NPASS Compound

Structure

CID117244 OpenBabel06191715472D 45 48 0 0 1 0 0 0 0 0999 V2000 -2.7802 2.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5729 -9.0582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1413 2.5908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1431 4.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8143 3.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2800 -8.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1766 -5.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4694 -5.7121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9177 -4.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6201 1.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5677 2.6724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7283 -6.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7814 1.1291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6248 -3.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6767 3.1264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6980 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3275 2.0019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1072 2.3320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9568 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0212 -7.3851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8904 1.5831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8380 2.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 1.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8721 2.8406 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0552 -7.1263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 -2.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 1.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2071 -2.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2071 1.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5137 3.7741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 4 45 1 0 0 0 0 5 22 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 17 28 2 0 0 0 0 19 38 1 0 0 0 0 20 23 1 0 0 0 0 21 23 2 0 0 0 0 21 39 1 0 0 0 0 22 3 1 6 0 0 0 23 25 1 0 0 0 0 24 40 2 0 0 0 0 25 28 1 0 0 0 0 26 16 1 1 0 0 0 26 31 1 0 0 0 0 26 35 1 0 0 0 0 27 20 1 1 0 0 0 27 32 1 0 0 0 0 27 36 1 0 0 0 0 28 39 1 0 0 0 0 29 18 1 6 0 0 0 29 33 1 0 0 0 0 29 38 1 0 0 0 0 30 22 1 1 0 0 0 30 34 1 0 0 0 0 30 37 1 0 0 0 0 31 36 2 3 0 0 0 31 41 1 0 0 0 0 32 37 2 3 0 0 0 32 42 1 0 0 0 0 33 35 2 3 0 0 0 33 43 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 39 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	623.37
Volume:	646.391
LogP:	3.789
LogD:	3.891
LogS:	-4.284
# Rotatable Bonds:	12
TPSA:	138.84
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.821
Fsp3:	0.618
Lipinski Rule-of-5:	Rejected
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:	-5.033
MDCK Permeability:	3.362275310792029e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.825
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	88.34745025634766%
Volume Distribution (VD):	0.43
Pgp-substrate:	4.557575225830078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.382
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	4.06
Half-life (T1/2):	0.704

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.729
Skin Sensitization:	0.044
Carcinogencity:	0.092
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC117244

Natural Product ID:	NPC117244
*Common Name:**	Apicidin
IUPAC Name:	(3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
Synonyms:	Acipidin
Standard InCHIKey:	JWOGUUIOCYMBPV-GMFLJSBRSA-N
Standard InCHI:	InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N2CCCC[C@@H]2C(=N[C@@H](CCCCCC(=O)CC)C(=N[C@@H](Cc2cn(c3ccccc23)OC)C(=N1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL430060
PubChem CID:	6918328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444718]
NPO11054	Fusarium fujikuroi	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195442]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24495105]
NPO11054	Fusarium fujikuroi	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26192387]
NPO11054	Fusarium fujikuroi	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	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	4
GI50	17
IC50	69
Ki	9
MIC	2
Others	14
Potency	2

Activity Type	# Activity
Cell Line	19
