NPASS Compound

Structure

NPC267078 OpenBabel07101718222D 26 30 0 0 0 0 0 0 0 0999 V2000 4.9409 0.6460 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 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 -3.3305 -2.6303 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 -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 -4.1965 -2.1303 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 -2.4644 -1.1303 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 4.1274 -1.1810 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 -0.7431 -0.6691 0.0000 C 0 0 0 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 -5.0625 -2.6303 0.0000 Br 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 -3.1226 0.3478 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 23 1 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 18 2 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 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:	404.03
Volume:	354.754
LogP:	5.118
LogD:	4.071
LogS:	-4.595
# Rotatable Bonds:	3
TPSA:	77.33
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	2.825
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152
MDCK Permeability:	5.950524155196035e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27
Plasma Protein Binding (PPB):	99.36886596679688%
Volume Distribution (VD):	1.346
Pgp-substrate:	0.8640003204345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.742
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	3.689
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.476
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.33
Rat Oral Acute Toxicity:	0.669
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.099
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.312
Respiratory Toxicity:	0.499

Download Data

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

Natural Product: NPC267078

Natural Product ID:	NPC267078
*Common Name:**	Bromodeoxytopsentin
IUPAC Name:	[5-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl]-(1H-indol-3-yl)methanone
Synonyms:
Standard InCHIKey:	RMAWSNVDVKZXDX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(25-18)19(26)15-9-22-16-4-2-1-3-12(15)16/h1-10,22-23H,(H,24,25)
SMILES:	Brc1ccc2c(c1)[nH]cc2c1c[nH]c(n1)C(=O)c1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL198814
PubChem CID:	400452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic 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
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217734]
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]
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
GI50	53
IC50	5
MIC	5
Others	9

Activity Type	# Activity
Cell Line	60
Individual Protein	2
NON-MOLECULAR	1
Organism	4
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	19.44	ug.mL-1	PMID[572503]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[572504]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[572504]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[572504]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[572504]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	11.48	ug ml-1	PMID[572504]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[572504]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	0.6	ug.mL-1	PMID[572505]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	40179.08	nM	PMID[572506]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	33884.42	nM	PMID[572506]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	48083.93	nM	PMID[572506]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	181.97	nM	PMID[572506]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	11015.39	nM	PMID[572506]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	17179.08	nM	PMID[572506]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	46665.94	nM	PMID[572506]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	33573.76	nM	PMID[572506]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	21379.62	nM	PMID[572506]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	18450.15	nM	PMID[572506]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	14256.08	nM	PMID[572506]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	35892.19	nM	PMID[572506]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	28119.01	nM	PMID[572506]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[572506]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	22233.1	nM	PMID[572506]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	31117.16	nM	PMID[572506]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	25763.21	nM	PMID[572506]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	24266.1	nM	PMID[572506]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	9594.01	nM	PMID[572506]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	46344.69	nM	PMID[572506]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	21727.01	nM	PMID[572506]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	32809.53	nM	PMID[572506]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	19498.45	nM	PMID[572506]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	16557.7	nM	PMID[572506]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	34197.94	nM	PMID[572506]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	34276.78	nM	PMID[572506]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	22803.42	nM	PMID[572506]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	29648.31	nM	PMID[572506]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[572506]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	21330.45	nM	PMID[572506]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	21281.39	nM	PMID[572506]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	13995.87	nM	PMID[572506]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	30690.22	nM	PMID[572506]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	19230.92	nM	PMID[572506]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[572506]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	48194.78	nM	PMID[572506]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	25468.3	nM	PMID[572506]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	26121.61	nM	PMID[572506]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	22908.68	nM	PMID[572506]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	39174.19	nM	PMID[572506]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	12735.03	nM	PMID[572506]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	34119.29	nM	PMID[572506]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10256.52	nM	PMID[572506]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[572506]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	48528.85	nM	PMID[572506]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	36643.76	nM	PMID[572506]
NPT6638	Individual Protein	Pyruvate kinase	Staphylococcus aureus (strain MRSA252)	IC50	=	60.0	nM	PMID[572508]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[572503]
NPT2	Others	Unspecified		IC50	=	60.0	nM	PMID[572507]
NPT2	Others	Unspecified		Selectivity ratio	=	166.0	n.a.	PMID[572507]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	6.25	ug.mL-1	PMID[572507]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[572507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	6.25	ug.mL-1	PMID[572508]
NPT2	Others	Unspecified		Selectivity ratio	=	166.0	n.a.	PMID[572508]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[572509]
NPT2	Others	Unspecified		IC50	=	16.0	nM	PMID[572509]

