NPASS Compound

Structure

NPC473218 OpenBabel07101718312D 26 30 0 0 1 0 0 0 0 0999 V2000 -3.3305 -2.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9409 0.6460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 0.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1220 -1.0765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -1.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5287 -0.1630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1274 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 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 6.5232 -0.0584 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 0.3478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -1.9901 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 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 1.8841 0.9013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 12 2 0 0 0 0 4 16 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 9 23 1 0 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 2 0 0 0 0 20 24 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.04
Volume:	357.39
LogP:	4.343
LogD:	3.687
LogS:	-4.129
# Rotatable Bonds:	3
TPSA:	80.49
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.329
Fsp3:	0.05
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.148
MDCK Permeability:	4.779477421834599e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.566

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	97.9762954711914%
Volume Distribution (VD):	0.908
Pgp-substrate:	1.47665274143219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.653
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	3.261
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.685
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.598
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.185
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC473218

Natural Product ID:	NPC473218
*Common Name:**	Spongotine B
IUPAC Name:	(6-bromo-1H-indol-3-yl)-[5-(1H-indol-3-yl)-4,5-dihydro-1H-imidazol-2-yl]methanone
Synonyms:
Standard InCHIKey:	CIFUWIGYZJXRFR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15BrN4O/c21-11-5-6-13-15(9-23-17(13)7-11)19(26)20-24-10-18(25-20)14-8-22-16-4-2-1-3-12(14)16/h1-9,18,22-23H,10H2,(H,24,25)
SMILES:	C1C(NC(=N1)C(=O)C2=CNC3=C2C=CC(=C3)Br)C4=CNC5=CC=CC=C54
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373574
PubChem CID:	16104848
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	5
MIC	20

Activity Type	# Activity
Cell Line	5
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[490422]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[490422]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[490422]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[490422]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[490422]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[490422]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25.0	ug.mL-1	PMID[490422]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[490422]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	25.0	ug.mL-1	PMID[490422]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[490422]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	=	25.0	ug.mL-1	PMID[490422]

☑ 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 NPC473218 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	780
0.1-0.2	11453
0.2-0.3	18939
0.3-0.4	6421
0.4-0.5	2019
0.5-0.6	1848
0.6-0.7	1020
0.7-0.8	184
0.8-0.85	25
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470702
0.9947	High Similarity	NPC470703
0.8894	High Similarity	NPC935
0.8894	High Similarity	NPC267078
0.8852	High Similarity	NPC474357
0.8756	High Similarity	NPC470323
