NPASS Compound

Structure

CID156003 OpenBabel06191715522D 22 25 0 0 0 0 0 0 0 0999 V2000 2.9921 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -4.3781 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -2.3968 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -4.1871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -2.8968 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 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 18 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 17 2 0 0 0 0 6 19 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.99
Volume:	290.893
LogP:	2.099
LogD:	2.071
LogS:	-4.121
# Rotatable Bonds:	2
TPSA:	90.64
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	3.02
Fsp3:	0.0
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:	-5.253
MDCK Permeability:	1.0467755600984674e-05
Pgp-inhibitor:	0.101
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.159
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	95.2060775756836%
Volume Distribution (VD):	1.037
Pgp-substrate:	6.039965629577637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.797
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	1.451
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.129
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.126

Download Data

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

Natural Product: NPC156003

Natural Product ID:	NPC156003
*Common Name:**	3-(6-Bromo-1H-Indol-3-Yl)-4-(1H-Imidazol-5-Yl)Pyrrole-2,5-Dione
IUPAC Name:	3-(6-bromo-1H-indol-3-yl)-4-(1H-imidazol-5-yl)pyrrole-2,5-dione
Synonyms:
Standard InCHIKey:	JAEXYIAXFPZAAX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H9BrN4O2/c16-7-1-2-8-9(4-18-10(8)3-7)12-13(11-5-17-6-19-11)15(22)20-14(12)21/h1-6,18H,(H,17,19)(H,20,21,22)
SMILES:	Brc1ccc2c(c1)[nH]cc2C1=C(C(=O)N=C1O)c1cnc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1789362
PubChem CID:	398495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO30955	Didemnum	Genus	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348447]
NPO30955	Didemnum	Genus	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358648]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
GI50	57

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	35481.34	nM	PMID[548438]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	53333.49	nM	PMID[548438]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	17660.38	nM	PMID[548438]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	43651.58	nM	PMID[548438]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	20417.38	nM	PMID[548438]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	21877.62	nM	PMID[548438]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	60534.09	nM	PMID[548438]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	11040.79	nM	PMID[548438]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	25585.86	nM	PMID[548438]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	12302.69	nM	PMID[548438]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	14521.12	nM	PMID[548438]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[548438]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	23878.11	nM	PMID[548438]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	32508.73	nM	PMID[548438]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	65162.84	nM	PMID[548438]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	31260.79	nM	PMID[548438]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	27861.21	nM	PMID[548438]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	55847.02	nM	PMID[548438]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	34914.03	nM	PMID[548438]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	31841.98	nM	PMID[548438]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	51641.64	nM	PMID[548438]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	21086.28	nM	PMID[548438]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	35645.11	nM	PMID[548438]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	30831.88	nM	PMID[548438]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	32136.61	nM	PMID[548438]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[548438]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	19498.45	nM	PMID[548438]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	22855.99	nM	PMID[548438]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	53088.44	nM	PMID[548438]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[548438]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	54450.27	nM	PMID[548438]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	29512.09	nM	PMID[548438]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	25822.6	nM	PMID[548438]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[548438]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	23442.29	nM	PMID[548438]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[548438]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	13091.82	nM	PMID[548438]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	48752.85	nM	PMID[548438]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	24043.63	nM	PMID[548438]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	25061.09	nM	PMID[548438]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	13182.57	nM	PMID[548438]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	16255.49	nM	PMID[548438]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	52722.99	nM	PMID[548438]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	28444.61	nM	PMID[548438]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[548438]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	15958.79	nM	PMID[548438]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[548438]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	1465.55	nM	PMID[548438]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	62086.9	nM	PMID[548438]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	26242.19	nM	PMID[548438]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	38994.2	nM	PMID[548438]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	15631.48	nM	PMID[548438]