☑ 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 NPC267078 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	1240
0.1-0.2	14765
0.2-0.3	18812
0.3-0.4	3442
0.4-0.5	2037
0.5-0.6	1641
0.6-0.7	623
0.7-0.8	121
0.8-0.85	4
0.85-0.9	7
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC935
0.9951	High Similarity	NPC474357
0.9854	High Similarity	NPC470323
0.9366	High Similarity	NPC267811
0.8894	High Similarity	NPC470702
0.8894	High Similarity	NPC473218
0.8852	High Similarity	NPC470703
0.8792	High Similarity	NPC116555
0.8613	High Similarity	NPC77101
0.823	Intermediate Similarity	NPC237414
0.8077	Intermediate Similarity	NPC326422
0.8067	Intermediate Similarity	NPC63109
0.8009	Intermediate Similarity	NPC156003
0.7887	Intermediate Similarity	NPC477004
0.784	Intermediate Similarity	NPC474389
0.782	Intermediate Similarity	NPC474180
0.782	Intermediate Similarity	NPC188821
0.782	Intermediate Similarity	NPC304203
0.7742	Intermediate Similarity	NPC317701
0.7721	Intermediate Similarity	NPC220797
0.7721	Intermediate Similarity	NPC474318
0.7721	Intermediate Similarity	NPC153123
0.7721	Intermediate Similarity	NPC475914
0.7721	Intermediate Similarity	NPC201266
0.7721	Intermediate Similarity	NPC268744
0.7707	Intermediate Similarity	NPC284775
0.7685	Intermediate Similarity	NPC77241
0.7685	Intermediate Similarity	NPC166209
0.7685	Intermediate Similarity	NPC13456
0.7685	Intermediate Similarity	NPC269203
0.7608	Intermediate Similarity	NPC110158
0.7596	Intermediate Similarity	NPC307191
0.7596	Intermediate Similarity	NPC191415
0.7559	Intermediate Similarity	NPC476460
0.7434	Intermediate Similarity	NPC282247
0.7393	Intermediate Similarity	NPC102755
0.7379	Intermediate Similarity	NPC74619
0.7358	Intermediate Similarity	NPC108011
0.7308	Intermediate Similarity	NPC477611
0.7306	Intermediate Similarity	NPC167710
0.7304	Intermediate Similarity	NPC475736
0.7277	Intermediate Similarity	NPC477003
0.7269	Intermediate Similarity	NPC231536
0.7261	Intermediate Similarity	NPC37152
0.7241	Intermediate Similarity	NPC474195
0.7217	Intermediate Similarity	NPC16659
0.7204	Intermediate Similarity	NPC240088
0.7204	Intermediate Similarity	NPC473380
0.7191	Intermediate Similarity	NPC474196
0.7189	Intermediate Similarity	NPC324091
0.717	Intermediate Similarity	NPC265710
0.7162	Intermediate Similarity	NPC19696
0.7162	Intermediate Similarity	NPC136957
0.7156	Intermediate Similarity	NPC474958
0.7155	Intermediate Similarity	NPC279189
0.7155	Intermediate Similarity	NPC200553
0.715	Intermediate Similarity	NPC274229
0.715	Intermediate Similarity	NPC17751
0.7149	Intermediate Similarity	NPC475286
0.7149	Intermediate Similarity	NPC174281
0.7149	Intermediate Similarity	NPC229893
0.7143	Intermediate Similarity	NPC252572
0.7104	Intermediate Similarity	NPC128244
0.7095	Intermediate Similarity	NPC174489
0.7095	Intermediate Similarity	NPC82331
0.7087	Intermediate Similarity	NPC471194
0.7087	Intermediate Similarity	NPC471193
0.7083	Intermediate Similarity	NPC308931
0.7083	Intermediate Similarity	NPC99939
0.7071	Intermediate Similarity	NPC69843
0.7066	Intermediate Similarity	NPC162002
0.7061	Intermediate Similarity	NPC201831
0.7061	Intermediate Similarity	NPC17487
0.7048	Intermediate Similarity	NPC82053
0.704	Intermediate Similarity	NPC471536
0.7037	Intermediate Similarity	NPC26641
0.7037	Intermediate Similarity	NPC21429
0.7033	Intermediate Similarity	NPC477108
0.7033	Intermediate Similarity	NPC477107
0.7033	Intermediate Similarity	NPC477109
0.7027	Intermediate Similarity	NPC48117
0.7027	Intermediate Similarity	NPC476526
0.7027	Intermediate Similarity	NPC329765
0.7019	Intermediate Similarity	NPC317105
0.6995	Remote Similarity	NPC151635
0.6986	Remote Similarity	NPC42372
0.6978	Remote Similarity	NPC205254
0.6978	Remote Similarity	NPC106771
0.6978	Remote Similarity	NPC23420
0.6978	Remote Similarity	NPC303820
