NPASS Compound

Structure

NPC476451 OpenBabel07101718192D 42 49 0 0 1 0 0 0 0 0999 V2000 3.6136 -0.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5684 -1.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4829 0.5961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3929 -0.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2664 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9085 1.3866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3300 -0.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9501 0.0986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7673 -2.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9434 1.5395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2791 -0.9140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5395 -0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7048 -1.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8817 -0.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0068 -3.2334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4559 -1.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3729 0.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1606 -3.7220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1700 -2.4303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1529 0.9651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3429 -2.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6218 -0.3020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1500 -1.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5744 -0.7905 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7330 -1.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0068 -2.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6218 -1.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7756 -1.7677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9099 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3355 -0.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 -2.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1606 -1.7677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9293 -0.3020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9293 -1.2791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7756 0.1866 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3143 -3.2334 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3637 -0.8119 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5928 -2.2523 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 6.5124 0.9735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 0.9972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 30 2 0 0 0 0 15 18 1 0 0 0 0 15 27 2 0 0 0 0 16 21 1 0 0 0 0 16 29 1 0 0 0 0 17 36 1 0 0 0 0 18 37 2 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 39 1 0 0 0 0 22 25 1 0 0 0 0 23 28 2 0 0 0 0 23 36 1 0 0 0 0 24 35 1 0 0 0 0 24 39 1 0 0 0 0 25 40 1 0 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 32 1 0 0 0 0 29 35 1 1 0 0 0 30 31 1 0 0 0 0 30 41 1 0 0 0 0 31 38 1 0 0 0 0 32 33 2 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 35 22 1 1 0 0 0 36 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.35
Volume:	600.6
LogP:	4.823
LogD:	3.89
LogS:	-3.127
# Rotatable Bonds:	1
TPSA:	75.62
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	6.626
Fsp3:	0.528
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:	-5.188
MDCK Permeability:	2.1424122678581625e-05
Pgp-inhibitor:	0.255
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.744

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.831
Plasma Protein Binding (PPB):	96.1670150756836%
Volume Distribution (VD):	2.715
Pgp-substrate:	5.396884918212891%

ADMET: Metabolism

CYP1A2-inhibitor:	0.384
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.161
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.63

ADMET: Excretion

Clearance (CL):	6.133
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.887
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.919
Carcinogencity:	0.142
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC476451

Natural Product ID:	NPC476451
*Common Name:**	8-Hydroxymanzamine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AMSNINGPDSUBHZ-FEPATLFLSA-N
Standard InCHI:	InChI=1S/C36H44N4O2/c41-30-14-11-13-26-27-15-18-37-32(33(27)38-31(26)30)28-23-36(42)17-8-4-1-2-5-9-19-39-21-16-29(28)35(24-39)22-25-12-7-3-6-10-20-40(25)34(35)36/h1,4,7,11-15,18,23,25,29,34,38,41-42H,2-3,5-6,8-10,16-17,19-22,24H2/b4-1-,12-7-/t25?,29-,34+,35-,36-/m0/s1
SMILES:	C1=CCC[C@@]2(C=C([C@@H]3CCN(CCCC1)C[C@]13CC3C=CCCCCN3[C@@H]21)c1c2c(ccn1)c1cccc(c1[nH]2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL612054
PubChem CID:	5468481
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32531	sponge sp.	Species	n.a.	n.a.	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia	2011-MAR	PMID[12828469]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]

☑ 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	3
GI50	59
IC50	49
MIC	13
Others	26