☑ 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 NPC156003 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	700
0.1-0.2	9537
0.2-0.3	20564
0.3-0.4	6222
0.4-0.5	2486
0.5-0.6	2004
0.6-0.7	1045
0.7-0.8	134
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9356	High Similarity	NPC282247
0.8203	Intermediate Similarity	NPC475736
0.8107	Intermediate Similarity	NPC77101
0.8044	Intermediate Similarity	NPC470323
0.8009	Intermediate Similarity	NPC935
0.8009	Intermediate Similarity	NPC267078
0.7974	Intermediate Similarity	NPC474357
0.7883	Intermediate Similarity	NPC474195
0.7867	Intermediate Similarity	NPC131887
0.7847	Intermediate Similarity	NPC188821
0.7847	Intermediate Similarity	NPC474180
0.7799	Intermediate Similarity	NPC477166
0.7799	Intermediate Similarity	NPC304187
0.7793	Intermediate Similarity	NPC106771
0.7793	Intermediate Similarity	NPC205254
0.7793	Intermediate Similarity	NPC23420
0.7793	Intermediate Similarity	NPC303820
0.7757	Intermediate Similarity	NPC94211
0.7757	Intermediate Similarity	NPC475935
0.7757	Intermediate Similarity	NPC52909
0.7743	Intermediate Similarity	NPC474196
0.7727	Intermediate Similarity	NPC473218
0.7727	Intermediate Similarity	NPC470702
0.7714	Intermediate Similarity	NPC473342
0.7714	Intermediate Similarity	NPC477167
0.77	Intermediate Similarity	NPC474389
0.7692	Intermediate Similarity	NPC470703
0.7686	Intermediate Similarity	NPC69843
0.7668	Intermediate Similarity	NPC477114
0.7585	Intermediate Similarity	NPC295452
0.7585	Intermediate Similarity	NPC17487
0.7585	Intermediate Similarity	NPC171393
0.7585	Intermediate Similarity	NPC201831
0.7572	Intermediate Similarity	NPC63109
0.7553	Intermediate Similarity	NPC477107
0.7553	Intermediate Similarity	NPC477108
0.7553	Intermediate Similarity	NPC477109
0.7545	Intermediate Similarity	NPC116555
0.7536	Intermediate Similarity	NPC307191
0.7523	Intermediate Similarity	NPC54981
0.7512	Intermediate Similarity	NPC88315
0.7479	Intermediate Similarity	NPC471536
0.7469	Intermediate Similarity	NPC74619
0.7455	Intermediate Similarity	NPC477610
0.7434	Intermediate Similarity	NPC267811
0.7419	Intermediate Similarity	NPC153123
0.7419	Intermediate Similarity	NPC201266
0.7419	Intermediate Similarity	NPC268744
0.7419	Intermediate Similarity	NPC220797
0.7419	Intermediate Similarity	NPC474318
0.7419	Intermediate Similarity	NPC475914
0.7411	Intermediate Similarity	NPC128084
0.7387	Intermediate Similarity	NPC71238
0.7385	Intermediate Similarity	NPC269203
0.7385	Intermediate Similarity	NPC77241
0.7385	Intermediate Similarity	NPC13456
0.7385	Intermediate Similarity	NPC166209
0.7381	Intermediate Similarity	NPC108011
0.7371	Intermediate Similarity	NPC117980
0.7358	Intermediate Similarity	NPC475746
0.7325	Intermediate Similarity	NPC469717
0.7319	Intermediate Similarity	NPC63031
0.7318	Intermediate Similarity	NPC473761
0.7318	Intermediate Similarity	NPC476073
0.7309	Intermediate Similarity	NPC476524
0.7297	Intermediate Similarity	NPC82053
0.7294	Intermediate Similarity	NPC67288
0.7257	Intermediate Similarity	NPC97902
0.7249	Intermediate Similarity	NPC264285
0.7241	Intermediate Similarity	NPC130570
0.723	Intermediate Similarity	NPC62749
0.7225	Intermediate Similarity	NPC473380
0.7225	Intermediate Similarity	NPC240088
0.719	Intermediate Similarity	NPC265710
0.7183	Intermediate Similarity	NPC15102
0.7182	Intermediate Similarity	NPC237414
0.7182	Intermediate Similarity	NPC477004
0.7175	Intermediate Similarity	NPC473376
0.7174	Intermediate Similarity	NPC477609
0.7171	Intermediate Similarity	NPC274229
0.7171	Intermediate Similarity	NPC17751
0.7156	Intermediate Similarity	NPC16659
0.7149	Intermediate Similarity	NPC39092
0.7143	Intermediate Similarity	NPC111275
0.7136	Intermediate Similarity	NPC49217
0.7124	Intermediate Similarity	NPC16352
0.7119	Intermediate Similarity	NPC477607
0.7119	Intermediate Similarity	NPC477608
0.7115	Intermediate Similarity	NPC82331
0.7109	Intermediate Similarity	NPC233050
0.7109	Intermediate Similarity	NPC276540