0.8571	High Similarity	NPC237414
0.8571	High Similarity	NPC477004
0.8477	Intermediate Similarity	NPC220797
0.8477	Intermediate Similarity	NPC153123
0.8477	Intermediate Similarity	NPC475914
0.8477	Intermediate Similarity	NPC474318
0.8477	Intermediate Similarity	NPC201266
0.8477	Intermediate Similarity	NPC268744
0.8434	Intermediate Similarity	NPC269203
0.8434	Intermediate Similarity	NPC77241
0.8434	Intermediate Similarity	NPC166209
0.8434	Intermediate Similarity	NPC13456
0.8404	Intermediate Similarity	NPC284775
0.8316	Intermediate Similarity	NPC326422
0.8316	Intermediate Similarity	NPC304203
0.8281	Intermediate Similarity	NPC110158
0.8269	Intermediate Similarity	NPC267811
0.8241	Intermediate Similarity	NPC474389
0.8214	Intermediate Similarity	NPC476460
0.8146	Intermediate Similarity	NPC116555
0.8131	Intermediate Similarity	NPC188821
0.8131	Intermediate Similarity	NPC474180
0.7958	Intermediate Similarity	NPC477611
0.7951	Intermediate Similarity	NPC317701
0.7908	Intermediate Similarity	NPC477003
0.7897	Intermediate Similarity	NPC191415
0.7778	Intermediate Similarity	NPC99939
0.7778	Intermediate Similarity	NPC308931
0.7736	Intermediate Similarity	NPC471194
0.7736	Intermediate Similarity	NPC471193
0.7727	Intermediate Similarity	NPC156003
0.7716	Intermediate Similarity	NPC307191
0.7677	Intermediate Similarity	NPC117027
0.7677	Intermediate Similarity	NPC102755
0.7676	Intermediate Similarity	NPC77101
0.7659	Intermediate Similarity	NPC167710
0.7638	Intermediate Similarity	NPC21429
0.7633	Intermediate Similarity	NPC23420
0.7633	Intermediate Similarity	NPC106771
0.7633	Intermediate Similarity	NPC303820
0.7633	Intermediate Similarity	NPC205254
0.7619	Intermediate Similarity	NPC82053
0.7606	Intermediate Similarity	NPC72956
0.7604	Intermediate Similarity	NPC17751
0.7604	Intermediate Similarity	NPC42372
0.7602	Intermediate Similarity	NPC474958
0.7596	Intermediate Similarity	NPC52909
0.7596	Intermediate Similarity	NPC475935
0.7596	Intermediate Similarity	NPC94211
0.7576	Intermediate Similarity	NPC88110
0.7576	Intermediate Similarity	NPC16659
0.757	Intermediate Similarity	NPC153980
0.757	Intermediate Similarity	NPC6865
0.7558	Intermediate Similarity	NPC475736
0.7537	Intermediate Similarity	NPC231536
0.7525	Intermediate Similarity	NPC265710
0.7513	Intermediate Similarity	NPC274229
0.75	Intermediate Similarity	NPC19696
0.75	Intermediate Similarity	NPC37152
0.75	Intermediate Similarity	NPC136957
0.7489	Intermediate Similarity	NPC474195
0.7488	Intermediate Similarity	NPC473666
0.7488	Intermediate Similarity	NPC174281
0.7488	Intermediate Similarity	NPC475286
0.7475	Intermediate Similarity	NPC240088
0.7475	Intermediate Similarity	NPC473380
0.7465	Intermediate Similarity	NPC471192
0.7463	Intermediate Similarity	NPC108011
0.7462	Intermediate Similarity	NPC293216
0.746	Intermediate Similarity	NPC141926
0.7451	Intermediate Similarity	NPC324091
0.7449	Intermediate Similarity	NPC82331
0.7437	Intermediate Similarity	NPC276540
0.7437	Intermediate Similarity	NPC233050
0.7432	Intermediate Similarity	NPC474196
0.7404	Intermediate Similarity	NPC471536
0.7398	Intermediate Similarity	NPC471943
0.7389	Intermediate Similarity	NPC200553
0.7389	Intermediate Similarity	NPC279189
0.7379	Intermediate Similarity	NPC477167
0.7379	Intermediate Similarity	NPC477166
0.7379	Intermediate Similarity	NPC473342
0.7379	Intermediate Similarity	NPC304187
0.7371	Intermediate Similarity	NPC247987
0.7368	Intermediate Similarity	NPC131887
0.7363	Intermediate Similarity	NPC275292
0.7363	Intermediate Similarity	NPC243381
0.7356	Intermediate Similarity	NPC329765
0.7356	Intermediate Similarity	NPC476526
0.7356	Intermediate Similarity	NPC48117
0.7343	Intermediate Similarity	NPC88315
0.734	Intermediate Similarity	NPC133003