Activity Type	# Activity
Cell Line	67
Individual Protein	3
NON-MOLECULAR	3
Organism	72
Others	4
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	Inhibition	=	86.7	%	PMID[560049]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	4800.0	nM	PMID[560049]
NPT168	Cell Line	P388	Mus musculus	IC50	>	20.0	ug.mL-1	PMID[560050]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	1100.0	ng/ml	PMID[560051]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.26	ug.mL-1	PMID[560052]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[560052]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	1.1	ug ml-1	PMID[560053]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.1	ug.mL-1	PMID[560054]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	Inhibition	=	86.7	%	PMID[560054]
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	=	1100.0	ug ml-1	PMID[560055]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.1	ug.mL-1	PMID[560057]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	891.25	nM	PMID[560058]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	770.9	nM	PMID[560058]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	912.01	nM	PMID[560058]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	1096.48	nM	PMID[560058]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	1438.8	nM	PMID[560058]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	225.94	nM	PMID[560058]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	666.81	nM	PMID[560058]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1713.96	nM	PMID[560058]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	1150.8	nM	PMID[560058]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	1592.21	nM	PMID[560058]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	1603.25	nM	PMID[560058]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	606.74	nM	PMID[560058]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	2243.88	nM	PMID[560058]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	893.31	nM	PMID[560058]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	639.73	nM	PMID[560058]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	763.84	nM	PMID[560058]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2172.7	nM	PMID[560058]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1081.43	nM	PMID[560058]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	1073.99	nM	PMID[560058]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	1145.51	nM	PMID[560058]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	1188.5	nM	PMID[560058]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	2685.34	nM	PMID[560058]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1896.71	nM	PMID[560058]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	578.1	nM	PMID[560058]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	1432.19	nM	PMID[560058]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1013.91	nM	PMID[560058]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1548.82	nM	PMID[560058]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	966.05	nM	PMID[560058]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	3396.25	nM	PMID[560058]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	609.54	nM	PMID[560058]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	679.2	nM	PMID[560058]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	736.21	nM	PMID[560058]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	1811.34	nM	PMID[560058]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	1472.31	nM	PMID[560058]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	2041.74	nM	PMID[560058]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	946.24	nM	PMID[560058]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	383.71	nM	PMID[560058]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	717.79	nM	PMID[560058]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1380.38	nM	PMID[560058]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	1581.25	nM	PMID[560058]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	699.84	nM	PMID[560058]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1233.1	nM	PMID[560058]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	737.9	nM	PMID[560058]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	1936.42	nM	PMID[560058]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	803.53	nM	PMID[560058]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	650.13	nM	PMID[560058]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1465.55	nM	PMID[560058]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	1671.09	nM	PMID[560058]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	797.99	nM	PMID[560058]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1745.82	nM	PMID[560058]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	1016.25	nM	PMID[560058]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	1629.3	nM	PMID[560058]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	1678.8	nM	PMID[560058]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	659.17	nM	PMID[560058]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	972.75	nM	PMID[560058]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	2213.09	nM	PMID[560058]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	796.16	nM	PMID[560058]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	1663.41	nM	PMID[560058]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	787.05	nM	PMID[560058]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	0.9	ug.mL-1	PMID[560048]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4.0	ug.mL-1	PMID[560048]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.0	