NPASS Compound

Structure

CID206061 OpenBabel06191715592D 37 41 0 0 1 0 0 0 0 0999 V2000 -1.2400 3.4771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7929 3.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1495 -3.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3693 -1.0677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5510 3.4503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9287 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9254 0.0342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1121 -1.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1055 0.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2922 -0.9164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6735 -1.0554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2443 -0.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9753 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4742 1.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6559 0.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 0.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3081 -0.3407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9115 -2.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4742 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6559 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6490 1.9124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6490 0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8376 1.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8113 2.3951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4639 2.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0133 1.9112 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8244 0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1656 3.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8075 3.3720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3895 2.2007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5077 2.7538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2133 -3.0614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3693 -0.0341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6559 2.9335 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 30 1 0 0 0 0 2 30 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 25 2 0 0 0 0 21 36 1 0 0 0 0 22 25 1 0 0 0 0 22 37 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 26 28 1 1 0 0 0 26 31 1 0 0 0 0 27 30 1 0 0 0 0 27 32 2 0 0 0 0 28 29 1 6 0 0 0 28 33 1 0 0 0 0 29 18 1 6 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	505.21
Volume:	513.521
LogP:	3.206
LogD:	3.208
LogS:	-4.695
# Rotatable Bonds:	7
TPSA:	97.69
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.532
Synthetic Accessibility Score:	3.987
Fsp3:	0.345
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.274
MDCK Permeability:	5.493584103533067e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.74
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.162
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.524
Plasma Protein Binding (PPB):	81.38732147216797%
Volume Distribution (VD):	1.291
Pgp-substrate:	6.885787010192871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.619
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.3
CYP2C9-substrate:	0.3
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	9.019
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.407
Human Hepatotoxicity (H-HT):	0.608
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.447
Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.36
Skin Sensitization:	0.034
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.75

Download Data

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

Natural Product: NPC206061

Natural Product ID:	NPC206061
*Common Name:**	Rocaglamide
IUPAC Name:	(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Synonyms:	Rocaglamide
Standard InCHIKey:	DAPAQENNNINUPW-IDAMAFBJSA-N
Standard InCHI:	InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)N(C)C)O)c(OC)cc(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL438139
PubChem CID:	331783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0014-2999(92)90156-X]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO28468	Aglaia duperreana	Species	Meliaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np990242g]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1039/C39820001150]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1039/C39820001150]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775404]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11170675]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32958	Streptocaulon juventas	Species	Apocynaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[14640513]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO40939	Syzygium corticosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30057155]
