NPASS Compound

Structure

NPC474195 OpenBabel07101718222D 22 24 0 0 1 0 0 0 0 0999 V2000 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.05
Volume:	307.359
LogP:	2.748
LogD:	2.141
LogS:	-3.763
# Rotatable Bonds:	3
TPSA:	72.42
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.876
Synthetic Accessibility Score:	3.692
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.731
MDCK Permeability:	1.7505348296253942e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.706

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	85.27318572998047%
Volume Distribution (VD):	0.974
Pgp-substrate:	29.418710708618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.393
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.492
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.554
CYP2C9-substrate:	0.445
CYP2D6-inhibitor:	0.494
CYP2D6-substrate:	0.714
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.937

ADMET: Excretion

Clearance (CL):	4.136
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.572
Skin Sensitization:	0.39
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC474195

Natural Product ID:	NPC474195
*Common Name:**	6-Bromo-1'-Methoxy-1',8-Dihydroaplysinopsin
IUPAC Name:	5-[(6-bromo-1H-indol-3-yl)methyl]-2-imino-5-methoxy-1,3-dimethylimidazolidin-4-one
Synonyms:
Standard InCHIKey:	QGMVWWCRCSOHMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H17BrN4O2/c1-19-13(21)15(22-3,20(2)14(19)17)7-9-8-18-12-6-10(16)4-5-11(9)12/h4-6,8,17-18H,7H2,1-3H3
SMILES:	CN1C(=O)C(N(C1=N)C)(CC2=CNC3=C2C=CC(=C3)Br)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463359
PubChem CID:	11508853
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	=	100.0	ug.mL-1	PMID[558409]

