NPASS Compound

Structure

CID227033 OpenBabel06191716022D 50 53 0 0 1 0 0 0 0 0999 V2000 -4.6805 -4.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8833 -5.3692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1675 0.2652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2778 -2.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0914 -1.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1327 -0.8013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4282 1.2525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6577 0.3874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9307 1.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0291 -4.1762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4964 -3.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5041 -4.3421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 -0.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9900 0.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1764 -3.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8767 -3.4866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9542 -4.3722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5241 -0.4998 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2871 -2.4740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1590 -1.3889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2671 -1.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6148 0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -3.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0221 -2.7099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0615 -0.2010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0867 -2.1630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5941 -2.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0132 -1.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1459 -3.0063 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2916 -1.9234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2671 -2.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3026 -3.5470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8977 -0.9043 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5941 -0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9400 -1.3162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 -4.2646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9481 -0.3166 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9179 -4.0261 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7050 1.0856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9923 -2.9506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0722 -3.3818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2843 -1.8062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1327 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9298 -4.3253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7438 -1.9103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0976 -5.2127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4945 0.7000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4483 -0.0862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7112 -0.3233 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 2 17 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 9 47 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 48 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 1 1 6 0 0 0 16 29 1 0 0 0 0 17 36 1 0 0 0 0 18 3 1 6 0 0 0 18 25 1 0 0 0 0 18 33 1 0 0 0 0 19 4 1 1 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 20 5 1 1 0 0 0 20 30 1 0 0 0 0 20 33 1 0 0 0 0 21 31 2 0 0 0 0 21 34 1 0 0 0 0 22 39 2 0 0 0 0 22 49 1 0 0 0 0 23 32 1 0 0 0 0 23 38 1 0 0 0 0 24 26 2 0 0 0 0 24 40 1 0 0 0 0 25 47 1 1 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 31 1 0 0 0 0 27 32 2 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 41 1 6 0 0 0 30 42 1 1 0 0 0 31 43 1 0 0 0 0 32 44 1 0 0 0 0 33 49 1 6 0 0 0 34 50 1 0 0 0 0 35 37 1 0 0 0 0 35 45 2 0 0 0 0 36 38 2 3 0 0 0 36 46 1 0 0 0 0 37 8 1 6 0 0 0 37 48 1 0 0 0 0 37 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	697.31
Volume:	701.761
LogP:	4.304
LogD:	2.775
LogS:	-2.825
# Rotatable Bonds:	3
TPSA:	201.31
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	6.802
Fsp3:	0.486
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:	-4.997
MDCK Permeability:	1.2912379133922514e-05
Pgp-inhibitor:	0.209
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.634

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	75.12488555908203%
Volume Distribution (VD):	1.264
Pgp-substrate:	14.429400444030762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.845

ADMET: Excretion

Clearance (CL):	1.231
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.485
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.725

Download Data

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

Natural Product: NPC227033

Natural Product ID:	NPC227033
*Common Name:**	Rifamycin
IUPAC Name:	n.a.
