NPASS Compound

Structure

NPC216314 OpenBabel07101718182D 25 27 0 0 0 0 0 0 0 0999 V2000 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 25 1 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	3.134
LogD:	2.886
LogS:	-4.666
# Rotatable Bonds:	5
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.121
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	6.458760617533699e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.731
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.302

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	76.42920684814453%
Volume Distribution (VD):	0.604
Pgp-substrate:	15.144377708435059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.55
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.437
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	7.257
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.297
Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.104
Skin Sensitization:	0.457
Carcinogencity:	0.061
Eye Corrosion:	0.004
Eye Irritation:	0.198
Respiratory Toxicity:	0.314

Download Data

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

Natural Product: NPC216314

Natural Product ID:	NPC216314
*Common Name:**	Sid503295
IUPAC Name:	7-methoxy-3-(2,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:	7,2',4',5'-Tetramethoxyisoflavone
Standard InCHIKey:	LMCHYXAZXISBOS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-21-11-5-6-12-16(7-11)25-10-14(19(12)20)13-8-17(23-3)18(24-4)9-15(13)22-2/h5-10H,1-4H3
SMILES:	COc1ccc2c(c1)occ(c2=O)c1cc(OC)c(cc1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478578
PubChem CID:	165203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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	4
GI50	67
IC50	6

Activity Type	# Activity
Cell Line	76
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	4.63	ug ml-1	PMID[469633]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	ED50	=	0.49	ug ml-1	PMID[469633]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.55	ug ml-1	PMID[469633]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.53	ug ml-1	PMID[469633]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	262.42	nM	PMID[469634]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	13273.94	nM	PMID[469634]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	82794.22	nM	PMID[469634]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	8669.62	nM	PMID[469634]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	34040.82	nM	PMID[469634]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	1811.34	nM	PMID[469634]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	734.51	nM	PMID[469634]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	2864.18	nM	PMID[469634]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	1552.39	nM	PMID[469634]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	3296.1	nM	PMID[469634]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	4539.42	nM	PMID[469634]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	1114.29	nM	PMID[469634]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	8452.79	nM	PMID[469634]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	1836.54	nM	PMID[469634]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1995.26	nM	PMID[469634]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	3723.92	nM	PMID[469634]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	2192.8	nM	PMID[469634]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	9727.47	nM	PMID[469634]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[469634]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	1845.02	nM	PMID[469634]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[469634]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	15310.87	nM	PMID[469634]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1267.65	nM	PMID[469634]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	31477.48	nM	PMID[469634]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	4149.54	nM	PMID[469634]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2328.09	nM	PMID[469634]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2741.57	nM	PMID[469634]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1279.38	nM	PMID[469634]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	4487.45	nM	PMID[469634]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	18323.14	nM	PMID[469634]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	2576.32	nM	PMID[469634]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	2349.63	nM	PMID[469634]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[469634]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	5508.08	nM	PMID[469634]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[469634]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	2269.86	nM	PMID[469634]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	2051.16	nM	PMID[469634]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	2944.42	nM	PMID[469634]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	5407.54	nM	PMID[469634]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	2264.64	nM	PMID[469634]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	1241.65	nM	PMID[469634]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	2280.34	nM	PMID[469634]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	4731.51	nM	PMID[469634]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	36057.86	nM	PMID[469634]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	4159.11	nM	PMID[469634]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	778.04	nM	PMID[469634]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	3019.95	nM	PMID[469634]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	6266.14	nM	PMID[469634]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	3019.95	nM	PMID[469634]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	6698.85	nM	PMID[469634]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	2483.13	nM	PMID[469634]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1967.89	nM	PMID[469634]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	3013.01	nM	PMID[469634]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1663.41	nM	PMID[469634]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	19230.92	nM	PMID[469634]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	1981.53	nM	PMID[469634]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	4111.5	nM	PMID[469634]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	5395.11	nM	PMID[469634]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	11324.0	nM	PMID[469634]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	4207.27	nM	PMID[469634]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	3953.67	nM	PMID[469634]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1555.97	nM	PMID[469634]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2349.63	nM	PMID[469634]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	43151.91	nM	PMID[469634]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	3647.54	nM	PMID[469634]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	2449.06	nM	PMID[469634]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	3318.94	nM	PMID[469634]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	10000.0	nM	PMID[469635]
NPT319	Cell Line	B16	Mus musculus	IC50	=	5200.0	nM	PMID[469635]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	9400.0	nM	PMID[469635]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	2640.0	nM	PMID[469635]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2040.0	nM	PMID[469635]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9170.0	nM	PMID[469635]