☑ 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 NPC474195 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	545
0.1-0.2	6757
0.2-0.3	22896
0.3-0.4	6441
0.4-0.5	2313
0.5-0.6	2309
0.6-0.7	1228
0.7-0.8	195
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC474196
0.9596	High Similarity	NPC475736
0.8878	High Similarity	NPC474389
0.8485	Intermediate Similarity	NPC188821
0.8485	Intermediate Similarity	NPC474180
0.8214	Intermediate Similarity	NPC17487
0.8214	Intermediate Similarity	NPC201831
0.8209	Intermediate Similarity	NPC88315
0.8178	Intermediate Similarity	NPC477109
0.8178	Intermediate Similarity	NPC477107
0.8178	Intermediate Similarity	NPC477108
0.8113	Intermediate Similarity	NPC54744
0.8077	Intermediate Similarity	NPC473376
0.7937	Intermediate Similarity	NPC63031
0.7892	Intermediate Similarity	NPC477167
0.7892	Intermediate Similarity	NPC473342
0.7883	Intermediate Similarity	NPC156003
0.785	Intermediate Similarity	NPC320968
0.7828	Intermediate Similarity	NPC240088
0.7828	Intermediate Similarity	NPC473380
0.7826	Intermediate Similarity	NPC262898
0.7799	Intermediate Similarity	NPC106771
0.7799	Intermediate Similarity	NPC205254
0.7799	Intermediate Similarity	NPC23420
0.7799	Intermediate Similarity	NPC303820
0.7789	Intermediate Similarity	NPC265710
0.7778	Intermediate Similarity	NPC179701
0.7762	Intermediate Similarity	NPC475935
0.7762	Intermediate Similarity	NPC52909
0.7762	Intermediate Similarity	NPC94211
0.775	Intermediate Similarity	NPC16659
0.7718	Intermediate Similarity	NPC304187
0.7718	Intermediate Similarity	NPC477166
0.7696	Intermediate Similarity	NPC17059
0.7689	Intermediate Similarity	NPC477176
0.7689	Intermediate Similarity	NPC477175
0.7689	Intermediate Similarity	NPC470729
0.7689	Intermediate Similarity	NPC470730
0.7674	Intermediate Similarity	NPC478158
0.7671	Intermediate Similarity	NPC477114
0.7667	Intermediate Similarity	NPC475914
0.7667	Intermediate Similarity	NPC220797
0.7667	Intermediate Similarity	NPC474318
0.7667	Intermediate Similarity	NPC268744
0.7667	Intermediate Similarity	NPC477004
0.7667	Intermediate Similarity	NPC153123
0.7667	Intermediate Similarity	NPC201266
0.7661	Intermediate Similarity	NPC478157
0.7659	Intermediate Similarity	NPC213629
0.7655	Intermediate Similarity	NPC475859
0.7655	Intermediate Similarity	NPC474877
0.7655	Intermediate Similarity	NPC475969
0.7655	Intermediate Similarity	NPC477177
0.765	Intermediate Similarity	NPC84827
0.765	Intermediate Similarity	NPC207020
0.765	Intermediate Similarity	NPC14113
0.765	Intermediate Similarity	NPC145885
0.763	Intermediate Similarity	NPC166209
0.763	Intermediate Similarity	NPC77241
0.763	Intermediate Similarity	NPC13456
0.763	Intermediate Similarity	NPC269203
0.7621	Intermediate Similarity	NPC165743
0.7619	Intermediate Similarity	NPC171317
0.7588	Intermediate Similarity	NPC63279
0.7555	Intermediate Similarity	NPC297642
0.7545	Intermediate Similarity	NPC64216
0.7544	Intermediate Similarity	NPC89987
0.7531	Intermediate Similarity	NPC263117
0.7531	Intermediate Similarity	NPC125181
0.7531	Intermediate Similarity	NPC242872
0.7512	Intermediate Similarity	NPC162860
0.75	Intermediate Similarity	NPC54420
0.7489	Intermediate Similarity	NPC473218
0.7489	Intermediate Similarity	NPC470702
0.7476	Intermediate Similarity	NPC94752
0.7465	Intermediate Similarity	NPC476525
0.7463	Intermediate Similarity	NPC228835
0.746	Intermediate Similarity	NPC321939
0.7455	Intermediate Similarity	NPC470703
0.7454	Intermediate Similarity	NPC82053
0.7451	Intermediate Similarity	NPC307191
0.7438	Intermediate Similarity	NPC126709
0.7438	Intermediate Similarity	NPC11126
0.7438	Intermediate Similarity	NPC248041
0.743	Intermediate Similarity	NPC475506
0.7424	Intermediate Similarity	NPC17751
0.7418	Intermediate Similarity	NPC100321
0.7418	Intermediate Similarity	NPC74413
0.7418	Intermediate Similarity	NPC293917
0.7416	Intermediate Similarity	NPC243716
0.7402	Intermediate Similarity	NPC469896
0.7395	Intermediate Similarity	NPC260900
0.7395	Intermediate Similarity	NPC473761
0.7395	Intermediate Similarity	NPC155143
0.7391	Intermediate Similarity	NPC315555
0.738	Intermediate Similarity	NPC69843
0.7371	Intermediate Similarity	NPC473640