Synonyms:	CB-01-11; Rifamycin; Rifamycin Sv; Rifomycin
Standard InCHIKey:	HJYYPODYNSCCOU-ODRIEIDWSA-N
Standard InCHI:	InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
SMILES:	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)cc(c(c2c(c3C)O)O)N=C(/C(=CC=C[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C)O
Synthetic Gene Cluster:	BGC0000136;BGC0000137;
ChEMBL Identifier:	CHEMBL437765
PubChem CID:	6324616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15916417]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17253854]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17323993]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19117399]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25256628]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31313922]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	2
GI50	9
IC50	17
Kd	1
Ki	8
MIC	34
Others	43

Activity Type	# Activity
Cell Line	1
Individual Protein	19
NON-MOLECULAR	16
Organism	54
Others	19
SINGLE PROTEIN	2
Tissue	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2613	Individual Protein	Bile salt export pump	Mus musculus	Activity	=	29.8	%	PMID[543876]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	Activity	=	110.0	%	PMID[543877]
NPT1733	Individual Protein	Solute carrier organic anion transporter family member 1A2	Homo sapiens	Ki	=	11000.0	nM	PMID[543880]
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	Ki	=	3000.0	nM	PMID[543880]
NPT305	Individual Protein	Solute carrier organic anion transporter family member 1A4	Rattus norvegicus	Ki	=	7300.0	nM	PMID[543885]
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	Inhibition	=	74.8	%	PMID[543886]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	62.46	ug.mL-1	PMID[543888]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	4.0	%	PMID[543864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	21.0	%	PMID[543864]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.0	%	PMID[543864]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.001	ug.mL-1	PMID[543864]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.004	ug.mL-1	PMID[543865]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.002	ug.mL-1	PMID[543865]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.008	ug.mL-1	PMID[543865]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	0.032	ug.mL-1	PMID[543865]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	1.0	ug.mL-1	PMID[543865]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.0	ug.mL-1	PMID[543865]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	32.0	ug.mL-1	PMID[543865]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	1.0	ug.mL-1	PMID[543865]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	8.0	ug.mL-1	PMID[543865]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	0.032	ug.mL-1	PMID[543865]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	0.125	ug.mL-1	PMID[543865]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.5	ug.mL-1	PMID[543865]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	ED50	=	0.93	mg.kg-1	PMID[543865]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	ED50	=	0.38	mg.kg-1	PMID[543865]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	MIC	>	32.0	ug.mL-1	PMID[543865]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	MIC50	>	128.0	ug.mL-1	PMID[543865]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	25.0	ug.mL-1	PMID[543866]
NPT317	Uncleic Acid	Nucleic Acid		IC50	=	85.0	nM/unit	PMID[543866]
NPT27	Others	Unspecified		Vd	=	1.2	L.kg-1	PMID[543867]
NPT27	Others	Unspecified		CL	=	80.0	mL.min-1.kg-1	PMID[543867]
NPT27	Others	Unspecified		T1/2	=	0.33	hr	PMID[543867]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	3.0	ug.mL-1	PMID[543868]
NPT317	Uncleic Acid	Nucleic Acid		IC50	=	15.0	nM/unit	PMID[543868]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.005	ug.mL-1	PMID[543869]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	100.0	ug.mL-1	PMID[543869]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	100.0	ug.mL-1	PMID[543869]
NPT1398	Organism	Salmonella paratyphi	Salmonella enterica subsp. enterica serovar Paratyphi A	MIC	=	100.0	ug.mL-1	PMID[543869]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.016	ug.mL-1	PMID[543871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[543871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[543871]
