NPASS Compound

Structure

NPC47672 OpenBabel07101718242D 32 33 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 6.9282 -4.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 7.7942 -4.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 29 1 0 0 0 0 3 31 1 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 10 32 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 1 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 28 2 3 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.98
Volume:	488.008
LogP:	4.073
LogD:	3.378
LogS:	-4.119
# Rotatable Bonds:	13
TPSA:	76.82
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	2.913
Fsp3:	0.435
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:	-5.239
MDCK Permeability:	1.4863988326396793e-05
Pgp-inhibitor:	0.577
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	96.39714813232422%
Volume Distribution (VD):	2.824
Pgp-substrate:	2.0940117835998535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.716
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	1.194
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.948
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.381
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC47672

Natural Product ID:	NPC47672
*Common Name:**	Suberedamine A
IUPAC Name:	(2S)-2-amino-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]ethyl]propanamide
Synonyms:
Standard InCHIKey:	CPOMDHYOIBOZBW-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C23H30Br3N3O3/c1-29(2)9-4-10-32-22-18(25)12-16(13-19(22)26)7-8-28-23(30)20(27)14-15-5-6-21(31-3)17(24)11-15/h5-6,11-13,20H,4,7-10,14,27H2,1-3H3,(H,28,30)/t20-/m0/s1
SMILES:	CN(C)CCCOc1c(cc(CCN=C([C@H](Cc2ccc(c(c2)Br)OC)N)O)cc1Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464660
PubChem CID:	10484217
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine and derivatives

*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
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425148]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473442]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964644]
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24758268]

☑ 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
IC50	2
MIC	23

Activity Type	# Activity
Cell Line	2
Organism	23

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	8.0	ug.mL-1	PMID[524165]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	9.0	ug.mL-1	PMID[524165]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.6	ug.mL-1	PMID[524165]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	50.0	ug.mL-1	PMID[524166]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	50.0	ug.mL-1	PMID[524166]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	128000.0	ug.mL-1	PMID[524166]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128000.0	ug.mL-1	PMID[524166]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	64000.0	ug.mL-1	PMID[524166]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	64000.0	ug.mL-1	PMID[524166]
NPT4276	Organism	Yersinia enterocolitica	Yersinia enterocolitica	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT2894	Organism	Providencia rettgeri	Providencia rettgeri	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128000.0	ug.mL-1	PMID[524166]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT1264	Organism	Burkholderia cepacia	Burkholderia cepacia	MIC	>	128000.0	ug.mL-1	PMID[524166]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	128000.0	ug.mL-1	PMID[524166]

