NPASS Compound

Structure

CID280272 OpenBabel06191716082D 35 40 0 0 1 0 0 0 0 0999 V2000 3.7553 1.6754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8531 4.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1804 1.5221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0122 1.0062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8298 -5.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2366 -4.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7035 -2.3394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2568 3.8896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9114 -1.3613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6943 3.5806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5259 -0.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3669 0.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9510 3.5295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2475 -4.4755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5352 1.5732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8532 2.2934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0611 1.3152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9999 3.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3180 0.6461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8353 -5.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2475 -2.6484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7920 2.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6543 -3.5620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6488 -3.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7828 -1.0012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1590 1.9333 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6941 2.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4862 1.8822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9907 -1.9793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1683 -0.6921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8567 -2.4793 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9022 2.6024 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.4286 -6.1981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6452 3.1693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2294 1.2131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 5 6 2 0 0 0 0 5 20 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 30 1 0 0 0 0 10 32 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 13 27 1 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 32 1 0 0 0 0 17 4 1 6 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 11 1 1 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 24 31 1 0 0 0 0 25 11 1 6 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 26 32 1 1 0 0 0 27 28 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	475.28
Volume:	499.707
LogP:	4.315
LogD:	4.112
LogS:	-2.731
# Rotatable Bonds:	5
TPSA:	69.75
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.061
Fsp3:	0.517
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:	-5.686
MDCK Permeability:	8.026024261198472e-06
Pgp-inhibitor:	0.148
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.9
30% Bioavailability (F30%):	0.386

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	78.43457794189453%
Volume Distribution (VD):	2.468
Pgp-substrate:	13.146965026855469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.824
CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	5.203
Half-life (T1/2):	0.695

ADMET: Toxicity

hERG Blockers:	0.951
Human Hepatotoxicity (H-HT):	0.662
Drug-inuced Liver Injury (DILI):	0.871
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.705
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC280272

Natural Product ID:	NPC280272
*Common Name:**	Tubulosine
IUPAC Name:	(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol
Synonyms:	Tubulosine
Standard InCHIKey:	JRVWIILYWSBUMC-PRUVNFMMSA-N
Standard InCHI:	InChI=1S/C29H37N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-6,13-15,17,19,25-26,30-31,33H,4,7-12,16H2,1-3H3/t17-,19-,25+,26-/m0/s1
SMILES:	CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@H]1NCCc2c1[nH]c1c2cc(cc1)O)cc(c(c3)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518568