NPT2	Others	Unspecified		Inhibition	=	0.7	%	PMID[543872]
NPT2	Others	Unspecified		IC50	=	31640.0	nM	PMID[543872]
NPT2	Others	Unspecified		IC50	=	8.6	nM	PMID[543873]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	12200.0	nM	PMID[543878]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	206500.0	nM	PMID[543878]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	230.0	nM	PMID[543879]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	2000.0	nM	PMID[543880]
NPT712	Individual Protein	Bile salt export pump	Rattus norvegicus	Ki	=	3800.0	nM	PMID[543881]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	Ki	=	31000.0	nM	PMID[543882]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	3000.0	nM	PMID[543880]
NPT752	Individual Protein	Solute carrier organic anion transporter family member 1A1	Rattus norvegicus	Ki	=	6600.0	nM	PMID[543885]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	101.4	%	PMID[543886]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	95.4	%	PMID[543886]
NPT2758	Organism	Streptomyces alboniger	Streptomyces alboniger	IZ	=	11.0	mm	PMID[543887]
NPT2758	Organism	Streptomyces alboniger	Streptomyces alboniger	IZ	=	21.0	mm	PMID[543887]
NPT2759	Organism	Streptomyces acidiscabies	Streptomyces acidiscabies	IZ	=	12.0	mm	PMID[543887]
NPT2760	Organism	Streptomyces scabiei	Streptomyces scabiei	IZ	=	11.0	mm	PMID[543887]
NPT35	Others	n.a.		LogP	=	3.71	n.a.	PMID[543888]
NPT2	Others	Unspecified		Selectivity Index	=	160.1	n.a.	PMID[543888]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	0.39	ug.mL-1	PMID[543888]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	5.0	n.a.	PMID[543889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	10.0	%	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (acute)	=	3.0	n.a.	PMID[543889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (acute)	=	2.3	%	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (cytolytic)	=	2.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (choleostasis)	=	2.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (severe hepatitis)	=	0.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (chronic liver disease)	=	0.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (cirrhosis)	=	0.0	n.a.	PMID[543889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (granulomatous hepatitis)	=	0.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (association with vascular disease)	=	0.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (steatosis)	=	0.0	n.a.	PMID[543889]
NPT2	Others	Unspecified		Hepatotoxicity (malignant tumour)	=	0.0	n.a.	PMID[543889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (benign tumour)	=	0.0	n.a.	PMID[543889]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	100.0	ug.mL-1	PMID[543890]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	100.0	ug.mL-1	PMID[543890]
NPT4078	Organism	Salmonella enterica subsp. enterica serovar Paratyphi B	Salmonella enterica subsp. enterica serovar Paratyphi B	MIC	=	100.0	ug.mL-1	PMID[543890]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.005	ug.mL-1	PMID[543890]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	4.0	nM	PMID[543891]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	2.0	nM	PMID[543891]
NPT35	Others	n.a.		LogD7.4	n.a.	1.19	n.a.	PMID[543892]
NPT27	Others	Unspecified		CL	<	3.0	uL.min-1.(10^6cells)-1	PMID[543892]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	10000.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	21400.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3200.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	14500.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	15500.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	18600.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	15900.0	nM	PMID[543893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	16600.0	nM	PMID[543893]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	990.0	nM	PMID[543894]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	49950.0	nM	PMID[543894]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41620.0	nM	PMID[543894]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15680.0	nM	PMID[543894]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	1500.0	nM	PMID[543894]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	13870.0	nM	PMID[543894]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	550.0	nM	PMID[543894]
