NPASS Compound

Structure

NPC474196 OpenBabel07101718222D 23 25 0 0 1 0 0 0 0 0999 V2000 2.7285 0.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8569 -1.8021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3584 0.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1333 -0.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8011 -3.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9351 -3.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6671 -2.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2138 -1.5818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5987 -0.4604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1919 -1.3739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6671 -3.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9351 -2.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8011 -1.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0847 -1.6158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5446 -0.8387 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5331 -3.5430 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7431 0.3705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5932 -0.5649 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 -1.2574 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1741 -2.5817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 -0.0351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 14 22 2 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.07
Volume:	324.655
LogP:	3.134
LogD:	2.368
LogS:	-3.964
# Rotatable Bonds:	4
TPSA:	72.42
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.858
Synthetic Accessibility Score:	3.724
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.639
MDCK Permeability:	2.1207266399869695e-05
Pgp-inhibitor:	0.136
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.268

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	85.5210952758789%
Volume Distribution (VD):	1.149
Pgp-substrate:	29.576078414916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.532
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.621
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.306
CYP2D6-substrate:	0.604
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.936

ADMET: Excretion

Clearance (CL):	4.388
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.726
Skin Sensitization:	0.342
Carcinogencity:	0.914
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC474196

Natural Product ID:	NPC474196
*Common Name:**	6-Bromo-1'-Ethoxy-1',8-Dihydroaplysinopsin
IUPAC Name:	5-[(6-bromo-1H-indol-3-yl)methyl]-5-ethoxy-2-imino-1,3-dimethylimidazolidin-4-one
Synonyms:
Standard InCHIKey:	RNZDQSFDNPIZJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H19BrN4O2/c1-4-23-16(14(22)20(2)15(18)21(16)3)8-10-9-19-13-7-11(17)5-6-12(10)13/h5-7,9,18-19H,4,8H2,1-3H3
SMILES:	CCOC1(C(=O)N(C(=N)N1C)C)CC2=CNC3=C2C=CC(=C3)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463360
PubChem CID:	11646570
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

*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
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374971]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975486]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	12.5	ug.mL-1	PMID[496869]