0.7368	Intermediate Similarity	NPC117980
0.7353	Intermediate Similarity	NPC283219
0.734	Intermediate Similarity	NPC267885
0.7333	Intermediate Similarity	NPC471536
0.7321	Intermediate Similarity	NPC321708
0.7321	Intermediate Similarity	NPC281049
0.7317	Intermediate Similarity	NPC91179
0.7308	Intermediate Similarity	NPC235684
0.7304	Intermediate Similarity	NPC111275
0.7297	Intermediate Similarity	NPC282247
0.7291	Intermediate Similarity	NPC203468
0.7291	Intermediate Similarity	NPC110500
0.7291	Intermediate Similarity	NPC149155
0.729	Intermediate Similarity	NPC470499
0.7286	Intermediate Similarity	NPC247987
0.7282	Intermediate Similarity	NPC141926
0.7273	Intermediate Similarity	NPC223791
0.7273	Intermediate Similarity	NPC107077
0.7268	Intermediate Similarity	NPC276540
0.7268	Intermediate Similarity	NPC233050
0.7256	Intermediate Similarity	NPC237414
0.7252	Intermediate Similarity	NPC128084
0.7246	Intermediate Similarity	NPC469358
0.7243	Intermediate Similarity	NPC227582
0.7241	Intermediate Similarity	NPC935
0.7241	Intermediate Similarity	NPC267078
0.7232	Intermediate Similarity	NPC470732
0.7232	Intermediate Similarity	NPC470731
0.7227	Intermediate Similarity	NPC476524
0.7222	Intermediate Similarity	NPC470497
0.7213	Intermediate Similarity	NPC475746
0.7212	Intermediate Similarity	NPC108011
0.7212	Intermediate Similarity	NPC110158
0.721	Intermediate Similarity	NPC474357
0.7209	Intermediate Similarity	NPC131887
0.7204	Intermediate Similarity	NPC154339
0.7198	Intermediate Similarity	NPC275292
0.7198	Intermediate Similarity	NPC71037
0.7198	Intermediate Similarity	NPC470323
0.7198	Intermediate Similarity	NPC243381
0.7193	Intermediate Similarity	NPC155444
0.7188	Intermediate Similarity	NPC474412
0.7186	Intermediate Similarity	NPC56109
0.7186	Intermediate Similarity	NPC191382
0.7184	Intermediate Similarity	NPC55772
0.7183	Intermediate Similarity	NPC267343
0.7181	Intermediate Similarity	NPC272174
0.7179	Intermediate Similarity	NPC245055
0.7178	Intermediate Similarity	NPC78020
0.7177	Intermediate Similarity	NPC15102
0.7175	Intermediate Similarity	NPC471194
0.7175	Intermediate Similarity	NPC6865
0.7175	Intermediate Similarity	NPC153980
0.7175	Intermediate Similarity	NPC75634
0.7175	Intermediate Similarity	NPC471193
0.7168	Intermediate Similarity	NPC477714
0.716	Intermediate Similarity	NPC314882
0.7157	Intermediate Similarity	NPC477611
0.7156	Intermediate Similarity	NPC36405
0.7143	Intermediate Similarity	NPC252338
0.7143	Intermediate Similarity	NPC171393
0.7143	Intermediate Similarity	NPC295452
0.7143	Intermediate Similarity	NPC477610
0.7137	Intermediate Similarity	NPC323752
0.713	Intermediate Similarity	NPC72956
0.713	Intermediate Similarity	NPC67288
0.713	Intermediate Similarity	NPC54981
0.7124	Intermediate Similarity	NPC472285
0.7124	Intermediate Similarity	NPC477715
0.7122	Intermediate Similarity	NPC280297
0.7108	Intermediate Similarity	NPC82331
0.7101	Intermediate Similarity	NPC219336
0.7097	Intermediate Similarity	NPC19696
0.7097	Intermediate Similarity	NPC136957
0.7095	Intermediate Similarity	NPC99939
0.7095	Intermediate Similarity	NPC308931
0.7095	Intermediate Similarity	NPC188387
0.7095	Intermediate Similarity	NPC163421
0.7093	Intermediate Similarity	NPC469717
0.7089	Intermediate Similarity	NPC117244
0.7089	Intermediate Similarity	NPC473763
0.7083	Intermediate Similarity	NPC174281
0.7083	Intermediate Similarity	NPC475286
0.708	Intermediate Similarity	NPC471192
0.7079	Intermediate Similarity	NPC280864
0.7078	Intermediate Similarity	NPC476874
0.7078	Intermediate Similarity	NPC476073
0.7074	Intermediate Similarity	NPC474896
0.7073	Intermediate Similarity	NPC161861
0.707	Intermediate Similarity	NPC294693
0.7062	Intermediate Similarity	NPC62749
0.7053	Intermediate Similarity	NPC217372
0.7053	Intermediate Similarity	NPC64436
0.7053	Intermediate Similarity	NPC15573
0.7053	Intermediate Similarity	NPC183662
0.705	Intermediate Similarity	NPC230869
0.7048	Intermediate Similarity	NPC477003
0.7048	Intermediate Similarity	NPC165495
0.7045	Intermediate Similarity	NPC478006
0.7044	Intermediate Similarity	NPC49217
0.7043	Intermediate Similarity	NPC31097
0.7037	Intermediate Similarity	NPC476526
0.7037	Intermediate Similarity	NPC329765

