NPASS Compound

Structure

CID151781 OpenBabel06191715522D 27 31 0 0 1 0 0 0 0 0999 V2000 0.8395 3.2120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3472 2.3323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3874 0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5486 1.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8710 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5482 -0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5164 1.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1938 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 -0.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7094 -0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0322 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3872 -0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6778 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7096 0.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0324 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5161 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 1.4529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8714 1.4516 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3550 -0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.2667 -0.5097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5159 -1.4846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8793 1.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3315 2.3325 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 2 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 7 16 2 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.11
Volume:	353.91
LogP:	1.765
LogD:	1.327
LogS:	-4.238
# Rotatable Bonds:	1
TPSA:	101.65
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	3.338
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981
MDCK Permeability:	1.3946629223937634e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	88.39118194580078%
Volume Distribution (VD):	0.912
Pgp-substrate:	6.599498748779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.483
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.286
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	11.765
Half-life (T1/2):	0.64

ADMET: Toxicity

hERG Blockers:	0.259
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.288
AMES Toxicity:	0.796
Rat Oral Acute Toxicity:	0.725
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.059
Carcinogencity:	0.624
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC151781

Natural Product ID:	NPC151781
*Common Name:**	Hydroxycamptothecin
IUPAC Name:	n.a.
Synonyms:	10-Hydroxy Camptothecin; 10-Hydroxy-Camptothecin; 10-Hydroxycamptothecin; 10-Hydroxycamptothecine; Hydroxycamptothecin
Standard InCHIKey:	HAWSQZCWOQZXHI-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1
SMILES:	CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4cc3Cn1c2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL273862
PubChem CID:	97226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000240] Camptothecins

*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
NPO21173	Culcita novaeguineae	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787432]
NPO21173	Culcita novaeguineae	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19133759]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21348469]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3735324]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18519	0thapodytes pittosporoides	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18519	0thapodytes pittosporoides	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21173	Culcita novaeguineae	Species	Oreasteridae	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	1
GI50	74
IC50	108
Others	98
Potency	18

Activity Type	# Activity
Cell Line	218
CELL-LINE	3
Individual Protein	21
NON-MOLECULAR	23
Organism	19
Others	13
Protein-Protein Interaction	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT604	Individual Protein	Serum albumin	Homo sapiens	K	=	130.0	1/Maa	PMID[567269]
NPT604	Individual Protein	Serum albumin	Homo sapiens	K	=	260.0	1/Maa	PMID[567269]
NPT604	Individual Protein	Serum albumin	Homo sapiens	Activity	=	1.7	n.a.	PMID[567269]
NPT168	Cell Line	P388	Mus musculus	IC50	=	12.0	nM	PMID[567270]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	CC50	=	1000.0	nM	PMID[567271]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	18.0	nM	PMID[567271]
NPT168	Cell Line	P388	Mus musculus	Dose range	=	8.0	mg kg-1	PMID[567272]
NPT168	Cell Line	P388	Mus musculus	DOSE	=	4.0	mg.kg-1	PMID[567272]
NPT168	Cell Line	P388	Mus musculus	DOSE	=	8.0	mg.kg-1	PMID[567272]
NPT3804	Cell Line	Human Tumor Cell lines		GI50	=	36.0	nM	PMID[567273]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	=	110.0	nM	PMID[567274]
NPT4468	Cell Line	P338	Mus musculus	T/C	=	297.0	%	PMID[567276]
NPT4468	Cell Line	P338	Mus musculus	No. of cures	=	0.0	n.a.	PMID[567276]
NPT4468	Cell Line	P338	Mus musculus	Active dose range	=	0.4	mg kg-1	PMID[567276]
NPT4468	Cell Line	P338	Mus musculus	Toxic dose	=	6.25	mg kg-1	PMID[567276]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	2470.0	nM	PMID[567277]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	148.0	nM	PMID[567277]