PubChem CID:	72341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514334]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1171883]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19500975]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1982768]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31513408]
NPO2719	Amauroascus aureus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5735362]
NPO24848	Acodontaster conspicuus	Species	Odontasteridae	Eukaryota	n.a.	Antarctic	n.a.	PMID[9358635]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23138	Swainsona salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18432	Poria corticola	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2719	Amauroascus aureus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24848	Acodontaster conspicuus	Species	Odontasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21010	Streptomyces avidinii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22548	Osteospermum jucundum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26637.1	Mentha aquatica var. citrata	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25098	Spinacia glabra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25360	Helminthosporium ravenelii	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25409	Ascochyta caulina	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24211	Parmelia cetrarioides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24521	Helichrysum revolutum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24880	Bacterial str	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23138	Swainsona salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24646	Coryphantha elephantidens	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23623	Hirsutella nivea	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5056	Helichrysum heterolasium	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

☑ 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
ED50	15
GI50	73
IC50	5
Others	15

Activity Type	# Activity
Cell Line	90
Individual Protein	1
NON-MOLECULAR	3
Organism	10
Others	1
PROTEIN FAMILY	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	<	1.0	10'-5 ug/ml	PMID[570074]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	1.0	10'-5 ug/ml	PMID[570074]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	<	1.0	10'-5 ug/ml	PMID[570074]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[570075]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	30.0	%	PMID[570076]
NPT168	Cell Line	P388	Mus musculus	Activity	=	80.0	%	PMID[570076]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[570076]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	0.05	ug ml-1	PMID[570076]
NPT91	Cell Line	KB	Homo sapiens	ED50	<	0.16	ug ml-1	PMID[570076]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.1	ug ml-1	PMID[570076]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	<	0.16	ug ml-1	PMID[570076]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	0.22	ug ml-1	PMID[570076]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	0.1	ug ml-1	PMID[570076]
NPT726	Cell Line	M109	Mus musculus	ED50	=	0.1	ug ml-1	PMID[570076]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	39.63	nM	PMID[570078]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	11.35	nM	PMID[570078]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	325.84	nM	PMID[570078]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	10.5	nM	PMID[570078]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	16.44	nM	PMID[570078]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	13.46	nM	PMID[570078]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	42.07	nM	PMID[570078]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	30.06	nM	PMID[570078]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	12.97	nM	PMID[570078]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	27.61	nM	PMID[570078]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	1733.8	nM	PMID[570078]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	10.3	nM	PMID[570078]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	15.35	nM	PMID[570078]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	12.53	nM	