NPT621	Tissue	Plasma	Homo sapiens	fCmax	=	3.153	uM	PMID[543895]
NPT712	Individual Protein	Bile salt export pump	Rattus norvegicus	IC50	=	3100.0	nM	PMID[543895]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	6300.0	nM	PMID[543895]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	9500.0	nM	PMID[543896]
NPT605	Organism	Homo sapiens	Homo sapiens	Cmax	=	2780.0	nM	PMID[543896]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-1.23	%	PMID[543898]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.1815	n.a.	PMID[543899]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	24.03	%	PMID[543900]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.02	%	PMID[543901]
NPT27627	SINGLE PROTEIN	B-cell lymphoma 6 protein	Homo sapiens	Kd	=	1000000.0	nM	PMID[543897]

☑ 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 NPC227033 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	373
0.1-0.2	1730
0.2-0.3	5285
0.3-0.4	11522
0.4-0.5	6394
0.5-0.6	9502
0.6-0.7	7788
0.7-0.8	99
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8884	High Similarity	NPC317567
0.784	Intermediate Similarity	NPC313453
0.7588	Intermediate Similarity	NPC251071
0.7512	Intermediate Similarity	NPC70340
0.7478	Intermediate Similarity	NPC240684
0.7445	Intermediate Similarity	NPC477828
0.7434	Intermediate Similarity	NPC290227
0.7345	Intermediate Similarity	NPC477827
0.7345	Intermediate Similarity	NPC477826
0.7339	Intermediate Similarity	NPC285254
0.7333	Intermediate Similarity	NPC474366
0.7308	Intermediate Similarity	NPC314987
0.7286	Intermediate Similarity	NPC477572
0.7286	Intermediate Similarity	NPC477571
0.7286	Intermediate Similarity	NPC477573
0.7281	Intermediate Similarity	NPC176113
0.7277	Intermediate Similarity	NPC132751
0.7277	Intermediate Similarity	NPC198160
0.7256	Intermediate Similarity	NPC475656
0.7256	Intermediate Similarity	NPC475148
0.7243	Intermediate Similarity	NPC288854
0.7237	Intermediate Similarity	NPC227361
0.7237	Intermediate Similarity	NPC217903
0.7237	Intermediate Similarity	NPC124658
0.7234	Intermediate Similarity	NPC13249
0.7232	Intermediate Similarity	NPC475768
0.7212	Intermediate Similarity	NPC121510
0.7212	Intermediate Similarity	NPC477825
0.7212	Intermediate Similarity	NPC85661
0.7212	Intermediate Similarity	NPC171882
0.72	Intermediate Similarity	NPC212123
0.7193	Intermediate Similarity	NPC116178
0.7193	Intermediate Similarity	NPC305542
0.7193	Intermediate Similarity	NPC91234
0.7188	Intermediate Similarity	NPC133156
0.7183	Intermediate Similarity	NPC199533
0.7183	Intermediate Similarity	NPC470454
0.7177	Intermediate Similarity	NPC225381
0.7168	Intermediate Similarity	NPC46679
0.7163	Intermediate Similarity	NPC245059
0.7163	Intermediate Similarity	NPC84494
0.7162	Intermediate Similarity	NPC30749
0.7162	Intermediate Similarity	NPC321166
0.7162	Intermediate Similarity	NPC315253
0.7156	Intermediate Similarity	NPC9475
0.7156	Intermediate Similarity	NPC473096
0.7156	Intermediate Similarity	NPC473095
0.7155	Intermediate Similarity	NPC256422
0.715	Intermediate Similarity	NPC312630
0.715	Intermediate Similarity	NPC324220
0.7149	Intermediate Similarity	NPC218303
0.7149	Intermediate Similarity	NPC61731
0.7149	Intermediate Similarity	NPC186569
0.7143	Intermediate Similarity	NPC159101
0.7136	Intermediate Similarity	NPC48474
0.713	Intermediate Similarity	NPC470453
0.713	Intermediate Similarity	NPC164047
0.713	Intermediate Similarity	NPC470452
0.713	Intermediate Similarity	NPC470448
0.7117	Intermediate Similarity	NPC316274
0.7117	Intermediate Similarity	NPC470198
0.7117	Intermediate Similarity	NPC470197
0.7117	Intermediate Similarity	NPC470196
0.7117	Intermediate Similarity	NPC470194
0.7117	Intermediate Similarity	NPC470195
0.7117	Intermediate Similarity	NPC470193
0.7117	Intermediate Similarity	NPC282474
0.7117	Intermediate Similarity	NPC470200
0.7109	Intermediate Similarity	NPC473094
0.7095	Intermediate Similarity	NPC314653
0.7095	Intermediate Similarity	NPC316262
0.7094	Intermediate Similarity	NPC7560
0.7091	Intermediate Similarity	NPC314672