ug.mL-1	PMID[560048]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	1.0	ug.mL-1	PMID[560048]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	590.0	nM	PMID[560048]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	6.25	ug.mL-1	PMID[560048]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	<	6.25	ug.mL-1	PMID[560048]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[560048]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	30000.0	nM	PMID[560048]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	LDH50	>	30.0	uM	PMID[560048]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	100.0	%	PMID[560050]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	<	6.25	ug.mL-1	PMID[560050]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.91	ug.mL-1	PMID[560051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.006	ug.mL-1	PMID[560051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.008	ug.mL-1	PMID[560051]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.2	ug.mL-1	PMID[560051]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4200.0	nM	PMID[560051]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	11.0	ug.mL-1	PMID[560051]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MIC	=	0.1	ug.mL-1	PMID[560052]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.008	ug.mL-1	PMID[560053]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.2	ug.mL-1	PMID[560053]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	0.9	ug.mL-1	PMID[560053]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4.0	ug.mL-1	PMID[560053]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.0	ug.mL-1	PMID[560053]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	1.0	ug.mL-1	PMID[560053]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	590.0	nM	PMID[560053]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	11.0	ug.mL-1	PMID[560053]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.9	ug.mL-1	PMID[560053]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.006	ug.mL-1	PMID[560053]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.9	ug.mL-1	PMID[560054]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.006	ug.mL-1	PMID[560054]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.008	ug.mL-1	PMID[560054]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.2	ug.mL-1	PMID[560054]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	0.9	ug.mL-1	PMID[560054]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4.0	ug.mL-1	PMID[560054]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.0	ug.mL-1	PMID[560054]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	1.0	ug.mL-1	PMID[560054]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	0.59	ug.mL-1	PMID[560054]
NPT4902	Protein Complex	Voltage-gated calcium channel	Homo sapiens	Inhibition	=	20.0	%	PMID[560054]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	11.0	ug.mL-1	PMID[560054]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.006	ug.mL-1	PMID[560055]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.008	ug.mL-1	PMID[560055]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.2	ug.mL-1	PMID[560055]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	11.0	ug.mL-1	PMID[560055]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	10.0	ug.mL-1	PMID[560055]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5.0	ug.mL-1	PMID[560055]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.0	ug.mL-1	PMID[560055]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5.0	ug.mL-1	PMID[560055]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	6.5	ug.mL-1	PMID[560055]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	0.25	ug.mL-1	PMID[560055]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	0.31	ug.mL-1	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	83.0	%	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	67.0	%	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	57.0	%	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	35.0	%	PMID[560055]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	32.0	%	PMID[560055]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11.0	nM	PMID[560056]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14.0	nM	PMID[560056]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	177.0	nM	PMID[560056]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3546.0	nM	PMID[560056]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	6205.0	nM	PMID[560056]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	10.0	uM	PMID[560057]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	500.0	nM	PMID[560057]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[560057]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	0.1	ug.mL-1	PMID[560057]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	2.0	ug.mL-1	PMID[560057]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3.5	ug.mL-1	PMID[560057]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	0.9	ug.mL-1	PMID[560057]
NPT2	Others	Unspecified		Ratio IC50	=	140.0	n.a.	PMID[560057]
NPT2	Others	Unspecified		Ratio IC50	=	25.0	n.a.	PMID[560057]
NPT2	Others	Unspecified		Ratio IC50	=	180.0	n.a.	PMID[560057]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.008	ug.mL-1	PMID[560057]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.006	ug.mL-1	PMID[560057]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.91	ug.mL-1	PMID[560057]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[560057]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	MST	>	28.0	%	PMID[560057]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	80.0	%	PMID[560057]

