NPASS Compound

Structure

CID265557 OpenBabel06191716062D 39 43 0 0 1 0 0 0 0 0999 V2000 5.8153 3.7378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2373 2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9146 4.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4119 3.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7374 0.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6735 -2.0798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3366 2.7591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1407 2.6284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3752 1.1592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3113 0.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0511 3.0816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1008 3.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3969 2.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7634 2.2564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0086 1.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4928 2.2752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5228 1.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0195 2.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2164 0.4592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8083 1.4467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1190 1.1780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3185 0.9579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2849 -0.0650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7315 2.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8596 -0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7525 1.5312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5036 1.5500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0072 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8733 0.9958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4732 1.4355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8992 2.7282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1743 0.1480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 -1.0080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5850 2.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7506 -0.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8211 -1.5431 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 1.1461 2.5030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7586 1.1130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 36 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 26 1 0 0 0 0 10 37 1 0 0 0 0 11 12 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 26 1 6 0 0 0 15 18 1 0 0 0 0 15 29 2 0 0 0 0 16 27 1 1 0 0 0 16 38 1 0 0 0 0 17 30 2 0 0 0 0 17 39 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 6 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 39 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 28 1 1 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 5 1 6 0 0 0 27 10 1 6 0 0 0 28 25 1 6 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.23
Volume:	530.935
LogP:	1.576
LogD:	0.805
LogS:	-4.232
# Rotatable Bonds:	6
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	6.641
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.375
MDCK Permeability:	9.234564640792087e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.11
20% Bioavailability (F20%):	0.619
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.382
Plasma Protein Binding (PPB):	76.62905883789062%
Volume Distribution (VD):	0.413
Pgp-substrate:	21.87672233581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	3.295
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.55
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.208
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC265557

Natural Product ID:	NPC265557
*Common Name:**	Bruceantin
IUPAC Name:	n.a.
Synonyms:	Bruceantin; Bruceantine
Standard InCHIKey:	IRQXZTBHNKVIRL-GOTQHHPNSA-N
Standard InCHI:	InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
SMILES:	CC(C)/C(=C/C(=O)O[C@@H]1[C@@H]2[C@]34CO[C@@]2([C@H]([C@@H]([C@@H]4[C@@]2(C)CC(=O)C(=C(C)[C@@H]2C[C@H]3OC1=O)O)O)O)C(=O)OC)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509895
PubChem CID:	5281304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