0.7327	Intermediate Similarity	NPC470205
0.7325	Intermediate Similarity	NPC174489
0.7323	Intermediate Similarity	NPC252572
0.7321	Intermediate Similarity	NPC227582
0.7317	Intermediate Similarity	NPC321708
0.731	Intermediate Similarity	NPC97343
0.7309	Intermediate Similarity	NPC229893
0.7293	Intermediate Similarity	NPC162002
0.7287	Intermediate Similarity	NPC288838
0.7286	Intermediate Similarity	NPC67288
0.7286	Intermediate Similarity	NPC280297
0.7277	Intermediate Similarity	NPC470677
0.7261	Intermediate Similarity	NPC26641
0.7251	Intermediate Similarity	NPC74413
0.725	Intermediate Similarity	NPC151635
0.7248	Intermediate Similarity	NPC207020
0.7245	Intermediate Similarity	NPC280864
0.7217	Intermediate Similarity	NPC252338
0.7216	Intermediate Similarity	NPC92796
0.7216	Intermediate Similarity	NPC135141
0.7212	Intermediate Similarity	NPC216550
0.721	Intermediate Similarity	NPC17487
0.721	Intermediate Similarity	NPC201831
0.7206	Intermediate Similarity	NPC467063
0.7198	Intermediate Similarity	NPC154339
0.7195	Intermediate Similarity	NPC477114
0.7194	Intermediate Similarity	NPC274981
0.719	Intermediate Similarity	NPC79356
0.719	Intermediate Similarity	NPC102592
0.7179	Intermediate Similarity	NPC477107
0.7179	Intermediate Similarity	NPC477108
0.7179	Intermediate Similarity	NPC477109
0.7177	Intermediate Similarity	NPC19342
0.7173	Intermediate Similarity	NPC53947
0.7162	Intermediate Similarity	NPC63031
0.7157	Intermediate Similarity	NPC115232
0.715	Intermediate Similarity	NPC260900
0.7143	Intermediate Similarity	NPC157828
0.7143	Intermediate Similarity	NPC476524
0.7143	Intermediate Similarity	NPC476525
0.7143	Intermediate Similarity	NPC195239
0.7137	Intermediate Similarity	NPC63109
0.7136	Intermediate Similarity	NPC17273
0.7136	Intermediate Similarity	NPC141612
0.7136	Intermediate Similarity	NPC135601
0.7136	Intermediate Similarity	NPC282247
0.713	Intermediate Similarity	NPC471191
0.7129	Intermediate Similarity	NPC47190
0.7129	Intermediate Similarity	NPC272458
0.7128	Intermediate Similarity	NPC474492
0.7117	Intermediate Similarity	NPC27041
0.7114	Intermediate Similarity	NPC469529
0.7109	Intermediate Similarity	NPC128244
0.7109	Intermediate Similarity	NPC179701
0.7109	Intermediate Similarity	NPC11445
0.7107	Intermediate Similarity	NPC149265
0.7107	Intermediate Similarity	NPC317105
0.7101	Intermediate Similarity	NPC17059
0.71	Intermediate Similarity	NPC54214
0.71	Intermediate Similarity	NPC97902
0.7098	Intermediate Similarity	NPC276657
0.7095	Intermediate Similarity	NPC267343
0.7087	Intermediate Similarity	NPC207686
0.7077	Intermediate Similarity	NPC216643
0.7075	Intermediate Similarity	NPC262898
0.707	Intermediate Similarity	NPC473761
0.707	Intermediate Similarity	NPC476073
0.7062	Intermediate Similarity	NPC34844
0.7059	Intermediate Similarity	NPC477610
0.7056	Intermediate Similarity	NPC470203
0.7056	Intermediate Similarity	NPC242116
0.7053	Intermediate Similarity	NPC63571
0.7053	Intermediate Similarity	NPC94752
0.7053	Intermediate Similarity	NPC476527
0.7045	Intermediate Similarity	NPC82370
0.7035	Intermediate Similarity	NPC49217
0.7031	Intermediate Similarity	NPC2272
0.7019	Intermediate Similarity	NPC278434
0.7019	Intermediate Similarity	NPC310633
0.7014	Intermediate Similarity	NPC477413
0.701	Intermediate Similarity	NPC325903
0.701	Intermediate Similarity	NPC11126
0.7005	Intermediate Similarity	NPC100104
0.7005	Intermediate Similarity	NPC470680
0.7005	Intermediate Similarity	NPC15102
0.7005	Intermediate Similarity	NPC470204
0.7	Intermediate Similarity	NPC138370
0.6986	Remote Similarity	NPC103119
0.6985	Remote Similarity	NPC233380
0.6981	Remote Similarity	NPC202812
0.6976	Remote Similarity	NPC477042
0.6976	Remote Similarity	NPC79777
