NPASS Compound

Structure

NPC233926 OpenBabel07101718302D 33 34 0 0 1 0 0 0 0 0999 V2000 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 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 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 6.0622 -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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 4.3301 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 32 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 11 33 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 29 2 3 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	647.0
Volume:	505.304
LogP:	4.555
LogD:	3.614
LogS:	-4.443
# Rotatable Bonds:	14
TPSA:	62.83
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	2.972
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.967
MDCK Permeability:	1.451195748813916e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	96.01241302490234%
Volume Distribution (VD):	2.573
Pgp-substrate:	3.1326255798339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.639
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.381
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	1.503
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.689
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.438
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC233926

Natural Product ID:	NPC233926
*Common Name:**	Suberedamine B
IUPAC Name:	(2S)-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]ethyl]-2-(methylamino)propanamide
Synonyms:
Standard InCHIKey:	MNNHZXNEKPRDII-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C24H32Br3N3O3/c1-28-21(15-16-6-7-22(32-4)18(25)12-16)24(31)29-9-8-17-13-19(26)23(20(27)14-17)33-11-5-10-30(2)3/h6-7,12-14,21,28H,5,8-11,15H2,1-4H3,(H,29,31)/t21-/m0/s1
SMILES:	CN[C@H](C(=NCCc1cc(Br)c(c(c1)Br)OCCCN(C)C)O)Cc1ccc(c(c1)Br)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465833
PubChem CID:	10258717
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
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]

☑ 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
GI50	2
IC50	2
MIC	23

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	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	=	8.6	ug.mL-1	PMID[536341]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[536341]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.6	ug.mL-1	PMID[536341]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4786.3	nM	PMID[536342]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5470.0	nM	PMID[536342]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	40.0	ug.mL-1	PMID[536342]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	40.0	ug.mL-1	PMID[536342]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	128000.0	ug.mL-1	PMID[536342]
NPT4276	Organism	Yersinia enterocolitica	Yersinia enterocolitica	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT2894	Organism	Providencia rettgeri	Providencia rettgeri	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128000.0	ug.mL-1	PMID[536342]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT1264	Organism	Burkholderia cepacia	Burkholderia cepacia	MIC	>	128000.0	ug.mL-1	PMID[536342]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	128000.0	ug.mL-1	PMID[536342]

☑ 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 NPC233926 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	233
0.1-0.2	2609
0.2-0.3	13041
0.3-0.4	4954
0.4-0.5	13600
0.5-0.6	7221
0.6-0.7	889
0.7-0.8	124
0.8-0.85	15
0.85-0.9	3
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC47672
0.9329	High Similarity	NPC156311
0.9252	High Similarity	NPC76412
0.906	High Similarity	NPC258222
0.9041	High Similarity	NPC78530
0.8912	High Similarity	NPC135349
0.8562	High Similarity	NPC109968
0.8411	Intermediate Similarity	NPC470472
0.8322	Intermediate Similarity	NPC470470
0.8311	Intermediate Similarity	NPC470471
0.8278	Intermediate Similarity	NPC474128
0.82	Intermediate Similarity	NPC474673