ED50	5
GI50	74
IC50	23
Others	11

Activity Type	# Activity
Cell Line	98
CELL-LINE	1
Individual Protein	2
NON-MOLECULAR	4
Organism	5
Others	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	=	514000.0	nM	PMID[560228]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	40.0	nM	PMID[560230]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	20.0	nM	PMID[560230]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	1.0	n.a.	PMID[560230]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[560231]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	<	0.015	ug.mL-1	PMID[560232]
NPT466	Cell Line	U-937	Homo sapiens	IC50	<	0.015	ug.mL-1	PMID[560232]
NPT1960	Cell Line	BV-173	Homo sapiens	IC50	<	0.015	ug.mL-1	PMID[560232]
NPT464	Cell Line	Daudi	Homo sapiens	IC50	<	0.015	ug.mL-1	PMID[560232]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[560232]
NPT2085	Cell Line	Kasumi 1		IC50	=	0.02	ug.mL-1	PMID[560232]
NPT2142	Cell Line	REH	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[560232]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	90.0	%	PMID[560232]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12.2	nM	PMID[560232]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	12.8	nM	PMID[560232]
NPT2015	Cell Line	U-266	Homo sapiens	IC50	=	49.0	nM	PMID[560232]
NPT389	Cell Line	RPMI-8226	Homo sapiens	Activity	=	36.6	%	PMID[560232]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio ED50	=	7.4	n.a.	PMID[560233]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.0	nM	PMID[560233]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	11.0	nM	PMID[560233]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	12.0	nM	PMID[560233]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.27	nM	PMID[560233]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	17.0	ug ml-1	PMID[560234]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	51.0	nM	PMID[560235]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	10.05	nM	PMID[560237]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	22.18	nM	PMID[560237]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	2.6	nM	PMID[560237]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	32.81	nM	PMID[560237]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	59.84	nM	PMID[560237]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	14.19	nM	PMID[560237]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	24.66	nM	PMID[560237]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	336.51	nM	PMID[560237]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	24.21	nM	PMID[560237]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	26.49	nM	PMID[560237]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	38.37	nM	PMID[560237]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	5.117	nM	PMID[560237]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	20.99	nM	PMID[560237]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	3.459	nM	PMID[560237]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	22.39	nM	PMID[560237]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	21.09	nM	PMID[560237]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	21.04	nM	PMID[560237]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	20.94	nM	PMID[560237]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	21.38	nM	PMID[560237]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	22.28	nM	PMID[560237]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	20.51	nM	PMID[560237]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	15.96	nM	PMID[560237]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	0.03499	nM	PMID[560237]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	15.31	nM	PMID[560237]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	22.03	nM	PMID[560237]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	18.79	nM	PMID[560237]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	24.38	nM	PMID[560237]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	29.24	nM	PMID[560237]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	0.3141	nM	PMID[560237]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	5.534	nM	PMID[560237]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	20.84	nM	PMID[560237]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	20.14	nM	PMID[560237]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	24.21	nM	PMID[560237]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	26.49	nM	PMID[560237]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	20.0	nM	PMID[560237]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	22.0	nM	PMID[560242]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	29.0	nM	PMID[560242]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.0008	ug.mL-1	PMID[560229]