0.6977	Remote Similarity	NPC88110
0.6971	Remote Similarity	NPC470203
0.697	Remote Similarity	NPC72956
0.697	Remote Similarity	NPC54981
0.6968	Remote Similarity	NPC473342
0.6968	Remote Similarity	NPC304187
0.6968	Remote Similarity	NPC477166
0.6968	Remote Similarity	NPC477167
0.6951	Remote Similarity	NPC102592
0.6951	Remote Similarity	NPC79356
0.6947	Remote Similarity	NPC475935
0.6947	Remote Similarity	NPC52909
0.6947	Remote Similarity	NPC94211
0.6942	Remote Similarity	NPC207686
0.694	Remote Similarity	NPC6865
0.694	Remote Similarity	NPC153980
0.6938	Remote Similarity	NPC247987
0.6923	Remote Similarity	NPC470204
0.6912	Remote Similarity	NPC117027
0.6895	Remote Similarity	NPC141612
0.6895	Remote Similarity	NPC135601
0.6895	Remote Similarity	NPC17273
0.6894	Remote Similarity	NPC477114
0.6894	Remote Similarity	NPC27041
0.6892	Remote Similarity	NPC216550
0.689	Remote Similarity	NPC253687
0.6885	Remote Similarity	NPC97902
0.6869	Remote Similarity	NPC293216
0.6869	Remote Similarity	NPC280297
0.6861	Remote Similarity	NPC19342
0.6855	Remote Similarity	NPC295452
0.6855	Remote Similarity	NPC171393
0.6852	Remote Similarity	NPC233050
0.6852	Remote Similarity	NPC276540
0.6851	Remote Similarity	NPC471192
0.6849	Remote Similarity	NPC133003
0.6845	Remote Similarity	NPC141926
0.684	Remote Similarity	NPC476525
0.684	Remote Similarity	NPC476524
0.684	Remote Similarity	NPC71238
0.6829	Remote Similarity	NPC235685
0.6825	Remote Similarity	NPC280864
0.6824	Remote Similarity	NPC82370
0.682	Remote Similarity	NPC117980
0.6808	Remote Similarity	NPC471943
0.6808	Remote Similarity	NPC97343
0.6804	Remote Similarity	NPC467063
0.6803	Remote Similarity	NPC63031
0.6802	Remote Similarity	NPC101350
0.6791	Remote Similarity	NPC317054
0.6789	Remote Similarity	NPC243381
0.6789	Remote Similarity	NPC275292
0.6786	Remote Similarity	NPC88315
0.6776	Remote Similarity	NPC54214
0.6773	Remote Similarity	NPC476341
0.677	Remote Similarity	NPC227582
0.6769	Remote Similarity	NPC473761
0.6762	Remote Similarity	NPC122141
0.6757	Remote Similarity	NPC473666
0.6746	Remote Similarity	NPC216643
0.6742	Remote Similarity	NPC476527
0.6742	Remote Similarity	NPC63571
0.6741	Remote Similarity	NPC272458
0.6722	Remote Similarity	NPC130570
0.6712	Remote Similarity	NPC470677
0.6712	Remote Similarity	NPC310633
0.6711	Remote Similarity	NPC74413
0.6709	Remote Similarity	NPC36405
0.6698	Remote Similarity	NPC274981
0.6695	Remote Similarity	NPC266249
0.6683	Remote Similarity	NPC325903
0.6683	Remote Similarity	NPC288838
0.6682	Remote Similarity	NPC470205
0.6682	Remote Similarity	NPC103119
0.6682	Remote Similarity	NPC321708
0.6681	Remote Similarity	NPC252338
0.6667	Remote Similarity	NPC111566
0.6667	Remote Similarity	NPC115232
0.6667	Remote Similarity	NPC131887
0.6667	Remote Similarity	NPC67288
0.6653	Remote Similarity	NPC207020
0.6653	Remote Similarity	NPC469717
0.6653	Remote Similarity	NPC477413
0.6652	Remote Similarity	NPC154339
0.6651	Remote Similarity	NPC157583
0.6651	Remote Similarity	NPC237188
0.6639	Remote Similarity	NPC470732
0.6639	Remote Similarity	NPC470731
0.6638	Remote Similarity	NPC88115
0.6638	Remote Similarity	NPC81535
0.6638	Remote Similarity	NPC123839
0.6635	Remote Similarity	NPC474492
0.6635	Remote Similarity	NPC135141
0.6635	Remote Similarity	NPC92796
0.6623	Remote Similarity	NPC260900
0.6623	Remote Similarity	NPC106757
0.6622	Remote Similarity	NPC210123
0.6606	Remote Similarity	NPC270834
0.6598	Remote Similarity	NPC276657
0.6593	Remote Similarity	NPC47190
0.6591	Remote Similarity	NPC314281
0.6591	Remote Similarity	NPC40530
0.6591	Remote Similarity	NPC73994
0.6587	Remote Similarity	NPC53947
0.658	Remote Similarity	NPC469308
0.6575	Remote Similarity	NPC178858
0.657	Remote Similarity	NPC114209
0.657	Remote Similarity	NPC469811
0.6567	Remote Similarity	NPC473376
0.6564	Remote Similarity	NPC267343