CELL-LINE	2
Individual Protein	57
NON-MOLECULAR	7
Organism	13
Others	8
Protein Complex	4
Protein Family	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4343	Individual Protein	Histone deacetylase	Cryptosporidium parvum	IC50	=	1.0	nM	PMID[469198]
NPT4343	Individual Protein	Histone deacetylase	Cryptosporidium parvum	IC50	=	1.0	nM	PMID[469200]
NPT4344	Individual Protein	Histone deacetylase	Cryptosporidium parvum	Ki	=	8.0	nM	PMID[469200]
NPT4344	Individual Protein	Histone deacetylase	Cryptosporidium parvum	IC50	=	0.008	ug.mL-1	PMID[469201]
NPT4344	Individual Protein	Histone deacetylase	Cryptosporidium parvum	IC50	=	1.0	nM	PMID[469201]
NPT165	Cell Line	HeLa	Homo sapiens	AP50	=	78.0	ng ml-1	PMID[469201]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	290.0	nM	PMID[469202]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	290.0	nM	PMID[469205]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI	=	98.0	%	PMID[469206]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	290.0	nM	PMID[469210]
NPT4346	Individual Protein	Histone deacetylase	Plasmodium falciparum	IC50	=	1.0	nM	PMID[469211]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	290.0	nM	PMID[469212]
NPT4347	Individual Protein	Histone deacetylase-like amidohydrolase	Alcaligenes sp. (strain DSM 11172) (Bordetella sp. (strain FB188))	Ki	=	9200.0	nM	PMID[469213]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	3000.0	nM	PMID[469215]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	7000.0	nM	PMID[469215]
NPT15	Cell Line	Jurkat	Homo sapiens	GI50	=	4000.0	nM	PMID[469215]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	900.0	nM	PMID[469215]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[469220]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	6800.0	nM	PMID[469222]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	1400.0	nM	PMID[469222]
NPT15	Cell Line	Jurkat	Homo sapiens	GI50	=	830.0	nM	PMID[469222]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	280.0	nM	PMID[469222]
NPT71	Cell Line	HEK293	Homo sapiens	GI50	=	11000.0	nM	PMID[469222]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	1500.0	nM	PMID[469223]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5000.0	nM	PMID[469223]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	1000.0	nM	PMID[469223]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	2000.0	nM	PMID[469223]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	1.0	nM	PMID[469198]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.058	ug.mL-1	PMID[469198]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	0.22	mg ml-1	PMID[469199]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	ED50	=	1.9	mg ml-1	PMID[469199]
NPT27	Others	Unspecified		ED50	=	0.2	mg ml-1	PMID[469199]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	1.0	nM	PMID[469200]
NPT2	Others	Unspecified		Ki	=	4.0	nM	PMID[469200]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.058	ug.mL-1	PMID[469200]
NPT3129	Organism	Eimeria tenella	Eimeria tenella	MIC	=	0.094	ug.mL-1	PMID[469200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	AP50	=	89.0	ng ml-1	PMID[469200]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	0.004	ug.mL-1	PMID[469201]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	1.0	nM	PMID[469201]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.057	ug.mL-1	PMID[469201]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	44.0	nM	PMID[469202]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<	0.28	uM	PMID[469203]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	Activity	=	12.0	%	PMID[469204]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	23.0	nM	PMID[469204]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	IC50	=	9.7	nM	PMID[469204]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	IC50	=	3600.0	nM	PMID[469204]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	IC50	=	8700.0	nM	PMID[469204]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	=	4300.0	nM	PMID[469204]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	44.0	nM	PMID[469205]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	13.0	nM	PMID[469206]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	Inhibition	=	0.3	%	PMID[469206]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	8.0	nM	PMID[469207]