PMID[570078]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	215.28	nM	PMID[570078]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	38.82	nM	PMID[570078]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	11.89	nM	PMID[570078]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	24.55	nM	PMID[570078]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	18.79	nM	PMID[570078]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	12.47	nM	PMID[570078]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	12.39	nM	PMID[570078]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	13.27	nM	PMID[570078]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	10.0	nM	PMID[570078]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	191.43	nM	PMID[570078]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	15.31	nM	PMID[570078]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	13.68	nM	PMID[570078]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	10.5	nM	PMID[570078]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	383.71	nM	PMID[570078]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	10.21	nM	PMID[570078]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	29.38	nM	PMID[570078]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	10.47	nM	PMID[570078]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	15.56	nM	PMID[570078]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	22.23	nM	PMID[570078]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	20.23	nM	PMID[570078]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	10.64	nM	PMID[570078]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	10.19	nM	PMID[570078]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	18.2	nM	PMID[570078]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	12.5	nM	PMID[570078]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	493.17	nM	PMID[570078]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	56.89	nM	PMID[570078]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	15.7	nM	PMID[570078]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	19.5	nM	PMID[570078]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	38.73	nM	PMID[570078]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	16.9	nM	PMID[570078]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	58.21	nM	PMID[570078]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	13.61	nM	PMID[570078]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	27.86	nM	PMID[570078]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	11.32	nM	PMID[570078]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	21.13	nM	PMID[570078]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	16.0	nM	PMID[570078]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	45.39	nM	PMID[570078]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	10.0	nM	PMID[570078]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2100.0	nM	PMID[570081]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[570081]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	400.0	nM	PMID[570081]
NPT140	Organism	Artemia	Artemia	LC50	=	0.02	ppm	PMID[570074]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	81.0	%	PMID[570074]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.8	10'-4 ug/ml	PMID[570074]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	10'-2 ug/ml	PMID[570074]
NPT2	Others	Unspecified		T/C	=	186.0	%	PMID[570074]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.1	ug ml-1	PMID[570076]
NPT25088	PROTEIN FAMILY	Janus Kinase (JAK)	Homo sapiens	Inhibition	>	65.0	%	PMID[570077]
NPT25088	PROTEIN FAMILY	Janus Kinase (JAK)	Homo sapiens	Inhibition	=	25.0	%	PMID[570077]
NPT207	Protein Family	MAP kinase p38	Homo sapiens	Inhibition	=	25.0	%	PMID[570077]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	1.6	ug.mL-1	PMID[570079]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-12.49	%	PMID[570080]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	3.63	%	PMID[570080]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	10.54	%	PMID[570080]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	2.67	%	PMID[570080]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-8.19	%	PMID[570080]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	2.68	%	PMID[570080]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	-0.53	%	PMID[570080]