NPO32958	Streptocaulon juventas	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120251]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496701]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214732]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868148]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8565	Dioscorea dumetorum	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8565	Dioscorea dumetorum	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1356	Bacillus circulans	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15626	Alternaria japonica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8565	Dioscorea dumetorum	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8409	Galium semiamictum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2867	Cotula coronopifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28468	Aglaia duperreana	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13865	Cucumaria chronhjelmi	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7567	Parmelia rigida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4528	Penicillium lapatayae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8281	Epimedium davidi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1360	Penicillium nordicum	Species	Aspergillaceae	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
AC50	2
EC50	3
ED50	4
GI50	60
IC50	22
Kd	1
MIC	3
Others	8
Potency	19

Activity Type	# Activity
Cell Line	70
Individual Protein	26
NON-MOLECULAR	5
Organism	9
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	156.0	%	PMID[487508]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.006	ug.mL-1	PMID[487508]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.006	ug.mL-1	PMID[487508]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	0.007	ug.mL-1	PMID[487508]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.005	ug.mL-1	PMID[487508]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	IC50	=	0.002	ug.mL-1	PMID[487508]
NPT672	Cell Line	TE-671	Homo sapiens	IC50	=	0.006	ug.mL-1	PMID[487508]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	=	2000.0	nM	PMID[487509]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	ED50	=	2.0	uM	PMID[487510]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	=	75.0	nM	PMID[487511]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	20.6	nM	PMID[487512]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	125.9	nM	PMID[487512]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	3.548	nM	PMID[487515]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	8.147	nM	PMID[487515]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	8.851	nM	PMID[487515]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3.436	nM	PMID[487515]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	15.85	nM	PMID[487515]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	13.77	nM	PMID[487515]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	3.828	nM	PMID[487515]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	8.091	nM	PMID[487515]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1.69	nM	PMID[487515]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	4.285	nM	PMID[487515]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	3.013	nM	PMID[487515]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	2.366	nM	PMID[487515]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	7.907	nM	PMID[487515]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	55.98	nM	PMID[487515]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1.919	nM	PMID[487515]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	9.727	nM	PMID[487515]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	6.053	nM	PMID[487515]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	30.55	nM	PMID[487515]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	9.908	nM	PMID[487515]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	10.91	nM	PMID[487515]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	7.762	nM	PMID[487515]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	267.3	nM	PMID[487515]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	14.55	nM	