NPT4345	Protein Complex	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Homo sapiens	IC50	=	15.8	nM	PMID[469207]
NPT4345	Protein Complex	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Homo sapiens	Ki	=	1.5	nM	PMID[469207]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	=	665.1	nM	PMID[469207]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	Ki	=	123.4	nM	PMID[469207]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	150.0	nM	PMID[469208]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	200.0	nM	PMID[469208]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	Inhibition	=	85.0	%	PMID[469208]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	Inhibition	=	80.0	%	PMID[469208]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	IC50	=	1.0	nM	PMID[469209]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	IC50	=	2.5	nM	PMID[469209]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	IC50	=	2.4	nM	PMID[469209]
NPT688	Individual Protein	Histone deacetylase 4	Homo sapiens	IC50	=	1.2	nM	PMID[469209]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	44.0	nM	PMID[469210]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	33.0	nM	PMID[469211]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	44.0	nM	PMID[469212]
NPT2	Others	Unspecified		IC50	=	670.0	nM	PMID[469213]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	44.0	nM	PMID[469213]
NPT2	Others	Unspecified		IC50	=	4.0	nM	PMID[469214]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	22.0	nM	PMID[469215]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	43.0	nM	PMID[469215]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	22.0	nM	PMID[469215]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	IC50	=	29.0	nM	PMID[469215]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	IC50	=	760.0	nM	PMID[469215]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	>	10000.0	nM	PMID[469215]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2500.0	nM	PMID[469215]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	0.7	nM	PMID[469216]
NPT685	Individual Protein	Histone deacetylase 2	Homo sapiens	IC50	=	1.0	nM	PMID[469216]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	IC50	=	0.6	nM	PMID[469216]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	=	9600.0	nM	PMID[469216]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	IC50	=	300.0	nM	PMID[469216]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	Ki	=	0.04	nM	PMID[469217]
NPT685	Individual Protein	Histone deacetylase 2	Homo sapiens	Ki	=	0.12	nM	PMID[469217]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	Ki	=	0.26	nM	PMID[469217]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	Ki	=	49.0	nM	PMID[469217]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	0.125	ug.mL-1	PMID[469218]
NPT2	Others	Unspecified		FC	=	100.0	n.a.	PMID[469221]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	22.0	nM	PMID[469221]
NPT4345	Protein Complex	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Homo sapiens	IC50	=	29.0	nM	PMID[469221]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	>	10000.0	nM	PMID[469221]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	IC50	=	755.0	nM	PMID[469221]
NPT685	Individual Protein	Histone deacetylase 2	Homo sapiens	IC50	=	35.0	nM	PMID[469222]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2700.0	nM	PMID[469223]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	>	10000.0	nM	PMID[469223]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	IC50	=	750.0	nM	PMID[469223]
NPT4345	Protein Complex	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Homo sapiens	IC50	=	13.0	nM	PMID[469223]
NPT685	Individual Protein	Histone deacetylase 2	Homo sapiens	IC50	=	34.0	nM	PMID[469223]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	11.0	nM	PMID[469223]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	22.0	nM	PMID[469223]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	200.0	nM	PMID[469224]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	100.0	%	PMID[469225]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	300.0	nM	PMID[469225]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[469220]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	800.0	nM	PMID[469227]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	800.0	nM	PMID[469228]