☑ 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 NPC47672 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	219
0.1-0.2	2495
0.2-0.3	12878
0.3-0.4	5114
0.4-0.5	13119
0.5-0.6	7725
0.6-0.7	996
0.7-0.8	124
0.8-0.85	15
0.85-0.9	3
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC233926
0.9388	High Similarity	NPC156311
0.9247	High Similarity	NPC258222
0.9231	High Similarity	NPC78530
0.9178	High Similarity	NPC76412
0.8966	High Similarity	NPC135349
0.8733	High Similarity	NPC109968
0.8446	Intermediate Similarity	NPC474128
0.8369	Intermediate Similarity	NPC110131
0.8367	Intermediate Similarity	NPC474673
0.8356	Intermediate Similarity	NPC470471
0.8333	Intermediate Similarity	NPC470472
0.8298	Intermediate Similarity	NPC272463
0.8243	Intermediate Similarity	NPC470470
0.817	Intermediate Similarity	NPC296085
0.8052	Intermediate Similarity	NPC71629
0.7962	Intermediate Similarity	NPC469711
0.7947	Intermediate Similarity	NPC128877
0.7908	Intermediate Similarity	NPC308571
0.7895	Intermediate Similarity	NPC83289
0.7895	Intermediate Similarity	NPC189724
0.7895	Intermediate Similarity	NPC212850
0.7838	Intermediate Similarity	NPC475735
0.7785	Intermediate Similarity	NPC307123
0.7785	Intermediate Similarity	NPC247018
0.7785	Intermediate Similarity	NPC97870
0.777	Intermediate Similarity	NPC474091
0.7763	Intermediate Similarity	NPC213471
0.7718	Intermediate Similarity	NPC473724
0.7692	Intermediate Similarity	NPC247298
0.7692	Intermediate Similarity	NPC263835
0.7665	Intermediate Similarity	NPC477255
0.7595	Intermediate Similarity	NPC245974
0.7586	Intermediate Similarity	NPC259071
0.7586	Intermediate Similarity	NPC77435
0.7572	Intermediate Similarity	NPC477254
0.7566	Intermediate Similarity	NPC303993
0.7558	Intermediate Similarity	NPC475396
0.7543	Intermediate Similarity	NPC475658
0.7543	Intermediate Similarity	NPC473892
0.7528	Intermediate Similarity	NPC227953
0.7514	Intermediate Similarity	NPC248822
0.75	Intermediate Similarity	NPC43275
0.7486	Intermediate Similarity	NPC8093
0.7486	Intermediate Similarity	NPC121571
0.7485	Intermediate Similarity	NPC469979
0.7483	Intermediate Similarity	NPC328267
0.7468	Intermediate Similarity	NPC470249
0.7447	Intermediate Similarity	NPC26524
0.7442	Intermediate Similarity	NPC473462
0.7442	Intermediate Similarity	NPC298981
0.7442	Intermediate Similarity	NPC207819
0.7442	Intermediate Similarity	NPC126128
0.7442	Intermediate Similarity	NPC110454
0.7434	Intermediate Similarity	NPC274732
0.7434	Intermediate Similarity	NPC471953
0.7432	Intermediate Similarity	NPC95733
0.7432	Intermediate Similarity	NPC62101
0.743	Intermediate Similarity	NPC474678
0.743	Intermediate Similarity	NPC471338
0.7401	Intermediate Similarity	NPC473409
0.7401	Intermediate Similarity	NPC82741
0.7401	Intermediate Similarity	NPC141405
0.7389	Intermediate Similarity	NPC475843
0.7384	Intermediate Similarity	NPC226001
0.7383	Intermediate Similarity	NPC29477
0.7383	Intermediate Similarity	NPC320242
0.7365	Intermediate Similarity	NPC211218
0.7355	Intermediate Similarity	NPC309667
0.7329	Intermediate Similarity	NPC321133
0.7326	Intermediate Similarity	NPC225130
0.732	Intermediate Similarity	NPC470392
0.7314	Intermediate Similarity	NPC301941
0.7314	Intermediate Similarity	NPC214188
0.7314	Intermediate Similarity	NPC74618
0.7308	Intermediate Similarity	NPC197045
0.7303	Intermediate Similarity	NPC147847
0.7303	Intermediate Similarity	NPC99280
0.7293	Intermediate Similarity	NPC202866
0.729	Intermediate Similarity	NPC235633
0.7288	Intermediate Similarity	NPC49172
0.7283	Intermediate Similarity	NPC471337
0.7273	Intermediate Similarity	NPC115803
0.7261	Intermediate Similarity	NPC40321
0.726	Intermediate Similarity	NPC256369
0.7255	Intermediate Similarity	NPC11449
0.7247	Intermediate Similarity	NPC471591
0.7247	Intermediate Similarity	NPC174607
0.7244	Intermediate Similarity	NPC470248
0.7226	Intermediate Similarity	NPC71888
0.7226	Intermediate Similarity	NPC120114
0.7215	Intermediate Similarity	NPC470709