PMID[487515]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1.622	nM	PMID[487515]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2.992	nM	PMID[487515]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	10.4	nM	PMID[487515]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2.944	nM	PMID[487515]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	3.266	nM	PMID[487515]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	9.727	nM	PMID[487515]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	5.546	nM	PMID[487515]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	20.65	nM	PMID[487515]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1.914	nM	PMID[487515]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	58.34	nM	PMID[487515]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	19.68	nM	PMID[487515]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	3.532	nM	PMID[487515]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	9.354	nM	PMID[487515]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	2.891	nM	PMID[487515]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	17.58	nM	PMID[487515]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	3.162	nM	PMID[487515]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	8.492	nM	PMID[487515]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	2.924	nM	PMID[487515]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	20.32	nM	PMID[487515]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	5.754	nM	PMID[487515]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	8.356	nM	PMID[487515]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	2.188	nM	PMID[487515]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	2.704	nM	PMID[487515]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	6.761	nM	PMID[487515]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	3.597	nM	PMID[487515]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	29.24	nM	PMID[487515]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	4.498	nM	PMID[487515]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	6.124	nM	PMID[487515]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	8.75	nM	PMID[487515]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	18.37	nM	PMID[487515]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	9.528	nM	PMID[487515]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	3.664	nM	PMID[487515]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	11.27	nM	PMID[487515]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2.244	nM	PMID[487515]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	6.887	nM	PMID[487515]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	20.56	nM	PMID[487515]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	6.471	nM	PMID[487515]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[487512]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[487512]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[487512]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[487512]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.005	uM	PMID[487517]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	9.2	nM	PMID[487512]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7.3	nM	PMID[487512]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[487512]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	14.6	nM	PMID[487512]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	20.0	nM	PMID[487522]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	Kd	=	156.0	nM	PMID[487522]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	IC50	=	4.7	nM	PMID[487522]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	IC50	=	47.0	nM	PMID[487522]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	IC50	=	135.0	nM	PMID[487522]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	IC50	=	231.0	nM	PMID[487522]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[487507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	77.6	%	PMID[487508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	90.5	%	PMID[487508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	85.5	%	PMID[487508]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	83.8	%	PMID[487508]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	80.0	nM	PMID[487509]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	4000.0	nM	PMID[487511]
NPT2	Others	Unspecified		Potency	n.a.	51.7	nM	PMID[487512]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	75.0	nM	PMID[487513]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	75.0	nM	PMID[487514]