0.7091	Intermediate Similarity	NPC29472
0.7075	Intermediate Similarity	NPC473202
0.7072	Intermediate Similarity	NPC314020
0.7067	Intermediate Similarity	NPC143050
0.7064	Intermediate Similarity	NPC106700
0.7062	Intermediate Similarity	NPC178851
0.7059	Intermediate Similarity	NPC315914
0.7056	Intermediate Similarity	NPC131862
0.7056	Intermediate Similarity	NPC98776
0.7056	Intermediate Similarity	NPC229051
0.7051	Intermediate Similarity	NPC219170
0.7051	Intermediate Similarity	NPC180253
0.7051	Intermediate Similarity	NPC477860
0.7051	Intermediate Similarity	NPC208069
0.7051	Intermediate Similarity	NPC475161
0.7047	Intermediate Similarity	NPC209981
0.7042	Intermediate Similarity	NPC17219
0.7042	Intermediate Similarity	NPC313717
0.7042	Intermediate Similarity	NPC298778
0.7042	Intermediate Similarity	NPC315306
0.704	Intermediate Similarity	NPC314687
0.7037	Intermediate Similarity	NPC313886
0.7037	Intermediate Similarity	NPC477683
0.7037	Intermediate Similarity	NPC477682
0.7035	Intermediate Similarity	NPC38961
0.7034	Intermediate Similarity	NPC252156
0.7032	Intermediate Similarity	NPC241847
0.7031	Intermediate Similarity	NPC25961
0.7028	Intermediate Similarity	NPC198075
0.7028	Intermediate Similarity	NPC76647
0.7027	Intermediate Similarity	NPC470199
0.7027	Intermediate Similarity	NPC314459
0.7024	Intermediate Similarity	NPC273483
0.7023	Intermediate Similarity	NPC474345
0.7023	Intermediate Similarity	NPC68381
0.7023	Intermediate Similarity	NPC63105
0.7019	Intermediate Similarity	NPC186113
0.7018	Intermediate Similarity	NPC475662
0.7018	Intermediate Similarity	NPC473631
0.7018	Intermediate Similarity	NPC293227
0.7018	Intermediate Similarity	NPC473717
0.7012	Intermediate Similarity	NPC316292
0.701	Intermediate Similarity	NPC119929
0.7	Intermediate Similarity	NPC282636
0.7	Intermediate Similarity	NPC294863
0.7	Intermediate Similarity	NPC174486
0.6995	Remote Similarity	NPC259905
0.6991	Remote Similarity	NPC475233
0.6991	Remote Similarity	NPC469345
0.699	Remote Similarity	NPC135522
0.699	Remote Similarity	NPC193200
0.6986	Remote Similarity	NPC313368
0.6983	Remote Similarity	NPC148391
0.6979	Remote Similarity	NPC157983
0.6979	Remote Similarity	NPC118154
0.6977	Remote Similarity	NPC213052
0.6977	Remote Similarity	NPC476311
0.6971	Remote Similarity	NPC212967
0.6971	Remote Similarity	NPC96342
0.6971	Remote Similarity	NPC164110
0.6971	Remote Similarity	NPC246647
0.6966	Remote Similarity	NPC316368
0.6966	Remote Similarity	NPC134702
0.6966	Remote Similarity	NPC284236
0.6963	Remote Similarity	NPC241874
0.6959	Remote Similarity	NPC476199
0.6959	Remote Similarity	NPC276060
0.6959	Remote Similarity	NPC5671
0.6959	Remote Similarity	NPC476210
0.6955	Remote Similarity	NPC473686
0.6955	Remote Similarity	NPC229817
0.6955	Remote Similarity	NPC197972
0.6955	Remote Similarity	NPC87583
0.6955	Remote Similarity	NPC221140
0.6955	Remote Similarity	NPC475220
0.6955	Remote Similarity	NPC475352
0.6953	Remote Similarity	NPC478048
0.6952	Remote Similarity	NPC117985
0.6949	Remote Similarity	NPC76478
0.6949	Remote Similarity	NPC329830
0.6949	Remote Similarity	NPC118189
0.6948	Remote Similarity	NPC225419
0.6948	Remote Similarity	NPC471180
0.6947	Remote Similarity	NPC131405
0.6944	Remote Similarity	NPC232412
0.6944	Remote Similarity	NPC98667
0.6944	Remote Similarity	NPC86809
0.6943	Remote Similarity	NPC315889
0.6942	Remote Similarity	NPC87708
0.6942	Remote Similarity	NPC474843
0.6942	Remote Similarity	NPC175978
0.6942	Remote Similarity	NPC271681
0.6941	Remote Similarity	NPC470332
0.6941	Remote Similarity	NPC22928
0.6938	Remote Similarity	NPC474373
0.6937	Remote Similarity	NPC289223
0.6934	Remote Similarity	NPC25361
0.6934	Remote Similarity	NPC7752
0.6933	Remote Similarity	NPC109403
0.6933	Remote Similarity	NPC261012
0.6933	Remote Similarity	NPC314738
0.693	Remote Similarity	NPC30432
0.693	Remote Similarity	NPC76128
0.693	Remote Similarity	NPC271385
0.693	Remote Similarity	NPC5029
0.693	Remote Similarity	NPC111536
0.693	Remote Similarity	NPC471181
0.693	Remote Similarity	NPC477836
0.6927	Remote Similarity	NPC277710
0.6927	Remote Similarity	NPC299149
0.6927	Remote Similarity	NPC244903
0.6927	Remote Similarity	NPC114257
0.6927	Remote Similarity	NPC240887
0.6927	Remote Similarity	NPC153578
0.6927	Remote Similarity	NPC329161