0.7203	Intermediate Similarity	NPC59387
0.72	Intermediate Similarity	NPC290534
0.7198	Intermediate Similarity	NPC469721
0.719	Intermediate Similarity	NPC135173
0.7189	Intermediate Similarity	NPC473450
0.7181	Intermediate Similarity	NPC471315
0.7181	Intermediate Similarity	NPC471314
0.716	Intermediate Similarity	NPC132771
0.7152	Intermediate Similarity	NPC136112
0.7152	Intermediate Similarity	NPC141739
0.7151	Intermediate Similarity	NPC144823
0.7143	Intermediate Similarity	NPC283760
0.7134	Intermediate Similarity	NPC475132
0.7134	Intermediate Similarity	NPC474587
0.7118	Intermediate Similarity	NPC254700
0.7097	Intermediate Similarity	NPC474753
0.7097	Intermediate Similarity	NPC123140
0.7092	Intermediate Similarity	NPC97811
0.7089	Intermediate Similarity	NPC318591
0.7089	Intermediate Similarity	NPC475293
0.7089	Intermediate Similarity	NPC231163
0.707	Intermediate Similarity	NPC237227
0.7059	Intermediate Similarity	NPC159987
0.7059	Intermediate Similarity	NPC78061
0.7059	Intermediate Similarity	NPC122359
0.7055	Intermediate Similarity	NPC82963
0.7051	Intermediate Similarity	NPC163810
0.7047	Intermediate Similarity	NPC318357
0.7045	Intermediate Similarity	NPC475615
0.7032	Intermediate Similarity	NPC114102
0.7027	Intermediate Similarity	NPC469731
0.7024	Intermediate Similarity	NPC287757
0.7024	Intermediate Similarity	NPC319320
0.7016	Intermediate Similarity	NPC471336
0.7016	Intermediate Similarity	NPC470746
0.7007	Intermediate Similarity	NPC38458
0.7007	Intermediate Similarity	NPC311737
0.7	Intermediate Similarity	NPC168861
0.6993	Remote Similarity	NPC301713
0.6989	Remote Similarity	NPC143450
0.6986	Remote Similarity	NPC303370
0.6981	Remote Similarity	NPC214988
0.698	Remote Similarity	NPC17388
0.698	Remote Similarity	NPC53596
0.698	Remote Similarity	NPC471308
0.698	Remote Similarity	NPC160120
0.698	Remote Similarity	NPC289330
0.6968	Remote Similarity	NPC195902
0.6968	Remote Similarity	NPC474087
0.6964	Remote Similarity	NPC56635
0.6957	Remote Similarity	NPC204546
0.6948	Remote Similarity	NPC251571
0.6944	Remote Similarity	NPC166837
0.6943	Remote Similarity	NPC267237
0.6937	Remote Similarity	NPC470250
0.6923	Remote Similarity	NPC470951
0.6923	Remote Similarity	NPC246591
0.6923	Remote Similarity	NPC326966
0.6918	Remote Similarity	NPC118202
0.6914	Remote Similarity	NPC470247
0.6909	Remote Similarity	NPC324081
0.6909	Remote Similarity	NPC277857
0.6909	Remote Similarity	NPC115144
0.6903	Remote Similarity	NPC325651
0.6903	Remote Similarity	NPC155838
0.6886	Remote Similarity	NPC475432
0.6883	Remote Similarity	NPC218323
0.6879	Remote Similarity	NPC42383
0.6879	Remote Similarity	NPC214869
0.6875	Remote Similarity	NPC204848
0.6875	Remote Similarity	NPC41473
0.6875	Remote Similarity	NPC473358
0.6875	Remote Similarity	NPC312770
0.6875	Remote Similarity	NPC160607
0.6875	Remote Similarity	NPC14600
0.6871	Remote Similarity	NPC317254
0.6868	Remote Similarity	NPC96275
0.6864	Remote Similarity	NPC207675
0.6864	Remote Similarity	NPC212699
0.6863	Remote Similarity	NPC236265
0.6863	Remote Similarity	NPC213414
0.6859	Remote Similarity	NPC35961
0.6859	Remote Similarity	NPC195749
0.6859	Remote Similarity	NPC52029
0.6842	Remote Similarity	NPC116562
0.6839	Remote Similarity	NPC202776
0.6839	Remote Similarity	NPC280736
0.6833	Remote Similarity	NPC475283
0.6833	Remote Similarity	NPC152205
0.6832	Remote Similarity	NPC299583
0.6805	Remote Similarity	NPC206372
0.6805	Remote Similarity	NPC203424
0.6802	Remote Similarity	NPC22014
0.6797	Remote Similarity	NPC255253
0.6788	Remote Similarity	NPC313414
0.6788	Remote Similarity	NPC9373
0.6779	Remote Similarity	NPC323948
0.6772	Remote Similarity	NPC166624
0.6772	Remote Similarity	NPC158078
0.677	Remote Similarity	NPC193528
0.6768	Remote Similarity	NPC63628
0.6768	Remote Similarity	NPC178466
0.6761	Remote Similarity	NPC470393
0.6755	Remote Similarity	NPC41801
0.6753	Remote Similarity	NPC471339
0.6738	Remote Similarity	NPC80514
0.6736	Remote Similarity	NPC96224
0.6736	Remote Similarity	NPC471495