NPT2	Others	Unspecified		Potency	n.a.	112.2	nM	PMID[487512]
NPT2	Others	Unspecified		AC50	<	260.0	nM	PMID[487512]
NPT2	Others	Unspecified		AC50	=	889.0	nM	PMID[487512]
NPT2	Others	Unspecified		Potency	n.a.	100000.0	nM	PMID[487512]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	>	200.0	ug.mL-1	PMID[487516]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	>	200.0	ug ml-1	PMID[487516]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	=	200.0	ug.mL-1	PMID[487516]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	=	66.0	ug ml-1	PMID[487516]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	25.0	ug.mL-1	PMID[487516]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	35.0	ug ml-1	PMID[487516]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	>	200.0	ug.mL-1	PMID[487516]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	=	8.0	ug.mL-1	PMID[487516]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	0.9	ug.mL-1	PMID[487516]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	=	0.08	uM	PMID[487517]
NPT27	Others	Unspecified		ED50	>	50.0	uM	PMID[487517]
NPT2	Others	Unspecified		Potency	n.a.	163.6	nM	PMID[487512]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	6.5	nM	PMID[487512]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[487512]
NPT2	Others	Unspecified		Potency	n.a.	0.1	nM	PMID[487512]
NPT2	Others	Unspecified		Potency	n.a.	58.0	nM	PMID[487512]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[487512]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3900.0	nM	PMID[487519]
NPT2	Others	Unspecified		IC50	=	2600.0	nM	PMID[487519]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	70.0	nM	PMID[487520]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	120.0	nM	PMID[487521]

☑ 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 NPC206061 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	282
0.1-0.2	1192
0.2-0.3	3221
0.3-0.4	9605
0.4-0.5	9466
0.5-0.6	7039
0.6-0.7	10734
0.7-0.8	1127
0.8-0.85	19
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.948	High Similarity	NPC308709
0.9111	High Similarity	NPC235698
0.8962	High Similarity	NPC79130
0.8956	High Similarity	NPC169605
0.8859	High Similarity	NPC258128
0.8763	High Similarity	NPC293347
0.875	High Similarity	NPC73422
0.875	High Similarity	NPC310399
0.869	High Similarity	NPC329743
0.869	High Similarity	NPC209473
0.8588	High Similarity	NPC90336
0.8305	Intermediate Similarity	NPC254071
0.8305	Intermediate Similarity	NPC271755
0.8305	Intermediate Similarity	NPC149502
0.8305	Intermediate Similarity	NPC222665
0.8284	Intermediate Similarity	NPC87363
0.8283	Intermediate Similarity	NPC475349
0.8283	Intermediate Similarity	NPC475292
0.8283	Intermediate Similarity	NPC475565
0.8283	Intermediate Similarity	NPC475442
0.8232	Intermediate Similarity	NPC184607
0.8171	Intermediate Similarity	NPC470937
0.8167	Intermediate Similarity	NPC23593
0.815	Intermediate Similarity	NPC475624
0.8144	Intermediate Similarity	NPC20360
0.8118	Intermediate Similarity	NPC51543
0.8111	Intermediate Similarity	NPC107739
0.8077	Intermediate Similarity	NPC236089
0.8066	Intermediate Similarity	NPC263955
0.8022	Intermediate Similarity	NPC29587
0.7949	Intermediate Similarity	NPC14390
0.7949	Intermediate Similarity	NPC197125
0.7871	Intermediate Similarity	NPC470846
0.7853	Intermediate Similarity	NPC470936
0.7765	Intermediate Similarity	NPC212697
0.7735	Intermediate Similarity	NPC129578
0.7654	Intermediate Similarity	NPC92589
0.7637	Intermediate Similarity	NPC476459
0.7627	Intermediate Similarity	NPC189730
0.76	Intermediate Similarity	NPC474772
0.76	Intermediate Similarity	NPC472636
0.76	Intermediate Similarity	NPC474744
0.76	Intermediate Similarity	NPC472423
0.76	Intermediate Similarity	NPC471675
0.7571	Intermediate Similarity	NPC164152
0.7557	Intermediate Similarity	NPC31627
0.7557	Intermediate Similarity	NPC473996
0.7557	Intermediate Similarity	NPC327269
0.7557	Intermediate Similarity	NPC285623
0.7557	Intermediate Similarity	NPC476238
0.7556	Intermediate Similarity	NPC96031
0.7543	Intermediate Similarity	NPC472421
0.7542	Intermediate Similarity	NPC469479
0.7514	Intermediate Similarity	NPC476244
0.7514	Intermediate Similarity	NPC303950
0.75	Intermediate Similarity	NPC471676
0.75	Intermediate Similarity	NPC263384
0.75	Intermediate Similarity	NPC28724
0.75	Intermediate Similarity	NPC472580
0.75	Intermediate Similarity	NPC471229
0.75	Intermediate Similarity	NPC472420
0.75	Intermediate Similarity	NPC470810
0.75	Intermediate Similarity	NPC471677