0.7105	Intermediate Similarity	NPC207020
0.7095	Intermediate Similarity	NPC474958
0.7094	Intermediate Similarity	NPC229893
0.7083	Intermediate Similarity	NPC213629
0.7081	Intermediate Similarity	NPC477611
0.708	Intermediate Similarity	NPC476525
0.7066	Intermediate Similarity	NPC37152
0.7061	Intermediate Similarity	NPC320968
0.7061	Intermediate Similarity	NPC72956
0.7056	Intermediate Similarity	NPC110158
0.7051	Intermediate Similarity	NPC154339
0.7045	Intermediate Similarity	NPC222018
0.7042	Intermediate Similarity	NPC275292
0.7042	Intermediate Similarity	NPC243381
0.7037	Intermediate Similarity	NPC278434
0.7031	Intermediate Similarity	NPC471603
0.7031	Intermediate Similarity	NPC471194
0.7031	Intermediate Similarity	NPC6865
0.7031	Intermediate Similarity	NPC153980
0.7031	Intermediate Similarity	NPC471193
0.7027	Intermediate Similarity	NPC136957
0.7027	Intermediate Similarity	NPC293917
0.7027	Intermediate Similarity	NPC19696
0.7024	Intermediate Similarity	NPC131718
0.7023	Intermediate Similarity	NPC188387
0.7023	Intermediate Similarity	NPC163421
0.7022	Intermediate Similarity	NPC470505
0.7014	Intermediate Similarity	NPC227582
0.7014	Intermediate Similarity	NPC174281
0.7014	Intermediate Similarity	NPC475286
0.6992	Remote Similarity	NPC245348
0.6991	Remote Similarity	NPC476121
0.6987	Remote Similarity	NPC82370
0.6986	Remote Similarity	NPC97343
0.6976	Remote Similarity	NPC230869
0.6974	Remote Similarity	NPC80596
0.6972	Remote Similarity	NPC231536
0.6968	Remote Similarity	NPC179701
0.6958	Remote Similarity	NPC279189
0.6958	Remote Similarity	NPC200553
0.6958	Remote Similarity	NPC207686
0.6957	Remote Similarity	NPC247987
0.6955	Remote Similarity	NPC267343
0.6953	Remote Similarity	NPC473310
0.6946	Remote Similarity	NPC141926
0.6942	Remote Similarity	NPC470204
0.694	Remote Similarity	NPC471192
0.6937	Remote Similarity	NPC262898
0.6933	Remote Similarity	NPC476491
0.693	Remote Similarity	NPC48938
0.6927	Remote Similarity	NPC321708
0.6926	Remote Similarity	NPC54744
0.6926	Remote Similarity	NPC31700
0.6923	Remote Similarity	NPC321939
0.692	Remote Similarity	NPC252338
0.6908	Remote Similarity	NPC470203
0.6906	Remote Similarity	NPC171317
0.6901	Remote Similarity	NPC59269
0.6901	Remote Similarity	NPC174489
0.6895	Remote Similarity	NPC83111
0.6892	Remote Similarity	NPC48117
0.6892	Remote Similarity	NPC242209
0.6892	Remote Similarity	NPC476526
0.6892	Remote Similarity	NPC329765
0.6891	Remote Similarity	NPC60006
0.6887	Remote Similarity	NPC280297
0.6884	Remote Similarity	NPC71037
0.6881	Remote Similarity	NPC17059
0.6881	Remote Similarity	NPC282531
0.688	Remote Similarity	NPC477633
0.6875	Remote Similarity	NPC102423
0.6872	Remote Similarity	NPC162002
0.6861	Remote Similarity	NPC77555
0.6857	Remote Similarity	NPC78020
0.6844	Remote Similarity	NPC26641
0.6842	Remote Similarity	NPC476124
0.6842	Remote Similarity	NPC280864
0.6838	Remote Similarity	NPC472285
0.6835	Remote Similarity	NPC94752
0.6832	Remote Similarity	NPC477634
0.6827	Remote Similarity	NPC253687
0.6822	Remote Similarity	NPC276657
0.6814	Remote Similarity	NPC300183
0.6812	Remote Similarity	NPC166492
0.6812	Remote Similarity	NPC92796
0.6812	Remote Similarity	NPC473362
0.6812	Remote Similarity	NPC135141
0.6808	Remote Similarity	NPC110500
0.6808	Remote Similarity	NPC149155
0.6808	Remote Similarity	NPC203468
0.6805	Remote Similarity	NPC470730
0.6805	Remote Similarity	NPC470729
0.6805	Remote Similarity	NPC477175
0.6805	Remote Similarity	NPC477176
0.68	Remote Similarity	NPC100321
0.6792	Remote Similarity	NPC323244
0.6791	Remote Similarity	NPC55772
0.6789	Remote Similarity	NPC308931
0.6789	Remote Similarity	NPC99939
0.6783	Remote Similarity	NPC263117
0.6783	Remote Similarity	NPC242872
0.6783	Remote Similarity	NPC125181
0.6779	Remote Similarity	NPC279918
0.6779	Remote Similarity	NPC122141
0.6777	Remote Similarity	NPC475969
0.6777	Remote Similarity	NPC474877
0.6777	Remote Similarity	NPC475859
0.6777	Remote Similarity	NPC477177
0.6776	Remote Similarity	NPC267885

