NPASS Compound

Structure

CID197141 OpenBabel06191715582D 24 26 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -2.0000 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 -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 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -2.5981 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -7.7942 -1.5000 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 7 2 0 0 0 0 2 11 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 1 1 1 0 0 0 10 17 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.06
Volume:	325.556
LogP:	3.809
LogD:	2.527
LogS:	-4.871
# Rotatable Bonds:	5
TPSA:	81.54
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	2.565
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	1.3685465091839433e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	99.47452545166016%
Volume Distribution (VD):	0.437
Pgp-substrate:	0.6866493225097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.328
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.356
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.763
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	0.86
Half-life (T1/2):	0.345

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.849
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.821
Carcinogencity:	0.612
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC197141

Natural Product ID:	NPC197141
*Common Name:**	(2R)-2-[4-(7-Chloroquinoxalin-2-Yl)Oxyphenoxy]Propanoic Acid
IUPAC Name:	(2R)-2-[4-(7-chloroquinoxalin-2-yl)oxyphenoxy]propanoic acid
Synonyms:
Standard InCHIKey:	NUQZXROIVGBRGR-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C17H13ClN2O4/c1-10(17(21)22)23-12-3-5-13(6-4-12)24-16-9-19-14-7-2-11(18)8-15(14)20-16/h2-10H,1H3,(H,21,22)/t10-/m1/s1
SMILES:	C[C@H](C(=O)O)Oc1ccc(cc1)Oc1cnc2c(n1)cc(cc2)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1741037
PubChem CID:	3246729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004676] 2-phenoxypropionic acids [CHEMONTID:0004674] Aryloxyphenoxypropionic acids

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	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
GI50	54
IC50	1
Others	12

Activity Type	# Activity
Cell Line	55
Individual Protein	1
NON-MOLECULAR	1
Organism	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	87902.25	nM	PMID[512511]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	37068.07	nM	PMID[512511]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	67452.8	nM	PMID[512511]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	95719.41	nM	PMID[512511]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	72777.98	nM	PMID[512511]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	85310.01	nM	PMID[512511]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	76559.66	nM	PMID[512511]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[512511]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	55462.57	nM	PMID[512511]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	94188.96	nM	PMID[512511]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	38994.2	nM	PMID[512511]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	66680.68	nM	PMID[512511]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	11220.18	nM	PMID[512511]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	82985.08	nM	PMID[512511]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	60117.37	nM	PMID[512511]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	97274.72	nM	PMID[512511]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512511]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	59292.53	nM	PMID[512511]
NPT2742	Individual Protein	Aldehyde oxidase	Homo sapiens	Retention_time	=	17.4	min	PMID[512513]
NPT611	Cell Line	Hepatocyte	Homo sapiens	CL	<	4.3	mL.min-1.kg-1	PMID[512513]
NPT32	Organism	Mus musculus	Mus musculus	Body weight loss	=	-8.0	%	PMID[512510]
NPT32	Organism	Mus musculus	Mus musculus	T/C	=	2.0	%	PMID[512510]
NPT32	Organism	Mus musculus	Mus musculus	Log kill	=	2.9	n.a.	PMID[512510]
NPT32	Organism	Mus musculus	Mus musculus	Activity rating	>	2.8	n.a.	PMID[512510]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	T1/2	=	13.5	hr	PMID[512512]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	T1/2	=	13.2	hr	PMID[512512]
NPT27	Others	Unspecified		Drugexcretion	=	7.0	%	PMID[512512]
NPT605	Organism	Homo sapiens	Homo sapiens	CL	<	1.0	mL.min-1.kg-1	PMID[512513]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	70000.0	nM	PMID[512514]
NPT27	Others	Unspecified		T1/2	=	13.5	hr	PMID[512515]
NPT27	Others	Unspecified		T1/2	=	13.2	hr	PMID[512515]