0.75	Intermediate Similarity	NPC472422
0.75	Intermediate Similarity	NPC476335
0.75	Intermediate Similarity	NPC244577
0.7486	Intermediate Similarity	NPC277032
0.7486	Intermediate Similarity	NPC475621
0.7486	Intermediate Similarity	NPC476340
0.7474	Intermediate Similarity	NPC83019
0.7474	Intermediate Similarity	NPC469437
0.7473	Intermediate Similarity	NPC471286
0.7473	Intermediate Similarity	NPC309692
0.7473	Intermediate Similarity	NPC214279
0.7471	Intermediate Similarity	NPC14875
0.7459	Intermediate Similarity	NPC74854
0.7459	Intermediate Similarity	NPC30655
0.7459	Intermediate Similarity	NPC45124
0.7459	Intermediate Similarity	NPC186228
0.7458	Intermediate Similarity	NPC477957
0.7458	Intermediate Similarity	NPC210597
0.7458	Intermediate Similarity	NPC473236
0.7458	Intermediate Similarity	NPC217149
0.7458	Intermediate Similarity	NPC475790
0.7458	Intermediate Similarity	NPC216035
0.7457	Intermediate Similarity	NPC311144
0.7446	Intermediate Similarity	NPC88378
0.7446	Intermediate Similarity	NPC211713
0.7444	Intermediate Similarity	NPC40583
0.7443	Intermediate Similarity	NPC267117
0.743	Intermediate Similarity	NPC78554
0.743	Intermediate Similarity	NPC474609
0.743	Intermediate Similarity	NPC109967
0.743	Intermediate Similarity	NPC164427
0.743	Intermediate Similarity	NPC20530
0.743	Intermediate Similarity	NPC208152
0.743	Intermediate Similarity	NPC10754
0.743	Intermediate Similarity	NPC474738
0.743	Intermediate Similarity	NPC78492
0.743	Intermediate Similarity	NPC129053
0.743	Intermediate Similarity	NPC215917
0.743	Intermediate Similarity	NPC469936
0.743	Intermediate Similarity	NPC321372
0.743	Intermediate Similarity	NPC165483
0.743	Intermediate Similarity	NPC475797
0.7427	Intermediate Similarity	NPC307287
0.7423	Intermediate Similarity	NPC204580
0.7419	Intermediate Similarity	NPC472584
0.7416	Intermediate Similarity	NPC7989
0.7416	Intermediate Similarity	NPC20907
0.7416	Intermediate Similarity	NPC203080
0.7416	Intermediate Similarity	NPC100134
0.7416	Intermediate Similarity	NPC223701
0.7416	Intermediate Similarity	NPC209760
0.7416	Intermediate Similarity	NPC244250
0.7416	Intermediate Similarity	NPC469405
0.7416	Intermediate Similarity	NPC472583
0.7414	Intermediate Similarity	NPC299011
0.7409	Intermediate Similarity	NPC264938
0.7403	Intermediate Similarity	NPC220582
0.7403	Intermediate Similarity	NPC304839
0.7403	Intermediate Similarity	NPC476337
0.7401	Intermediate Similarity	NPC319910
0.7401	Intermediate Similarity	NPC278476
0.7401	Intermediate Similarity	NPC474023
0.7401	Intermediate Similarity	NPC474021
0.7401	Intermediate Similarity	NPC254412
0.7401	Intermediate Similarity	NPC262039
0.7401	Intermediate Similarity	NPC262038
0.7399	Intermediate Similarity	NPC113770
0.7396	Intermediate Similarity	NPC474687
0.7391	Intermediate Similarity	NPC43065
0.7391	Intermediate Similarity	NPC476277
0.7391	Intermediate Similarity	NPC53640
0.7391	Intermediate Similarity	NPC119589
0.7391	Intermediate Similarity	NPC82330
0.7386	Intermediate Similarity	NPC472628
0.7386	Intermediate Similarity	NPC317492
0.7377	Intermediate Similarity	NPC472581
0.7377	Intermediate Similarity	NPC63438
0.7377	Intermediate Similarity	NPC124038
0.7374	Intermediate Similarity	NPC108937
0.7374	Intermediate Similarity	NPC471116
0.7374	Intermediate Similarity	NPC470681
0.7374	Intermediate Similarity	NPC217706
0.7374	Intermediate Similarity	NPC207809
0.7374	Intermediate Similarity	NPC304207
0.7374	Intermediate Similarity	NPC477530
0.7374	Intermediate Similarity	NPC476169
0.7374	Intermediate Similarity	NPC48579
0.7374	Intermediate Similarity	NPC259710
0.7374	Intermediate Similarity	NPC477958
0.7374	Intermediate Similarity	NPC279218
0.7371	Intermediate Similarity	NPC470646
0.7371	Intermediate Similarity	NPC472918
0.7371	Intermediate Similarity	NPC473133
0.7371	Intermediate Similarity	NPC44721
0.7371	Intermediate Similarity	NPC122828
0.7371	Intermediate Similarity	NPC202494
0.7371	Intermediate Similarity	NPC308200
0.7371	Intermediate Similarity	NPC211466
0.7371	Intermediate Similarity	NPC3779
0.7371	Intermediate Similarity	NPC472627
0.7371	Intermediate Similarity	NPC47388
0.7371	Intermediate Similarity	NPC470670
0.7371	Intermediate Similarity	NPC176869
0.7371	Intermediate Similarity	NPC476182
0.7371	Intermediate Similarity	NPC40086
0.7366	Intermediate Similarity	NPC120220
0.7366	Intermediate Similarity	NPC91043
0.7366	Intermediate Similarity	NPC279209
0.7366	Intermediate Similarity	NPC102277
0.7363	Intermediate Similarity	NPC97812
0.736	Intermediate Similarity	NPC243171