NPT2	Others	Unspecified		Inhibition	=	70.0	%	PMID[560230]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<	0.015	ug.mL-1	PMID[560232]
NPT27	Others	Unspecified		Activity	=	90.0	%	PMID[560232]
NPT24234	CELL-LINE	NCI-H929	Homo sapiens	IC50	=	115.0	nM	PMID[560232]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5.0	nM	PMID[560235]
NPT2	Others	Unspecified		INH	=	0.41	uM	PMID[560235]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.019	ug.mL-1	PMID[560238]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	47.77	%	PMID[560239]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.42	%	PMID[560240]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.02	%	PMID[560241]

☑ 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 NPC265557 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	256
0.1-0.2	1498
0.2-0.3	4160
0.3-0.4	6877
0.4-0.5	10746
0.5-0.6	9382
0.6-0.7	5918
0.7-0.8	3281
0.8-0.85	420
0.85-0.9	75
0.9-0.95	64
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC105926
1.0	High Similarity	NPC91693
1.0	High Similarity	NPC18945
0.9912	High Similarity	NPC476729
0.9912	High Similarity	NPC312833
0.9739	High Similarity	NPC24651
0.9652	High Similarity	NPC67251
0.9649	High Similarity	NPC470779
0.9407	High Similarity	NPC476008
0.9386	High Similarity	NPC17772
0.9381	High Similarity	NPC16081
0.9381	High Similarity	NPC173686
0.9322	High Similarity	NPC477745
0.9304	High Similarity	NPC470777
0.9298	High Similarity	NPC473590
0.9298	High Similarity	NPC470778
0.9298	High Similarity	NPC146432
0.9292	High Similarity	NPC45218
0.9292	High Similarity	NPC143268
0.9292	High Similarity	NPC268238
0.9292	High Similarity	NPC323821
0.9237	High Similarity	NPC470922
0.9217	High Similarity	NPC470776
0.9211	High Similarity	NPC328374
0.9211	High Similarity	NPC96312
0.9211	High Similarity	NPC40632
0.9211	High Similarity	NPC213084
0.9211	High Similarity	NPC251236
0.9211	High Similarity	NPC190185
0.9211	High Similarity	NPC89929
0.9204	High Similarity	NPC94509
0.9187	High Similarity	NPC262813
0.913	High Similarity	NPC470854
0.913	High Similarity	NPC287343
0.913	High Similarity	NPC474654
0.913	High Similarity	NPC122033
0.913	High Similarity	NPC97908
0.9123	High Similarity	NPC299849
0.9123	High Similarity	NPC473798
0.9113	High Similarity	NPC141215
0.9113	High Similarity	NPC251998
0.9113	High Similarity	NPC471089
0.9113	High Similarity	NPC190065
0.906	High Similarity	NPC109607
0.906	High Similarity	NPC107338
0.9052	High Similarity	NPC297179
0.9052	High Similarity	NPC251310
0.9043	High Similarity	NPC474734
0.904	High Similarity	NPC140045
0.904	High Similarity	NPC596
0.904	High Similarity	NPC295885
0.9035	High Similarity	NPC49451
0.8974	High Similarity	NPC476529
0.8974	High Similarity	NPC475775
0.8966	High Similarity	NPC176513
0.8966	High Similarity	NPC470775
0.8898	High Similarity	NPC112038
0.8889	High Similarity	NPC204552
0.8889	High Similarity	NPC188667
0.8879	High Similarity	NPC134869
0.8879	High Similarity	NPC152199
0.8879	High Similarity	NPC235539
0.8871	High Similarity	NPC168879
0.887	High Similarity	NPC208998
0.887	High Similarity	NPC7921
0.8824	High Similarity	NPC477046
0.8824	High Similarity	NPC102822
0.8793	High Similarity	NPC18547
0.8793	High Similarity	NPC474906
0.879	High Similarity	NPC102316
0.877	High Similarity	NPC470780
0.8718	High Similarity	NPC474046
0.8718	High Similarity	NPC470628
0.8718	High Similarity	NPC207217
0.8718	High Similarity	NPC259306
0.8707	High Similarity	NPC198539
0.8699	High Similarity	NPC475636
0.8699	High Similarity	NPC295220
0.8696	High Similarity	NPC171888
0.8696	High Similarity	NPC146945
0.8689	High Similarity	NPC181999
0.8689	High Similarity	NPC87662
0.8655	High Similarity	NPC469488
0.8644	High Similarity	NPC473968
