8882	High Similarity	NPC116604
0.8875	High Similarity	NPC144288
0.8874	High Similarity	NPC296030
0.8874	High Similarity	NPC39929
0.8874	High Similarity	NPC317492
0.8867	High Similarity	NPC130581
0.8867	High Similarity	NPC12148
0.8861	High Similarity	NPC179015
0.8861	High Similarity	NPC173149
0.8859	High Similarity	NPC171656
0.8839	High Similarity	NPC65504
0.8831	High Similarity	NPC198490
0.8831	High Similarity	NPC474542
0.8828	High Similarity	NPC254741
0.8828	High Similarity	NPC29638
0.8824	High Similarity	NPC5871
0.8824	High Similarity	NPC67654
0.8816	High Similarity	NPC230713
0.8816	High Similarity	NPC78335
0.8808	High Similarity	NPC168085
0.8808	High Similarity	NPC135325
0.8805	High Similarity	NPC323137
0.88	High Similarity	NPC210826
0.88	High Similarity	NPC300267
0.88	High Similarity	NPC51641
0.8797	High Similarity	NPC65846
0.8797	High Similarity	NPC155640
0.8792	High Similarity	NPC184702
0.8773	High Similarity	NPC107244
0.8773	High Similarity	NPC325176
0.8767	High Similarity	NPC38153
0.8766	High Similarity	NPC183874
0.8766	High Similarity	NPC472462
0.8765	High Similarity	NPC233956
0.8765	High Similarity	NPC72455
0.8758	High Similarity	NPC51404
0.8758	High Similarity	NPC156244
0.875	High Similarity	NPC37208
0.875	High Similarity	NPC247743
0.875	High Similarity	NPC221868
0.875	High Similarity	NPC178202
0.875	High Similarity	NPC164299
0.8742	High Similarity	NPC259007
0.8742	High Similarity	NPC329215
0.8742	High Similarity	NPC204088
0.8741	High Similarity	NPC175159
0.8734	High Similarity	NPC193998
0.8733	High Similarity	NPC294365
0.8733	High Similarity	NPC179970
0.8712	High Similarity	NPC53917
0.8712	High Similarity	NPC224165
0.871	High Similarity	NPC108937
0.871	High Similarity	NPC148938
0.871	High Similarity	NPC279218
0.8701	High Similarity	NPC253872
0.8699	High Similarity	NPC161196
0.8693	High Similarity	NPC474735
0.869	High Similarity	NPC229128
0.8684	High Similarity	NPC272194
0.8681	High Similarity	NPC55147
0.8681	High Similarity	NPC54503
0.8681	High Similarity	NPC229646
0.8675	High Similarity	NPC473927
0.8675	High Similarity	NPC470322
0.8675	High Similarity	NPC154217
0.8671	High Similarity	NPC472517
0.8671	High Similarity	NPC264293
0.8667	High Similarity	NPC470932
0.8667	High Similarity	NPC302181
0.8667	High Similarity	NPC225884
0.8662	High Similarity	NPC40583
0.8658	High Similarity	NPC22467
0.8658	High Similarity	NPC297985
0.8654	High Similarity	NPC469936
0.8654	High Similarity	NPC474738
0.8654	High Similarity	NPC321372
0.8654	High Similarity	NPC129053
0.8654	High Similarity	NPC78554
0.8654	High Similarity	NPC474609
0.8654	High Similarity	NPC109967
0.8654	High Similarity	NPC475797
0.8649	High Similarity	NPC11566
0.8645	High Similarity	NPC186507
0.8645	High Similarity	NPC235333
0.8642	High Similarity	NPC120220
0.8642	High Similarity	NPC281835
0.8639	High Similarity	NPC259685
0.8636	High Similarity	NPC318424
0.8634	High Similarity	NPC320789
0.863	High Similarity	NPC46869
0.8625	High Similarity	NPC136641
0.8621	High Similarity	NPC223354
0.8621	High Similarity	NPC292998
0.8618	High Similarity	NPC471285
0.8618	High Similarity	NPC282335
0.8618	High Similarity	NPC17816
0.8618	High Similarity	NPC218300
0.8616	High Similarity	NPC219861
0.8609	High Similarity	NPC230943
0.8609	High Similarity	NPC1886
0.8609	High Similarity	NPC311741
0.8609	High Similarity	NPC196137
0.8609	High Similarity	NPC469953
0.8609	High Similarity	NPC234629
0.8608	High Similarity	NPC43971
0.8608	High Similarity	NPC19554
0.8608	High Similarity	NPC74749
0.86	High Similarity	NPC294432
0.86	High Similarity	NPC470556
0.86	High Similarity	NPC36181
0.86	High Similarity	NPC112829
0.86	High Similarity	NPC53192
0.86	High Similarity	NPC472344
0.8599	High Similarity	NPC268360
0.8599	High Similarity	NPC164110
0.8599	High Similarity	NPC96342
0.8599	High Similarity	NPC212967
0.8599	High Similarity	NPC246647
0.8591	High Similarity	NPC474037
0.8591	High Similarity	NPC472409
0.859	High Similarity	NPC213936
0.859	High Similarity	NPC297531
0.8589	High Similarity	NPC472584
0.8581	High Similarity	NPC476238
0.8581	High Similarity	NPC327269
0.8581	High Similarity	NPC207624

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 NPC191104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	972
0.2-0.3	1697
0.3-0.4	2731
0.4-0.5	1910
0.5-0.6	1014
0.6-0.7	316
0.7-0.8	102
0.8-0.85	26
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.979	High Similarity	NPD920	Approved
0.965	High Similarity	NPD642	Clinical (unspecified phase)
0.951	High Similarity	NPD643	Clinical (unspecified phase)
0.9301	High Similarity	NPD1243	Approved
0.9026	High Similarity	NPD919	Approved
0.8699	High Similarity	NPD2796	Approved
0.8671	High Similarity	NPD1247	Approved
0.8487	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8365	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8261	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8217	Intermediate Similarity	NPD6599	Discontinued
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.8146	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3748	Approved
0.8133	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2533	Approved
0.8129	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD2534	Approved
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8101	Intermediate Similarity	NPD4380	Phase 2
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8082	Intermediate Similarity	NPD6832	Phase 2
0.8079	Intermediate Similarity	NPD1551	Phase 2
0.8075	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD1240	Approved