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 NPC156003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	794
0.2-0.3	1082
0.3-0.4	2482
0.4-0.5	1933
0.5-0.6	1892
0.6-0.7	611
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8153	Intermediate Similarity	NPD6165	Phase 2
0.8153	Intermediate Similarity	NPD6164	Phase 2
0.786	Intermediate Similarity	NPD6970	Phase 2
0.7773	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2443	Approved
0.7545	Intermediate Similarity	NPD2442	Approved
0.7534	Intermediate Similarity	NPD2008	Discontinued
0.7511	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7415	Suspended
0.7354	Intermediate Similarity	NPD2408	Discontinued
0.7333	Intermediate Similarity	NPD2411	Approved
0.7327	Intermediate Similarity	NPD2880	Discontinued
0.729	Intermediate Similarity	NPD1043	Phase 3
0.7286	Intermediate Similarity	NPD1895	Discontinued
0.726	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6999	Discontinued
0.7252	Intermediate Similarity	NPD5426	Phase 3
0.7232	Intermediate Similarity	NPD7665	Phase 2
0.7232	Intermediate Similarity	NPD7666	Phase 3
0.72	Intermediate Similarity	NPD1600	Suspended
0.7188	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7856	Phase 2
0.7149	Intermediate Similarity	NPD7857	Phase 3
0.7111	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD460	Discontinued
0.7108	Intermediate Similarity	NPD6458	Discontinued
0.708	Intermediate Similarity	NPD4612	Discontinued
0.7076	Intermediate Similarity	NPD2349	Phase 3
0.707	Intermediate Similarity	NPD706	Phase 1
0.7067	Intermediate Similarity	NPD7001	Phase 3
0.7056	Intermediate Similarity	NPD2813	Phase 3
0.7056	Intermediate Similarity	NPD8256	Approved
0.7056	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8257	Approved
0.7035	Intermediate Similarity	NPD1506	Discontinued
0.7027	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4414	Discontinued
0.7008	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2127	Suspended
0.6957	Remote Similarity	NPD4852	Phase 2
0.6955	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7465	Suspended
0.6943	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3013	Phase 3
0.6939	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2881	Approved
0.6933	Remote Similarity	NPD2879	Approved
0.6923	Remote Similarity	NPD534	Phase 2
0.6923	Remote Similarity	NPD537	Phase 2
0.6916	Remote Similarity	NPD6595	Phase 3
0.6913	Remote Similarity	NPD949	Phase 1
0.6909	Remote Similarity	NPD4615	Phase 2
0.6897	Remote Similarity	NPD7970	Approved
0.6897	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5827	Discontinued
0.6881	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6850	Phase 2
0.6878	Remote Similarity	NPD6849	Phase 2
0.6872	Remote Similarity	NPD1915	Phase 1
0.6867	Remote Similarity	NPD6957	Approved
0.6867	Remote Similarity	NPD6958	Approved
0.6864	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5807	Phase 2
0.684	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1571	Phase 2
0.6833	Remote Similarity	NPD3430	Approved
0.6833	Remote Similarity	NPD3431	Approved
0.6831	Remote Similarity	NPD6142	Phase 3
0.683	Remote Similarity	NPD1249	Clinical (unspecified phase)
0.683	Remote Similarity	NPD1982	Phase 1
0.6822	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3905	Phase 3
0.6812	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6470	Phase 3
0.6808	Remote Similarity	NPD482	Approved
0.6808	Remote Similarity	NPD5065	Approved
0.6806	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1707	Approved
0.6806	Remote Similarity	NPD1708	Approved
0.6804	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5428	Discontinued
0.6798	Remote Similarity	NPD5901	Discontinued
0.6795	Remote Similarity	NPD6711	Approved
0.6792	Remote Similarity	NPD8292	Phase 2
0.6792	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3830	Phase 1