0.8194	Intermediate Similarity	NPC110131
0.8129	Intermediate Similarity	NPC296085
0.8125	Intermediate Similarity	NPC272463
0.8013	Intermediate Similarity	NPC71629
0.7974	Intermediate Similarity	NPC212850
0.7974	Intermediate Similarity	NPC83289
0.7974	Intermediate Similarity	NPC189724
0.7925	Intermediate Similarity	NPC469711
0.7908	Intermediate Similarity	NPC128877
0.7871	Intermediate Similarity	NPC308571
0.7867	Intermediate Similarity	NPC97870
0.7867	Intermediate Similarity	NPC247018
0.7867	Intermediate Similarity	NPC307123
0.7771	Intermediate Similarity	NPC247298
0.7682	Intermediate Similarity	NPC475735
0.7673	Intermediate Similarity	NPC245974
0.7633	Intermediate Similarity	NPC477255
0.7616	Intermediate Similarity	NPC474091
0.7613	Intermediate Similarity	NPC213471
0.7598	Intermediate Similarity	NPC227953
0.7584	Intermediate Similarity	NPC248822
0.7566	Intermediate Similarity	NPC473724
0.7557	Intermediate Similarity	NPC259071
0.7557	Intermediate Similarity	NPC77435
0.7543	Intermediate Similarity	NPC477254
0.7534	Intermediate Similarity	NPC263835
0.7529	Intermediate Similarity	NPC475396
0.7516	Intermediate Similarity	NPC274732
0.7514	Intermediate Similarity	NPC475658
0.7514	Intermediate Similarity	NPC473892
0.7467	Intermediate Similarity	NPC320242
0.7459	Intermediate Similarity	NPC475843
0.7458	Intermediate Similarity	NPC121571
0.7458	Intermediate Similarity	NPC8093
0.745	Intermediate Similarity	NPC328267
0.7436	Intermediate Similarity	NPC470249
0.7419	Intermediate Similarity	NPC303993
0.7403	Intermediate Similarity	NPC471338
0.7403	Intermediate Similarity	NPC474678
0.7403	Intermediate Similarity	NPC471953
0.7356	Intermediate Similarity	NPC469979
0.7351	Intermediate Similarity	NPC471337
0.7351	Intermediate Similarity	NPC473450
0.7347	Intermediate Similarity	NPC43275
0.7314	Intermediate Similarity	NPC110454
0.7314	Intermediate Similarity	NPC298981
0.7314	Intermediate Similarity	NPC126128
0.7314	Intermediate Similarity	NPC473462
0.7314	Intermediate Similarity	NPC207819
0.7292	Intermediate Similarity	NPC26524
0.7285	Intermediate Similarity	NPC62101
0.7285	Intermediate Similarity	NPC95733
0.7278	Intermediate Similarity	NPC197045
0.7278	Intermediate Similarity	NPC141405
0.7278	Intermediate Similarity	NPC82741
0.7278	Intermediate Similarity	NPC473409
0.7278	Intermediate Similarity	NPC147847
0.7268	Intermediate Similarity	NPC202866
0.7261	Intermediate Similarity	NPC235633
0.7257	Intermediate Similarity	NPC226001
0.7237	Intermediate Similarity	NPC141739
0.7237	Intermediate Similarity	NPC136112
0.7237	Intermediate Similarity	NPC29477
0.7233	Intermediate Similarity	NPC40321
0.7222	Intermediate Similarity	NPC174607
0.7219	Intermediate Similarity	NPC211218
0.7215	Intermediate Similarity	NPC309667
0.7215	Intermediate Similarity	NPC470248
0.72	Intermediate Similarity	NPC225130
0.7193	Intermediate Similarity	NPC254700
0.7191	Intermediate Similarity	NPC301941
0.7191	Intermediate Similarity	NPC214188
0.7191	Intermediate Similarity	NPC74618
0.7188	Intermediate Similarity	NPC470709
0.7181	Intermediate Similarity	NPC321133
0.7179	Intermediate Similarity	NPC470392
0.717	Intermediate Similarity	NPC231163
0.717	Intermediate Similarity	NPC318591
0.7167	Intermediate Similarity	NPC49172
0.7161	Intermediate Similarity	NPC99280
0.7161	Intermediate Similarity	NPC135173
0.7134	Intermediate Similarity	NPC132771
0.7127	Intermediate Similarity	NPC471591
0.7123	Intermediate Similarity	NPC115803
0.7115	Intermediate Similarity	NPC11449
0.7114	Intermediate Similarity	NPC283760
0.7114	Intermediate Similarity	NPC256369
0.7101	Intermediate Similarity	NPC287757
0.7101	Intermediate Similarity	NPC319320
0.7089	Intermediate Similarity	NPC71888
0.7089	Intermediate Similarity	NPC120114
0.7088	Intermediate Similarity	NPC246591
0.7083	Intermediate Similarity	NPC471336
0.7083	Intermediate Similarity	NPC470746
0.7081	Intermediate Similarity	NPC168861
0.7081	Intermediate Similarity	NPC469721
0.7079	Intermediate Similarity	NPC290534