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 NPC267078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	518
0.1-0.2	944
0.2-0.3	1619
0.3-0.4	2367
0.4-0.5	1817
0.5-0.6	1439
0.6-0.7	417
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8341	Intermediate Similarity	NPD2008	Discontinued
0.8279	Intermediate Similarity	NPD2411	Approved
0.8009	Intermediate Similarity	NPD2442	Approved
0.8009	Intermediate Similarity	NPD2443	Approved
0.7944	Intermediate Similarity	NPD2881	Approved
0.7944	Intermediate Similarity	NPD2879	Approved
0.789	Intermediate Similarity	NPD1600	Suspended
0.788	Intermediate Similarity	NPD1506	Discontinued
0.7808	Intermediate Similarity	NPD2408	Discontinued
0.7798	Intermediate Similarity	NPD3905	Phase 3
0.7653	Intermediate Similarity	NPD460	Discontinued
0.7578	Intermediate Similarity	NPD4863	Approved
0.7533	Intermediate Similarity	NPD6470	Phase 3
0.7512	Intermediate Similarity	NPD1982	Phase 1
0.7512	Intermediate Similarity	NPD1895	Discontinued
0.7465	Intermediate Similarity	NPD2880	Discontinued
0.7333	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7657	Approved
0.7313	Intermediate Similarity	NPD7656	Approved
0.7313	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5446	Phase 2
0.7281	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD8257	Approved
0.7261	Intermediate Similarity	NPD8256	Approved
0.7261	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6579	Phase 2
0.7235	Intermediate Similarity	NPD1658	Discontinued
0.7227	Intermediate Similarity	NPD1952	Discontinued
0.7182	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6715	Discontinued
0.7156	Intermediate Similarity	NPD6229	Phase 2
0.7137	Intermediate Similarity	NPD6986	Phase 1
0.7131	Intermediate Similarity	NPD6165	Phase 2
0.7131	Intermediate Similarity	NPD6164	Phase 2
0.713	Intermediate Similarity	NPD2793	Discontinued
0.7125	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5199	Approved
0.7124	Intermediate Similarity	NPD5198	Approved
0.7123	Intermediate Similarity	NPD3430	Approved
0.7123	Intermediate Similarity	NPD3431	Approved
0.7112	Intermediate Similarity	NPD5643	Phase 2
0.7111	Intermediate Similarity	NPD2364	Suspended
0.7103	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6210	Phase 3
0.7093	Intermediate Similarity	NPD3840	Phase 2
0.7093	Intermediate Similarity	NPD3839	Phase 2
0.7082	Intermediate Similarity	NPD4541	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4299	Phase 1
0.708	Intermediate Similarity	NPD7207	Approved
0.708	Intermediate Similarity	NPD7209	Approved
0.708	Intermediate Similarity	NPD7208	Approved
0.7056	Intermediate Similarity	NPD2363	Discontinued
0.7031	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6837	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3360	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4854	Phase 3
0.6992	Remote Similarity	NPD5831	Discontinued
0.6983	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5962	Phase 2
0.6968	Remote Similarity	NPD1896	Approved
0.6962	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD5415	Approved
0.6953	Remote Similarity	NPD4395	Phase 1
0.6943	Remote Similarity	NPD7445	Phase 1
0.6923	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8317	Phase 2
0.6901	Remote Similarity	NPD8316	Phase 2
0.69	Remote Similarity	NPD6271	Approved
0.688	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1871	Approved
0.687	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD5854	Approved
0.6847	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.684	Remote Similarity	NPD2333	Discontinued
0.684	Remote Similarity	NPD6459	Phase 2
0.6833	Remote Similarity	NPD5016	Approved
0.6826	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6458	Discontinued
0.6818	Remote Similarity	NPD4940	Approved
0.6818	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7887	Approved
0.6818	Remote Similarity	NPD7888	Approved
0.6816	Remote Similarity	NPD6465	Phase 2
0.6814	Remote Similarity	NPD7459	Phase 2
0.6805	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7857	Phase 3