0.6976	Remote Similarity	NPC73994
0.6971	Remote Similarity	NPC111566
0.697	Remote Similarity	NPC214106
0.6966	Remote Similarity	NPC235685
0.6961	Remote Similarity	NPC237188
0.6961	Remote Similarity	NPC59269
0.6961	Remote Similarity	NPC157583
0.6957	Remote Similarity	NPC228835
0.695	Remote Similarity	NPC114637
0.6939	Remote Similarity	NPC74357

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 NPC473218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	827
0.2-0.3	1187
0.3-0.4	2441
0.4-0.5	2098
0.5-0.6	1699
0.6-0.7	511
0.7-0.8	23
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
0.7874	Intermediate Similarity	NPD2008	Discontinued
0.782	Intermediate Similarity	NPD2411	Approved
0.7547	Intermediate Similarity	NPD2443	Approved
0.7547	Intermediate Similarity	NPD2442	Approved
0.7476	Intermediate Similarity	NPD2879	Approved
0.7476	Intermediate Similarity	NPD2881	Approved
0.7463	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2408	Discontinued
0.7349	Intermediate Similarity	NPD1600	Suspended
0.7336	Intermediate Similarity	NPD3905	Phase 3
0.7295	Intermediate Similarity	NPD4922	Phase 2
0.722	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4848	Phase 1
0.7176	Intermediate Similarity	NPD1506	Discontinued
0.7143	Intermediate Similarity	NPD2481	Approved
0.7143	Intermediate Similarity	NPD2479	Phase 3
0.7143	Intermediate Similarity	NPD2509	Approved
0.7143	Intermediate Similarity	NPD5473	Discontinued
0.7143	Intermediate Similarity	NPD2510	Approved
0.7123	Intermediate Similarity	NPD1982	Phase 1
0.7101	Intermediate Similarity	NPD4988	Discontinued
0.7095	Intermediate Similarity	NPD460	Discontinued
0.7078	Intermediate Similarity	NPD4051	Discontinued
0.7075	Intermediate Similarity	NPD6664	Approved
0.7064	Intermediate Similarity	NPD6459	Phase 2
0.7062	Intermediate Similarity	NPD7619	Phase 3
0.7062	Intermediate Similarity	NPD7618	Phase 3
0.7059	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5199	Approved
0.7054	Intermediate Similarity	NPD5198	Approved
0.7045	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7564	Discontinued
0.703	Intermediate Similarity	NPD4128	Approved
0.7024	Intermediate Similarity	NPD1895	Discontinued
0.7005	Intermediate Similarity	NPD5426	Phase 3
0.7	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2880	Discontinued
0.6987	Remote Similarity	NPD6165	Phase 2
0.6987	Remote Similarity	NPD6164	Phase 2
0.6976	Remote Similarity	NPD6595	Phase 3
0.6968	Remote Similarity	NPD4863	Approved
0.6961	Remote Similarity	NPD4181	Approved
0.6948	Remote Similarity	NPD2290	Phase 3
0.6948	Remote Similarity	NPD2289	Phase 3
0.6941	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6470	Phase 3
0.692	Remote Similarity	NPD3389	Approved
0.692	Remote Similarity	NPD3394	Approved
0.692	Remote Similarity	NPD3393	Approved
0.6916	Remote Similarity	NPD5446	Phase 2
0.691	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1996	Discontinued
0.6863	Remote Similarity	NPD482	Approved
0.686	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4299	Phase 1
0.6849	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7666	Phase 3
0.6833	Remote Similarity	NPD7665	Phase 2
0.6829	Remote Similarity	NPD4075	Phase 2
0.6827	Remote Similarity	NPD3318	Approved
0.6827	Remote Similarity	NPD3320	Approved
0.6827	Remote Similarity	NPD3319	Phase 1
0.6822	Remote Similarity	NPD5855	Phase 3
0.6822	Remote Similarity	NPD5853	Phase 3
0.6809	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2096	Phase 2
0.6794	Remote Similarity	NPD2091	Phase 2
0.6791	Remote Similarity	NPD7027	Phase 3
0.6789	Remote Similarity	NPD786	Approved
0.6777	Remote Similarity	NPD3961	Discontinued
0.6774	Remote Similarity	NPD6999	Discontinued
0.6774	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5854	Approved