☑ 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 NPC474196 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	461
0.1-0.2	4939
0.2-0.3	22923
0.3-0.4	8185
0.4-0.5	2381
0.5-0.6	2418
0.6-0.7	1209
0.7-0.8	169
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC474195
0.9406	High Similarity	NPC475736
0.87	High Similarity	NPC474389
0.8317	Intermediate Similarity	NPC474180
0.8317	Intermediate Similarity	NPC188821
0.8216	Intermediate Similarity	NPC54744
0.815	Intermediate Similarity	NPC17487
0.815	Intermediate Similarity	NPC201831
0.8114	Intermediate Similarity	NPC477109
0.8114	Intermediate Similarity	NPC477107
0.8114	Intermediate Similarity	NPC477108
0.8049	Intermediate Similarity	NPC88315
0.8009	Intermediate Similarity	NPC473376
0.7876	Intermediate Similarity	NPC63031
0.787	Intermediate Similarity	NPC320968
0.7826	Intermediate Similarity	NPC473342
0.7826	Intermediate Similarity	NPC477167
0.7778	Intermediate Similarity	NPC478158
0.7763	Intermediate Similarity	NPC478157
0.7743	Intermediate Similarity	NPC156003
0.7736	Intermediate Similarity	NPC303820
0.7736	Intermediate Similarity	NPC23420
0.7736	Intermediate Similarity	NPC205254
0.7736	Intermediate Similarity	NPC106771
0.7719	Intermediate Similarity	NPC89987
0.7709	Intermediate Similarity	NPC470729
0.7709	Intermediate Similarity	NPC470730
0.7709	Intermediate Similarity	NPC477176
0.7709	Intermediate Similarity	NPC477175
0.77	Intermediate Similarity	NPC94211
0.77	Intermediate Similarity	NPC52909
0.77	Intermediate Similarity	NPC475935
0.7685	Intermediate Similarity	NPC16659
0.7678	Intermediate Similarity	NPC262898
0.7675	Intermediate Similarity	NPC474877
0.7675	Intermediate Similarity	NPC477177
0.7675	Intermediate Similarity	NPC475969
0.7675	Intermediate Similarity	NPC475859
0.7673	Intermediate Similarity	NPC473380
0.7673	Intermediate Similarity	NPC240088
0.7656	Intermediate Similarity	NPC477166
0.7656	Intermediate Similarity	NPC304187
0.7644	Intermediate Similarity	NPC64216
0.7642	Intermediate Similarity	NPC165743
0.7635	Intermediate Similarity	NPC265710
0.7633	Intermediate Similarity	NPC17059
0.763	Intermediate Similarity	NPC179701
0.7623	Intermediate Similarity	NPC263117
0.7623	Intermediate Similarity	NPC125181
0.7623	Intermediate Similarity	NPC242872
0.7613	Intermediate Similarity	NPC477114
0.7609	Intermediate Similarity	NPC63279
0.7606	Intermediate Similarity	NPC475914
0.7606	Intermediate Similarity	NPC477004
0.7606	Intermediate Similarity	NPC220797
0.7606	Intermediate Similarity	NPC474318
0.7606	Intermediate Similarity	NPC201266
0.7606	Intermediate Similarity	NPC268744
0.7606	Intermediate Similarity	NPC153123
0.7596	Intermediate Similarity	NPC213629
0.7591	Intermediate Similarity	NPC207020
0.7576	Intermediate Similarity	NPC297642
0.757	Intermediate Similarity	NPC269203
0.757	Intermediate Similarity	NPC166209
0.757	Intermediate Similarity	NPC77241
0.757	Intermediate Similarity	NPC13456
0.7559	Intermediate Similarity	NPC171317
0.755	Intermediate Similarity	NPC321939
0.7534	Intermediate Similarity	NPC162860
0.7523	Intermediate Similarity	NPC54420
0.75	Intermediate Similarity	NPC84827
0.75	Intermediate Similarity	NPC14113
0.75	Intermediate Similarity	NPC145885
0.7454	Intermediate Similarity	NPC475506
0.7442	Intermediate Similarity	NPC100321
0.7441	Intermediate Similarity	NPC243716
0.7432	Intermediate Similarity	NPC473218
0.7432	Intermediate Similarity	NPC470702
0.7422	Intermediate Similarity	NPC281049
0.7419	Intermediate Similarity	NPC155143
0.7416	Intermediate Similarity	NPC94752
0.7409	Intermediate Similarity	NPC476525
0.7404	Intermediate Similarity	NPC228835
0.7399	Intermediate Similarity	NPC470703
0.7395	Intermediate Similarity	NPC473640
0.7391	Intermediate Similarity	NPC307191
0.7361	Intermediate Similarity	NPC74413
0.7361	Intermediate Similarity	NPC293917
0.7339	Intermediate Similarity	NPC260900
0.7339	Intermediate Similarity	NPC473761
0.7333	Intermediate Similarity	NPC315555
0.7328	Intermediate Similarity	NPC69843
0.7325	Intermediate Similarity	NPC314882
0.732	Intermediate Similarity	NPC117980
0.7318	Intermediate Similarity	NPC82053
0.7297	Intermediate Similarity	NPC223791
0.7297	Intermediate Similarity	NPC107077