0.864	High Similarity	NPC478154
0.8632	High Similarity	NPC470919
0.8632	High Similarity	NPC469877
0.8629	High Similarity	NPC309096
0.8629	High Similarity	NPC476851
0.8629	High Similarity	NPC54614
0.8621	High Similarity	NPC269530
0.8621	High Similarity	NPC474516
0.8621	High Similarity	NPC11252
0.8621	High Similarity	NPC289312
0.8596	High Similarity	NPC293850
0.8595	High Similarity	NPC269642
0.8583	High Similarity	NPC478051
0.8571	High Similarity	NPC478151
0.856	High Similarity	NPC478065
0.856	High Similarity	NPC476852
0.856	High Similarity	NPC475167
0.856	High Similarity	NPC45346
0.856	High Similarity	NPC475377
0.856	High Similarity	NPC172374
0.856	High Similarity	NPC25998
0.856	High Similarity	NPC173435
0.856	High Similarity	NPC262796
0.856	High Similarity	NPC134914
0.856	High Similarity	NPC478064
0.856	High Similarity	NPC478155
0.856	High Similarity	NPC264566
0.856	High Similarity	NPC476074
0.856	High Similarity	NPC301639
0.856	High Similarity	NPC329993
0.8548	High Similarity	NPC188291
0.8548	High Similarity	NPC476859
0.8547	High Similarity	NPC477126
0.8547	High Similarity	NPC51978
0.8537	High Similarity	NPC293112
0.8537	High Similarity	NPC473635
0.8534	High Similarity	NPC201992
0.8525	High Similarity	NPC227397
0.8525	High Similarity	NPC11895
0.8522	High Similarity	NPC27814
0.8516	High Similarity	NPC243014
0.8509	High Similarity	NPC144854
0.8509	High Similarity	NPC3316
0.85	High Similarity	NPC77689
0.85	High Similarity	NPC473636
0.8492	Intermediate Similarity	NPC100390
0.8492	Intermediate Similarity	NPC478150
0.8492	Intermediate Similarity	NPC478153
0.8492	Intermediate Similarity	NPC254614
0.8492	Intermediate Similarity	NPC478152
0.8492	Intermediate Similarity	NPC476193
0.8487	Intermediate Similarity	NPC98249
0.8487	Intermediate Similarity	NPC134430
0.8487	Intermediate Similarity	NPC469684
0.8487	Intermediate Similarity	NPC53396
0.8487	Intermediate Similarity	NPC58662
0.848	Intermediate Similarity	NPC476854
0.848	Intermediate Similarity	NPC477196
0.848	Intermediate Similarity	NPC231529
0.8475	Intermediate Similarity	NPC117712
0.8468	Intermediate Similarity	NPC470882
0.8462	Intermediate Similarity	NPC317687
0.8462	Intermediate Similarity	NPC472002
0.8462	Intermediate Similarity	NPC302146
0.8455	Intermediate Similarity	NPC81736
0.8455	Intermediate Similarity	NPC172154
0.8443	Intermediate Similarity	NPC222688
0.8443	Intermediate Similarity	NPC170538
0.8435	Intermediate Similarity	NPC154608
0.8435	Intermediate Similarity	NPC192813
0.8435	Intermediate Similarity	NPC289702
0.8435	Intermediate Similarity	NPC208461
0.8435	Intermediate Similarity	NPC277017
0.843	Intermediate Similarity	NPC251226
0.843	Intermediate Similarity	NPC109973
0.843	Intermediate Similarity	NPC476961
0.843	Intermediate Similarity	NPC472004
0.8417	Intermediate Similarity	NPC240509
0.8417	Intermediate Similarity	NPC284707
0.8413	Intermediate Similarity	NPC476855
0.8413	Intermediate Similarity	NPC477197
0.8403	Intermediate Similarity	NPC270478
0.8403	Intermediate Similarity	NPC179626
0.84	Intermediate Similarity	NPC329923
0.84	Intermediate Similarity	NPC477078
0.84	Intermediate Similarity	NPC477194
0.84	Intermediate Similarity	NPC477713
0.84	Intermediate Similarity	NPC477192
0.84	Intermediate Similarity	NPC475281
0.84	Intermediate Similarity	NPC477193
0.84	Intermediate Similarity	NPC477075
0.84	Intermediate Similarity	NPC477712
0.84	Intermediate Similarity	NPC477191
0.839	Intermediate Similarity	NPC471204
0.839	Intermediate Similarity	NPC478212
0.839	Intermediate Similarity	NPC159333
0.839	Intermediate Similarity	NPC25909
0.8387	Intermediate Similarity	NPC285091
0.8387	Intermediate Similarity	NPC225049
0.8376	Intermediate Similarity	NPC34315
0.8376	Intermediate Similarity	NPC157476
0.8376	Intermediate Similarity	NPC317107
0.8376	Intermediate Similarity	NPC474846
0.8376	Intermediate Similarity	NPC469655
0.8376	Intermediate Similarity	NPC469656
0.8374	Intermediate Similarity	NPC120724
0.8374	Intermediate Similarity	NPC469789
0.8362	Intermediate Similarity	NPC141350
0.8362	Intermediate Similarity	NPC42662
0.8361	Intermediate Similarity	NPC275675
0.8361	Intermediate Similarity	NPC472000
0.8361	Intermediate Similarity	NPC4021
0.8361	Intermediate Similarity	NPC159456
0.8361	Intermediate Similarity	NPC471999