NPT547	Cell Line	BGC-823	Homo sapiens	Activity	=	4.78	%	PMID[567278]
NPT547	Cell Line	BGC-823	Homo sapiens	Activity	=	13.2	%	PMID[567278]
NPT547	Cell Line	BGC-823	Homo sapiens	Activity	=	6.47	%	PMID[567278]
NPT547	Cell Line	BGC-823	Homo sapiens	Activity	=	3.72	%	PMID[567278]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	5.4	nM	PMID[567279]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	9.1	nM	PMID[567279]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	8.8	nM	PMID[567279]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.024	ug.mL-1	PMID[567281]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	0.62	ug.mL-1	PMID[567281]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	410.0	nM	PMID[567282]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	280.0	nM	PMID[567282]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	19120.0	nM	PMID[567283]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	38550.0	nM	PMID[567283]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	29880.0	nM	PMID[567283]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4100.0	nM	PMID[567284]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	400.0	nM	PMID[567284]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	110.0	nM	PMID[567285]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	210.0	nM	PMID[567285]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	600.0	nM	PMID[567286]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	700.0	nM	PMID[567286]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	200.0	nM	PMID[567286]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	140.0	nM	PMID[567288]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	160.0	nM	PMID[567289]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	360.0	nM	PMID[567289]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3700.0	nM	PMID[567290]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	40.0	nM	PMID[567290]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	30.0	nM	PMID[567290]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	110.0	nM	PMID[567290]
NPT1226	Individual Protein	Caspase-7	Homo sapiens	Potency	=	15848.9	nM	PMID[567291]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PMID[567291]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	10000.0	nM	PMID[567291]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	35481.3	nM	PMID[567291]
NPT2930	Individual Protein	Hemoglobin beta chain	Homo sapiens	Potency	=	12589.3	nM	PMID[567291]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1584.9	nM	PMID[567291]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	15848.9	nM	PMID[567291]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[567291]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[567291]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	829.0	nM	PMID[567292]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	981.0	nM	PMID[567292]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	92.0	%	PMID[567294]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	12.85	nM	PMID[567295]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	141.58	nM	PMID[567295]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	11.56	nM	PMID[567295]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	17.58	nM	PMID[567295]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	23.44	nM	PMID[567295]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	27.73	nM	PMID[567295]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	16.07	nM	PMID[567295]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PMID[567295]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	8.26	nM	PMID[567295]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	27.61	nM	PMID[567295]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	49.77	nM	PMID[567295]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	86.3	nM	PMID[567295]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	31.48	nM	PMID[567295]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	45.71	nM	PMID[567295]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	9.441	nM	PMID[567295]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	23.17	nM	PMID[567295]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	10.91	nM	PMID[567295]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	7.499	nM	PMID[567295]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	46.99	nM	PMID[567295]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	14.16	nM	PMID[567295]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	866.96	nM	PMID[567295]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	8.414	nM	PMID[567295]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	17.7	nM	PMID[567295]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PMID[567295]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	2685.34	nM	PMID[567295]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	24.6	nM	PMID[567295]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	51.29	nM	PMID[567295]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	10.54	nM	PMID[567295]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	105.44	nM	PMID[567295]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	33.57	nM	