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 NPC474195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	678
0.2-0.3	1159
0.3-0.4	2179
0.4-0.5	2253
0.5-0.6	2191
0.6-0.7	403
0.7-0.8	29
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
0.783	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7970	Approved
0.7418	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7470	Discontinued
0.7352	Intermediate Similarity	NPD4520	Approved
0.7349	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD482	Approved
0.7246	Intermediate Similarity	NPD2094	Phase 2
0.7246	Intermediate Similarity	NPD2092	Phase 2
0.7246	Intermediate Similarity	NPD2095	Phase 2
0.7217	Intermediate Similarity	NPD7730	Approved
0.7217	Intermediate Similarity	NPD6164	Phase 2
0.7217	Intermediate Similarity	NPD7731	Approved
0.7217	Intermediate Similarity	NPD6165	Phase 2
0.7212	Intermediate Similarity	NPD2096	Phase 2
0.7212	Intermediate Similarity	NPD2091	Phase 2
0.721	Intermediate Similarity	NPD7951	Approved
0.721	Intermediate Similarity	NPD7953	Approved
0.721	Intermediate Similarity	NPD7790	Approved
0.721	Intermediate Similarity	NPD7950	Approved
0.721	Intermediate Similarity	NPD7952	Approved
0.721	Intermediate Similarity	NPD7789	Approved
0.721	Intermediate Similarity	NPD7791	Approved
0.7205	Intermediate Similarity	NPD7271	Approved
0.7186	Intermediate Similarity	NPD7780	Approved
0.7186	Intermediate Similarity	NPD7781	Approved
0.7169	Intermediate Similarity	NPD5426	Phase 3
0.7162	Intermediate Similarity	NPD7717	Approved
0.7162	Intermediate Similarity	NPD7716	Approved
0.7157	Intermediate Similarity	NPD750	Phase 2
0.7155	Intermediate Similarity	NPD7824	Approved
0.7136	Intermediate Similarity	NPD7001	Phase 3
0.7124	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1996	Discontinued
0.7083	Intermediate Similarity	NPD2880	Discontinued
0.7067	Intermediate Similarity	NPD6595	Phase 3
0.7059	Intermediate Similarity	NPD2008	Discontinued
0.7018	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8272	Phase 2
0.7	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD2443	Approved
0.6996	Remote Similarity	NPD2442	Approved
0.6991	Remote Similarity	NPD7618	Phase 3
0.6991	Remote Similarity	NPD7619	Phase 3
0.6982	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8271	Discontinued
0.6951	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6664	Approved
0.6926	Remote Similarity	NPD4558	Phase 2
0.692	Remote Similarity	NPD2510	Approved
0.692	Remote Similarity	NPD2509	Approved
0.6916	Remote Similarity	NPD8094	Discontinued
0.6916	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7944	Discontinued
0.6909	Remote Similarity	NPD484	Approved
0.6893	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2144	Approved
0.6875	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2411	Approved
0.6872	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8093	Discontinued
0.6864	Remote Similarity	NPD6999	Discontinued
0.6864	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2408	Discontinued
0.6812	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7711	Discontinued
0.6792	Remote Similarity	NPD3038	Discontinued
0.6791	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3961	Discontinued
0.6791	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6268	Phase 1
0.677	Remote Similarity	NPD7665	Phase 2
0.677	Remote Similarity	NPD7666	Phase 3
0.677	Remote Similarity	NPD2189	Approved
0.677	Remote Similarity	NPD2187	Approved
0.6769	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4602	Approved
0.6756	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5559	Phase 2
0.674	Remote Similarity	NPD1600	Suspended
0.6737	Remote Similarity	NPD7603	Discontinued