0.7074	Intermediate Similarity	NPC123140
0.7063	Intermediate Similarity	NPC214988
0.7055	Intermediate Similarity	NPC59387
0.7044	Intermediate Similarity	NPC237227
0.7039	Intermediate Similarity	NPC471314
0.7039	Intermediate Similarity	NPC471315
0.7037	Intermediate Similarity	NPC204546
0.7033	Intermediate Similarity	NPC96275
0.7033	Intermediate Similarity	NPC144823
0.7025	Intermediate Similarity	NPC267237
0.7	Intermediate Similarity	NPC474587
0.7	Intermediate Similarity	NPC475132
0.6988	Remote Similarity	NPC324081
0.6966	Remote Similarity	NPC143450
0.6962	Remote Similarity	NPC474753
0.6957	Remote Similarity	NPC475293
0.6954	Remote Similarity	NPC17388
0.6954	Remote Similarity	NPC53596
0.6954	Remote Similarity	NPC471308
0.6954	Remote Similarity	NPC289330
0.6954	Remote Similarity	NPC160120
0.6944	Remote Similarity	NPC97811
0.6943	Remote Similarity	NPC474087
0.6943	Remote Similarity	NPC195902
0.6941	Remote Similarity	NPC56635
0.6927	Remote Similarity	NPC475615
0.6923	Remote Similarity	NPC78061
0.6923	Remote Similarity	NPC159987
0.6923	Remote Similarity	NPC122359
0.6918	Remote Similarity	NPC163810
0.6915	Remote Similarity	NPC469731
0.6914	Remote Similarity	NPC470250
0.6913	Remote Similarity	NPC82963
0.6908	Remote Similarity	NPC318357
0.6902	Remote Similarity	NPC470951
0.6899	Remote Similarity	NPC114102
0.6899	Remote Similarity	NPC326966
0.6898	Remote Similarity	NPC80514
0.6882	Remote Similarity	NPC206372
0.6882	Remote Similarity	NPC203424
0.6879	Remote Similarity	NPC22014
0.6867	Remote Similarity	NPC38458
0.6867	Remote Similarity	NPC311737
0.6859	Remote Similarity	NPC301713
0.6846	Remote Similarity	NPC303370
0.6846	Remote Similarity	NPC317254
0.6842	Remote Similarity	NPC207675
0.6842	Remote Similarity	NPC212699
0.6815	Remote Similarity	NPC280736
0.6815	Remote Similarity	NPC251571
0.6813	Remote Similarity	NPC475283
0.6813	Remote Similarity	NPC152205
0.6803	Remote Similarity	NPC166837
0.6788	Remote Similarity	NPC470247
0.6786	Remote Similarity	NPC277857
0.6786	Remote Similarity	NPC115144
0.6779	Remote Similarity	NPC118202
0.6774	Remote Similarity	NPC255253
0.6772	Remote Similarity	NPC155838
0.6772	Remote Similarity	NPC471321
0.6772	Remote Similarity	NPC471306
0.6772	Remote Similarity	NPC325651
0.6766	Remote Similarity	NPC313414
0.6766	Remote Similarity	NPC9373
0.6765	Remote Similarity	NPC475432
0.676	Remote Similarity	NPC164608
0.6755	Remote Similarity	NPC65714
0.6752	Remote Similarity	NPC218323
0.675	Remote Similarity	NPC214869
0.675	Remote Similarity	NPC471335
0.6748	Remote Similarity	NPC312770
0.6748	Remote Similarity	NPC160607
0.6748	Remote Similarity	NPC14600
0.6748	Remote Similarity	NPC204848
0.6748	Remote Similarity	NPC41473
0.6736	Remote Similarity	NPC42383
0.6735	Remote Similarity	NPC473358
0.6735	Remote Similarity	NPC471339
0.6733	Remote Similarity	NPC10286
0.6733	Remote Similarity	NPC213
0.6731	Remote Similarity	NPC236265
0.6731	Remote Similarity	NPC213414
0.673	Remote Similarity	NPC52029
0.673	Remote Similarity	NPC35961
0.673	Remote Similarity	NPC195749
0.671	Remote Similarity	NPC116562
0.671	Remote Similarity	NPC298486
0.6709	Remote Similarity	NPC202776
0.6708	Remote Similarity	NPC243404
0.6707	Remote Similarity	NPC299583
0.6687	Remote Similarity	NPC70485

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 NPC233926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	612
0.2-0.3	1220
0.3-0.4	1913
0.4-0.5	2958
0.5-0.6	1713
0.6-0.7	511
0.7-0.8	69
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
0.7987	Intermediate Similarity	NPD2458	Approved
0.7987	Intermediate Similarity	NPD2460	Phase 3
0.7987	Intermediate Similarity	NPD2459	Approved
0.7867	Intermediate Similarity	NPD1423	Approved
0.7829	Intermediate Similarity	NPD3054	Approved
0.7829	Intermediate Similarity	NPD3052	Approved
0.78	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2874	Phase 2
0.7564	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1818	Approved
0.7467	Intermediate Similarity	NPD1820	Approved