☑ 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 NPC476451 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	656
0.1-0.2	3367
0.2-0.3	13679
0.3-0.4	16319
0.4-0.5	4140
0.5-0.6	2514
0.6-0.7	1723
0.7-0.8	267
0.8-0.85	16
0.85-0.9	9
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC6215
0.9401	High Similarity	NPC471891
0.9395	High Similarity	NPC473312
0.8991	High Similarity	NPC41679
0.8878	High Similarity	NPC166492
0.8878	High Similarity	NPC473362
0.8824	High Similarity	NPC81175
0.8673	High Similarity	NPC250835
0.8578	High Similarity	NPC192315
0.8537	High Similarity	NPC476167
0.8505	High Similarity	NPC476041
0.8505	High Similarity	NPC304926
0.8444	Intermediate Similarity	NPC477861
0.8398	Intermediate Similarity	NPC265576
0.838	Intermediate Similarity	NPC473310
0.8364	Intermediate Similarity	NPC473757
0.8333	Intermediate Similarity	NPC475070
0.8265	Intermediate Similarity	NPC471506
0.8224	Intermediate Similarity	NPC5145
0.8208	Intermediate Similarity	NPC475288
0.8203	Intermediate Similarity	NPC472027
0.808	Intermediate Similarity	NPC476492
0.8047	Intermediate Similarity	NPC477111
0.8018	Intermediate Similarity	NPC101543
0.8018	Intermediate Similarity	NPC469554
0.8009	Intermediate Similarity	NPC476116
0.7965	Intermediate Similarity	NPC314954
0.7955	Intermediate Similarity	NPC8022
0.7955	Intermediate Similarity	NPC470799
0.7953	Intermediate Similarity	NPC477113
0.792	Intermediate Similarity	NPC476491
0.7915	Intermediate Similarity	NPC232130
0.7885	Intermediate Similarity	NPC253580
0.7876	Intermediate Similarity	NPC475338
0.7876	Intermediate Similarity	NPC909
0.7873	Intermediate Similarity	NPC251936
0.7873	Intermediate Similarity	NPC477110
0.786	Intermediate Similarity	NPC476138
0.786	Intermediate Similarity	NPC245816
0.7841	Intermediate Similarity	NPC470126
0.7835	Intermediate Similarity	NPC295228
0.7824	Intermediate Similarity	NPC470500
0.781	Intermediate Similarity	NPC324149
0.7804	Intermediate Similarity	NPC249040
0.7763	Intermediate Similarity	NPC475258
0.7738	Intermediate Similarity	NPC26679
0.7725	Intermediate Similarity	NPC99666
0.7719	Intermediate Similarity	NPC103687
0.7719	Intermediate Similarity	NPC132631
0.7713	Intermediate Similarity	NPC183407
0.7689	Intermediate Similarity	NPC213530
0.7689	Intermediate Similarity	NPC193267
0.7682	Intermediate Similarity	NPC185782
0.7664	Intermediate Similarity	NPC77555
0.7656	Intermediate Similarity	NPC171171
0.7655	Intermediate Similarity	NPC132642
0.765	Intermediate Similarity	NPC211813
0.7623	Intermediate Similarity	NPC477610
0.7623	Intermediate Similarity	NPC476287
0.7619	Intermediate Similarity	NPC326363
0.7615	Intermediate Similarity	NPC475774
0.7608	Intermediate Similarity	NPC314002
0.7596	Intermediate Similarity	NPC220765
0.7595	Intermediate Similarity	NPC171393
0.7595	Intermediate Similarity	NPC295452
0.7588	Intermediate Similarity	NPC162748
0.7583	Intermediate Similarity	NPC471564
0.7578	Intermediate Similarity	NPC94157
0.7569	Intermediate Similarity	NPC470678
0.7564	Intermediate Similarity	NPC325976
0.756	Intermediate Similarity	NPC204717
0.7558	Intermediate Similarity	NPC176538
0.7532	Intermediate Similarity	NPC473185
0.7524	Intermediate Similarity	NPC15102
0.7512	Intermediate Similarity	NPC48938
0.75	Intermediate Similarity	NPC473764
0.75	Intermediate Similarity	NPC314940
0.749	Intermediate Similarity	NPC476493
0.7489	Intermediate Similarity	NPC60006
0.7479	Intermediate Similarity	NPC207686
0.7479	Intermediate Similarity	NPC26543
0.7477	Intermediate Similarity	NPC19872
0.7467	Intermediate Similarity	NPC310118
0.7453	Intermediate Similarity	NPC46580
0.7414	Intermediate Similarity	NPC214980
0.7412	Intermediate Similarity	NPC477609
0.7411	Intermediate Similarity	NPC475422
0.7411	Intermediate Similarity	NPC167860
0.7411	Intermediate Similarity	NPC123976
0.7404	Intermediate Similarity	NPC184964
0.7403	Intermediate Similarity	NPC130570
0.7403	Intermediate Similarity	NPC167908
0.7389	Intermediate Similarity	NPC471080
0.7389	Intermediate Similarity	NPC469592
0.7384	Intermediate Similarity	NPC477549
0.7379	Intermediate Similarity	NPC252590
0.7376	Intermediate Similarity	NPC200836
0.7376	Intermediate Similarity	NPC223427