PMID[567295]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	26.24	nM	PMID[567295]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	106.91	nM	PMID[567295]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	156.31	nM	PMID[567295]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	92.04	nM	PMID[567295]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	33.73	nM	PMID[567295]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	20.32	nM	PMID[567295]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	54.33	nM	PMID[567295]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	473.15	nM	PMID[567295]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	50.58	nM	PMID[567295]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	83.37	nM	PMID[567295]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	35.16	nM	PMID[567295]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	14.0	nM	PMID[567295]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	295.12	nM	PMID[567295]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	15.67	nM	PMID[567295]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	16.41	nM	PMID[567295]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	83.95	nM	PMID[567295]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	62.95	nM	PMID[567295]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	7.499	nM	PMID[567295]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	150.31	nM	PMID[567295]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	13.61	nM	PMID[567295]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	22.7	nM	PMID[567295]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	13.93	nM	PMID[567295]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	10.0	nM	PMID[567295]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	7.499	nM	PMID[567295]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	30.41	nM	PMID[567295]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	45.29	nM	PMID[567295]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	9.705	nM	PMID[567295]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	476.43	nM	PMID[567295]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	18.41	nM	PMID[567295]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	24.1	nM	PMID[567295]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	1042.32	nM	PMID[567295]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	23.12	nM	PMID[567295]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	41.21	nM	PMID[567295]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	247.74	nM	PMID[567295]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	7.499	nM	PMID[567295]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	1196.74	nM	PMID[567295]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	13.4	nM	PMID[567295]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	118.3	nM	PMID[567295]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	74.47	nM	PMID[567295]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	23.6	nM	PMID[567295]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	125.31	nM	PMID[567295]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	109.14	nM	PMID[567295]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	10.0	nM	PMID[567295]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	31.2	nM	PMID[567296]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	33.6	nM	PMID[567296]
NPT3140	Cell Line	MGC-803	Homo sapiens	GI	=	29.1	%	PMID[567297]
NPT1872	Cell Line	Bcap37	Homo sapiens	GI	=	28.1	%	PMID[567297]
NPT886	Cell Line	NIH3T3	Mus musculus	GI	=	9.3	%	PMID[567297]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	>	20000.0	nM	PMID[567297]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	20000.0	nM	PMID[567297]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	17.37	%	PMID[567297]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	18.66	%	PMID[567297]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	24.95	%	PMID[567297]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	78.0	nM	PMID[567298]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	4.0	nM	PMID[567298]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-5.24	%	PMID[567299]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	29500.0	nM	PMID[567300]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	58.0	nM	PMID[567291]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20.6	nM	PMID[567291]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	600.0	nM	PMID[567301]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	300.0	nM	PMID[567301]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	200.0	nM	PMID[567301]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	70.0	nM	PMID[567301]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	60.0	nM	PMID[567301]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	150.0	nM	PMID[567302]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	300.0	nM	PMID[567302]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	250.0	nM	PMID[567302]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	17.0	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	8.3	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	38.2	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	19.8	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	12.8	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	11.9	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	7.4	%	PMID[567303]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	5.7	%	PMID[567303]