0.7973	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2313	Discontinued
0.7964	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2344	Approved
0.7901	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1607	Approved
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.784	Intermediate Similarity	NPD2801	Approved
0.7824	Intermediate Similarity	NPD5953	Discontinued
0.7815	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7286	Phase 2
0.7799	Intermediate Similarity	NPD5403	Approved
0.7791	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD1934	Approved
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7725	Intermediate Similarity	NPD6808	Phase 2
0.7722	Intermediate Similarity	NPD1511	Approved
0.7707	Intermediate Similarity	NPD2309	Approved
0.7706	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5844	Phase 1
0.7703	Intermediate Similarity	NPD1019	Discontinued
0.7702	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6959	Discontinued
0.7636	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1512	Approved
0.7616	Intermediate Similarity	NPD1296	Phase 2
0.758	Intermediate Similarity	NPD2654	Approved
0.7564	Intermediate Similarity	NPD1471	Phase 3
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7561	Intermediate Similarity	NPD6279	Approved
0.7561	Intermediate Similarity	NPD6280	Approved
0.7551	Intermediate Similarity	NPD9717	Approved
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD3266	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD4307	Phase 2
0.7515	Intermediate Similarity	NPD5710	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7429	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6166	Phase 2
0.7419	Intermediate Similarity	NPD6651	Approved
0.7399	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD5890	Approved
0.7394	Intermediate Similarity	NPD5889	Approved
0.7386	Intermediate Similarity	NPD3268	Approved
0.7374	Intermediate Similarity	NPD4287	Approved
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7356	Intermediate Similarity	NPD7074	Phase 3
0.7356	Intermediate Similarity	NPD7472	Approved
0.7355	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5124	Phase 1
0.7355	Intermediate Similarity	NPD1933	Approved
0.7355	Intermediate Similarity	NPD447	Suspended
0.7351	Intermediate Similarity	NPD2798	Approved
0.7326	Intermediate Similarity	NPD2403	Approved
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7314	Intermediate Similarity	NPD6797	Phase 2
0.7305	Intermediate Similarity	NPD1465	Phase 2
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD7251	Discontinued
0.7257	Intermediate Similarity	NPD1729	Discontinued
0.7255	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD230	Phase 1
0.7232	Intermediate Similarity	NPD7808	Phase 3
0.723	Intermediate Similarity	NPD17	Approved
0.7229	Intermediate Similarity	NPD6585	Discontinued
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7216	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5760	Phase 2
0.7202	Intermediate Similarity	NPD5761	Phase 2
0.72	Intermediate Similarity	NPD3972	Approved
0.7168	Intermediate Similarity	NPD5242	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.716	Intermediate Similarity	NPD2296	Approved
0.716	Intermediate Similarity	NPD3887	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6004	Phase 3
0.7125	Intermediate Similarity	NPD6002	Phase 3
0.7125	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6005	Phase 3
0.7107	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3225	Approved
0.7095	Intermediate Similarity	NPD9545	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7081	Intermediate Similarity	NPD4361	Phase 2
0.7081	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD943	Approved
0.707	Intermediate Similarity	NPD2979	Phase 3
0.7066	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD5353	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7051	Intermediate Similarity	NPD3764	Approved
0.7051	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7027	Intermediate Similarity	NPD4360	Phase 2
0.7027	Intermediate Similarity	NPD4363	Phase 3
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD2353	Approved
0.7019	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7003	Approved
0.6993	Remote Similarity	NPD1876	Approved
0.6988	Remote Similarity	NPD6273	Approved
0.6982	Remote Similarity	NPD6385	Approved
0.6982	Remote Similarity	NPD6386	Approved
0.6975	Remote Similarity	NPD2424	Discontinued
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7390	Discontinued
0.6962	Remote Similarity	NPD3142	Approved
0.6962	Remote Similarity	NPD3140	Approved
0.6959	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9493	Approved
0.6957	Remote Similarity	NPD4477	Approved
0.6957	Remote Similarity	NPD4476	Approved
0.6948	Remote Similarity	NPD1164	Approved
0.6943	Remote Similarity	NPD6798	Discontinued
0.6941	Remote Similarity	NPD37	Approved
0.6933	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD4908	Phase 1
0.6919	Remote Similarity	NPD4966	Approved
0.6919	Remote Similarity	NPD4965	Approved
0.6919	Remote Similarity	NPD4967	Phase 2
0.6918	Remote Similarity	NPD5535	Approved
0.6908	Remote Similarity	NPD1281	Approved
0.6906	Remote Similarity	NPD8313	Approved
0.6906	Remote Similarity	NPD8312	Approved
0.6901	Remote Similarity	NPD8455	Phase 2
0.6889	Remote Similarity	NPD6104	Discontinued
0.6886	Remote Similarity	NPD5049	Phase 3
0.6886	Remote Similarity	NPD2186	Approved
0.6879	Remote Similarity	NPD6971	Discontinued
0.6878	Remote Similarity	NPD8285	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