0.7376	Intermediate Similarity	NPC53144
0.7375	Intermediate Similarity	NPC39092
0.7371	Intermediate Similarity	NPC245348
0.7361	Intermediate Similarity	NPC329541
0.7359	Intermediate Similarity	NPC280272
0.735	Intermediate Similarity	NPC477608
0.7345	Intermediate Similarity	NPC294620
0.7339	Intermediate Similarity	NPC24370
0.7339	Intermediate Similarity	NPC319232
0.7339	Intermediate Similarity	NPC156704
0.7336	Intermediate Similarity	NPC469594
0.7328	Intermediate Similarity	NPC53534
0.7325	Intermediate Similarity	NPC469928
0.7321	Intermediate Similarity	NPC18348
0.7321	Intermediate Similarity	NPC87755
0.7318	Intermediate Similarity	NPC45459
0.7318	Intermediate Similarity	NPC329793
0.7318	Intermediate Similarity	NPC315491
0.7311	Intermediate Similarity	NPC472294
0.7309	Intermediate Similarity	NPC476124
0.7309	Intermediate Similarity	NPC476121
0.7308	Intermediate Similarity	NPC110151
0.7304	Intermediate Similarity	NPC292958
0.7304	Intermediate Similarity	NPC473179
0.7302	Intermediate Similarity	NPC3715
0.7301	Intermediate Similarity	NPC208284
0.7288	Intermediate Similarity	NPC475253
0.7285	Intermediate Similarity	NPC232727
0.7284	Intermediate Similarity	NPC470501
0.728	Intermediate Similarity	NPC184225
0.728	Intermediate Similarity	NPC473183
0.7277	Intermediate Similarity	NPC477607
0.7256	Intermediate Similarity	NPC32771
0.7251	Intermediate Similarity	NPC478032
0.7248	Intermediate Similarity	NPC133366
0.7244	Intermediate Similarity	NPC314957
0.7241	Intermediate Similarity	NPC470502
0.7238	Intermediate Similarity	NPC59269
0.7237	Intermediate Similarity	NPC475602
0.7227	Intermediate Similarity	NPC180504
0.7222	Intermediate Similarity	NPC152620
0.722	Intermediate Similarity	NPC476098
0.7217	Intermediate Similarity	NPC314394
0.7217	Intermediate Similarity	NPC469727
0.7215	Intermediate Similarity	NPC242209
0.7215	Intermediate Similarity	NPC477112
0.7213	Intermediate Similarity	NPC178858
0.7212	Intermediate Similarity	NPC469589
0.7204	Intermediate Similarity	NPC88363
0.7202	Intermediate Similarity	NPC307963
0.7197	Intermediate Similarity	NPC473184
0.7191	Intermediate Similarity	NPC202503
0.719	Intermediate Similarity	NPC150048
0.719	Intermediate Similarity	NPC203754
0.7188	Intermediate Similarity	NPC329708
0.7188	Intermediate Similarity	NPC264166
0.7188	Intermediate Similarity	NPC165349
0.7188	Intermediate Similarity	NPC118832
0.7188	Intermediate Similarity	NPC47059
0.7188	Intermediate Similarity	NPC274291
0.7182	Intermediate Similarity	NPC267928
0.7181	Intermediate Similarity	NPC199667
0.7181	Intermediate Similarity	NPC85273
0.7179	Intermediate Similarity	NPC470503
0.7176	Intermediate Similarity	NPC246700
0.7168	Intermediate Similarity	NPC475910
0.7162	Intermediate Similarity	NPC213308
0.716	Intermediate Similarity	NPC475746
0.7155	Intermediate Similarity	NPC323752
0.715	Intermediate Similarity	NPC284678
0.7143	Intermediate Similarity	NPC27041
0.7143	Intermediate Similarity	NPC95783
0.7143	Intermediate Similarity	NPC469497
0.7143	Intermediate Similarity	NPC106833
0.7137	Intermediate Similarity	NPC473181
0.7137	Intermediate Similarity	NPC153400
0.7136	Intermediate Similarity	NPC251090
0.7131	Intermediate Similarity	NPC74619
0.7131	Intermediate Similarity	NPC33949
0.7125	Intermediate Similarity	NPC182222
0.7124	Intermediate Similarity	NPC276657
0.7123	Intermediate Similarity	NPC474177
0.7123	Intermediate Similarity	NPC232340
0.7118	Intermediate Similarity	NPC473180
0.7117	Intermediate Similarity	NPC128823
0.7115	Intermediate Similarity	NPC317430
0.7112	Intermediate Similarity	NPC264285
0.7112	Intermediate Similarity	NPC477714
0.7111	Intermediate Similarity	NPC285558
0.7111	Intermediate Similarity	NPC470505
0.711	Intermediate Similarity	NPC92111
0.7106	Intermediate Similarity	NPC229893
0.7101	Intermediate Similarity	NPC471178
0.71	Intermediate Similarity	NPC330009
0.71	Intermediate Similarity	NPC170114
0.7098	Intermediate Similarity	NPC315467
0.7097	Intermediate Similarity	NPC128751
0.7097	Intermediate Similarity	NPC213629
0.7095	Intermediate Similarity	NPC471294
0.7094	Intermediate Similarity	NPC473317
0.7094	Intermediate Similarity	NPC60621
0.7093	Intermediate Similarity	NPC82548