NPT492	Cell Line	Caco-2	Homo sapiens	Peff	=	7.88	ucm/s	PMID[567304]
NPT492	Cell Line	Caco-2	Homo sapiens	Peff	=	1.01	ucm/s	PMID[567304]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	85.4	%	PMID[567305]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	24.5	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	7.6	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	4.7	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	8.6	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	5.8	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	2.0	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	3.0	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	1.8	%	PMID[567306]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	1.2	%	PMID[567306]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	17.1	%	PMID[567307]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	37.0	%	PMID[567307]
NPT1872	Cell Line	Bcap37	Homo sapiens	GI	=	8.8	%	PMID[567307]
NPT1872	Cell Line	Bcap37	Homo sapiens	GI	=	33.5	%	PMID[567307]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	128.0	nM	PMID[567308]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	499.0	nM	PMID[567308]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	1.3	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	1.8	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	3.5	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	2.1	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	6.0	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	9.1	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	3.8	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	7.3	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	Activity	=	18.6	%	PMID[567309]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	29100.0	nM	PMID[567310]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	=	28100.0	nM	PMID[567310]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	27800.0	nM	PMID[567310]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48200.0	nM	PMID[567310]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	29100.0	nM	PMID[567311]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	34500.0	nM	PMID[567311]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	=	28100.0	nM	PMID[567311]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	27800.0	nM	PMID[567311]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48200.0	nM	PMID[567311]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	82.0	nM	PMID[567313]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2270.0	nM	PMID[567313]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3500.0	nM	PMID[567315]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2400.0	nM	PMID[567315]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	10100.0	nM	PMID[567315]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	800.0	nM	PMID[567315]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	10040.0	nM	PMID[567316]
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	5530.0	nM	PMID[567317]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	5520.0	nM	PMID[567317]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4910.0	nM	PMID[567317]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	15190.0	nM	PMID[567317]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	29160.0	nM	PMID[567317]
NPT65	Cell Line	HepG2	Homo sapiens	TGI	=	71.6	%	PMID[567317]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	10300.0	nM	PMID[567318]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	800.0	nM	PMID[567318]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2800.0	nM	PMID[567318]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3200.0	nM	PMID[567318]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	18200.0	nM	PMID[567318]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	6550.0	nM	PMID[567319]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3190.0	nM	PMID[567319]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1750.0	nM	PMID[567319]
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	11830.0	nM	PMID[567319]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	6550.0	nM	PMID[567321]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	16590.0	nM	PMID[567321]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2750.0	nM	PMID[567321]
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	11830.0	nM	PMID[567321]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1470.0	nM	PMID[567323]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3580.0	nM	PMID[567323]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	10210.0	nM	PMID[567324]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10080.0	nM	PMID[567324]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	9710.0	nM	PMID[567324]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9130.0	nM	PMID[567324]