NPT2	Others	Unspecified		FC	=	1.0	n.a.	PMID[469229]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	22.0	nM	PMID[469229]
NPT685	Individual Protein	Histone deacetylase 2	Homo sapiens	IC50	=	35.0	nM	PMID[469229]
NPT686	Individual Protein	Histone deacetylase 3	Homo sapiens	IC50	=	29.0	nM	PMID[469229]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	IC50	=	760.0	nM	PMID[469229]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	IC50	>	10000.0	nM	PMID[469229]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	13.0	nM	PMID[469230]
NPT27	Others	Unspecified		AUC Ratio	=	0.4733	n.a.	PMID[469231]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	AUC	=	379.9	n.a.	PMID[469231]
NPT22224	CELL-LINE	Vero C1008	Chlorocebus sabaeus	AUC cytotoxicity	=	179.8	n.a.	PMID[469231]
NPT22224	CELL-LINE	Vero C1008	Chlorocebus sabaeus	pCC50	~	11.15	n.a.	PMID[469231]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	999684595.59	nM	PMID[469231]

☑ 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 NPC117244 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	294
0.1-0.2	1510
0.2-0.3	11209
0.3-0.4	20977
0.4-0.5	3461
0.5-0.6	2618
0.6-0.7	1982
0.7-0.8	597
0.8-0.85	40
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473763
0.8667	High Similarity	NPC213629
0.8556	High Similarity	NPC94752
0.8495	Intermediate Similarity	NPC171317
0.8466	Intermediate Similarity	NPC469938
0.8457	Intermediate Similarity	NPC475506
0.8444	Intermediate Similarity	NPC228835
0.8444	Intermediate Similarity	NPC165495
0.8438	Intermediate Similarity	NPC478158
0.8438	Intermediate Similarity	NPC162860
0.8429	Intermediate Similarity	NPC54420
0.8427	Intermediate Similarity	NPC248462
0.8413	Intermediate Similarity	NPC155143
0.8396	Intermediate Similarity	NPC473640
0.8376	Intermediate Similarity	NPC281049
0.8351	Intermediate Similarity	NPC100321
0.8325	Intermediate Similarity	NPC473376
0.8306	Intermediate Similarity	NPC17059
0.8278	Intermediate Similarity	NPC15840
0.8254	Intermediate Similarity	NPC293917
0.8247	Intermediate Similarity	NPC223791
0.8247	Intermediate Similarity	NPC107077
0.8223	Intermediate Similarity	NPC478157
0.8222	Intermediate Similarity	NPC11126
0.8214	Intermediate Similarity	NPC75634
0.8173	Intermediate Similarity	NPC54744
0.8167	Intermediate Similarity	NPC64436
0.8163	Intermediate Similarity	NPC320968
0.8152	Intermediate Similarity	NPC478077
0.8115	Intermediate Similarity	NPC470497
0.8108	Intermediate Similarity	NPC472323
0.8105	Intermediate Similarity	NPC470499
0.8079	Intermediate Similarity	NPC160105
0.8054	Intermediate Similarity	NPC235684
0.8022	Intermediate Similarity	NPC248041
0.8022	Intermediate Similarity	NPC283219
0.8022	Intermediate Similarity	NPC126709
0.8011	Intermediate Similarity	NPC267885
0.801	Intermediate Similarity	NPC477714
0.8	Intermediate Similarity	NPC314603
0.799	Intermediate Similarity	NPC64216
0.7979	Intermediate Similarity	NPC243716
0.7978	Intermediate Similarity	NPC91179
0.7967	Intermediate Similarity	NPC145885
0.7967	Intermediate Similarity	NPC14113
0.7967	Intermediate Similarity	NPC84827
0.7956	Intermediate Similarity	NPC110500
0.7956	Intermediate Similarity	NPC149155
0.7956	Intermediate Similarity	NPC203468
0.794	Intermediate Similarity	NPC31385
0.794	Intermediate Similarity	NPC110602
0.794	Intermediate Similarity	NPC75726
0.7938	Intermediate Similarity	NPC476874
0.7935	Intermediate Similarity	NPC113626
0.7917	Intermediate Similarity	NPC149708
0.7913	Intermediate Similarity	NPC319232
0.7913	Intermediate Similarity	NPC24370
0.7892	Intermediate Similarity	NPC143533
0.7877	Intermediate Similarity	NPC474561
0.7877	Intermediate Similarity	NPC49954
0.7872	Intermediate Similarity	NPC321708
0.7871	Intermediate Similarity	NPC477715
0.7849	Intermediate Similarity	NPC258480
0.7841	Intermediate Similarity	NPC129721
0.7826	Intermediate Similarity	NPC219336
0.7795	Intermediate Similarity	NPC300183
0.7772	Intermediate Similarity	NPC15573
0.7772	Intermediate Similarity	NPC183662
0.7772	Intermediate Similarity	NPC217372
0.7772	Intermediate Similarity	NPC234987
0.7761	Intermediate Similarity	NPC6865
0.7761	Intermediate Similarity	NPC153980
0.776	Intermediate Similarity	NPC294693
0.7735	Intermediate Similarity	NPC78020
0.773	Intermediate Similarity	NPC213468
0.772	Intermediate Similarity	NPC11445
0.7714	Intermediate Similarity	NPC326363