0.6927	Remote Similarity	NPC470091
0.6923	Remote Similarity	NPC314914
0.6923	Remote Similarity	NPC146211
0.6923	Remote Similarity	NPC478047
0.6923	Remote Similarity	NPC321226
0.6923	Remote Similarity	NPC328856
0.6923	Remote Similarity	NPC180924
0.6923	Remote Similarity	NPC180210
0.6923	Remote Similarity	NPC478046
0.6923	Remote Similarity	NPC294244
0.6919	Remote Similarity	NPC473961
0.6919	Remote Similarity	NPC216752

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 NPC227033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	709
0.2-0.3	1224
0.3-0.4	2342
0.4-0.5	2659
0.5-0.6	1513
0.6-0.7	406
0.7-0.8	17
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8067	Phase 3
0.8884	High Similarity	NPD8367	Approved
0.8728	High Similarity	NPD8492	Approved
0.8255	Intermediate Similarity	NPD8461	Discontinued
0.7418	Intermediate Similarity	NPD1898	Discontinued
0.7391	Intermediate Similarity	NPD8366	Approved
0.7381	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD8469	Approved
0.7265	Intermediate Similarity	NPD8491	Approved
0.7225	Intermediate Similarity	NPD7801	Approved
0.7212	Intermediate Similarity	NPD8151	Discontinued
0.7167	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8357	Approved
0.7155	Intermediate Similarity	NPD6625	Approved
0.7149	Intermediate Similarity	NPD7783	Phase 2
0.7149	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7654	Discontinued
0.7069	Intermediate Similarity	NPD8404	Phase 2
0.7009	Intermediate Similarity	NPD2339	Phase 3
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7696	Phase 3
0.6991	Remote Similarity	NPD7698	Approved
0.6991	Remote Similarity	NPD7697	Approved
0.6974	Remote Similarity	NPD6296	Discontinued
0.6974	Remote Similarity	NPD7584	Approved
0.6964	Remote Similarity	NPD6874	Approved
0.696	Remote Similarity	NPD7870	Phase 2
0.696	Remote Similarity	NPD7871	Phase 2
0.6947	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6823	Phase 2
0.6944	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7701	Phase 2
0.6933	Remote Similarity	NPD6782	Approved
0.6933	Remote Similarity	NPD6777	Approved
0.6933	Remote Similarity	NPD6780	Approved
0.6933	Remote Similarity	NPD6781	Approved
0.6933	Remote Similarity	NPD6779	Approved
0.6933	Remote Similarity	NPD6776	Approved
0.6933	Remote Similarity	NPD6778	Approved
0.692	Remote Similarity	NPD4668	Phase 2
0.6916	Remote Similarity	NPD7435	Discontinued
0.6908	Remote Similarity	NPD7819	Suspended
0.6895	Remote Similarity	NPD8150	Discontinued
0.6892	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6212	Phase 3
0.6892	Remote Similarity	NPD6213	Phase 3
0.689	Remote Similarity	NPD3453	Discontinued
0.6886	Remote Similarity	NPD8320	Phase 1
0.6886	Remote Similarity	NPD8319	Approved
0.6864	Remote Similarity	NPD2899	Discontinued
0.6852	Remote Similarity	NPD6184	Discontinued
0.6837	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7473	Discontinued
0.682	Remote Similarity	NPD6559	Discontinued
0.681	Remote Similarity	NPD7075	Discontinued
0.6809	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7907	Approved
0.6805	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7585	Approved
0.6792	Remote Similarity	NPD3925	Approved
0.6789	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6807	Phase 3
0.6779	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7700	Phase 2
0.677	Remote Similarity	NPD7699	Phase 2
0.6766	Remote Similarity	NPD7930	Approved
0.6765	Remote Similarity	NPD2533	Approved
0.6765	Remote Similarity	NPD2532	Approved
0.6765	Remote Similarity	NPD2534	Approved
0.6761	Remote Similarity	NPD5711	Approved
0.6761	Remote Similarity	NPD5710	Approved
0.6759	Remote Similarity	NPD3965	Phase 1
0.6758	Remote Similarity	NPD7546	Discontinued
0.6756	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7583	Approved
0.6741	Remote Similarity	NPD7125	Discontinued
0.6736	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD8059	Phase 3
0.673	Remote Similarity	NPD955	Approved
0.6726	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5005	Approved
0.6725	Remote Similarity	NPD5006	Approved
0.6714	Remote Similarity	NPD6959	Discontinued
0.6711	Remote Similarity	NPD6535	Approved
0.6711	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6534	Approved
0.6709	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7417	Discontinued