NPT2351	Cell Line	MG-63	Homo sapiens	IC50	=	10690.0	nM	PMID[567324]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	80.0	nM	PMID[567327]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	21.0	nM	PMID[567327]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	330.0	nM	PMID[567327]
NPT27	Others	Unspecified		T1/2	=	0.3683	hr	PMID[567269]
NPT27	Others	Unspecified		T1/2	=	0.3517	hr	PMID[567269]
NPT27	Others	Unspecified		T free	=	4.0	ns	PMID[567269]
NPT605	Organism	Homo sapiens	Homo sapiens	T bound	=	5.4	ns	PMID[567269]
NPT605	Organism	Homo sapiens	Homo sapiens	T bound	=	5.5	ns	PMID[567269]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	36.5	%	PMID[567270]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	21.0	uM kg-1	PMID[567271]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	78.0	%	PMID[567271]
NPT32	Organism	Mus musculus	Mus musculus	T/C	=	314.0	%	PMID[567272]
NPT27	Others	Unspecified		Therapeutic index	=	8.0	n.a.	PMID[567272]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.02	ug ml-1	PMID[567272]
NPT605	Organism	Homo sapiens	Homo sapiens	T1/2	=	0.3683	hr	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	16.0	%	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	T1/2	=	0.3517	hr	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	4.0	%	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	T1/2	=	0.31	hr	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	6.0	%	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	K	=	135.0	1/Maa	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	K	=	264.0	1/Maa	PMID[567275]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	=	1.7	n.a.	PMID[567275]
NPT35	Others	n.a.		Solubility	=	13700.0	nM	PMID[567279]
NPT35	Others	n.a.		Solubility	=	137000.0	nM	PMID[567279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.9	nM	PMID[567279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6490.0	nM	PMID[567283]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	370.0	nM	PMID[567287]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1090.0	nM	PMID[567287]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	22387.2	nM	PMID[567291]
NPT2	Others	Unspecified		Potency	=	15848.9	nM	PMID[567291]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	50.1	nM	PMID[567291]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	496.0	nM	PMID[567292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	230.0	nM	PMID[567293]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1040.0	nM	PMID[567293]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	6.63	%	PMID[567299]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21300.0	nM	PMID[567300]
NPT2	Others	Unspecified		Potency	n.a.	112.2	nM	PMID[567291]
NPT2	Others	Unspecified		Potency	n.a.	1258.9	nM	PMID[567291]
NPT2	Others	Unspecified		Potency	n.a.	251.2	nM	PMID[567291]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	7.3	%	PMID[567307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	26.5	%	PMID[567307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	181.0	nM	PMID[567308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	835.0	nM	PMID[567308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34500.0	nM	PMID[567310]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	58620.0	nM	PMID[567313]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	91.99	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	68.37	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	54.55	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	29.44	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	27.97	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	23.92	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	20.0	%	PMID[567314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	21.68	%	PMID[567314]
NPT21742	CELL-LINE	L02	Homo sapiens	IC50	=	20400.0	nM	PMID[567318]
NPT2	Others	Unspecified		IC50	=	12630.0	nM	PMID[567321]
NPT21742	CELL-LINE	L02	Homo sapiens	IC50	=	12830.0	nM	PMID[567321]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-9.33	%	PMID[567322]
NPT35	Others	n.a.		Solubility	=	0.94	ug.mL-1	PMID[567323]
NPT21742	CELL-LINE	L02	Homo sapiens	IC50	=	10230.0	nM	PMID[567324]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-10.86	%	PMID[567325]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.16	%	PMID[567326]

☑ 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 NPC151781 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	368
0.1-0.2	1939
0.2-0.3	8284
0.3-0.4	9265
0.4-0.5	14424
0.5-0.6	5943
0.6-0.7	2093
0.7-0.8	365
0.8-0.85	3
0.85-0.9	3
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC316181
1.0	High Similarity	NPC74562
0.901	High Similarity	NPC128115
0.8942	High Similarity	NPC129909
0.8639	High Similarity	NPC61435
0.8632	High Similarity	NPC311858
0.8622	High Similarity	NPC192674
0.8526	High Similarity	NPC470003
0.8263	Intermediate Similarity	NPC28848
0.8263	Intermediate Similarity	NPC14325
0.7799	Intermediate Similarity	NPC53344
0.7778	Intermediate Similarity	NPC211813
0.7751	Intermediate Similarity	NPC474145
0.7751	Intermediate Similarity	NPC475841
0.7725	Intermediate Similarity	NPC477548
0.77	Intermediate Similarity	NPC472098
0.7696	Intermediate Similarity	NPC472099
0.7681	Intermediate Similarity	NPC249040
0.7667	Intermediate Similarity	NPC472111
0.7644	Intermediate Similarity	NPC477549