☑ 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 NPC216314 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	513
0.1-0.2	1979
0.2-0.3	4930
0.3-0.4	11761
0.4-0.5	5839
0.5-0.6	3970
0.6-0.7	5539
0.7-0.8	5006
0.8-0.85	1873
0.85-0.9	944
0.9-0.95	305
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120924
1.0	High Similarity	NPC195919
0.9856	High Similarity	NPC182842
0.9712	High Similarity	NPC185607
0.9653	High Similarity	NPC262623
0.9648	High Similarity	NPC205522
0.964	High Similarity	NPC58229
0.9583	High Similarity	NPC156953
0.9583	High Similarity	NPC239363
0.958	High Similarity	NPC63256
0.958	High Similarity	NPC10304
0.9577	High Similarity	NPC40818
0.9577	High Similarity	NPC106461
0.9577	High Similarity	NPC110639
0.9577	High Similarity	NPC215932
0.9577	High Similarity	NPC14958
0.9521	High Similarity	NPC186507
0.9521	High Similarity	NPC478213
0.9521	High Similarity	NPC124714
0.9514	High Similarity	NPC238366
0.951	High Similarity	NPC85233
0.9507	High Similarity	NPC471590
0.9507	High Similarity	NPC136278
0.9504	High Similarity	NPC476054
0.9452	High Similarity	NPC216769
0.9452	High Similarity	NPC209487
0.9452	High Similarity	NPC269451
0.9452	High Similarity	NPC35763
0.9452	High Similarity	NPC291802
0.9452	High Similarity	NPC181209
0.9452	High Similarity	NPC121522
0.9452	High Similarity	NPC131266
0.9452	High Similarity	NPC245382
0.9452	High Similarity	NPC100263
0.9452	High Similarity	NPC100971
0.9452	High Similarity	NPC153008
0.9452	High Similarity	NPC148497
0.9441	High Similarity	NPC302408
0.9441	High Similarity	NPC231013
0.9441	High Similarity	NPC283002
0.9437	High Similarity	NPC23955
0.9437	High Similarity	NPC113089
0.9424	High Similarity	NPC44573
0.9388	High Similarity	NPC250557
0.9388	High Similarity	NPC57211
0.9388	High Similarity	NPC472408
0.9388	High Similarity	NPC280937
0.9388	High Similarity	NPC128961
0.9384	High Similarity	NPC45291
0.9384	High Similarity	NPC279061
0.9384	High Similarity	NPC19980
0.9379	High Similarity	NPC69752
0.9375	High Similarity	NPC93034
0.9375	High Similarity	NPC119660
0.9375	High Similarity	NPC474999
0.9371	High Similarity	NPC165512
0.9366	High Similarity	NPC9966
0.9366	High Similarity	NPC70853
0.9329	High Similarity	NPC19097
0.9324	High Similarity	NPC478238
0.9324	High Similarity	NPC39184
0.9324	High Similarity	NPC130589
0.9324	High Similarity	NPC134287
0.932	High Similarity	NPC52623
0.932	High Similarity	NPC166201
0.9315	High Similarity	NPC10467
0.9315	High Similarity	NPC259058
0.9315	High Similarity	NPC201547
0.931	High Similarity	NPC476058
0.9306	High Similarity	NPC12377
0.9301	High Similarity	NPC293201
0.9296	High Similarity	NPC124467
0.9296	High Similarity	NPC214919
0.9296	High Similarity	NPC29536
0.9262	High Similarity	NPC180340
0.9257	High Similarity	NPC472915
0.9252	High Similarity	NPC226973
0.9252	High Similarity	NPC208043
0.9252	High Similarity	NPC308451
0.9247	High Similarity	NPC139293
0.9247	High Similarity	NPC264289
0.9247	High Similarity	NPC181250
0.9247	High Similarity	NPC92722
0.9247	High Similarity	NPC200060
0.9247	High Similarity	NPC142876
0.9247	High Similarity	NPC333691
0.9247	High Similarity	NPC40290
0.9247	High Similarity	NPC102003
0.9247	High Similarity	NPC264550
0.9247	High Similarity	NPC69430
0.9247	High Similarity	NPC195763
0.9241	High Similarity	NPC299923
0.9241	High Similarity	NPC470511
0.9209	High Similarity	NPC143649
0.92	High Similarity	NPC181960
0.92	High Similarity	NPC476981