0.7713	Intermediate Similarity	NPC472107
0.7713	Intermediate Similarity	NPC79062
0.7711	Intermediate Similarity	NPC72956
0.7709	Intermediate Similarity	NPC282231
0.7703	Intermediate Similarity	NPC476491
0.7689	Intermediate Similarity	NPC220852
0.7689	Intermediate Similarity	NPC323752
0.7688	Intermediate Similarity	NPC469896
0.7681	Intermediate Similarity	NPC155444
0.768	Intermediate Similarity	NPC56233
0.7676	Intermediate Similarity	NPC326575
0.7673	Intermediate Similarity	NPC471193
0.7673	Intermediate Similarity	NPC471194
0.7672	Intermediate Similarity	NPC66210
0.7672	Intermediate Similarity	NPC62749
0.7668	Intermediate Similarity	NPC157828
0.7668	Intermediate Similarity	NPC57994
0.7668	Intermediate Similarity	NPC195239
0.7668	Intermediate Similarity	NPC289299
0.7667	Intermediate Similarity	NPC194640
0.7667	Intermediate Similarity	NPC56109
0.7667	Intermediate Similarity	NPC191382
0.7665	Intermediate Similarity	NPC57398
0.7664	Intermediate Similarity	NPC184225
0.766	Intermediate Similarity	NPC472119
0.7659	Intermediate Similarity	NPC473310
0.7654	Intermediate Similarity	NPC279918
0.7647	Intermediate Similarity	NPC471192
0.7647	Intermediate Similarity	NPC233936
0.7644	Intermediate Similarity	NPC470111
0.7642	Intermediate Similarity	NPC89987
0.7637	Intermediate Similarity	NPC63751
0.7634	Intermediate Similarity	NPC55772
0.7634	Intermediate Similarity	NPC133261
0.7629	Intermediate Similarity	NPC472116
0.7627	Intermediate Similarity	NPC70922
0.7627	Intermediate Similarity	NPC80597
0.7627	Intermediate Similarity	NPC212376
0.7627	Intermediate Similarity	NPC75540
0.7627	Intermediate Similarity	NPC211572
0.7622	Intermediate Similarity	NPC472122
0.7622	Intermediate Similarity	NPC24594
0.7619	Intermediate Similarity	NPC62510
0.7592	Intermediate Similarity	NPC175474
0.759	Intermediate Similarity	NPC262898
0.7582	Intermediate Similarity	NPC54988
0.7581	Intermediate Similarity	NPC285343
0.7579	Intermediate Similarity	NPC474707
0.7571	Intermediate Similarity	NPC259644
0.7571	Intermediate Similarity	NPC25008
0.7571	Intermediate Similarity	NPC73952
0.7571	Intermediate Similarity	NPC469760
0.7571	Intermediate Similarity	NPC469763
0.7571	Intermediate Similarity	NPC469786
0.7571	Intermediate Similarity	NPC469765
0.757	Intermediate Similarity	NPC325976
0.7569	Intermediate Similarity	NPC311276
0.7569	Intermediate Similarity	NPC478182
0.7552	Intermediate Similarity	NPC472112
0.7551	Intermediate Similarity	NPC212213
0.7542	Intermediate Similarity	NPC469762
0.7538	Intermediate Similarity	NPC179701
0.7536	Intermediate Similarity	NPC315804
0.7536	Intermediate Similarity	NPC313804
0.7527	Intermediate Similarity	NPC203754
0.7527	Intermediate Similarity	NPC150048
0.7525	Intermediate Similarity	NPC271862
0.7514	Intermediate Similarity	NPC194881
0.7514	Intermediate Similarity	NPC161861
0.7514	Intermediate Similarity	NPC477976
0.7513	Intermediate Similarity	NPC159125
0.7513	Intermediate Similarity	NPC472097
0.7512	Intermediate Similarity	NPC475969
0.7512	Intermediate Similarity	NPC313640
0.7512	Intermediate Similarity	NPC475859
0.7512	Intermediate Similarity	NPC474877
0.75	Intermediate Similarity	NPC472105
0.75	Intermediate Similarity	NPC28945
0.75	Intermediate Similarity	NPC227582
0.75	Intermediate Similarity	NPC173028
0.75	Intermediate Similarity	NPC65215
0.75	Intermediate Similarity	NPC187827
0.7487	Intermediate Similarity	NPC59269
0.7487	Intermediate Similarity	NPC193761
0.7487	Intermediate Similarity	NPC328318
0.7487	Intermediate Similarity	NPC328596
0.7486	Intermediate Similarity	NPC114637
0.7486	Intermediate Similarity	NPC469785
0.7475	Intermediate Similarity	NPC258062
0.7475	Intermediate Similarity	NPC127677
0.7475	Intermediate Similarity	NPC252338
0.7474	Intermediate Similarity	NPC46895
0.7473	Intermediate Similarity	NPC271797
0.7473	Intermediate Similarity	NPC21174
0.7465	Intermediate Similarity	NPC477176
0.7465	Intermediate Similarity	NPC470730
0.7465	Intermediate Similarity	NPC470729
0.7465	Intermediate Similarity	NPC477175
0.7462	Intermediate Similarity	NPC239954
0.7461	Intermediate Similarity	NPC95783
0.7454	Intermediate Similarity	NPC478028
0.745	Intermediate Similarity	NPC98715
0.7448	Intermediate Similarity	NPC204565
0.7447	Intermediate Similarity	NPC12649
0.7446	Intermediate Similarity	NPC201700
0.7442	Intermediate Similarity	NPC63279