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 NPC476451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	598
0.2-0.3	888
0.3-0.4	1817
0.4-0.5	2671
0.5-0.6	1978
0.6-0.7	829
0.7-0.8	63
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
0.7876	Intermediate Similarity	NPD7603	Discontinued
0.783	Intermediate Similarity	NPD7948	Phase 1
0.7773	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7112	Discontinued
0.7578	Intermediate Similarity	NPD3330	Phase 1
0.7566	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4886	Phase 2
0.7522	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5065	Approved
0.7352	Intermediate Similarity	NPD8395	Approved
0.7352	Intermediate Similarity	NPD2176	Approved
0.7352	Intermediate Similarity	NPD8396	Approved
0.7352	Intermediate Similarity	NPD2177	Approved
0.7352	Intermediate Similarity	NPD2175	Phase 3
0.7325	Intermediate Similarity	NPD5612	Discontinued
0.7318	Intermediate Similarity	NPD484	Approved
0.7316	Intermediate Similarity	NPD7726	Phase 1
0.7308	Intermediate Similarity	NPD9690	Approved
0.7301	Intermediate Similarity	NPD5939	Approved
0.7301	Intermediate Similarity	NPD5936	Approved
0.7238	Intermediate Similarity	NPD6159	Phase 2
0.7233	Intermediate Similarity	NPD424	Approved
0.7233	Intermediate Similarity	NPD425	Approved
0.7227	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4511	Phase 1
0.7206	Intermediate Similarity	NPD112	Approved
0.7206	Intermediate Similarity	NPD9705	Discontinued
0.7202	Intermediate Similarity	NPD1038	Approved
0.7202	Intermediate Similarity	NPD9695	Approved
0.72	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4122	Approved
0.7188	Intermediate Similarity	NPD32	Approved
0.7188	Intermediate Similarity	NPD4038	Approved
0.7188	Intermediate Similarity	NPD31	Approved
0.7188	Intermediate Similarity	NPD4034	Approved
0.7188	Intermediate Similarity	NPD4039	Approved
0.7188	Intermediate Similarity	NPD4036	Approved
0.7188	Intermediate Similarity	NPD4033	Approved
0.7188	Intermediate Similarity	NPD4035	Approved
0.7188	Intermediate Similarity	NPD4037	Approved
0.7185	Intermediate Similarity	NPD3746	Discontinued
0.7156	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD1856	Discontinued
0.7124	Intermediate Similarity	NPD6290	Phase 2
0.7101	Intermediate Similarity	NPD7824	Approved
0.7097	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7666	Phase 3
0.7093	Intermediate Similarity	NPD7665	Phase 2
0.7089	Intermediate Similarity	NPD6595	Phase 3
0.7082	Intermediate Similarity	NPD3402	Phase 1
0.708	Intermediate Similarity	NPD5530	Phase 1
0.708	Intermediate Similarity	NPD8442	Discontinued
0.7074	Intermediate Similarity	NPD4502	Phase 2
0.7073	Intermediate Similarity	NPD5255	Approved
0.7072	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5559	Phase 2
0.7051	Intermediate Similarity	NPD8431	Approved
0.7048	Intermediate Similarity	NPD7222	Phase 2
0.7046	Intermediate Similarity	NPD6352	Phase 2
0.7045	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8358	Approved
0.7045	Intermediate Similarity	NPD802	Phase 2
0.7035	Intermediate Similarity	NPD4795	Phase 2
0.702	Intermediate Similarity	NPD6456	Discontinued
0.7017	Intermediate Similarity	NPD7731	Approved
0.7017	Intermediate Similarity	NPD7730	Approved
0.7013	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2615	Phase 3
0.7013	Intermediate Similarity	NPD2616	Phase 3
0.7012	Intermediate Similarity	NPD7558	Phase 2
0.7009	Intermediate Similarity	NPD537	Phase 2
0.7009	Intermediate Similarity	NPD534	Phase 2
0.7004	Intermediate Similarity	NPD7271	Approved
0.7004	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7925	Phase 2
0.7004	Intermediate Similarity	NPD7924	Phase 2
0.7	Intermediate Similarity	NPD3404	Approved
0.6984	Remote Similarity	NPD6961	Discontinued
0.697	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8093	Discontinued
0.696	Remote Similarity	NPD5426	Phase 3
0.6959	Remote Similarity	NPD2762	Phase 2
0.6948	Remote Similarity	NPD5644	Phase 1
0.6948	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8430	Approved