0.92	High Similarity	NPC78103
0.9195	High Similarity	NPC213622
0.9195	High Similarity	NPC37392
0.9195	High Similarity	NPC20830
0.9195	High Similarity	NPC472909
0.9195	High Similarity	NPC256612
0.9189	High Similarity	NPC40033
0.9189	High Similarity	NPC134677
0.9184	High Similarity	NPC189270
0.9184	High Similarity	NPC306821
0.9184	High Similarity	NPC5840
0.9178	High Similarity	NPC194653
0.9178	High Similarity	NPC15329
0.9178	High Similarity	NPC139364
0.9178	High Similarity	NPC80710
0.9178	High Similarity	NPC203747
0.9178	High Similarity	NPC254702
0.9178	High Similarity	NPC131451
0.9178	High Similarity	NPC287395
0.9178	High Similarity	NPC183655
0.9178	High Similarity	NPC218490
0.9178	High Similarity	NPC476342
0.9172	High Similarity	NPC310259
0.9145	High Similarity	NPC165549
0.9139	High Similarity	NPC215375
0.9139	High Similarity	NPC62518
0.9137	High Similarity	NPC223354
0.9133	High Similarity	NPC472916
0.9133	High Similarity	NPC303255
0.9128	High Similarity	NPC231018
0.9128	High Similarity	NPC47781
0.9128	High Similarity	NPC86485
0.9128	High Similarity	NPC69394
0.9128	High Similarity	NPC160951
0.9128	High Similarity	NPC176775
0.9128	High Similarity	NPC183878
0.9128	High Similarity	NPC145379
0.9128	High Similarity	NPC22519
0.9128	High Similarity	NPC255350
0.9128	High Similarity	NPC274327
0.9122	High Similarity	NPC149614
0.9122	High Similarity	NPC117579
0.9122	High Similarity	NPC474663
0.9122	High Similarity	NPC256406
0.9122	High Similarity	NPC198615
0.9116	High Similarity	NPC328119
0.911	High Similarity	NPC125449
0.911	High Similarity	NPC188074
0.9097	High Similarity	NPC119663
0.9079	High Similarity	NPC476980
0.9079	High Similarity	NPC298093
0.9078	High Similarity	NPC157944
0.9078	High Similarity	NPC474274
0.9073	High Similarity	NPC474208
0.9073	High Similarity	NPC472911
0.9073	High Similarity	NPC162869
0.9073	High Similarity	NPC48208
0.9073	High Similarity	NPC167595
0.9073	High Similarity	NPC210084
0.9073	High Similarity	NPC475267
0.9073	High Similarity	NPC472914
0.9073	High Similarity	NPC258644
0.9073	High Similarity	NPC99597
0.9073	High Similarity	NPC245758
0.9073	High Similarity	NPC222814
0.9073	High Similarity	NPC474836
0.9073	High Similarity	NPC96167
0.9073	High Similarity	NPC472913
0.9073	High Similarity	NPC472910
0.9073	High Similarity	NPC156057
0.9073	High Similarity	NPC470402
0.9067	High Similarity	NPC241774
0.9067	High Similarity	NPC34725
0.9067	High Similarity	NPC138360
0.9067	High Similarity	NPC280339
0.9067	High Similarity	NPC50715
0.9067	High Similarity	NPC183597
0.9067	High Similarity	NPC196439
0.9067	High Similarity	NPC189960
0.9067	High Similarity	NPC2928
0.9067	High Similarity	NPC208197
0.9067	High Similarity	NPC163780
0.9067	High Similarity	NPC4455
0.9067	High Similarity	NPC276059
0.9067	High Similarity	NPC227325
0.9067	High Similarity	NPC167815
0.9067	High Similarity	NPC92659
0.9067	High Similarity	NPC122623
0.9067	High Similarity	NPC31018
0.9067	High Similarity	NPC255807
0.9067	High Similarity	NPC201136
0.9067	High Similarity	NPC146165
0.9067	High Similarity	NPC2476
0.9067	High Similarity	NPC32557
0.9067	High Similarity	NPC128863
0.9065	High Similarity	NPC182428
0.906	High Similarity	NPC156222
0.906	High Similarity	NPC222830
0.906	High Similarity	NPC301323
0.906	High Similarity	NPC68882
0.906	High Similarity	NPC292460
0.906	High Similarity	NPC83508
0.906	High Similarity	NPC162313
0.906	High Similarity	NPC293183