0.8348	Intermediate Similarity	NPC202524
0.8347	Intermediate Similarity	NPC268958

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 NPC265557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1673
0.2-0.3	3692
0.3-0.4	2226
0.4-0.5	742
0.5-0.6	326
0.6-0.7	158
0.7-0.8	106
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD8328	Phase 3
0.813	Intermediate Similarity	NPD6319	Approved
0.8047	Intermediate Similarity	NPD7319	Approved
0.7899	Intermediate Similarity	NPD6373	Approved
0.7899	Intermediate Similarity	NPD6372	Approved
0.7899	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7115	Discovery
0.7874	Intermediate Similarity	NPD7492	Approved
0.7851	Intermediate Similarity	NPD8297	Approved
0.784	Intermediate Similarity	NPD6059	Approved
0.784	Intermediate Similarity	NPD6054	Approved
0.7833	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7736	Approved
0.7812	Intermediate Similarity	NPD6616	Approved
0.7812	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD6402	Approved
0.7797	Intermediate Similarity	NPD5739	Approved
0.7797	Intermediate Similarity	NPD6675	Approved
0.7797	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD6921	Approved
0.7769	Intermediate Similarity	NPD6649	Approved
0.7769	Intermediate Similarity	NPD6650	Approved
0.7752	Intermediate Similarity	NPD7078	Approved
0.7752	Intermediate Similarity	NPD8293	Discontinued
0.7742	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6370	Approved
0.7667	Intermediate Similarity	NPD6881	Approved
0.7667	Intermediate Similarity	NPD7320	Approved
0.7667	Intermediate Similarity	NPD6686	Approved
0.7667	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD4632	Approved
0.7638	Intermediate Similarity	NPD6015	Approved
0.7638	Intermediate Similarity	NPD6016	Approved
0.7586	Intermediate Similarity	NPD4225	Approved
0.7583	Intermediate Similarity	NPD5697	Approved
0.7583	Intermediate Similarity	NPD5701	Approved
0.7583	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5988	Approved
0.7561	Intermediate Similarity	NPD6882	Approved
0.7541	Intermediate Similarity	NPD7290	Approved
0.7541	Intermediate Similarity	NPD6883	Approved
0.7541	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD8513	Phase 3
0.75	Intermediate Similarity	NPD8516	Approved
0.75	Intermediate Similarity	NPD8515	Approved
0.75	Intermediate Similarity	NPD8517	Approved
0.748	Intermediate Similarity	NPD8130	Phase 1
0.748	Intermediate Similarity	NPD6847	Approved
0.748	Intermediate Similarity	NPD6617	Approved
0.748	Intermediate Similarity	NPD6869	Approved
0.748	Intermediate Similarity	NPD7516	Approved
0.746	Intermediate Similarity	NPD6009	Approved
0.7459	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6014	Approved
0.7459	Intermediate Similarity	NPD6012	Approved
0.7459	Intermediate Similarity	NPD6013	Approved
0.7436	Intermediate Similarity	NPD7638	Approved
0.7402	Intermediate Similarity	NPD7328	Approved
0.7402	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD4634	Approved
0.7385	Intermediate Similarity	NPD7604	Phase 2
0.7377	Intermediate Similarity	NPD6011	Approved
0.7373	Intermediate Similarity	NPD7639	Approved
0.7373	Intermediate Similarity	NPD7640	Approved
0.7364	Intermediate Similarity	NPD5983	Phase 2
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6412	Phase 2
0.7293	Intermediate Similarity	NPD6033	Approved
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7259	Intermediate Similarity	NPD7260	Phase 2
0.7231	Intermediate Similarity	NPD8378	Approved
0.7231	Intermediate Similarity	NPD8335	Approved
0.7231	Intermediate Similarity	NPD7503	Approved
0.7231	Intermediate Similarity	NPD8380	Approved
0.7231	Intermediate Similarity	NPD8379	Approved
0.7231	Intermediate Similarity	NPD8296	Approved
0.7213	Intermediate Similarity	NPD6008	Approved
0.7203	Intermediate Similarity	NPD6084	Phase 2
0.7203	Intermediate Similarity	NPD7902	Approved
0.7203	Intermediate Similarity	NPD6083	Phase 2
0.7203	Intermediate Similarity	NPD4755	Approved
0.7154	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7109	Intermediate Similarity	NPD6274	Approved
0.7107	Intermediate Similarity	NPD5211	Phase 2
0.7099	Intermediate Similarity	NPD8033	Approved
0.7094	Intermediate Similarity	NPD7748	Approved
0.709	Intermediate Similarity	NPD8074	Phase 3