0.7436	Intermediate Similarity	NPC474177
0.7436	Intermediate Similarity	NPC198673
0.743	Intermediate Similarity	NPC477177
0.7427	Intermediate Similarity	NPC65408
0.7426	Intermediate Similarity	NPC323927
0.7426	Intermediate Similarity	NPC225821
0.7426	Intermediate Similarity	NPC46225
0.7424	Intermediate Similarity	NPC81535
0.7421	Intermediate Similarity	NPC472110
0.7421	Intermediate Similarity	NPC472109
0.7419	Intermediate Similarity	NPC472123
0.7418	Intermediate Similarity	NPC242116
0.7407	Intermediate Similarity	NPC297642
0.7407	Intermediate Similarity	NPC24864
0.7405	Intermediate Similarity	NPC32534
0.7403	Intermediate Similarity	NPC293487
0.7398	Intermediate Similarity	NPC133366

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 NPC117244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	484
0.2-0.3	635
0.3-0.4	1710
0.4-0.5	2357
0.5-0.6	2434
0.6-0.7	1163
0.7-0.8	181
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD7944	Discontinued
0.8457	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8238	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD8272	Phase 2
0.8202	Intermediate Similarity	NPD750	Phase 2
0.8135	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD7618	Phase 3
0.8042	Intermediate Similarity	NPD7619	Phase 3
0.7989	Intermediate Similarity	NPD2092	Phase 2
0.7989	Intermediate Similarity	NPD2095	Phase 2
0.7989	Intermediate Similarity	NPD2094	Phase 2
0.798	Intermediate Similarity	NPD7470	Discontinued
0.798	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD482	Approved
0.7946	Intermediate Similarity	NPD2096	Phase 2
0.7946	Intermediate Similarity	NPD2091	Phase 2
0.7929	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD5017	Discontinued
0.7871	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2511	Approved
0.7846	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7731	Approved
0.7788	Intermediate Similarity	NPD7730	Approved
0.7784	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6999	Discontinued
0.7783	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD7953	Approved
0.7773	Intermediate Similarity	NPD7952	Approved
0.7773	Intermediate Similarity	NPD7790	Approved
0.7773	Intermediate Similarity	NPD7950	Approved
0.7773	Intermediate Similarity	NPD7789	Approved
0.7773	Intermediate Similarity	NPD7951	Approved
0.7773	Intermediate Similarity	NPD7791	Approved
0.7749	Intermediate Similarity	NPD6665	Discontinued
0.7739	Intermediate Similarity	NPD7665	Phase 2
0.7739	Intermediate Similarity	NPD7666	Phase 3
0.7714	Intermediate Similarity	NPD7824	Approved
0.7692	Intermediate Similarity	NPD7271	Approved
0.7692	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD7970	Approved
0.7685	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD8115	Approved
0.7677	Intermediate Similarity	NPD8114	Approved
0.7668	Intermediate Similarity	NPD4602	Approved
0.7667	Intermediate Similarity	NPD7780	Approved
0.7667	Intermediate Similarity	NPD7781	Approved
0.766	Intermediate Similarity	NPD7482	Phase 2
0.766	Intermediate Similarity	NPD7483	Phase 2
0.7656	Intermediate Similarity	NPD7603	Discontinued
0.7638	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7001	Phase 3
0.7638	Intermediate Similarity	NPD7957	Phase 1
0.7614	Intermediate Similarity	NPD7817	Phase 1
0.7596	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6595	Phase 3
0.7592	Intermediate Similarity	NPD7234	Approved
0.7592	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7233	Approved
0.759	Intermediate Similarity	NPD6664	Approved
0.7586	Intermediate Similarity	NPD8093	Discontinued
0.7577	Intermediate Similarity	NPD4427	Phase 2
0.7565	Intermediate Similarity	NPD5505	Discontinued
0.7554	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8431	Approved
0.7538	Intermediate Similarity	NPD8072	Approved
0.7526	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5426	Phase 3
0.7488	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8123	Approved
0.7487	Intermediate Similarity	NPD8073	Approved
0.7487	Intermediate Similarity	NPD8122	Approved
0.7473	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD3321	Discontinued
0.746	Intermediate Similarity	NPD8408	Discontinued
0.7459	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3961	Discontinued
0.7448	Intermediate Similarity	NPD8021	Approved
0.7448	Intermediate Similarity	NPD8020	Approved