☑ 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 NPC197141 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	519
0.1-0.2	6903
0.2-0.3	11160
0.3-0.4	15234
0.4-0.5	6333
0.5-0.6	2259
0.6-0.7	283
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7416	Intermediate Similarity	NPC226202
0.7353	Intermediate Similarity	NPC219963
0.733	Intermediate Similarity	NPC20249
0.7308	Intermediate Similarity	NPC110741
0.7294	Intermediate Similarity	NPC308392
0.7281	Intermediate Similarity	NPC471736
0.7268	Intermediate Similarity	NPC266551
0.7268	Intermediate Similarity	NPC161887
0.7268	Intermediate Similarity	NPC118776
0.7079	Intermediate Similarity	NPC1527
0.7018	Intermediate Similarity	NPC470586
0.701	Intermediate Similarity	NPC121658
0.701	Intermediate Similarity	NPC14651
0.698	Remote Similarity	NPC472435
0.6978	Remote Similarity	NPC476287
0.6961	Remote Similarity	NPC476518
0.6929	Remote Similarity	NPC472434
0.6912	Remote Similarity	NPC267928
0.6895	Remote Similarity	NPC472436
0.683	Remote Similarity	NPC287208
0.6812	Remote Similarity	NPC111624
0.6783	Remote Similarity	NPC314270
0.6777	Remote Similarity	NPC124300
0.6769	Remote Similarity	NPC288349
0.6763	Remote Similarity	NPC258773
0.6749	Remote Similarity	NPC285635
0.6749	Remote Similarity	NPC291609
0.6742	Remote Similarity	NPC19872
0.6694	Remote Similarity	NPC310618
0.6667	Remote Similarity	NPC25899
0.6652	Remote Similarity	NPC245816
0.6652	Remote Similarity	NPC476138
0.6634	Remote Similarity	NPC79911
0.6626	Remote Similarity	NPC471614
0.662	Remote Similarity	NPC206251
0.662	Remote Similarity	NPC74382
0.6612	Remote Similarity	NPC316224
0.6598	Remote Similarity	NPC99891
0.6585	Remote Similarity	NPC120798
0.6577	Remote Similarity	NPC168911
0.6577	Remote Similarity	NPC239954
0.6558	Remote Similarity	NPC156059
0.6553	Remote Similarity	NPC48192
0.6547	Remote Similarity	NPC187558
0.6545	Remote Similarity	NPC84853
0.6542	Remote Similarity	NPC300114
0.6522	Remote Similarity	NPC258048
0.6504	Remote Similarity	NPC475774
0.6502	Remote Similarity	NPC212213
0.65	Remote Similarity	NPC220523
0.65	Remote Similarity	NPC469961
0.6494	Remote Similarity	NPC26679
0.6491	Remote Similarity	NPC316403
0.6488	Remote Similarity	NPC141053
0.6485	Remote Similarity	NPC186351
0.6484	Remote Similarity	NPC134079
0.6483	Remote Similarity	NPC60621
0.6481	Remote Similarity	NPC470799
0.6481	Remote Similarity	NPC8022
0.6476	Remote Similarity	NPC47059
0.6476	Remote Similarity	NPC264166
0.6476	Remote Similarity	NPC274291
0.6476	Remote Similarity	NPC329708
0.6476	Remote Similarity	NPC118832
0.6476	Remote Similarity	NPC165349
0.6466	Remote Similarity	NPC161801
0.6462	Remote Similarity	NPC328029
0.6462	Remote Similarity	NPC95898
0.6441	Remote Similarity	NPC128115
0.6438	Remote Similarity	NPC224327
0.6435	Remote Similarity	NPC185782
0.6425	Remote Similarity	NPC195268
0.6425	Remote Similarity	NPC133140
0.642	Remote Similarity	NPC323198
0.6406	Remote Similarity	NPC320394
0.6404	Remote Similarity	NPC470500
0.64	Remote Similarity	NPC313421
0.6398	Remote Similarity	NPC313804
0.6398	Remote Similarity	NPC315804
0.6396	Remote Similarity	NPC198673
0.6394	Remote Similarity	NPC177404
0.6391	Remote Similarity	NPC82548
0.6379	Remote Similarity	NPC469554
0.6372	Remote Similarity	NPC149402
0.6368	Remote Similarity	NPC153452
0.6364	Remote Similarity	NPC174672
0.6364	Remote Similarity	NPC174758
0.636	Remote Similarity	NPC65277
0.6352	Remote Similarity	NPC323752
0.6352	Remote Similarity	NPC202605
0.6352	Remote Similarity	NPC112206
0.6349	Remote Similarity	NPC110151
0.6348	Remote Similarity	NPC193238
0.6341	Remote Similarity	NPC36168
0.6337	Remote Similarity	NPC260434