0.6776	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4998	Phase 3
0.6771	Remote Similarity	NPD4999	Phase 3
0.6771	Remote Similarity	NPD8113	Phase 2
0.6769	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2793	Discontinued
0.6754	Remote Similarity	NPD2364	Suspended
0.6751	Remote Similarity	NPD6210	Phase 3
0.675	Remote Similarity	NPD6352	Phase 2
0.6749	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD1572	Phase 2
0.6747	Remote Similarity	NPD3962	Phase 2
0.6747	Remote Similarity	NPD3959	Phase 2
0.6743	Remote Similarity	NPD2091	Phase 2
0.6743	Remote Similarity	NPD2096	Phase 2
0.6736	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4558	Phase 2
0.6726	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3814	Phase 1
0.6724	Remote Similarity	NPD5072	Discontinued
0.6713	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD8094	Discontinued
0.6709	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8316	Phase 2
0.6708	Remote Similarity	NPD8317	Phase 2
0.6707	Remote Similarity	NPD2348	Phase 3
0.6697	Remote Similarity	NPD2092	Phase 2
0.6697	Remote Similarity	NPD2095	Phase 2
0.6697	Remote Similarity	NPD2094	Phase 2
0.6696	Remote Similarity	NPD8641	Approved
0.6695	Remote Similarity	NPD7423	Phase 2
0.6695	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4863	Approved
0.6694	Remote Similarity	NPD7767	Approved
0.6682	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7711	Discontinued
0.6667	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3917	Approved
0.6667	Remote Similarity	NPD3918	Approved
0.6667	Remote Similarity	NPD1197	Approved
0.6653	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5425	Phase 1
0.6639	Remote Similarity	NPD4403	Phase 3
0.6639	Remote Similarity	NPD4401	Phase 2
0.6638	Remote Similarity	NPD6132	Phase 1
0.6637	Remote Similarity	NPD5446	Phase 2
0.6636	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD8271	Discontinued
0.6624	Remote Similarity	NPD3915	Approved
0.6624	Remote Similarity	NPD7470	Discontinued
0.6623	Remote Similarity	NPD484	Approved
0.662	Remote Similarity	NPD2333	Discontinued
0.661	Remote Similarity	NPD5413	Phase 2
0.661	Remote Similarity	NPD7188	Phase 3
0.6609	Remote Similarity	NPD4886	Phase 2
0.6608	Remote Similarity	NPD6469	Phase 3
0.6608	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD996	Phase 2
0.6607	Remote Similarity	NPD994	Phase 2
0.6606	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5962	Phase 2
0.66	Remote Similarity	NPD5821	Approved
0.6598	Remote Similarity	NPD6829	Phase 2
0.6598	Remote Similarity	NPD3222	Phase 2
0.6596	Remote Similarity	NPD7656	Approved
0.6596	Remote Similarity	NPD8093	Discontinued
0.6596	Remote Similarity	NPD7657	Approved
0.6595	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD796	Phase 2
0.6594	Remote Similarity	NPD8629	Discontinued
0.6593	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7689	Approved
0.659	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7694	Discontinued
0.6578	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5199	Approved
0.6569	Remote Similarity	NPD5198	Approved
0.6568	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2509	Approved
0.6567	Remote Similarity	NPD2510	Approved
0.6557	Remote Similarity	NPD5140	Approved
0.6557	Remote Similarity	NPD5138	Approved
0.6545	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD2844	Phase 3
0.6542	Remote Similarity	NPD1996	Discontinued
0.654	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2803	Discontinued
0.6529	Remote Similarity	NPD6753	Phase 1
0.6529	Remote Similarity	NPD6752	Phase 1
0.6528	Remote Similarity	NPD750	Phase 2
0.6528	Remote Similarity	NPD5509	Phase 1
0.6527	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1313	Approved
0.6525	Remote Similarity	NPD2794	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