0.7087	Intermediate Similarity	NPD8133	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.708	Intermediate Similarity	NPD6845	Suspended
0.7077	Intermediate Similarity	NPD7101	Approved
0.7077	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7515	Phase 2
0.7063	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6053	Discontinued
0.7	Intermediate Similarity	NPD6335	Approved
0.6992	Remote Similarity	NPD5141	Approved
0.6984	Remote Similarity	NPD6371	Approved
0.6983	Remote Similarity	NPD46	Approved
0.6983	Remote Similarity	NPD6698	Approved
0.6975	Remote Similarity	NPD4697	Phase 3
0.697	Remote Similarity	NPD6909	Approved
0.697	Remote Similarity	NPD6908	Approved
0.6967	Remote Similarity	NPD5224	Approved
0.6967	Remote Similarity	NPD5226	Approved
0.6967	Remote Similarity	NPD4633	Approved
0.6967	Remote Similarity	NPD5225	Approved
0.6949	Remote Similarity	NPD5282	Discontinued
0.6949	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7900	Approved
0.6935	Remote Similarity	NPD4768	Approved
0.6935	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD6317	Approved
0.6911	Remote Similarity	NPD5175	Approved
0.6911	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD5328	Approved
0.6891	Remote Similarity	NPD5695	Phase 3
0.6885	Remote Similarity	NPD5223	Approved
0.6885	Remote Similarity	NPD5344	Discontinued
0.6879	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD3573	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6864	Remote Similarity	NPD6399	Phase 3
0.6846	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5222	Approved
0.6833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5221	Approved
0.6829	Remote Similarity	NPD7632	Discontinued
0.6825	Remote Similarity	NPD4729	Approved
0.6825	Remote Similarity	NPD4730	Approved
0.681	Remote Similarity	NPD5737	Approved
0.681	Remote Similarity	NPD6672	Approved
0.6783	Remote Similarity	NPD3618	Phase 1
0.678	Remote Similarity	NPD5693	Phase 1
0.678	Remote Similarity	NPD6079	Approved
0.678	Remote Similarity	NPD6411	Approved
0.6777	Remote Similarity	NPD5173	Approved
0.6774	Remote Similarity	NPD4754	Approved
0.675	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5779	Approved
0.6723	Remote Similarity	NPD5778	Approved
0.6719	Remote Similarity	NPD5248	Approved
0.6719	Remote Similarity	NPD5247	Approved
0.6719	Remote Similarity	NPD5251	Approved
0.6719	Remote Similarity	NPD5250	Approved
0.6719	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD1694	Approved
0.6693	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD7983	Approved
0.6612	Remote Similarity	NPD4629	Approved
0.6612	Remote Similarity	NPD5210	Approved
0.6612	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6080	Approved
0.661	Remote Similarity	NPD6904	Approved
0.661	Remote Similarity	NPD4753	Phase 2
0.661	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6673	Approved
0.661	Remote Similarity	NPD6101	Approved
0.6583	Remote Similarity	NPD4202	Approved
0.6573	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5956	Approved
0.6538	Remote Similarity	NPD5216	Approved
0.6538	Remote Similarity	NPD5215	Approved
0.6538	Remote Similarity	NPD5217	Approved
0.6532	Remote Similarity	NPD6648	Approved
0.6525	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6110	Phase 1
0.6509	Remote Similarity	NPD8434	Phase 2
0.6503	Remote Similarity	NPD8415	Approved
0.65	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD8035	Phase 2
0.6496	Remote Similarity	NPD6067	Discontinued
0.6496	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6409	Approved
0.6496	Remote Similarity	NPD7334	Approved
0.6496	Remote Similarity	NPD5330	Approved
0.6496	Remote Similarity	NPD6684	Approved
0.6496	Remote Similarity	NPD7521	Approved
0.6496	Remote Similarity	NPD7146	Approved
0.6488	Remote Similarity	NPD8407	Phase 2
0.6483	Remote Similarity	NPD6334	Approved
0.6483	Remote Similarity	NPD6333	Approved
0.648	Remote Similarity	NPD1700	Approved
0.6471	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7799	Discontinued
0.6462	Remote Similarity	NPD5169	Approved
0.6462	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5135	Approved
0.6435	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5127	Approved
0.6407	Remote Similarity	NPD8368	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data