☑ 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 NPC280272 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	504
0.1-0.2	2559
0.2-0.3	13938
0.3-0.4	5109
0.4-0.5	13350
0.5-0.6	4165
0.6-0.7	2392
0.7-0.8	634
0.8-0.85	31
0.85-0.9	9
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9378	High Similarity	NPC295228
0.87	High Similarity	NPC249040
0.8663	High Similarity	NPC223427
0.8647	High Similarity	NPC266931
0.8522	High Similarity	NPC199277
0.8522	High Similarity	NPC135887
0.8454	Intermediate Similarity	NPC476116
0.8424	Intermediate Similarity	NPC329793
0.8381	Intermediate Similarity	NPC471080
0.8381	Intermediate Similarity	NPC469592
0.8333	Intermediate Similarity	NPC316981
0.8309	Intermediate Similarity	NPC472111
0.8257	Intermediate Similarity	NPC470126
0.823	Intermediate Similarity	NPC475910
0.8224	Intermediate Similarity	NPC469594
0.8219	Intermediate Similarity	NPC253580
0.8186	Intermediate Similarity	NPC213530
0.8186	Intermediate Similarity	NPC193267
0.8182	Intermediate Similarity	NPC193777
0.8178	Intermediate Similarity	NPC476041
0.8178	Intermediate Similarity	NPC304926
0.816	Intermediate Similarity	NPC112206
0.816	Intermediate Similarity	NPC202605
0.8131	Intermediate Similarity	NPC183407
0.8122	Intermediate Similarity	NPC478074
0.8107	Intermediate Similarity	NPC4071
0.8107	Intermediate Similarity	NPC476578
0.8107	Intermediate Similarity	NPC476582
0.8068	Intermediate Similarity	NPC329747
0.8066	Intermediate Similarity	NPC471304
0.804	Intermediate Similarity	NPC176127
0.8039	Intermediate Similarity	NPC307963
0.8019	Intermediate Similarity	NPC469589
0.8009	Intermediate Similarity	NPC313189
0.8	Intermediate Similarity	NPC476581
0.8	Intermediate Similarity	NPC475070
0.8	Intermediate Similarity	NPC16452
0.8	Intermediate Similarity	NPC36229
0.7991	Intermediate Similarity	NPC48353
0.799	Intermediate Similarity	NPC99666
0.7982	Intermediate Similarity	NPC472099
0.7981	Intermediate Similarity	NPC176538
0.7965	Intermediate Similarity	NPC473183
0.7961	Intermediate Similarity	NPC251090
0.7944	Intermediate Similarity	NPC208284
0.7941	Intermediate Similarity	NPC92111
0.7923	Intermediate Similarity	NPC70956
0.7923	Intermediate Similarity	NPC243834
0.7919	Intermediate Similarity	NPC312872
0.7907	Intermediate Similarity	NPC53069
0.7907	Intermediate Similarity	NPC296482
0.7907	Intermediate Similarity	NPC202768
0.7902	Intermediate Similarity	NPC133140
0.7902	Intermediate Similarity	NPC195268
0.7897	Intermediate Similarity	NPC123976
0.7897	Intermediate Similarity	NPC167860
0.7897	Intermediate Similarity	NPC290689
0.7895	Intermediate Similarity	NPC234197
0.7892	Intermediate Similarity	NPC76748
0.7876	Intermediate Similarity	NPC473184
0.786	Intermediate Similarity	NPC217554
0.7857	Intermediate Similarity	NPC31930
0.7848	Intermediate Similarity	NPC284685
0.7843	Intermediate Similarity	NPC296527
0.784	Intermediate Similarity	NPC135549
0.7832	Intermediate Similarity	NPC473182
0.783	Intermediate Similarity	NPC329708
0.783	Intermediate Similarity	NPC274291
0.783	Intermediate Similarity	NPC285558
0.783	Intermediate Similarity	NPC118832
0.783	Intermediate Similarity	NPC47059
0.783	Intermediate Similarity	NPC165349
0.783	Intermediate Similarity	NPC264166
0.7826	Intermediate Similarity	NPC131017
0.7822	Intermediate Similarity	NPC477531
0.7815	Intermediate Similarity	NPC191489
0.7812	Intermediate Similarity	NPC252251
0.781	Intermediate Similarity	NPC477019
0.7808	Intermediate Similarity	NPC96321
0.7805	Intermediate Similarity	NPC469497
0.7805	Intermediate Similarity	NPC106833
0.7793	Intermediate Similarity	NPC474145
0.7793	Intermediate Similarity	NPC475841
0.7783	Intermediate Similarity	NPC162484
0.7778	Intermediate Similarity	NPC209174
0.7773	Intermediate Similarity	NPC11408
0.7768	Intermediate Similarity	NPC473185
0.7767	Intermediate Similarity	NPC201697
0.7763	Intermediate Similarity	NPC305984
0.7759	Intermediate Similarity	NPC284141
0.7756	Intermediate Similarity	NPC128751
0.7756	Intermediate Similarity	NPC477186
0.7756	Intermediate Similarity	NPC246700
0.7751	Intermediate Similarity	NPC153042
0.7749	Intermediate Similarity	NPC478082