0.7295	Intermediate Similarity	NPC11126
0.7295	Intermediate Similarity	NPC248041
0.7295	Intermediate Similarity	NPC126709
0.7293	Intermediate Similarity	NPC155444
0.7284	Intermediate Similarity	NPC56109
0.7284	Intermediate Similarity	NPC471536
0.7284	Intermediate Similarity	NPC191382
0.7277	Intermediate Similarity	NPC245055
0.7277	Intermediate Similarity	NPC17751
0.7273	Intermediate Similarity	NPC469358
0.7264	Intermediate Similarity	NPC321708
0.726	Intermediate Similarity	NPC469896
0.726	Intermediate Similarity	NPC91179
0.7257	Intermediate Similarity	NPC470732
0.7257	Intermediate Similarity	NPC470731
0.7251	Intermediate Similarity	NPC235684
0.7235	Intermediate Similarity	NPC470499
0.7234	Intermediate Similarity	NPC323752
0.7225	Intermediate Similarity	NPC71037
0.7225	Intermediate Similarity	NPC243381
0.7225	Intermediate Similarity	NPC275292
0.7212	Intermediate Similarity	NPC283219
0.7206	Intermediate Similarity	NPC478006
0.7202	Intermediate Similarity	NPC237414
0.72	Intermediate Similarity	NPC75634
0.7198	Intermediate Similarity	NPC267885
0.7191	Intermediate Similarity	NPC267078
0.7191	Intermediate Similarity	NPC935
0.7189	Intermediate Similarity	NPC227582
0.7182	Intermediate Similarity	NPC476874
0.7175	Intermediate Similarity	NPC476524
0.7169	Intermediate Similarity	NPC470497
0.7168	Intermediate Similarity	NPC282247
0.7166	Intermediate Similarity	NPC475746
0.7163	Intermediate Similarity	NPC111275
0.7161	Intermediate Similarity	NPC474357
0.7156	Intermediate Similarity	NPC131887
0.7156	Intermediate Similarity	NPC67288
0.7156	Intermediate Similarity	NPC110158
0.7156	Intermediate Similarity	NPC108011
0.715	Intermediate Similarity	NPC149155
0.715	Intermediate Similarity	NPC203468
0.715	Intermediate Similarity	NPC110500
0.715	Intermediate Similarity	NPC154339
0.7149	Intermediate Similarity	NPC470323
0.7149	Intermediate Similarity	NPC472285
0.7143	Intermediate Similarity	NPC247987
0.7137	Intermediate Similarity	NPC474412
0.7136	Intermediate Similarity	NPC141926
0.713	Intermediate Similarity	NPC267343
0.713	Intermediate Similarity	NPC272174
0.7129	Intermediate Similarity	NPC276540
0.7129	Intermediate Similarity	NPC233050
0.7124	Intermediate Similarity	NPC153980
0.7124	Intermediate Similarity	NPC471194
0.7124	Intermediate Similarity	NPC24370
0.7124	Intermediate Similarity	NPC471193
0.7124	Intermediate Similarity	NPC128084
0.7124	Intermediate Similarity	NPC319232
0.7124	Intermediate Similarity	NPC6865
0.7123	Intermediate Similarity	NPC15102
0.7123	Intermediate Similarity	NPC188387
0.7123	Intermediate Similarity	NPC163421
0.7118	Intermediate Similarity	NPC477714
0.7105	Intermediate Similarity	NPC36405
0.7105	Intermediate Similarity	NPC471192
0.7104	Intermediate Similarity	NPC193761
0.7101	Intermediate Similarity	NPC477611
0.7097	Intermediate Similarity	NPC294693
0.7095	Intermediate Similarity	NPC295452
0.7095	Intermediate Similarity	NPC171393
0.7094	Intermediate Similarity	NPC124920
0.7094	Intermediate Similarity	NPC34580
0.7094	Intermediate Similarity	NPC118559
0.7094	Intermediate Similarity	NPC304307
0.7093	Intermediate Similarity	NPC477610
0.7093	Intermediate Similarity	NPC229348
0.7091	Intermediate Similarity	NPC252338
0.7085	Intermediate Similarity	NPC277350
0.7082	Intermediate Similarity	NPC125597
0.708	Intermediate Similarity	NPC54981
0.708	Intermediate Similarity	NPC72956
0.7074	Intermediate Similarity	NPC477715
0.7064	Intermediate Similarity	NPC100547
0.7063	Intermediate Similarity	NPC314056
0.7059	Intermediate Similarity	NPC311276
0.7048	Intermediate Similarity	NPC55772
0.7048	Intermediate Similarity	NPC118940
0.7045	Intermediate Similarity	NPC136957
0.7045	Intermediate Similarity	NPC19696
0.7043	Intermediate Similarity	NPC469717
0.7042	Intermediate Similarity	NPC308931
0.7042	Intermediate Similarity	NPC99939
0.7039	Intermediate Similarity	NPC78020
0.7037	Intermediate Similarity	NPC117244
0.7037	Intermediate Similarity	NPC473763
0.7036	Intermediate Similarity	NPC315467
0.7034	Intermediate Similarity	NPC322135
0.7034	Intermediate Similarity	NPC223409
0.7034	Intermediate Similarity	NPC95240
0.7032	Intermediate Similarity	NPC174281
0.7032	Intermediate Similarity	NPC475286
0.7027	Intermediate Similarity	NPC476073