0.6787	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7856	Phase 2
0.6774	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5853	Phase 3
0.6756	Remote Similarity	NPD8641	Approved
0.6756	Remote Similarity	NPD5855	Phase 3
0.6756	Remote Similarity	NPD7406	Phase 2
0.6753	Remote Similarity	NPD5489	Phase 1
0.6753	Remote Similarity	NPD5491	Phase 3
0.6745	Remote Similarity	NPD1313	Approved
0.6741	Remote Similarity	NPD4922	Phase 2
0.6736	Remote Similarity	NPD1996	Discontinued
0.6736	Remote Similarity	NPD5827	Discontinued
0.6733	Remote Similarity	NPD3962	Phase 2
0.6733	Remote Similarity	NPD3959	Phase 2
0.6722	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2400	Phase 2
0.6714	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1708	Approved
0.6712	Remote Similarity	NPD1707	Approved
0.6712	Remote Similarity	NPD4988	Discontinued
0.6711	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2446	Approved
0.6711	Remote Similarity	NPD2445	Approved
0.671	Remote Similarity	NPD4446	Approved
0.6709	Remote Similarity	NPD4051	Discontinued
0.6706	Remote Similarity	NPD3811	Discontinued
0.6696	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6268	Phase 1
0.6696	Remote Similarity	NPD5462	Discontinued
0.6693	Remote Similarity	NPD5985	Phase 2
0.6693	Remote Similarity	NPD8484	Phase 2
0.6682	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5465	Phase 2
0.668	Remote Similarity	NPD6970	Phase 2
0.668	Remote Similarity	NPD8159	Discontinued
0.6667	Remote Similarity	NPD3786	Phase 3
0.6667	Remote Similarity	NPD7173	Approved
0.6667	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7172	Approved
0.6667	Remote Similarity	NPD5508	Phase 1
0.6667	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6469	Phase 3
0.6667	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4615	Phase 2
0.6652	Remote Similarity	NPD2457	Phase 2
0.6652	Remote Similarity	NPD2456	Phase 2
0.6652	Remote Similarity	NPD5685	Approved
0.6652	Remote Similarity	NPD5686	Approved
0.6652	Remote Similarity	NPD4848	Phase 1
0.6652	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6521	Phase 3
0.6624	Remote Similarity	NPD6520	Phase 3
0.6611	Remote Similarity	NPD2813	Phase 3
0.6611	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3265	Phase 1
0.6609	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3860	Discontinued
0.6594	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6721	Phase 1
0.6592	Remote Similarity	NPD4902	Discontinued
0.6592	Remote Similarity	NPD2591	Phase 2
0.6591	Remote Similarity	NPD2479	Phase 3
0.6591	Remote Similarity	NPD2481	Approved
0.6589	Remote Similarity	NPD1333	Phase 3
0.6581	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1015	Phase 2
0.6573	Remote Similarity	NPD1016	Phase 2
0.6573	Remote Similarity	NPD7415	Suspended
0.6571	Remote Similarity	NPD7694	Discontinued
0.6569	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5072	Discontinued
0.6567	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6265	Discontinued
0.6562	Remote Similarity	NPD3246	Discontinued
0.6558	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD2510	Approved
0.6553	Remote Similarity	NPD2509	Approved
0.655	Remote Similarity	NPD3830	Phase 1
0.655	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7709	Discontinued
0.6547	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3432	Approved
0.6545	Remote Similarity	NPD7767	Approved
0.6537	Remote Similarity	NPD6816	Phase 3
0.6523	Remote Similarity	NPD4558	Phase 2
0.6523	Remote Similarity	NPD8523	Approved
0.6522	Remote Similarity	NPD5821	Approved
0.6518	Remote Similarity	NPD2872	Phase 2
0.6518	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6849	Phase 2
0.6516	Remote Similarity	NPD6850	Phase 2
0.6516	Remote Similarity	NPD5473	Discontinued
0.6515	Remote Similarity	NPD5533	Discontinued
0.6513	Remote Similarity	NPD6954	Phase 2
0.6513	Remote Similarity	NPD4352	Phase 1
0.6511	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4142	Discontinued

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