0.7749	Intermediate Similarity	NPC477067
0.7745	Intermediate Similarity	NPC204385
0.7745	Intermediate Similarity	NPC171171
0.7743	Intermediate Similarity	NPC201508
0.7742	Intermediate Similarity	NPC171409
0.7742	Intermediate Similarity	NPC96405
0.7738	Intermediate Similarity	NPC132642
0.7736	Intermediate Similarity	NPC475085
0.7736	Intermediate Similarity	NPC291535
0.7736	Intermediate Similarity	NPC475112
0.7734	Intermediate Similarity	NPC84478
0.7733	Intermediate Similarity	NPC314954
0.7733	Intermediate Similarity	NPC476997
0.7731	Intermediate Similarity	NPC5145
0.7731	Intermediate Similarity	NPC11464
0.7727	Intermediate Similarity	NPC204446
0.7723	Intermediate Similarity	NPC206201
0.7721	Intermediate Similarity	NPC470931
0.7719	Intermediate Similarity	NPC277351
0.7717	Intermediate Similarity	NPC148183
0.7717	Intermediate Similarity	NPC152768
0.7717	Intermediate Similarity	NPC469928
0.7711	Intermediate Similarity	NPC88363
0.77	Intermediate Similarity	NPC476098
0.7699	Intermediate Similarity	NPC476996
0.7699	Intermediate Similarity	NPC476998
0.7696	Intermediate Similarity	NPC314002
0.7689	Intermediate Similarity	NPC232727
0.7689	Intermediate Similarity	NPC6215
0.7686	Intermediate Similarity	NPC88923
0.7686	Intermediate Similarity	NPC100734
0.7686	Intermediate Similarity	NPC315634
0.7679	Intermediate Similarity	NPC21638
0.7675	Intermediate Similarity	NPC255800
0.7675	Intermediate Similarity	NPC96584
0.7672	Intermediate Similarity	NPC478081
0.7668	Intermediate Similarity	NPC162748
0.7661	Intermediate Similarity	NPC472098
0.7661	Intermediate Similarity	NPC94157
0.7655	Intermediate Similarity	NPC476994
0.7652	Intermediate Similarity	NPC184680
0.7647	Intermediate Similarity	NPC204717
0.7644	Intermediate Similarity	NPC214980
0.7632	Intermediate Similarity	NPC474192
0.7632	Intermediate Similarity	NPC475720
0.7629	Intermediate Similarity	NPC477066
0.7626	Intermediate Similarity	NPC149471
0.7626	Intermediate Similarity	NPC271215
0.7623	Intermediate Similarity	NPC477532
0.7619	Intermediate Similarity	NPC470785
0.7619	Intermediate Similarity	NPC470784
0.7617	Intermediate Similarity	NPC17437
0.7613	Intermediate Similarity	NPC473179
0.7611	Intermediate Similarity	NPC157931
0.7611	Intermediate Similarity	NPC478078
0.7609	Intermediate Similarity	NPC272549
0.7606	Intermediate Similarity	NPC267423
0.76	Intermediate Similarity	NPC472123
0.7598	Intermediate Similarity	NPC220765
0.7594	Intermediate Similarity	NPC128823
0.7589	Intermediate Similarity	NPC118121
0.7583	Intermediate Similarity	NPC77555
0.758	Intermediate Similarity	NPC251160
0.7578	Intermediate Similarity	NPC174049
0.7577	Intermediate Similarity	NPC311906
0.7571	Intermediate Similarity	NPC326634
0.7569	Intermediate Similarity	NPC199667
0.7569	Intermediate Similarity	NPC188420
0.7568	Intermediate Similarity	NPC473041
0.7568	Intermediate Similarity	NPC303658
0.756	Intermediate Similarity	NPC324149
0.7547	Intermediate Similarity	NPC72211
0.7546	Intermediate Similarity	NPC476106
0.7545	Intermediate Similarity	NPC310118
0.7538	Intermediate Similarity	NPC317430
0.7537	Intermediate Similarity	NPC72980
0.7532	Intermediate Similarity	NPC81939
0.7523	Intermediate Similarity	NPC473181
0.7512	Intermediate Similarity	NPC472108
0.7512	Intermediate Similarity	NPC139291
0.7511	Intermediate Similarity	NPC122463
0.75	Intermediate Similarity	NPC264176
0.75	Intermediate Similarity	NPC475666
0.75	Intermediate Similarity	NPC303374
0.75	Intermediate Similarity	NPC478080
0.7489	Intermediate Similarity	NPC100079
0.7489	Intermediate Similarity	NPC23614
0.7489	Intermediate Similarity	NPC173080
0.7479	Intermediate Similarity	NPC81175
0.7478	Intermediate Similarity	NPC469554
0.7478	Intermediate Similarity	NPC101543
0.7477	Intermediate Similarity	NPC170114
0.7477	Intermediate Similarity	NPC8022
0.7477	Intermediate Similarity	NPC315957
0.7477	Intermediate Similarity	NPC470799
0.7477	Intermediate Similarity	NPC330009
0.7476	Intermediate Similarity	NPC280964
0.7476	Intermediate Similarity	NPC114335
0.7476	Intermediate Similarity	NPC141915
0.7468	Intermediate Similarity	NPC82472
0.7467	Intermediate Similarity	NPC60621
0.7466	Intermediate Similarity	NPC162530
0.7456	Intermediate Similarity	NPC110151