0.7447	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD4638	Approved
0.7446	Intermediate Similarity	NPD4640	Approved
0.7446	Intermediate Similarity	NPD4639	Approved
0.7437	Intermediate Similarity	NPD7727	Phase 2
0.7435	Intermediate Similarity	NPD5555	Phase 1
0.7427	Intermediate Similarity	NPD201	Phase 2
0.7427	Intermediate Similarity	NPD200	Phase 2
0.7426	Intermediate Similarity	NPD8322	Phase 2
0.7415	Intermediate Similarity	NPD4852	Phase 2
0.7413	Intermediate Similarity	NPD8169	Discontinued
0.7406	Intermediate Similarity	NPD7711	Discontinued
0.7406	Intermediate Similarity	NPD8289	Discontinued
0.7389	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD4600	Approved
0.7387	Intermediate Similarity	NPD4601	Approved
0.7384	Intermediate Similarity	NPD2896	Discontinued
0.7382	Intermediate Similarity	NPD6178	Phase 3
0.7379	Intermediate Similarity	NPD8094	Discontinued
0.7377	Intermediate Similarity	NPD3583	Phase 2
0.7376	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8326	Phase 3
0.7356	Intermediate Similarity	NPD8325	Phase 3
0.7356	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8356	Approved
0.7345	Intermediate Similarity	NPD4703	Approved
0.7345	Intermediate Similarity	NPD4702	Approved
0.7323	Intermediate Similarity	NPD6206	Phase 1
0.732	Intermediate Similarity	NPD4334	Discontinued
0.7308	Intermediate Similarity	NPD5255	Approved
0.7306	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7564	Discontinued
0.7291	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8430	Approved
0.7287	Intermediate Similarity	NPD5065	Approved
0.7286	Intermediate Similarity	NPD4397	Phase 1
0.7278	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5487	Phase 1
0.7273	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4326	Phase 2
0.7249	Intermediate Similarity	NPD4075	Phase 2
0.7247	Intermediate Similarity	NPD1661	Suspended
0.7245	Intermediate Similarity	NPD2336	Approved
0.7238	Intermediate Similarity	NPD2809	Approved
0.7238	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7948	Phase 1
0.7233	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6173	Approved
0.7225	Intermediate Similarity	NPD5898	Approved
0.7225	Intermediate Similarity	NPD5899	Approved
0.7225	Intermediate Similarity	NPD5897	Approved
0.7216	Intermediate Similarity	NPD7026	Phase 2
0.7216	Intermediate Similarity	NPD5809	Phase 3
0.7214	Intermediate Similarity	NPD484	Approved
0.7212	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2144	Approved
0.7202	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4957	Phase 2
0.72	Intermediate Similarity	NPD7777	Approved
0.72	Intermediate Similarity	NPD7778	Approved
0.72	Intermediate Similarity	NPD53	Approved
0.7196	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD8063	Discontinued
0.7194	Intermediate Similarity	NPD4499	Approved
0.7193	Intermediate Similarity	NPD8246	Approved
0.7193	Intermediate Similarity	NPD8247	Approved
0.7191	Intermediate Similarity	NPD7469	Discontinued
0.7188	Intermediate Similarity	NPD3038	Discontinued
0.7184	Intermediate Similarity	NPD4520	Approved
0.7173	Intermediate Similarity	NPD4076	Approved
0.7173	Intermediate Similarity	NPD4079	Approved
0.7166	Intermediate Similarity	NPD5862	Discovery
0.7165	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7308	Discontinued
0.7163	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5100	Phase 3
0.7157	Intermediate Similarity	NPD6987	Phase 1
0.7156	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2915	Discontinued
0.715	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7187	Phase 2
0.7135	Intermediate Similarity	NPD8026	Phase 1
0.7135	Intermediate Similarity	NPD6771	Discontinued
0.7135	Intermediate Similarity	NPD6452	Discontinued
0.7129	Intermediate Similarity	NPD6787	Phase 2
0.7128	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7168	Phase 3
0.7121	Intermediate Similarity	NPD4315	Phase 2
0.712	Intermediate Similarity	NPD3506	Approved
0.712	Intermediate Similarity	NPD3505	Approved
0.712	Intermediate Similarity	NPD4181	Approved
0.7119	Intermediate Similarity	NPD3717	Discontinued
0.7113	Intermediate Similarity	NPD1096	Discontinued
0.7113	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3576	Approved
0.7111	Intermediate Similarity	NPD3575	Approved
0.7107	Intermediate Similarity	NPD6281	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