0.7594	Intermediate Similarity	NPC82548
0.7593	Intermediate Similarity	NPC469928
0.7577	Intermediate Similarity	NPC474183
0.7577	Intermediate Similarity	NPC470785
0.7577	Intermediate Similarity	NPC470784
0.7566	Intermediate Similarity	NPC272549
0.7547	Intermediate Similarity	NPC270918
0.7533	Intermediate Similarity	NPC184680
0.7532	Intermediate Similarity	NPC472435
0.7524	Intermediate Similarity	NPC295898
0.7524	Intermediate Similarity	NPC276517
0.7489	Intermediate Similarity	NPC157931
0.7488	Intermediate Similarity	NPC476098
0.7464	Intermediate Similarity	NPC280714
0.7437	Intermediate Similarity	NPC472436
0.7416	Intermediate Similarity	NPC239954
0.7416	Intermediate Similarity	NPC212213
0.7406	Intermediate Similarity	NPC53144
0.7406	Intermediate Similarity	NPC200836
0.7402	Intermediate Similarity	NPC66083
0.7401	Intermediate Similarity	NPC323752
0.7401	Intermediate Similarity	NPC323198
0.7399	Intermediate Similarity	NPC473449
0.7391	Intermediate Similarity	NPC475816
0.7387	Intermediate Similarity	NPC478141
0.7383	Intermediate Similarity	NPC88008
0.7378	Intermediate Similarity	NPC311906
0.7373	Intermediate Similarity	NPC264176
0.7368	Intermediate Similarity	NPC156704
0.7353	Intermediate Similarity	NPC194040
0.7348	Intermediate Similarity	NPC82472
0.7333	Intermediate Similarity	NPC168911
0.7315	Intermediate Similarity	NPC469589
0.7313	Intermediate Similarity	NPC14288
0.7302	Intermediate Similarity	NPC193238
0.7289	Intermediate Similarity	NPC319232
0.7289	Intermediate Similarity	NPC24370
0.7286	Intermediate Similarity	NPC90229
0.7285	Intermediate Similarity	NPC96321
0.7284	Intermediate Similarity	NPC99891
0.7281	Intermediate Similarity	NPC475720
0.7281	Intermediate Similarity	NPC474192
0.7273	Intermediate Similarity	NPC148183
0.7273	Intermediate Similarity	NPC152768
0.7269	Intermediate Similarity	NPC287208
0.7265	Intermediate Similarity	NPC472434
0.7257	Intermediate Similarity	NPC473800
0.7257	Intermediate Similarity	NPC34580
0.7257	Intermediate Similarity	NPC257851
0.7257	Intermediate Similarity	NPC118559
0.7257	Intermediate Similarity	NPC124920
0.7257	Intermediate Similarity	NPC304307
0.7255	Intermediate Similarity	NPC320394
0.7243	Intermediate Similarity	NPC223427
0.7235	Intermediate Similarity	NPC476116
0.7235	Intermediate Similarity	NPC174672
0.7235	Intermediate Similarity	NPC174758
0.7232	Intermediate Similarity	NPC280272
0.7225	Intermediate Similarity	NPC198673
0.7225	Intermediate Similarity	NPC100547
0.7225	Intermediate Similarity	NPC230403
0.722	Intermediate Similarity	NPC478006
0.7209	Intermediate Similarity	NPC329708
0.7209	Intermediate Similarity	NPC475070
0.7209	Intermediate Similarity	NPC47059
0.7209	Intermediate Similarity	NPC165349
0.7209	Intermediate Similarity	NPC274291
0.7209	Intermediate Similarity	NPC264166
0.7209	Intermediate Similarity	NPC118832
0.7207	Intermediate Similarity	NPC469594
0.7207	Intermediate Similarity	NPC303658
0.7202	Intermediate Similarity	NPC85273
0.7202	Intermediate Similarity	NPC471304
0.7195	Intermediate Similarity	NPC330009
0.7193	Intermediate Similarity	NPC322135
0.7193	Intermediate Similarity	NPC223409
0.7193	Intermediate Similarity	NPC95240
0.7186	Intermediate Similarity	NPC65080
0.7185	Intermediate Similarity	NPC181081
0.7184	Intermediate Similarity	NPC315467
0.7182	Intermediate Similarity	NPC471080
0.7182	Intermediate Similarity	NPC469592
0.7181	Intermediate Similarity	NPC261251
0.7175	Intermediate Similarity	NPC313804
0.7175	Intermediate Similarity	NPC315804
0.7174	Intermediate Similarity	NPC284888
0.7168	Intermediate Similarity	NPC21638
0.7167	Intermediate Similarity	NPC303374
0.7162	Intermediate Similarity	NPC469727
0.7156	Intermediate Similarity	NPC220851
0.7154	Intermediate Similarity	NPC478009
0.7154	Intermediate Similarity	NPC478010
0.7149	Intermediate Similarity	NPC194740
0.7149	Intermediate Similarity	NPC471762
0.7143	Intermediate Similarity	NPC79293
0.7143	Intermediate Similarity	NPC279401
0.7137	Intermediate Similarity	NPC214142
0.713	Intermediate Similarity	NPC54803
0.713	Intermediate Similarity	NPC321592
0.713	Intermediate Similarity	NPC314270
0.7125	Intermediate Similarity	NPC314882
0.7125	Intermediate Similarity	NPC329982
0.7123	Intermediate Similarity	NPC309845
0.7123	Intermediate Similarity	NPC5145
0.7122	Intermediate Similarity	NPC176127
0.7115	Intermediate Similarity	NPC183805
0.7109	Intermediate Similarity	NPC57994
0.7109	Intermediate Similarity	NPC289299
0.7105	Intermediate Similarity	NPC186351
0.7104	Intermediate Similarity	NPC266931
0.7103	Intermediate Similarity	NPC329793
0.7103	Intermediate Similarity	NPC315491
0.7103	Intermediate Similarity	NPC45459
0.7101	Intermediate Similarity	NPC171171
0.7101	Intermediate Similarity	NPC204385
0.71	Intermediate Similarity	NPC141053
0.7098	Intermediate Similarity	NPC74360
0.7097	Intermediate Similarity	NPC277350
0.7094	Intermediate Similarity	NPC283152
0.7089	Intermediate Similarity	NPC306376
0.7089	Intermediate Similarity	NPC469734
0.7085	Intermediate Similarity	NPC305984
0.7083	Intermediate Similarity	NPC189079
0.7079	Intermediate Similarity	NPC312872
0.7076	Intermediate Similarity	NPC316224
0.7076	Intermediate Similarity	NPC188400
0.7075	Intermediate Similarity	NPC245916
0.7072	Intermediate Similarity	NPC16066