0.673	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5901	Discontinued
0.6695	Remote Similarity	NPD5199	Approved
0.6695	Remote Similarity	NPD5198	Approved
0.6695	Remote Similarity	NPD4890	Phase 2
0.6681	Remote Similarity	NPD8257	Approved
0.6681	Remote Similarity	NPD8256	Approved
0.6681	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5017	Discontinued
0.6651	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4499	Approved
0.6639	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1707	Approved
0.6636	Remote Similarity	NPD1708	Approved
0.6636	Remote Similarity	NPD802	Phase 2
0.6636	Remote Similarity	NPD1038	Approved
0.6635	Remote Similarity	NPD4128	Approved
0.6633	Remote Similarity	NPD786	Approved
0.662	Remote Similarity	NPD8386	Phase 2
0.6609	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7957	Phase 1
0.6604	Remote Similarity	NPD4075	Phase 2
0.6603	Remote Similarity	NPD2844	Phase 3
0.6597	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6665	Discontinued
0.659	Remote Similarity	NPD7026	Phase 2
0.659	Remote Similarity	NPD706	Phase 1
0.659	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2172	Phase 1
0.6579	Remote Similarity	NPD1506	Discontinued
0.6579	Remote Similarity	NPD8322	Phase 2
0.6574	Remote Similarity	NPD1096	Discontinued
0.6573	Remote Similarity	NPD4181	Approved
0.6571	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7415	Suspended
0.6567	Remote Similarity	NPD3394	Approved
0.6567	Remote Similarity	NPD3389	Approved
0.6567	Remote Similarity	NPD3393	Approved
0.6564	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6458	Discontinued
0.6558	Remote Similarity	NPD1895	Discontinued
0.6558	Remote Similarity	NPD3178	Discontinued
0.6557	Remote Similarity	NPD5065	Approved
0.6555	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8073	Approved
0.6538	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2813	Phase 3
0.6537	Remote Similarity	NPD3915	Approved
0.6537	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4600	Approved
0.6533	Remote Similarity	NPD4601	Approved
0.6533	Remote Similarity	NPD4501	Approved
0.6533	Remote Similarity	NPD4500	Approved
0.6532	Remote Similarity	NPD8641	Approved
0.653	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8119	Discontinued
0.6529	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6242	Discontinued
0.6524	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8072	Approved
0.6514	Remote Similarity	NPD6217	Discontinued
0.6509	Remote Similarity	NPD4852	Phase 2
0.6509	Remote Similarity	NPD3917	Approved
0.6509	Remote Similarity	NPD3918	Approved
0.6509	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7817	Phase 1
0.6502	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5072	Discontinued
0.6491	Remote Similarity	NPD3947	Discontinued
0.6484	Remote Similarity	NPD8431	Approved
0.6482	Remote Similarity	NPD1722	Approved
0.6476	Remote Similarity	NPD2879	Approved
0.6476	Remote Similarity	NPD2639	Approved
0.6476	Remote Similarity	NPD2881	Approved
0.6476	Remote Similarity	NPD2642	Approved
0.6473	Remote Similarity	NPD5003	Discontinued
0.6471	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5818	Discontinued
0.6466	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4079	Approved
0.6465	Remote Similarity	NPD4076	Approved
0.6461	Remote Similarity	NPD4885	Approved
0.6456	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7175	Phase 1
0.6453	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3100	Discontinued
0.645	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5891	Approved
0.6447	Remote Similarity	NPD6176	Phase 1
0.6445	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1982	Phase 1

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