0.6329	Remote Similarity	NPC213530
0.6329	Remote Similarity	NPC193267
0.6327	Remote Similarity	NPC476578
0.6327	Remote Similarity	NPC4071
0.6327	Remote Similarity	NPC182222
0.6327	Remote Similarity	NPC476582
0.6322	Remote Similarity	NPC314954
0.6318	Remote Similarity	NPC216612
0.63	Remote Similarity	NPC315957
0.63	Remote Similarity	NPC176538
0.6291	Remote Similarity	NPC253810
0.6287	Remote Similarity	NPC473822
0.6286	Remote Similarity	NPC118511
0.6285	Remote Similarity	NPC165964
0.6281	Remote Similarity	NPC244536
0.6276	Remote Similarity	NPC90019
0.6275	Remote Similarity	NPC476995
0.6275	Remote Similarity	NPC177056
0.6273	Remote Similarity	NPC314573
0.6272	Remote Similarity	NPC232727
0.6266	Remote Similarity	NPC123976
0.6266	Remote Similarity	NPC5145
0.6266	Remote Similarity	NPC167860
0.6266	Remote Similarity	NPC290689
0.6261	Remote Similarity	NPC214827
0.6261	Remote Similarity	NPC314930
0.6261	Remote Similarity	NPC476581
0.6261	Remote Similarity	NPC16452
0.6261	Remote Similarity	NPC472259
0.6261	Remote Similarity	NPC36229
0.626	Remote Similarity	NPC56271
0.6256	Remote Similarity	NPC55038
0.6256	Remote Similarity	NPC476167
0.6255	Remote Similarity	NPC151781
0.6255	Remote Similarity	NPC316181
0.6255	Remote Similarity	NPC74562
0.625	Remote Similarity	NPC79293
0.625	Remote Similarity	NPC279401
0.625	Remote Similarity	NPC26850
0.625	Remote Similarity	NPC85879
0.625	Remote Similarity	NPC53255
0.625	Remote Similarity	NPC475301
0.625	Remote Similarity	NPC326930
0.6245	Remote Similarity	NPC101543
0.6244	Remote Similarity	NPC314940
0.6244	Remote Similarity	NPC232872
0.6244	Remote Similarity	NPC473764
0.6231	Remote Similarity	NPC328928
0.6228	Remote Similarity	NPC234197
0.6228	Remote Similarity	NPC477019
0.6227	Remote Similarity	NPC42591
0.6226	Remote Similarity	NPC13603
0.6223	Remote Similarity	NPC469589
0.6215	Remote Similarity	NPC316756
0.6211	Remote Similarity	NPC192315
0.6209	Remote Similarity	NPC263439
0.6208	Remote Similarity	NPC310118
0.6207	Remote Similarity	NPC313189
0.6207	Remote Similarity	NPC152620
0.6205	Remote Similarity	NPC324149
0.6204	Remote Similarity	NPC476999
0.6203	Remote Similarity	NPC274982
0.62	Remote Similarity	NPC148889
0.6198	Remote Similarity	NPC289423
0.6198	Remote Similarity	NPC212766
0.6195	Remote Similarity	NPC109922
0.6192	Remote Similarity	NPC17565
0.6192	Remote Similarity	NPC292958
0.6189	Remote Similarity	NPC476997
0.6188	Remote Similarity	NPC470403
0.6188	Remote Similarity	NPC470404
0.6188	Remote Similarity	NPC470394
0.6186	Remote Similarity	NPC266931
0.6186	Remote Similarity	NPC250448
0.6184	Remote Similarity	NPC18487
0.6182	Remote Similarity	NPC284559
0.6182	Remote Similarity	NPC284678
0.618	Remote Similarity	NPC475024
0.6178	Remote Similarity	NPC289786
0.6175	Remote Similarity	NPC283152
0.6172	Remote Similarity	NPC116573
0.6169	Remote Similarity	NPC318935
0.6167	Remote Similarity	NPC54066
0.6166	Remote Similarity	NPC475533
0.6163	Remote Similarity	NPC476998
0.6163	Remote Similarity	NPC476996
0.616	Remote Similarity	NPC227824
0.6157	Remote Similarity	NPC312872
0.6157	Remote Similarity	NPC26543
0.6154	Remote Similarity	NPC473833
0.6151	Remote Similarity	NPC173080
0.6145	Remote Similarity	NPC472061
0.6144	Remote Similarity	NPC53069
0.6144	Remote Similarity	NPC244856
0.6144	Remote Similarity	NPC202768
0.6144	Remote Similarity	NPC296482
0.6142	Remote Similarity	NPC475315
0.6142	Remote Similarity	NPC324619
0.6137	Remote Similarity	NPC135549
0.6135	Remote Similarity	NPC284348
0.613	Remote Similarity	NPC31930
0.6128	Remote Similarity	NPC123839
0.6128	Remote Similarity	NPC470020
0.6128	Remote Similarity	NPC219664
0.6127	Remote Similarity	NPC470395