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 NPC47672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	626
0.2-0.3	1227
0.3-0.4	1911
0.4-0.5	2951
0.5-0.6	1681
0.6-0.7	547
0.7-0.8	58
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
0.7908	Intermediate Similarity	NPD2459	Approved
0.7908	Intermediate Similarity	NPD2458	Approved
0.7908	Intermediate Similarity	NPD2460	Phase 3
0.7785	Intermediate Similarity	NPD1423	Approved
0.7748	Intermediate Similarity	NPD3054	Approved
0.7748	Intermediate Similarity	NPD3052	Approved
0.7718	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2874	Phase 2
0.7484	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2429	Approved
0.7483	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2428	Approved
0.7448	Intermediate Similarity	NPD2556	Approved
0.7448	Intermediate Similarity	NPD2554	Approved
0.7434	Intermediate Similarity	NPD7477	Discontinued
0.7417	Intermediate Similarity	NPD5163	Phase 2
0.7391	Intermediate Similarity	NPD2184	Approved
0.7391	Intermediate Similarity	NPD2183	Approved
0.7389	Intermediate Similarity	NPD7153	Discontinued
0.7383	Intermediate Similarity	NPD1820	Approved
0.7383	Intermediate Similarity	NPD1818	Approved
0.7383	Intermediate Similarity	NPD1817	Approved
0.7383	Intermediate Similarity	NPD1819	Approved
0.7383	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7131	Phase 3
0.7329	Intermediate Similarity	NPD3985	Discontinued
0.7329	Intermediate Similarity	NPD2668	Approved
0.7329	Intermediate Similarity	NPD2667	Approved
0.7303	Intermediate Similarity	NPD3165	Approved
0.7303	Intermediate Similarity	NPD3164	Approved
0.7303	Intermediate Similarity	NPD3167	Approved
0.7303	Intermediate Similarity	NPD3166	Approved
0.7285	Intermediate Similarity	NPD4993	Discontinued
0.7284	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD52	Approved
0.7284	Intermediate Similarity	NPD7526	Approved
0.7284	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6072	Discontinued
0.726	Intermediate Similarity	NPD3049	Approved
0.7248	Intermediate Similarity	NPD6582	Phase 2
0.7248	Intermediate Similarity	NPD6583	Phase 3
0.7233	Intermediate Similarity	NPD4162	Approved
0.7222	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3536	Discontinued
0.7208	Intermediate Similarity	NPD5745	Approved
0.719	Intermediate Similarity	NPD3179	Approved
0.719	Intermediate Similarity	NPD3180	Approved
0.7181	Intermediate Similarity	NPD2231	Phase 2
0.7181	Intermediate Similarity	NPD2235	Phase 2
0.7172	Intermediate Similarity	NPD3596	Phase 2
0.717	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8031	Discontinued
0.716	Intermediate Similarity	NPD6087	Phase 1
0.7152	Intermediate Similarity	NPD1794	Approved
0.7143	Intermediate Similarity	NPD3692	Discontinued
0.7135	Intermediate Similarity	NPD7484	Phase 3
0.7135	Intermediate Similarity	NPD7485	Phase 3
0.7133	Intermediate Similarity	NPD821	Approved
0.7125	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7019	Approved
0.7117	Intermediate Similarity	NPD7020	Approved
0.7117	Intermediate Similarity	NPD6419	Discontinued
0.7105	Intermediate Similarity	NPD7451	Discontinued
0.7105	Intermediate Similarity	NPD6584	Phase 3
0.7097	Intermediate Similarity	NPD3530	Approved
0.7097	Intermediate Similarity	NPD3531	Approved
0.7097	Intermediate Similarity	NPD3532	Approved
0.7093	Intermediate Similarity	NPD7608	Discontinued
0.7089	Intermediate Similarity	NPD2154	Approved
0.7089	Intermediate Similarity	NPD2156	Approved
0.7089	Intermediate Similarity	NPD2155	Approved
0.7089	Intermediate Similarity	NPD6380	Phase 1
0.7083	Intermediate Similarity	NPD5773	Approved
0.7083	Intermediate Similarity	NPD5772	Approved
0.7078	Intermediate Similarity	NPD6179	Discontinued
0.7078	Intermediate Similarity	NPD5746	Approved
0.7078	Intermediate Similarity	NPD9718	Approved
0.7075	Intermediate Similarity	NPD6581	Approved
0.7075	Intermediate Similarity	NPD6580	Approved
0.7067	Intermediate Similarity	NPD2562	Approved
0.7067	Intermediate Similarity	NPD2561	Approved
0.7048	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3156	Discontinued
0.7037	Intermediate Similarity	NPD5160	Discontinued
0.7034	Intermediate Similarity	NPD595	Approved
0.7034	Intermediate Similarity	NPD593	Approved
0.7032	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2595	Approved
0.7027	Intermediate Similarity	NPD2594	Approved