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 NPC474196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	657
0.2-0.3	1148
0.3-0.4	2173
0.4-0.5	2301
0.5-0.6	2195
0.6-0.7	409
0.7-0.8	27
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
0.7767	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7970	Approved
0.7466	Intermediate Similarity	NPD7470	Discontinued
0.7361	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7731	Approved
0.7316	Intermediate Similarity	NPD7730	Approved
0.7309	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7951	Approved
0.7308	Intermediate Similarity	NPD7953	Approved
0.7308	Intermediate Similarity	NPD7950	Approved
0.7308	Intermediate Similarity	NPD7791	Approved
0.7308	Intermediate Similarity	NPD7790	Approved
0.7308	Intermediate Similarity	NPD7789	Approved
0.7308	Intermediate Similarity	NPD7952	Approved
0.7304	Intermediate Similarity	NPD7271	Approved
0.7297	Intermediate Similarity	NPD4520	Approved
0.7294	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7781	Approved
0.7284	Intermediate Similarity	NPD7780	Approved
0.7277	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7717	Approved
0.7261	Intermediate Similarity	NPD7716	Approved
0.7253	Intermediate Similarity	NPD7824	Approved
0.724	Intermediate Similarity	NPD7001	Phase 3
0.7205	Intermediate Similarity	NPD1996	Discontinued
0.7198	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2095	Phase 2
0.719	Intermediate Similarity	NPD2094	Phase 2
0.719	Intermediate Similarity	NPD2092	Phase 2
0.7167	Intermediate Similarity	NPD6164	Phase 2
0.7167	Intermediate Similarity	NPD6165	Phase 2
0.7156	Intermediate Similarity	NPD2096	Phase 2
0.7156	Intermediate Similarity	NPD2091	Phase 2
0.715	Intermediate Similarity	NPD482	Approved
0.7149	Intermediate Similarity	NPD8271	Discontinued
0.7117	Intermediate Similarity	NPD5426	Phase 3
0.7085	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8272	Phase 2
0.7032	Intermediate Similarity	NPD2880	Discontinued
0.7022	Intermediate Similarity	NPD2510	Approved
0.7022	Intermediate Similarity	NPD2509	Approved
0.7019	Intermediate Similarity	NPD750	Phase 2
0.7014	Intermediate Similarity	NPD6595	Phase 3
0.7009	Intermediate Similarity	NPD2008	Discontinued
0.6996	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2443	Approved
0.6947	Remote Similarity	NPD2442	Approved
0.6941	Remote Similarity	NPD7618	Phase 3
0.6941	Remote Similarity	NPD7619	Phase 3
0.6941	Remote Similarity	NPD7944	Discontinued
0.6919	Remote Similarity	NPD2144	Approved
0.6903	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4558	Phase 2
0.6878	Remote Similarity	NPD6664	Approved
0.6875	Remote Similarity	NPD6268	Phase 1
0.6875	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8094	Discontinued
0.6858	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5559	Phase 2
0.6842	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8093	Discontinued
0.6826	Remote Similarity	NPD2411	Approved
0.6822	Remote Similarity	NPD3038	Discontinued
0.6816	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6999	Discontinued
0.6812	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD484	Approved
0.6769	Remote Similarity	NPD2408	Discontinued
0.6765	Remote Similarity	NPD7711	Discontinued
0.6743	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3961	Discontinued
0.6743	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7666	Phase 3
0.6725	Remote Similarity	NPD2187	Approved
0.6725	Remote Similarity	NPD2189	Approved
0.6725	Remote Similarity	NPD7665	Phase 2
0.6712	Remote Similarity	NPD4602	Approved
0.6695	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7603	Discontinued
0.6682	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3394	Approved
0.6667	Remote Similarity	NPD3389	Approved
0.6667	Remote Similarity	NPD3393	Approved