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 NPC197141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	880
0.2-0.3	1015
0.3-0.4	2159
0.4-0.5	2883
0.5-0.6	1626
0.6-0.7	322
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9793	High Similarity	NPD2314	Clinical (unspecified phase)
0.9793	High Similarity	NPD2772	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4454	Phase 2
0.7378	Intermediate Similarity	NPD7548	Discontinued
0.7356	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD2785	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2831	Approved
0.7204	Intermediate Similarity	NPD4372	Phase 1
0.7181	Intermediate Similarity	NPD1856	Discontinued
0.7162	Intermediate Similarity	NPD5640	Discontinued
0.7143	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9548	Phase 2
0.7089	Intermediate Similarity	NPD4529	Approved
0.7089	Intermediate Similarity	NPD4526	Approved
0.7089	Intermediate Similarity	NPD4528	Approved
0.7059	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4131	Phase 3
0.7	Intermediate Similarity	NPD4889	Approved
0.6968	Remote Similarity	NPD6728	Phase 3
0.6963	Remote Similarity	NPD6569	Phase 2
0.6944	Remote Similarity	NPD3477	Phase 2
0.6944	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7405	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7069	Discontinued
0.691	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6219	Discontinued
0.6894	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5450	Discontinued
0.6878	Remote Similarity	NPD565	Phase 2
0.6849	Remote Similarity	NPD3338	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5420	Discontinued
0.6844	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1622	Discontinued
0.6818	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2077	Approved
0.6812	Remote Similarity	NPD2076	Approved
0.6797	Remote Similarity	NPD3280	Approved
0.6796	Remote Similarity	NPD5319	Approved
0.6796	Remote Similarity	NPD5320	Approved
0.6792	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1213	Phase 3
0.6789	Remote Similarity	NPD6550	Discontinued
0.6789	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD9596	Approved
0.6784	Remote Similarity	NPD9595	Approved
0.678	Remote Similarity	NPD3302	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6298	Discontinued
0.6758	Remote Similarity	NPD1229	Phase 2
0.674	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1638	Discovery
0.6723	Remote Similarity	NPD7426	Phase 1
0.6712	Remote Similarity	NPD5512	Phase 3
0.6709	Remote Similarity	NPD5022	Discontinued
0.6709	Remote Similarity	NPD5842	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7022	Phase 2
0.6698	Remote Similarity	NPD1034	Phase 3
0.6698	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4296	Phase 2
0.668	Remote Similarity	NPD7413	Phase 3
0.6667	Remote Similarity	NPD6759	Phase 2
0.6653	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4314	Approved
0.6653	Remote Similarity	NPD4313	Approved
0.665	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4072	Approved
0.6635	Remote Similarity	NPD4071	Approved
0.6626	Remote Similarity	NPD4309	Approved
0.6626	Remote Similarity	NPD6537	Approved
0.6626	Remote Similarity	NPD6536	Approved
0.662	Remote Similarity	NPD4203	Approved
0.662	Remote Similarity	NPD4204	Approved
0.6613	Remote Similarity	NPD4303	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7467	Discontinued
0.6594	Remote Similarity	NPD5067	Phase 2
0.6594	Remote Similarity	NPD5066	Phase 2
0.6591	Remote Similarity	NPD3396	Approved
0.6591	Remote Similarity	NPD3395	Approved
0.6583	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6482	Phase 1
0.6546	Remote Similarity	NPD5482	Discontinued
0.6544	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7963	Phase 3
0.6532	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6988	Phase 1
0.6528	Remote Similarity	NPD7407	Discontinued
0.6525	Remote Similarity	NPD8356	Approved
0.6516	Remote Similarity	NPD6590	Discontinued