0.736	Intermediate Similarity	NPC10807
0.736	Intermediate Similarity	NPC161881
0.736	Intermediate Similarity	NPC138288
0.736	Intermediate Similarity	NPC150123
0.736	Intermediate Similarity	NPC56232
0.736	Intermediate Similarity	NPC35567
0.736	Intermediate Similarity	NPC171651
0.736	Intermediate Similarity	NPC244583
0.7356	Intermediate Similarity	NPC303185
0.7356	Intermediate Similarity	NPC124780
0.7356	Intermediate Similarity	NPC87486
0.7356	Intermediate Similarity	NPC184649
0.7353	Intermediate Similarity	NPC475836
0.7349	Intermediate Similarity	NPC162801
0.7345	Intermediate Similarity	NPC476509
0.7345	Intermediate Similarity	NPC476185
0.7345	Intermediate Similarity	NPC321896
0.7345	Intermediate Similarity	NPC105136
0.7345	Intermediate Similarity	NPC471115
0.7345	Intermediate Similarity	NPC29777
0.7337	Intermediate Similarity	NPC3049
0.7337	Intermediate Similarity	NPC300053
0.7333	Intermediate Similarity	NPC198489
0.7333	Intermediate Similarity	NPC61112
0.733	Intermediate Similarity	NPC39195
0.733	Intermediate Similarity	NPC145467

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 NPC206061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	622
0.2-0.3	1271
0.3-0.4	2452
0.4-0.5	2455
0.5-0.6	1416
0.6-0.7	702
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7814	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7199	Phase 2
0.7409	Intermediate Similarity	NPD4363	Phase 3
0.7409	Intermediate Similarity	NPD4360	Phase 2
0.7377	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4361	Phase 2
0.7371	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7497	Discontinued
0.7263	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7466	Approved
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2238	Phase 2
0.72	Intermediate Similarity	NPD7213	Phase 3
0.72	Intermediate Similarity	NPD7212	Phase 2
0.7186	Intermediate Similarity	NPD2493	Approved
0.7186	Intermediate Similarity	NPD2494	Approved
0.7182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1934	Approved
0.7164	Intermediate Similarity	NPD4583	Approved
0.7164	Intermediate Similarity	NPD4582	Approved
0.7159	Intermediate Similarity	NPD7447	Phase 1
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7157	Intermediate Similarity	NPD2973	Approved
0.7157	Intermediate Similarity	NPD2974	Approved
0.7157	Intermediate Similarity	NPD2975	Approved
0.7151	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4380	Phase 2
0.7151	Intermediate Similarity	NPD6005	Phase 3
0.7151	Intermediate Similarity	NPD6002	Phase 3
0.7151	Intermediate Similarity	NPD6004	Phase 3
0.7151	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6166	Phase 2
0.7151	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7136	Intermediate Similarity	NPD4580	Approved
0.7135	Intermediate Similarity	NPD7033	Discontinued
0.7127	Intermediate Similarity	NPD5761	Phase 2
0.7127	Intermediate Similarity	NPD5760	Phase 2
0.7127	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4004	Approved
0.7114	Intermediate Similarity	NPD4002	Approved
0.7104	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3452	Approved
0.71	Intermediate Similarity	NPD3450	Approved
0.7094	Intermediate Similarity	NPD7584	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3818	Discontinued
0.7072	Intermediate Similarity	NPD7577	Discontinued
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7062	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4965	Approved
0.7049	Intermediate Similarity	NPD4966	Approved
0.7049	Intermediate Similarity	NPD4967	Phase 2
0.7049	Intermediate Similarity	NPD3882	Suspended
0.7049	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2801	Approved
0.7027	Intermediate Similarity	NPD5494	Approved
0.702	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7075	Discontinued
0.7011	Intermediate Similarity	NPD1549	Phase 2
0.6994	Remote Similarity	NPD2796	Approved
0.699	Remote Similarity	NPD2488	Approved
0.699	Remote Similarity	NPD2490	Approved
0.6984	Remote Similarity	NPD7177	Discontinued
0.6982	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD37	Approved
0.6978	Remote Similarity	NPD6801	Discontinued
0.6973	Remote Similarity	NPD6234	Discontinued
0.6971	Remote Similarity	NPD2654	Approved
0.6966	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6355	Discontinued
0.6952	Remote Similarity	NPD7229	Phase 3
0.6952	Remote Similarity	NPD7315	Approved
0.6952	Remote Similarity	NPD3787	Discontinued
0.6944	Remote Similarity	NPD4210	Discontinued
0.694	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7930	Approved