0.707	Intermediate Similarity	NPC471944
0.7069	Intermediate Similarity	NPC33064
0.7069	Intermediate Similarity	NPC245055
0.7064	Intermediate Similarity	NPC474905
0.7056	Intermediate Similarity	NPC241024
0.7056	Intermediate Similarity	NPC32200
0.7053	Intermediate Similarity	NPC314002
0.7047	Intermediate Similarity	NPC260909
0.7044	Intermediate Similarity	NPC288943
0.7042	Intermediate Similarity	NPC133609
0.704	Intermediate Similarity	NPC274982
0.704	Intermediate Similarity	NPC322064
0.7037	Intermediate Similarity	NPC123019
0.7031	Intermediate Similarity	NPC470126
0.7027	Intermediate Similarity	NPC478074
0.7026	Intermediate Similarity	NPC220852
0.7024	Intermediate Similarity	NPC24864
0.7023	Intermediate Similarity	NPC213308
0.7019	Intermediate Similarity	NPC66210
0.7018	Intermediate Similarity	NPC472287
0.7018	Intermediate Similarity	NPC472286
0.7014	Intermediate Similarity	NPC99666
0.7014	Intermediate Similarity	NPC55493
0.7012	Intermediate Similarity	NPC478012
0.7012	Intermediate Similarity	NPC478011
0.701	Intermediate Similarity	NPC326575
0.7009	Intermediate Similarity	NPC285343
0.7009	Intermediate Similarity	NPC184225
0.7009	Intermediate Similarity	NPC312645
0.7009	Intermediate Similarity	NPC102008
0.7005	Intermediate Similarity	NPC204717
0.7005	Intermediate Similarity	NPC317572
0.7005	Intermediate Similarity	NPC476115
0.7004	Intermediate Similarity	NPC314056
0.7	Intermediate Similarity	NPC66777
0.7	Intermediate Similarity	NPC144381
0.6996	Remote Similarity	NPC477979
0.6995	Remote Similarity	NPC303225
0.699	Remote Similarity	NPC206201
0.6986	Remote Similarity	NPC472323
0.6986	Remote Similarity	NPC321428
0.6984	Remote Similarity	NPC314176
0.6982	Remote Similarity	NPC112206
0.6982	Remote Similarity	NPC235900
0.6982	Remote Similarity	NPC202605
0.6981	Remote Similarity	NPC307963
0.6976	Remote Similarity	NPC72980
0.6974	Remote Similarity	NPC26872
0.6971	Remote Similarity	NPC313587
0.6971	Remote Similarity	NPC315893
0.6971	Remote Similarity	NPC316110
0.6964	Remote Similarity	NPC74969

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 NPC151781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	595
0.2-0.3	784
0.3-0.4	1469
0.4-0.5	2760
0.5-0.6	2332
0.6-0.7	850
0.7-0.8	108
0.8-0.85	4
0.85-0.9	7
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9947	High Similarity	NPD4897	Phase 2
0.9643	High Similarity	NPD5506	Approved
0.9643	High Similarity	NPD5507	Approved
0.9216	High Similarity	NPD7589	Clinical (unspecified phase)
0.9126	High Similarity	NPD7796	Approved
0.9126	High Similarity	NPD7797	Approved
0.9026	High Similarity	NPD4901	Clinical (unspecified phase)
0.8942	High Similarity	NPD3785	Clinical (unspecified phase)
0.8711	High Similarity	NPD6206	Phase 1
0.8692	High Similarity	NPD7025	Clinical (unspecified phase)
0.8667	High Similarity	NPD6261	Phase 3
0.8657	High Similarity	NPD4900	Clinical (unspecified phase)
0.8632	High Similarity	NPD5444	Phase 1
0.8622	High Similarity	NPD6249	Phase 2
0.8622	High Similarity	NPD3800	Clinical (unspecified phase)
0.8622	High Similarity	NPD6248	Phase 2
0.845	Intermediate Similarity	NPD5487	Phase 1
0.8446	Intermediate Similarity	NPD4334	Discontinued
0.8358	Intermediate Similarity	NPD3777	Phase 3
0.8223	Intermediate Similarity	NPD4315	Phase 2
0.8119	Intermediate Similarity	NPD5427	Suspended
0.7981	Intermediate Similarity	NPD5834	Phase 3
0.7981	Intermediate Similarity	NPD5835	Phase 3
0.77	Intermediate Similarity	NPD7573	Discontinued
0.7653	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7222	Phase 2
0.7512	Intermediate Similarity	NPD7218	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD8463	Approved
0.7489	Intermediate Similarity	NPD4328	Approved
0.7466	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4418	Discontinued
0.7415	Intermediate Similarity	NPD3321	Discontinued
0.7413	Intermediate Similarity	NPD4204	Approved
0.7413	Intermediate Similarity	NPD4203	Approved
0.7389	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5293	Phase 2
0.7302	Intermediate Similarity	NPD7453	Approved
0.7302	Intermediate Similarity	NPD7452	Approved
0.7301	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5658	Approved
0.7257	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6716	Phase 1
0.7252	Intermediate Similarity	NPD3258	Approved
0.7249	Intermediate Similarity	NPD4373	Phase 2
0.7248	Intermediate Similarity	NPD5416	Discontinued
0.7246	Intermediate Similarity	NPD8102	Discontinued
0.7225	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3263	Phase 3
0.7209	Intermediate Similarity	NPD4035	Approved
0.7209	Intermediate Similarity	NPD32	Approved
0.7209	Intermediate Similarity	NPD4033	Approved
0.7209	Intermediate Similarity	NPD4122	Approved
0.7209	Intermediate Similarity	NPD4037	Approved
0.7209	Intermediate Similarity	NPD4039	Approved
0.7209	Intermediate Similarity	NPD31	Approved
0.7209	Intermediate Similarity	NPD4036	Approved
0.7209	Intermediate Similarity	NPD4034	Approved
0.7209	Intermediate Similarity	NPD4038	Approved
0.7207	Intermediate Similarity	NPD7395	Discontinued
0.7206	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4885	Approved
0.7189	Intermediate Similarity	NPD2916	Discontinued
0.7174	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8016	Phase 3