0.7454	Intermediate Similarity	NPC476138
0.7454	Intermediate Similarity	NPC245816

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 NPC280272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	598
0.2-0.3	914
0.3-0.4	1203
0.4-0.5	2513
0.5-0.6	2399
0.6-0.7	1037
0.7-0.8	214
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8955	High Similarity	NPD5658	Approved
0.8374	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD4885	Approved
0.8269	Intermediate Similarity	NPD7222	Phase 2
0.8216	Intermediate Similarity	NPD5612	Discontinued
0.813	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD3920	Phase 2
0.8039	Intermediate Similarity	NPD1038	Approved
0.8009	Intermediate Similarity	NPD7453	Approved
0.8009	Intermediate Similarity	NPD7452	Approved
0.7982	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD4502	Phase 2
0.7917	Intermediate Similarity	NPD5903	Approved
0.7917	Intermediate Similarity	NPD5902	Approved
0.7907	Intermediate Similarity	NPD3815	Phase 1
0.7907	Intermediate Similarity	NPD3816	Phase 1
0.7902	Intermediate Similarity	NPD3924	Approved
0.7902	Intermediate Similarity	NPD3921	Approved
0.7902	Intermediate Similarity	NPD3923	Approved
0.7902	Intermediate Similarity	NPD3922	Approved
0.79	Intermediate Similarity	NPD5930	Phase 3
0.7877	Intermediate Similarity	NPD5530	Phase 1
0.7877	Intermediate Similarity	NPD3003	Approved
0.7871	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7956	Approved
0.7848	Intermediate Similarity	NPD7955	Approved
0.7844	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6494	Phase 2
0.783	Intermediate Similarity	NPD4039	Approved
0.783	Intermediate Similarity	NPD4122	Approved
0.783	Intermediate Similarity	NPD4036	Approved
0.783	Intermediate Similarity	NPD4037	Approved
0.783	Intermediate Similarity	NPD31	Approved
0.783	Intermediate Similarity	NPD4034	Approved
0.783	Intermediate Similarity	NPD4035	Approved
0.783	Intermediate Similarity	NPD4033	Approved
0.783	Intermediate Similarity	NPD32	Approved
0.783	Intermediate Similarity	NPD4038	Approved
0.7815	Intermediate Similarity	NPD7708	Approved
0.7773	Intermediate Similarity	NPD7194	Discontinued
0.774	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD7803	Approved
0.7675	Intermediate Similarity	NPD7558	Phase 2
0.7668	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7219	Approved
0.7668	Intermediate Similarity	NPD7221	Approved
0.7667	Intermediate Similarity	NPD7948	Phase 1
0.7664	Intermediate Similarity	NPD4795	Phase 2
0.7657	Intermediate Similarity	NPD8091	Phase 3
0.7656	Intermediate Similarity	NPD4418	Discontinued
0.7635	Intermediate Similarity	NPD4203	Approved
0.7635	Intermediate Similarity	NPD4204	Approved
0.7632	Intermediate Similarity	NPD7796	Approved
0.7632	Intermediate Similarity	NPD7797	Approved
0.7617	Intermediate Similarity	NPD8358	Approved
0.7607	Intermediate Similarity	NPD6230	Discontinued
0.7606	Intermediate Similarity	NPD4511	Phase 1
0.7598	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1768	Approved
0.7589	Intermediate Similarity	NPD1954	Phase 1
0.7568	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD2176	Approved
0.7512	Intermediate Similarity	NPD2175	Phase 3
0.7512	Intermediate Similarity	NPD2177	Approved
0.7511	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD8016	Phase 3
0.75	Intermediate Similarity	NPD5559	Phase 2
0.75	Intermediate Similarity	NPD6242	Discontinued
0.7489	Intermediate Similarity	NPD7620	Phase 2
0.7488	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1740	Approved
0.7477	Intermediate Similarity	NPD7112	Discontinued
0.7477	Intermediate Similarity	NPD1739	Approved
0.7475	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5939	Approved
0.7455	Intermediate Similarity	NPD5936	Approved
0.743	Intermediate Similarity	NPD3825	Phase 3
0.7417	Intermediate Similarity	NPD7859	Phase 2
0.7411	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6985	Discontinued
0.7406	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7671	Approved
0.7397	Intermediate Similarity	NPD2187	Approved
0.7397	Intermediate Similarity	NPD2189	Approved
0.7397	Intermediate Similarity	NPD7672	Approved
0.7387	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3763	Approved
0.7376	Intermediate Similarity	NPD4131	Phase 3