0.6923	Remote Similarity	NPD7411	Suspended
0.6923	Remote Similarity	NPD6072	Discontinued
0.6919	Remote Similarity	NPD4466	Phase 1
0.6919	Remote Similarity	NPD3749	Approved
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6799	Approved
0.6906	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5006	Approved
0.6897	Remote Similarity	NPD5005	Approved
0.6897	Remote Similarity	NPD6032	Approved
0.6895	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7427	Discontinued
0.6885	Remote Similarity	NPD6844	Discontinued
0.6882	Remote Similarity	NPD6315	Phase 2
0.6882	Remote Similarity	NPD6798	Discontinued
0.6872	Remote Similarity	NPD7019	Approved
0.6872	Remote Similarity	NPD7020	Approved
0.6869	Remote Similarity	NPD7296	Approved
0.6868	Remote Similarity	NPD6599	Discontinued
0.6862	Remote Similarity	NPD3051	Approved
0.6859	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5844	Phase 1
0.6856	Remote Similarity	NPD2971	Approved
0.6856	Remote Similarity	NPD2968	Approved
0.6845	Remote Similarity	NPD2904	Discontinued
0.6845	Remote Similarity	NPD6746	Phase 2
0.6845	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5647	Approved
0.6845	Remote Similarity	NPD7583	Approved
0.6845	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1510	Phase 2
0.6839	Remote Similarity	NPD6559	Discontinued
0.6837	Remote Similarity	NPD4663	Approved
0.6837	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4628	Phase 3
0.6825	Remote Similarity	NPD2969	Approved
0.6825	Remote Similarity	NPD5242	Approved
0.6825	Remote Similarity	NPD2970	Approved
0.6823	Remote Similarity	NPD7074	Phase 3
0.6821	Remote Similarity	NPD8053	Approved
0.6821	Remote Similarity	NPD8054	Approved
0.6818	Remote Similarity	NPD2424	Discontinued
0.6816	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1511	Approved
0.6812	Remote Similarity	NPD7585	Approved
0.6811	Remote Similarity	NPD3817	Phase 2
0.6811	Remote Similarity	NPD2560	Approved
0.6811	Remote Similarity	NPD2563	Approved
0.6809	Remote Similarity	NPD6959	Discontinued
0.6806	Remote Similarity	NPD7228	Approved
0.6806	Remote Similarity	NPD3751	Discontinued
0.6806	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6620	Discovery
0.6802	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1613	Approved
0.68	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD4477	Approved
0.68	Remote Similarity	NPD4476	Approved
0.68	Remote Similarity	NPD6099	Approved
0.6798	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7783	Phase 2
0.6794	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6502	Phase 2
0.6774	Remote Similarity	NPD7768	Phase 2
0.6772	Remote Similarity	NPD5710	Approved
0.6772	Remote Similarity	NPD5711	Approved
0.6772	Remote Similarity	NPD6232	Discontinued
0.6771	Remote Similarity	NPD6020	Phase 2
0.6771	Remote Similarity	NPD7054	Approved
0.6771	Remote Similarity	NPD6042	Phase 2
0.6771	Remote Similarity	NPD42	Phase 2
0.6769	Remote Similarity	NPD4578	Approved
0.6769	Remote Similarity	NPD4577	Approved
0.6757	Remote Similarity	NPD7819	Suspended
0.6757	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7473	Discontinued
0.6753	Remote Similarity	NPD7039	Approved
0.6753	Remote Similarity	NPD7685	Pre-registration
0.6753	Remote Similarity	NPD7038	Approved
0.6749	Remote Similarity	NPD7810	Phase 3
0.6749	Remote Similarity	NPD7811	Phase 3
0.6747	Remote Similarity	NPD1610	Phase 2
0.6745	Remote Similarity	NPD7047	Phase 3
0.6744	Remote Similarity	NPD6233	Phase 2
0.674	Remote Similarity	NPD1512	Approved
0.6736	Remote Similarity	NPD7472	Approved
0.6731	Remote Similarity	NPD7701	Phase 2
0.6729	Remote Similarity	NPD4665	Approved
0.6729	Remote Similarity	NPD4111	Phase 1
0.6724	Remote Similarity	NPD6653	Approved
0.672	Remote Similarity	NPD5402	Approved
0.6717	Remote Similarity	NPD7906	Approved
0.6713	Remote Similarity	NPD6997	Phase 2
0.6706	Remote Similarity	NPD2861	Phase 2
0.6705	Remote Similarity	NPD1240	Approved
0.6705	Remote Similarity	NPD5712	Approved
0.6703	Remote Similarity	NPD5403	Approved
0.6702	Remote Similarity	NPD2489	Approved
0.6702	Remote Similarity	NPD27	Approved
0.6702	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3823	Discontinued
0.6701	Remote Similarity	NPD6797	Phase 2
0.6701	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4420	Approved
0.6686	Remote Similarity	NPD2200	Suspended
0.6685	Remote Similarity	NPD4662	Approved
0.6685	Remote Similarity	NPD2800	Approved
0.6685	Remote Similarity	NPD4661	Approved
0.6685	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5177	Phase 3

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