0.7162	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5488	Discontinued
0.7156	Intermediate Similarity	NPD8356	Approved
0.7156	Intermediate Similarity	NPD5512	Phase 3
0.715	Intermediate Similarity	NPD3390	Phase 2
0.7149	Intermediate Similarity	NPD5559	Phase 2
0.7143	Intermediate Similarity	NPD8479	Phase 2
0.7137	Intermediate Similarity	NPD7603	Discontinued
0.7136	Intermediate Similarity	NPD5075	Discontinued
0.7136	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5104	Approved
0.7123	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2915	Discontinued
0.7118	Intermediate Similarity	NPD4952	Phase 3
0.7117	Intermediate Similarity	NPD5612	Discontinued
0.7116	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6376	Discontinued
0.7109	Intermediate Similarity	NPD4602	Approved
0.7105	Intermediate Similarity	NPD8430	Approved
0.7103	Intermediate Similarity	NPD484	Approved
0.7098	Intermediate Similarity	NPD2882	Phase 1
0.7097	Intermediate Similarity	NPD5530	Phase 1
0.7094	Intermediate Similarity	NPD6159	Phase 2
0.708	Intermediate Similarity	NPD6209	Approved
0.7075	Intermediate Similarity	NPD6550	Discontinued
0.7072	Intermediate Similarity	NPD3257	Approved
0.7067	Intermediate Similarity	NPD2383	Phase 1
0.7064	Intermediate Similarity	NPD5429	Discontinued
0.7061	Intermediate Similarity	NPD7426	Phase 1
0.7059	Intermediate Similarity	NPD7069	Discontinued
0.7054	Intermediate Similarity	NPD3354	Phase 2
0.7054	Intermediate Similarity	NPD8370	Discontinued
0.7051	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7548	Discontinued
0.7047	Intermediate Similarity	NPD8460	Approved
0.7047	Intermediate Similarity	NPD8459	Approved
0.7042	Intermediate Similarity	NPD5003	Discontinued
0.7033	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3925	Approved
0.7013	Intermediate Similarity	NPD6962	Phase 2
0.7013	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD53	Approved
0.7009	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7778	Approved
0.7009	Intermediate Similarity	NPD7777	Approved
0.7005	Intermediate Similarity	NPD5513	Phase 2
0.7	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6242	Discontinued
0.6987	Remote Similarity	NPD5640	Discontinued
0.6982	Remote Similarity	NPD5866	Approved
0.6981	Remote Similarity	NPD1038	Approved
0.6981	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7022	Phase 2
0.6957	Remote Similarity	NPD8467	Approved
0.6957	Remote Similarity	NPD8465	Approved
0.6957	Remote Similarity	NPD8466	Approved
0.6957	Remote Similarity	NPD4086	Phase 1
0.6947	Remote Similarity	NPD7194	Discontinued
0.6939	Remote Similarity	NPD7955	Approved
0.6939	Remote Similarity	NPD7956	Approved
0.6929	Remote Similarity	NPD3809	Discontinued
0.6923	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6158	Phase 2
0.692	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2565	Phase 2
0.6919	Remote Similarity	NPD2564	Approved
0.6914	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4511	Phase 1
0.691	Remote Similarity	NPD7031	Phase 1
0.6909	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5632	Approved
0.6894	Remote Similarity	NPD7853	Phase 2
0.689	Remote Similarity	NPD8429	Approved
0.689	Remote Similarity	NPD8428	Approved
0.689	Remote Similarity	NPD8427	Approved
0.6889	Remote Similarity	NPD7112	Discontinued
0.6887	Remote Similarity	NPD1924	Approved
0.6884	Remote Similarity	NPD6988	Phase 1
0.6883	Remote Similarity	NPD4845	Discontinued
0.688	Remote Similarity	NPD8421	Discontinued
0.6875	Remote Similarity	NPD3243	Approved
0.6875	Remote Similarity	NPD3794	Approved
0.6875	Remote Similarity	NPD3795	Approved
0.6872	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7859	Phase 2
0.6866	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4501	Approved
0.6866	Remote Similarity	NPD4601	Approved
0.6866	Remote Similarity	NPD4500	Approved
0.6866	Remote Similarity	NPD4600	Approved
0.6864	Remote Similarity	NPD5601	Phase 2
0.6864	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3003	Approved
0.686	Remote Similarity	NPD5897	Approved
0.686	Remote Similarity	NPD5899	Approved
0.686	Remote Similarity	NPD5898	Approved
0.686	Remote Similarity	NPD8101	Phase 3
0.6858	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4989	Phase 2
0.6857	Remote Similarity	NPD6961	Discontinued
0.6854	Remote Similarity	NPD6569	Phase 2
0.6853	Remote Similarity	NPD5014	Discontinued
0.6851	Remote Similarity	NPD6963	Approved
0.6851	Remote Similarity	NPD6964	Approved
0.6849	Remote Similarity	NPD6991	Approved
0.6849	Remote Similarity	NPD6176	Phase 1
0.6848	Remote Similarity	NPD8426	Approved
0.6848	Remote Similarity	NPD8425	Approved
0.6846	Remote Similarity	NPD6276	Discontinued
0.6846	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7996	Phase 2
0.6844	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5149	Phase 2
0.6842	Remote Similarity	NPD7708	Approved
0.6835	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8091	Phase 3
0.6828	Remote Similarity	NPD6568	Discontinued
0.6825	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5022	Discontinued
0.682	Remote Similarity	NPD2176	Approved
0.682	Remote Similarity	NPD2177	Approved
0.682	Remote Similarity	NPD2175	Phase 3
0.682	Remote Similarity	NPD1768	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