0.6682	Remote Similarity	NPD6232	Discontinued
0.6682	Remote Similarity	NPD5844	Phase 1
0.6681	Remote Similarity	NPD7827	Phase 1
0.668	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7565	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4605	Approved
0.6652	Remote Similarity	NPD4604	Approved
0.6651	Remote Similarity	NPD2366	Approved
0.664	Remote Similarity	NPD1852	Discontinued
0.6636	Remote Similarity	NPD3818	Discontinued
0.6636	Remote Similarity	NPD7808	Phase 3
0.6635	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6801	Discontinued
0.6609	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4361	Phase 2
0.6607	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8361	Approved
0.6607	Remote Similarity	NPD8360	Approved
0.6607	Remote Similarity	NPD8435	Approved
0.6606	Remote Similarity	NPD8313	Approved
0.6606	Remote Similarity	NPD8312	Approved
0.6602	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7251	Discontinued
0.6585	Remote Similarity	NPD1505	Phase 2
0.6583	Remote Similarity	NPD4665	Approved
0.6583	Remote Similarity	NPD4111	Phase 1
0.6579	Remote Similarity	NPD8485	Approved
0.6571	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3398	Discontinued
0.656	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5402	Approved
0.655	Remote Similarity	NPD4420	Approved
0.6548	Remote Similarity	NPD1483	Discontinued
0.6545	Remote Similarity	NPD6797	Phase 2
0.6542	Remote Similarity	NPD6198	Phase 1
0.654	Remote Similarity	NPD7803	Approved
0.6538	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3882	Suspended
0.6524	Remote Similarity	NPD3684	Discontinued
0.6524	Remote Similarity	NPD6599	Discontinued
0.6522	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8285	Discontinued
0.6518	Remote Similarity	NPD5037	Approved
0.6518	Remote Similarity	NPD5038	Approved
0.6512	Remote Similarity	NPD6746	Phase 2
0.6512	Remote Similarity	NPD5494	Approved
0.6511	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7627	Approved
0.6509	Remote Similarity	NPD7626	Approved
0.6509	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4003	Phase 3
0.6502	Remote Similarity	NPD8407	Phase 2
0.65	Remote Similarity	NPD7074	Phase 3
0.6496	Remote Similarity	NPD7999	Approved
0.6495	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4360	Phase 2
0.6491	Remote Similarity	NPD4363	Phase 3
0.6479	Remote Similarity	NPD3817	Phase 2
0.6473	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5036	Approved
0.6471	Remote Similarity	NPD3823	Discontinued
0.6471	Remote Similarity	NPD5488	Discontinued
0.6468	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2248	Approved
0.6468	Remote Similarity	NPD2246	Approved
0.6466	Remote Similarity	NPD3450	Approved
0.6466	Remote Similarity	NPD3452	Approved
0.6466	Remote Similarity	NPD2494	Approved
0.6466	Remote Similarity	NPD2493	Approved
0.6466	Remote Similarity	NPD6723	Discontinued
0.6455	Remote Similarity	NPD7054	Approved
0.6454	Remote Similarity	NPD4846	Phase 2
0.6453	Remote Similarity	NPD4583	Approved
0.6453	Remote Similarity	NPD4582	Approved
0.645	Remote Similarity	NPD5608	Approved
0.645	Remote Similarity	NPD5609	Approved
0.6449	Remote Similarity	NPD7768	Phase 2
0.6444	Remote Similarity	NPD8434	Phase 2
0.6435	Remote Similarity	NPD2975	Approved
0.6435	Remote Similarity	NPD2974	Approved
0.6435	Remote Similarity	NPD2973	Approved
0.6426	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7472	Approved
0.6422	Remote Similarity	NPD4580	Approved
0.6419	Remote Similarity	NPD3749	Approved
0.6415	Remote Similarity	NPD7411	Suspended
0.6413	Remote Similarity	NPD5026	Approved
0.6413	Remote Similarity	NPD5034	Approved
0.6413	Remote Similarity	NPD36	Approved
0.6413	Remote Similarity	NPD4955	Approved
0.6413	Remote Similarity	NPD5028	Approved
0.6413	Remote Similarity	NPD4954	Approved
0.6413	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2802	Phase 3
0.6411	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4004	Approved
0.641	Remote Similarity	NPD4002	Approved
0.6408	Remote Similarity	NPD7278	Phase 2
0.6408	Remote Similarity	NPD7279	Phase 2
0.6406	Remote Similarity	NPD2247	Approved
0.6406	Remote Similarity	NPD2821	Approved
0.6406	Remote Similarity	NPD2249	Approved
0.6405	Remote Similarity	NPD7292	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