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 NPC216314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1025
0.2-0.3	1773
0.3-0.4	2720
0.4-0.5	1761
0.5-0.6	898
0.6-0.7	374
0.7-0.8	107
0.8-0.85	27
0.85-0.9	11
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9128	High Similarity	NPD2801	Approved
0.9079	High Similarity	NPD5494	Approved
0.8816	High Similarity	NPD3817	Phase 2
0.8811	High Similarity	NPD2796	Approved
0.8808	High Similarity	NPD1934	Approved
0.8654	High Similarity	NPD1247	Approved
0.8636	High Similarity	NPD3882	Suspended
0.8627	High Similarity	NPD2393	Clinical (unspecified phase)
0.8611	High Similarity	NPD1510	Phase 2
0.8523	High Similarity	NPD1511	Approved
0.85	High Similarity	NPD3818	Discontinued
0.8477	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD4380	Phase 2
0.8411	Intermediate Similarity	NPD1512	Approved
0.8375	Intermediate Similarity	NPD6166	Phase 2
0.8375	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1240	Approved
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD3926	Phase 2
0.8291	Intermediate Similarity	NPD919	Approved
0.8278	Intermediate Similarity	NPD6799	Approved
0.8242	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7054	Approved
0.8219	Intermediate Similarity	NPD1607	Approved
0.8217	Intermediate Similarity	NPD5402	Approved
0.8188	Intermediate Similarity	NPD1549	Phase 2
0.8171	Intermediate Similarity	NPD7074	Phase 3
0.8171	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8082	Intermediate Similarity	NPD943	Approved
0.8077	Intermediate Similarity	NPD6599	Discontinued
0.8054	Intermediate Similarity	NPD2935	Discontinued
0.8024	Intermediate Similarity	NPD7808	Phase 3
0.8012	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7251	Discontinued
0.7911	Intermediate Similarity	NPD7411	Suspended
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3748	Approved
0.7866	Intermediate Similarity	NPD5242	Approved
0.7829	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD1243	Approved
0.7771	Intermediate Similarity	NPD5403	Approved
0.7764	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5401	Approved
0.7742	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5536	Phase 2
0.7702	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6386	Approved
0.7688	Intermediate Similarity	NPD6385	Approved
0.7679	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2798	Approved
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7667	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD5353	Approved
0.7643	Intermediate Similarity	NPD2534	Approved
0.7643	Intermediate Similarity	NPD2533	Approved
0.7643	Intermediate Similarity	NPD2532	Approved
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7635	Intermediate Similarity	NPD3027	Phase 3
0.7613	Intermediate Similarity	NPD3750	Approved
0.7584	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2654	Approved
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7543	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD3972	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7468	Intermediate Similarity	NPD1551	Phase 2
0.7467	Intermediate Similarity	NPD2313	Discontinued
0.7455	Intermediate Similarity	NPD3749	Approved
0.7436	Intermediate Similarity	NPD2800	Approved
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7403	Intermediate Similarity	NPD2799	Discontinued
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4965	Approved