0.7467	Intermediate Similarity	NPD1819	Approved
0.7467	Intermediate Similarity	NPD1817	Approved
0.745	Intermediate Similarity	NPD2428	Approved
0.745	Intermediate Similarity	NPD2429	Approved
0.7423	Intermediate Similarity	NPD7131	Phase 3
0.7415	Intermediate Similarity	NPD2554	Approved
0.7415	Intermediate Similarity	NPD2556	Approved
0.7407	Intermediate Similarity	NPD3985	Discontinued
0.7403	Intermediate Similarity	NPD7477	Discontinued
0.7386	Intermediate Similarity	NPD3165	Approved
0.7386	Intermediate Similarity	NPD3164	Approved
0.7386	Intermediate Similarity	NPD3166	Approved
0.7386	Intermediate Similarity	NPD5163	Phase 2
0.7386	Intermediate Similarity	NPD3167	Approved
0.7358	Intermediate Similarity	NPD7153	Discontinued
0.7351	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6072	Discontinued
0.7337	Intermediate Similarity	NPD8031	Discontinued
0.7333	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4162	Approved
0.731	Intermediate Similarity	NPD7485	Phase 3
0.731	Intermediate Similarity	NPD7484	Phase 3
0.7301	Intermediate Similarity	NPD3536	Discontinued
0.7301	Intermediate Similarity	NPD6419	Discontinued
0.7301	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3180	Approved
0.7273	Intermediate Similarity	NPD3179	Approved
0.7256	Intermediate Similarity	NPD2183	Approved
0.7256	Intermediate Similarity	NPD52	Approved
0.7256	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7526	Approved
0.7256	Intermediate Similarity	NPD2184	Approved
0.7255	Intermediate Similarity	NPD4993	Discontinued
0.7244	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6087	Phase 1
0.7237	Intermediate Similarity	NPD1794	Approved
0.723	Intermediate Similarity	NPD3049	Approved
0.7219	Intermediate Similarity	NPD6583	Phase 3
0.7219	Intermediate Similarity	NPD6582	Phase 2
0.7205	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2668	Approved
0.7181	Intermediate Similarity	NPD2667	Approved
0.7179	Intermediate Similarity	NPD5745	Approved
0.7179	Intermediate Similarity	NPD3531	Approved
0.7179	Intermediate Similarity	NPD3530	Approved
0.7179	Intermediate Similarity	NPD3532	Approved
0.717	Intermediate Similarity	NPD2156	Approved
0.717	Intermediate Similarity	NPD2154	Approved
0.717	Intermediate Similarity	NPD2155	Approved
0.7161	Intermediate Similarity	NPD6179	Discontinued
0.7152	Intermediate Similarity	NPD2561	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2562	Approved
0.7143	Intermediate Similarity	NPD3596	Phase 2
0.7143	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5160	Discontinued
0.7117	Intermediate Similarity	NPD3692	Discontinued
0.7114	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6584	Phase 3
0.7078	Intermediate Similarity	NPD7451	Discontinued
0.7069	Intermediate Similarity	NPD7608	Discontinued
0.7063	Intermediate Similarity	NPD6380	Phase 1
0.7059	Intermediate Similarity	NPD5772	Approved
0.7059	Intermediate Similarity	NPD5773	Approved
0.7051	Intermediate Similarity	NPD5746	Approved
0.7047	Intermediate Similarity	NPD6581	Approved
0.7047	Intermediate Similarity	NPD6580	Approved
0.7039	Intermediate Similarity	NPD2231	Phase 2
0.7039	Intermediate Similarity	NPD2235	Phase 2
0.7019	Intermediate Similarity	NPD2239	Approved
0.7019	Intermediate Similarity	NPD2240	Approved
0.7019	Intermediate Similarity	NPD3156	Discontinued
0.7007	Intermediate Similarity	NPD593	Approved
0.7007	Intermediate Similarity	NPD595	Approved
0.7006	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2595	Approved
0.7	Intermediate Similarity	NPD3552	Approved
0.7	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3554	Approved
0.7	Intermediate Similarity	NPD3553	Approved
0.7	Intermediate Similarity	NPD2594	Approved
0.7	Intermediate Similarity	NPD3555	Approved
0.6994	Remote Similarity	NPD6364	Approved
0.6994	Remote Similarity	NPD44	Approved
0.6994	Remote Similarity	NPD5062	Approved
0.6994	Remote Similarity	NPD5061	Approved
0.6994	Remote Similarity	NPD3060	Approved
0.6988	Remote Similarity	NPD4123	Phase 3