0.6946	Remote Similarity	NPD6978	Phase 2
0.6946	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7791	Approved
0.6942	Remote Similarity	NPD7790	Approved
0.6942	Remote Similarity	NPD7952	Approved
0.6942	Remote Similarity	NPD7789	Approved
0.6942	Remote Similarity	NPD7953	Approved
0.6942	Remote Similarity	NPD7950	Approved
0.6942	Remote Similarity	NPD7951	Approved
0.6939	Remote Similarity	NPD8016	Phase 3
0.6939	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD706	Phase 1
0.6926	Remote Similarity	NPD7470	Discontinued
0.6923	Remote Similarity	NPD5164	Discontinued
0.6923	Remote Similarity	NPD7068	Approved
0.6923	Remote Similarity	NPD7067	Approved
0.692	Remote Similarity	NPD8356	Approved
0.692	Remote Similarity	NPD7219	Approved
0.692	Remote Similarity	NPD7221	Approved
0.6919	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4044	Discontinued
0.6913	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.69	Remote Similarity	NPD796	Phase 2
0.6897	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2383	Phase 1
0.6895	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3013	Phase 3
0.6883	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6975	Discontinued
0.687	Remote Similarity	NPD2916	Discontinued
0.687	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6376	Discontinued
0.687	Remote Similarity	NPD5658	Approved
0.6864	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD1740	Approved
0.6858	Remote Similarity	NPD1739	Approved
0.6856	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4131	Phase 3
0.6852	Remote Similarity	NPD8349	Phase 1
0.6852	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6569	Phase 2
0.6847	Remote Similarity	NPD9689	Approved
0.684	Remote Similarity	NPD1325	Approved
0.684	Remote Similarity	NPD1326	Approved
0.6838	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4442	Phase 2
0.6833	Remote Similarity	NPD6281	Approved
0.6833	Remote Similarity	NPD8063	Discontinued
0.683	Remote Similarity	NPD3477	Phase 2
0.683	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7453	Approved
0.6826	Remote Similarity	NPD7452	Approved
0.6818	Remote Similarity	NPD6968	Phase 2
0.6818	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6969	Phase 2
0.6816	Remote Similarity	NPD3006	Discontinued
0.6814	Remote Similarity	NPD3825	Phase 3
0.6814	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3814	Phase 1
0.6814	Remote Similarity	NPD5999	Phase 2
0.6814	Remote Similarity	NPD6999	Discontinued
0.6812	Remote Similarity	NPD5901	Discontinued
0.6811	Remote Similarity	NPD8246	Approved
0.6811	Remote Similarity	NPD8247	Approved
0.6802	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3343	Phase 3
0.6795	Remote Similarity	NPD8094	Discontinued
0.6793	Remote Similarity	NPD7194	Discontinued
0.6791	Remote Similarity	NPD5100	Phase 3
0.6789	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8101	Phase 3
0.6784	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8363	Approved
0.6782	Remote Similarity	NPD8364	Approved
0.678	Remote Similarity	NPD7423	Phase 2
0.6778	Remote Similarity	NPD4945	Discontinued
0.6777	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD925	Approved
0.6777	Remote Similarity	NPD926	Approved
0.6774	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8370	Discontinued
0.6763	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7674	Phase 3
0.6763	Remote Similarity	NPD7675	Phase 3
0.6753	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1392	Approved
0.675	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8512	Phase 3
0.6743	Remote Similarity	NPD7867	Phase 1
0.6742	Remote Similarity	NPD1034	Phase 3
0.6742	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3961	Discontinued
0.6742	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8020	Approved
0.6742	Remote Similarity	NPD8021	Approved
0.674	Remote Similarity	NPD4548	Discontinued
0.6739	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6164	Phase 2

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