0.702	Intermediate Similarity	NPD1669	Approved
0.7019	Intermediate Similarity	NPD44	Approved
0.7019	Intermediate Similarity	NPD6364	Approved
0.7013	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4123	Phase 3
0.6986	Remote Similarity	NPD2557	Approved
0.6981	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6331	Phase 2
0.697	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2486	Discontinued
0.6957	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2239	Approved
0.6937	Remote Similarity	NPD2240	Approved
0.6937	Remote Similarity	NPD1725	Approved
0.6928	Remote Similarity	NPD4098	Discontinued
0.6923	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3555	Approved
0.6918	Remote Similarity	NPD3553	Approved
0.6918	Remote Similarity	NPD3552	Approved
0.6918	Remote Similarity	NPD3554	Approved
0.6914	Remote Similarity	NPD5061	Approved
0.6914	Remote Similarity	NPD5062	Approved
0.6914	Remote Similarity	NPD3060	Approved
0.6913	Remote Similarity	NPD6382	Discontinued
0.6909	Remote Similarity	NPD2504	Approved
0.6909	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2505	Approved
0.6908	Remote Similarity	NPD4129	Approved
0.6908	Remote Similarity	NPD3685	Discontinued
0.6894	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7018	Phase 2
0.6883	Remote Similarity	NPD2990	Approved
0.6883	Remote Similarity	NPD2987	Approved
0.6883	Remote Similarity	NPD3690	Phase 2
0.6883	Remote Similarity	NPD3691	Phase 2
0.6882	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4474	Approved
0.6879	Remote Similarity	NPD2245	Discovery
0.6879	Remote Similarity	NPD3163	Approved
0.6879	Remote Similarity	NPD4475	Approved
0.6879	Remote Similarity	NPD840	Approved
0.6879	Remote Similarity	NPD839	Approved
0.6879	Remote Similarity	NPD3162	Approved
0.6863	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8070	Approved
0.6859	Remote Similarity	NPD3136	Phase 2
0.6855	Remote Similarity	NPD2157	Approved
0.6842	Remote Similarity	NPD3560	Approved
0.6842	Remote Similarity	NPD2233	Approved
0.6842	Remote Similarity	NPD3556	Approved
0.6842	Remote Similarity	NPD3558	Approved
0.6842	Remote Similarity	NPD3557	Approved
0.6842	Remote Similarity	NPD2232	Approved
0.6842	Remote Similarity	NPD2230	Approved
0.6842	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1712	Approved
0.6832	Remote Similarity	NPD2161	Phase 2
0.6829	Remote Similarity	NPD2677	Approved
0.6824	Remote Similarity	NPD5355	Approved
0.6824	Remote Similarity	NPD5356	Approved
0.6821	Remote Similarity	NPD3294	Phase 2
0.6818	Remote Similarity	NPD3568	Approved
0.6818	Remote Similarity	NPD3567	Approved
0.6813	Remote Similarity	NPD1536	Approved
0.681	Remote Similarity	NPD4237	Approved
0.681	Remote Similarity	NPD4236	Phase 3
0.6805	Remote Similarity	NPD4675	Approved
0.6805	Remote Similarity	NPD4179	Approved
0.6805	Remote Similarity	NPD4678	Approved
0.6805	Remote Similarity	NPD4180	Approved
0.68	Remote Similarity	NPD3445	Approved
0.68	Remote Similarity	NPD3444	Approved
0.68	Remote Similarity	NPD3443	Approved
0.6797	Remote Similarity	NPD6543	Approved
0.6797	Remote Similarity	NPD6542	Approved
0.6797	Remote Similarity	NPD6539	Approved
0.6797	Remote Similarity	NPD6540	Phase 3
0.6795	Remote Similarity	NPD2614	Approved
0.679	Remote Similarity	NPD3656	Approved
0.6788	Remote Similarity	NPD6667	Approved
0.6788	Remote Similarity	NPD6666	Approved
0.6786	Remote Similarity	NPD3336	Discovery
0.6786	Remote Similarity	NPD5267	Discontinued
0.6784	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1411	Approved
0.6779	Remote Similarity	NPD318	Approved
0.6779	Remote Similarity	NPD317	Approved
0.6774	Remote Similarity	NPD558	Phase 2
0.6772	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7438	Suspended
0.6761	Remote Similarity	NPD2216	Approved
0.6761	Remote Similarity	NPD2215	Approved
0.6753	Remote Similarity	NPD196	Phase 1
0.6753	Remote Similarity	NPD6538	Approved
0.6753	Remote Similarity	NPD6541	Approved
0.6743	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2802	Phase 3
0.6735	Remote Similarity	NPD594	Approved
0.6735	Remote Similarity	NPD592	Approved
0.6731	Remote Similarity	NPD2250	Discontinued
0.6731	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1538	Phase 1
0.6728	Remote Similarity	NPD1537	Approved
0.6728	Remote Similarity	NPD1519	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