0.6513	Remote Similarity	NPD7675	Phase 3
0.6513	Remote Similarity	NPD7674	Phase 3
0.6513	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD8479	Phase 2
0.6509	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1418	Phase 2
0.6504	Remote Similarity	NPD4875	Phase 3
0.6504	Remote Similarity	NPD8116	Phase 3
0.6504	Remote Similarity	NPD8117	Approved
0.6504	Remote Similarity	NPD4876	Phase 3
0.65	Remote Similarity	NPD9243	Approved
0.65	Remote Similarity	NPD9689	Approved
0.6495	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5429	Discontinued
0.6488	Remote Similarity	NPD7558	Phase 2
0.6485	Remote Similarity	NPD8430	Approved
0.6481	Remote Similarity	NPD5612	Discontinued
0.648	Remote Similarity	NPD4916	Discontinued
0.6476	Remote Similarity	NPD4039	Approved
0.6476	Remote Similarity	NPD4122	Approved
0.6476	Remote Similarity	NPD32	Approved
0.6476	Remote Similarity	NPD4034	Approved
0.6476	Remote Similarity	NPD4035	Approved
0.6476	Remote Similarity	NPD4038	Approved
0.6476	Remote Similarity	NPD4037	Approved
0.6476	Remote Similarity	NPD4036	Approved
0.6476	Remote Similarity	NPD31	Approved
0.6476	Remote Similarity	NPD4033	Approved
0.6475	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4343	Phase 1
0.6473	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4548	Discontinued
0.6468	Remote Similarity	NPD6500	Approved
0.6468	Remote Similarity	NPD6501	Approved
0.6465	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3931	Approved
0.646	Remote Similarity	NPD3928	Approved
0.6458	Remote Similarity	NPD5559	Phase 2
0.6457	Remote Similarity	NPD2952	Discontinued
0.6457	Remote Similarity	NPD6207	Discovery
0.6455	Remote Similarity	NPD4148	Approved
0.6455	Remote Similarity	NPD1924	Approved
0.6454	Remote Similarity	NPD5878	Approved
0.6454	Remote Similarity	NPD5875	Approved
0.6453	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4989	Phase 2
0.645	Remote Similarity	NPD3939	Suspended
0.645	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3580	Discontinued
0.6443	Remote Similarity	NPD8247	Approved
0.6443	Remote Similarity	NPD8246	Approved
0.6441	Remote Similarity	NPD7180	Phase 3
0.6441	Remote Similarity	NPD1602	Discontinued
0.6438	Remote Similarity	NPD4021	Phase 2
0.6437	Remote Similarity	NPD5922	Phase 3
0.6432	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD772	Phase 3
0.6429	Remote Similarity	NPD6197	Approved
0.6426	Remote Similarity	NPD7395	Discontinued
0.6425	Remote Similarity	NPD3923	Approved
0.6425	Remote Similarity	NPD3924	Approved
0.6425	Remote Similarity	NPD3921	Approved
0.6425	Remote Similarity	NPD3922	Approved
0.6423	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1392	Approved
0.6417	Remote Similarity	NPD4328	Approved
0.6414	Remote Similarity	NPD8101	Phase 3
0.6407	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1867	Approved
0.6391	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7221	Approved
0.6387	Remote Similarity	NPD7219	Approved
0.6385	Remote Similarity	NPD158	Discontinued
0.6384	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD2959	Phase 3
0.6383	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6750	Phase 2
0.6379	Remote Similarity	NPD3570	Phase 2
0.6379	Remote Similarity	NPD5416	Discontinued
0.6376	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD8324	Phase 2
0.6368	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7659	Discontinued
0.636	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4429	Discontinued
0.6356	Remote Similarity	NPD6568	Discontinued
0.6352	Remote Similarity	NPD6494	Phase 2
0.6352	Remote Similarity	NPD5866	Approved
0.635	Remote Similarity	NPD5018	Phase 3
0.6348	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7222	Phase 2
0.6347	Remote Similarity	NPD4921	Phase 3
0.6347	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD4919	Phase 3
0.6346	Remote Similarity	NPD7673	Phase 3
0.6343	Remote Similarity	NPD3781	Phase 2

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