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD6651	Approved
0.7368	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1613	Approved
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2983	Phase 2
0.7347	Intermediate Similarity	NPD2982	Phase 2
0.7346	Intermediate Similarity	NPD3226	Approved
0.7342	Intermediate Similarity	NPD6190	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6844	Discontinued
0.731	Intermediate Similarity	NPD3751	Discontinued
0.7308	Intermediate Similarity	NPD2346	Discontinued
0.7308	Intermediate Similarity	NPD2344	Approved
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.7305	Intermediate Similarity	NPD6234	Discontinued
0.7294	Intermediate Similarity	NPD2403	Approved
0.7284	Intermediate Similarity	NPD1653	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7390	Discontinued
0.725	Intermediate Similarity	NPD4357	Discontinued
0.7229	Intermediate Similarity	NPD5978	Approved
0.7229	Intermediate Similarity	NPD5977	Approved
0.72	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7125	Intermediate Similarity	NPD2309	Approved
0.7123	Intermediate Similarity	NPD9268	Approved
0.7097	Intermediate Similarity	NPD5006	Approved
0.7097	Intermediate Similarity	NPD5005	Approved
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7081	Intermediate Similarity	NPD6780	Approved
0.7081	Intermediate Similarity	NPD6776	Approved
0.7081	Intermediate Similarity	NPD6781	Approved
0.7081	Intermediate Similarity	NPD6778	Approved
0.7081	Intermediate Similarity	NPD6777	Approved
0.7081	Intermediate Similarity	NPD6782	Approved
0.7081	Intermediate Similarity	NPD6779	Approved
0.7076	Intermediate Similarity	NPD5711	Approved
0.7076	Intermediate Similarity	NPD5710	Approved
0.7075	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7055	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD9269	Phase 2
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7025	Intermediate Similarity	NPD3539	Phase 1
0.702	Intermediate Similarity	NPD1470	Approved
0.702	Intermediate Similarity	NPD1203	Approved
0.7019	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3887	Approved
0.7013	Intermediate Similarity	NPD3268	Approved
0.7013	Intermediate Similarity	NPD1296	Phase 2
0.7011	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD6280	Approved
0.7006	Intermediate Similarity	NPD6279	Approved
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.6994	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4908	Phase 1
0.6981	Remote Similarity	NPD3540	Phase 1
0.6977	Remote Similarity	NPD7229	Phase 3
0.6973	Remote Similarity	NPD4420	Approved
0.6968	Remote Similarity	NPD7696	Phase 3
0.6968	Remote Similarity	NPD7697	Approved
0.6968	Remote Similarity	NPD6233	Phase 2
0.6968	Remote Similarity	NPD7698	Approved
0.6968	Remote Similarity	NPD7435	Discontinued
0.6962	Remote Similarity	NPD4308	Phase 3
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5890	Approved
0.6946	Remote Similarity	NPD6873	Phase 2
0.6946	Remote Similarity	NPD5889	Approved
0.6944	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD1548	Phase 1
0.6933	Remote Similarity	NPD9717	Approved
0.6933	Remote Similarity	NPD1608	Approved
0.6931	Remote Similarity	NPD7871	Phase 2
0.6931	Remote Similarity	NPD7870	Phase 2
0.6923	Remote Similarity	NPD4288	Approved
0.6919	Remote Similarity	NPD8090	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