0.7376	Intermediate Similarity	NPD4083	Discontinued
0.7371	Intermediate Similarity	NPD4080	Discontinued
0.7352	Intermediate Similarity	NPD6290	Phase 2
0.7352	Intermediate Similarity	NPD1392	Approved
0.7348	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5913	Phase 3
0.7346	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6244	Phase 3
0.7333	Intermediate Similarity	NPD6243	Phase 3
0.7311	Intermediate Similarity	NPD6569	Phase 2
0.7308	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8403	Phase 1
0.7301	Intermediate Similarity	NPD3402	Phase 1
0.7297	Intermediate Similarity	NPD5066	Phase 2
0.7297	Intermediate Similarity	NPD5067	Phase 2
0.7294	Intermediate Similarity	NPD6991	Approved
0.7293	Intermediate Similarity	NPD7719	Discontinued
0.7289	Intermediate Similarity	NPD5164	Discontinued
0.7286	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8442	Discontinued
0.7282	Intermediate Similarity	NPD7479	Phase 2
0.7281	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4897	Phase 2
0.7273	Intermediate Similarity	NPD7298	Approved
0.7269	Intermediate Similarity	NPD3814	Phase 1
0.7265	Intermediate Similarity	NPD6963	Approved
0.7265	Intermediate Similarity	NPD6964	Approved
0.7261	Intermediate Similarity	NPD7675	Phase 3
0.7261	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7674	Phase 3
0.7241	Intermediate Similarity	NPD1325	Approved
0.7241	Intermediate Similarity	NPD1326	Approved
0.7241	Intermediate Similarity	NPD8512	Phase 3
0.724	Intermediate Similarity	NPD2916	Discontinued
0.7237	Intermediate Similarity	NPD5507	Approved
0.7237	Intermediate Similarity	NPD5506	Approved
0.7235	Intermediate Similarity	NPD484	Approved
0.7235	Intermediate Similarity	NPD4601	Approved
0.7235	Intermediate Similarity	NPD4600	Approved
0.722	Intermediate Similarity	NPD5065	Approved
0.7217	Intermediate Similarity	NPD6246	Approved
0.7212	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6634	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6633	Phase 2
0.7189	Intermediate Similarity	NPD8396	Approved
0.7189	Intermediate Similarity	NPD8395	Approved
0.7184	Intermediate Similarity	NPD8244	Phase 2
0.7171	Intermediate Similarity	NPD8364	Approved
0.7171	Intermediate Similarity	NPD8363	Approved
0.7167	Intermediate Similarity	NPD6969	Phase 2
0.7167	Intermediate Similarity	NPD6968	Phase 2
0.7163	Intermediate Similarity	NPD6590	Discontinued
0.7162	Intermediate Similarity	NPD7726	Phase 1
0.7162	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5256	Discontinued
0.7155	Intermediate Similarity	NPD6517	Phase 3
0.7155	Intermediate Similarity	NPD4875	Phase 3
0.7155	Intermediate Similarity	NPD4876	Phase 3
0.7154	Intermediate Similarity	NPD7169	Suspended
0.715	Intermediate Similarity	NPD6159	Phase 2
0.7149	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5905	Phase 1
0.7143	Intermediate Similarity	NPD6220	Phase 3
0.7123	Intermediate Similarity	NPD2383	Phase 1
0.7117	Intermediate Similarity	NPD5429	Discontinued
0.7115	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7603	Discontinued
0.711	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5632	Approved
0.7095	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5007	Approved
0.7078	Intermediate Similarity	NPD4558	Phase 2
0.7076	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8466	Approved
0.707	Intermediate Similarity	NPD8467	Approved
0.707	Intermediate Similarity	NPD8465	Approved
0.7067	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4996	Approved
0.7064	Intermediate Similarity	NPD4995	Approved
0.7056	Intermediate Similarity	NPD1856	Discontinued
0.7054	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3477	Phase 2
0.7051	Intermediate Similarity	NPD5512	Phase 3
0.7051	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3037	Phase 1
0.7048	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7426	Phase 1
0.7039	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4551	Phase 2
0.7033	Intermediate Similarity	NPD5539	Phase 2
0.7032	Intermediate Similarity	NPD4548	Discontinued
0.7032	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7395	Discontinued
0.7023	Intermediate Similarity	NPD5641	Discontinued
0.7021	Intermediate Similarity	NPD4925	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