0.6667	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5901	Discontinued
0.6653	Remote Similarity	NPD5198	Approved
0.6653	Remote Similarity	NPD4890	Phase 2
0.6653	Remote Similarity	NPD5199	Approved
0.6638	Remote Similarity	NPD8257	Approved
0.6638	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7957	Phase 1
0.6638	Remote Similarity	NPD8256	Approved
0.6638	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD8119	Discontinued
0.6623	Remote Similarity	NPD1600	Suspended
0.6615	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8322	Phase 2
0.6608	Remote Similarity	NPD5017	Discontinued
0.6606	Remote Similarity	NPD4499	Approved
0.6606	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5072	Discontinued
0.6595	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3947	Discontinued
0.6594	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4128	Approved
0.6578	Remote Similarity	NPD5003	Discontinued
0.6574	Remote Similarity	NPD8386	Phase 2
0.6568	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4600	Approved
0.6564	Remote Similarity	NPD4501	Approved
0.6564	Remote Similarity	NPD4601	Approved
0.6564	Remote Similarity	NPD4500	Approved
0.656	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4075	Phase 2
0.6557	Remote Similarity	NPD2844	Phase 3
0.6557	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8072	Approved
0.655	Remote Similarity	NPD6176	Phase 1
0.6547	Remote Similarity	NPD6665	Discontinued
0.6545	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7026	Phase 2
0.6545	Remote Similarity	NPD5891	Approved
0.6545	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7573	Discontinued
0.6537	Remote Similarity	NPD2172	Phase 1
0.6537	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7817	Phase 1
0.6531	Remote Similarity	NPD7415	Suspended
0.653	Remote Similarity	NPD1096	Discontinued
0.6528	Remote Similarity	NPD4181	Approved
0.6524	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD6458	Discontinued
0.6522	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD802	Phase 2
0.6518	Remote Similarity	NPD1038	Approved
0.6516	Remote Similarity	NPD7688	Phase 1
0.6514	Remote Similarity	NPD3178	Discontinued
0.6514	Remote Similarity	NPD1707	Approved
0.6514	Remote Similarity	NPD1708	Approved
0.6514	Remote Similarity	NPD1895	Discontinued
0.6512	Remote Similarity	NPD5065	Approved
0.6507	Remote Similarity	NPD8073	Approved
0.65	Remote Similarity	NPD786	Approved
0.6498	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD2813	Phase 3
0.6498	Remote Similarity	NPD4079	Approved
0.6498	Remote Similarity	NPD4076	Approved
0.6498	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3915	Approved
0.6494	Remote Similarity	NPD5491	Phase 3
0.6494	Remote Similarity	NPD5489	Phase 1
0.6491	Remote Similarity	NPD6479	Discontinued
0.649	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8641	Approved
0.6488	Remote Similarity	NPD8289	Discontinued
0.6486	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6242	Discontinued
0.6471	Remote Similarity	NPD6217	Discontinued
0.6471	Remote Similarity	NPD706	Phase 1
0.6468	Remote Similarity	NPD3917	Approved
0.6468	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3918	Approved
0.6468	Remote Similarity	NPD4852	Phase 2
0.6466	Remote Similarity	NPD1506	Discontinued
0.6463	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2564	Approved
0.6457	Remote Similarity	NPD5482	Discontinued
0.6457	Remote Similarity	NPD2565	Phase 2
0.6453	Remote Similarity	NPD7465	Suspended
0.6452	Remote Similarity	NPD3506	Approved
0.6452	Remote Similarity	NPD3505	Approved
0.645	Remote Similarity	NPD8169	Discontinued
0.6444	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8431	Approved
0.6438	Remote Similarity	NPD7947	Clinical (unspecified phase)

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