0.6773	Remote Similarity	NPD7208	Approved
0.6773	Remote Similarity	NPD7209	Approved
0.6773	Remote Similarity	NPD7207	Approved
0.6771	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1952	Discontinued
0.6756	Remote Similarity	NPD6787	Phase 2
0.6749	Remote Similarity	NPD1343	Approved
0.6748	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2094	Phase 2
0.6746	Remote Similarity	NPD2092	Phase 2
0.6746	Remote Similarity	NPD2095	Phase 2
0.6745	Remote Similarity	NPD7175	Phase 1
0.6744	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.674	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2172	Phase 1
0.673	Remote Similarity	NPD7026	Phase 2
0.6726	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7970	Approved
0.6725	Remote Similarity	NPD6579	Phase 2
0.6719	Remote Similarity	NPD1722	Approved
0.6713	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5017	Discontinued
0.6712	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3246	Discontinued
0.6697	Remote Similarity	NPD5901	Discontinued
0.6697	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5415	Approved
0.6667	Remote Similarity	NPD8256	Approved
0.6667	Remote Similarity	NPD7001	Phase 3
0.6667	Remote Similarity	NPD2837	Discontinued
0.6667	Remote Similarity	NPD8257	Approved
0.6667	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3431	Approved
0.6651	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2793	Discontinued
0.6651	Remote Similarity	NPD6217	Discontinued
0.6651	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3430	Approved
0.6639	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6986	Phase 1
0.6637	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7656	Approved
0.6637	Remote Similarity	NPD7657	Approved
0.6636	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5686	Approved
0.6636	Remote Similarity	NPD7817	Phase 1
0.6636	Remote Similarity	NPD5685	Approved
0.6636	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1270	Approved
0.6622	Remote Similarity	NPD6229	Phase 2
0.662	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1708	Approved
0.6619	Remote Similarity	NPD1707	Approved
0.6619	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5065	Approved
0.6608	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1658	Discontinued
0.6605	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3583	Phase 2
0.6599	Remote Similarity	NPD3100	Discontinued
0.6594	Remote Similarity	NPD5643	Phase 2
0.6593	Remote Similarity	NPD6152	Phase 1
0.6592	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2367	Phase 2
0.6585	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6210	Phase 3
0.657	Remote Similarity	NPD750	Phase 2
0.6564	Remote Similarity	NPD7454	Approved
0.6564	Remote Similarity	NPD6954	Phase 2
0.6564	Remote Similarity	NPD7455	Approved
0.6562	Remote Similarity	NPD3840	Phase 2
0.6562	Remote Similarity	NPD3839	Phase 2
0.6561	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6987	Phase 1
0.6545	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD1248	Discontinued
0.6524	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.652	Remote Similarity	NPD3323	Discontinued
0.652	Remote Similarity	NPD7470	Discontinued
0.6518	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5016	Approved
0.6509	Remote Similarity	NPD6242	Discontinued
0.6505	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7459	Phase 2
0.6498	Remote Similarity	NPD1896	Approved
0.6494	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4852	Phase 2
0.6481	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6458	Discontinued
0.6476	Remote Similarity	NPD2144	Approved
0.6476	Remote Similarity	NPD6204	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