0.6988	Remote Similarity	NPD7019	Approved
0.6988	Remote Similarity	NPD7020	Approved
0.6987	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD821	Approved
0.6962	Remote Similarity	NPD3162	Approved
0.6962	Remote Similarity	NPD3163	Approved
0.6959	Remote Similarity	NPD2557	Approved
0.6959	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD9718	Approved
0.6936	Remote Similarity	NPD8070	Approved
0.6923	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3558	Approved
0.6919	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3557	Approved
0.6919	Remote Similarity	NPD3560	Approved
0.6919	Remote Similarity	NPD3556	Approved
0.6914	Remote Similarity	NPD1725	Approved
0.6909	Remote Similarity	NPD2677	Approved
0.6905	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5356	Approved
0.6901	Remote Similarity	NPD5722	Discontinued
0.6901	Remote Similarity	NPD5355	Approved
0.6887	Remote Similarity	NPD6382	Discontinued
0.6886	Remote Similarity	NPD2505	Approved
0.6886	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2504	Approved
0.6883	Remote Similarity	NPD1669	Approved
0.6882	Remote Similarity	NPD4180	Approved
0.6882	Remote Similarity	NPD4179	Approved
0.6871	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD317	Approved
0.6867	Remote Similarity	NPD318	Approved
0.686	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2987	Approved
0.6859	Remote Similarity	NPD7018	Phase 2
0.6859	Remote Similarity	NPD2990	Approved
0.6855	Remote Similarity	NPD2245	Discovery
0.6848	Remote Similarity	NPD6331	Phase 2
0.6845	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7438	Suspended
0.6839	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2216	Approved
0.6836	Remote Similarity	NPD2215	Approved
0.6829	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2486	Discontinued
0.6815	Remote Similarity	NPD2250	Discontinued
0.6813	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4227	Discontinued
0.68	Remote Similarity	NPD5709	Phase 3
0.6795	Remote Similarity	NPD4098	Discontinued
0.6791	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4237	Approved
0.6788	Remote Similarity	NPD4236	Phase 3
0.6784	Remote Similarity	NPD4675	Approved
0.6784	Remote Similarity	NPD4678	Approved
0.6778	Remote Similarity	NPD6042	Phase 2
0.6778	Remote Similarity	NPD42	Phase 2
0.6774	Remote Similarity	NPD3685	Discontinued
0.6774	Remote Similarity	NPD6542	Approved
0.6774	Remote Similarity	NPD6543	Approved
0.6774	Remote Similarity	NPD4129	Approved
0.6774	Remote Similarity	NPD6539	Approved
0.6774	Remote Similarity	NPD6540	Phase 3
0.6768	Remote Similarity	NPD3336	Discovery
0.6766	Remote Similarity	NPD6667	Approved
0.6766	Remote Similarity	NPD6666	Approved
0.6765	Remote Similarity	NPD5267	Discontinued
0.6761	Remote Similarity	NPD4666	Phase 3
0.6755	Remote Similarity	NPD856	Approved
0.6755	Remote Similarity	NPD16	Approved
0.6752	Remote Similarity	NPD3690	Phase 2
0.6752	Remote Similarity	NPD3691	Phase 2
0.675	Remote Similarity	NPD6405	Approved
0.675	Remote Similarity	NPD4474	Approved
0.675	Remote Similarity	NPD7265	Discontinued
0.675	Remote Similarity	NPD839	Approved
0.675	Remote Similarity	NPD6407	Approved
0.675	Remote Similarity	NPD4475	Approved
0.675	Remote Similarity	NPD840	Approved
0.6748	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6677	Suspended
0.6744	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4083	Discontinued
0.6731	Remote Similarity	NPD6541	Approved
0.6731	Remote Similarity	NPD6538	Approved
0.673	Remote Similarity	NPD3136	Phase 2
0.6728	Remote Similarity	NPD2157	Approved
0.6727	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7598	Phase 2
0.671	Remote Similarity	NPD2233	Approved
0.671	Remote Similarity	NPD2232	Approved
0.671	Remote Similarity	NPD2230	Approved
0.6709	Remote Similarity	NPD1712	Approved
0.6707	Remote Similarity	NPD2161	Phase 2
0.6707	Remote Similarity	NPD5241	Discontinued
0.6706	Remote Similarity	NPD3033	Phase 2
0.6703	Remote Similarity	NPD6339	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