NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	235.1
Volume:	258.318
LogP:	3.18
LogD:	3.131
LogS:	-4.125
# Rotatable Bonds:	1
TPSA:	22.0
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	1.79
Fsp3:	0.062
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:	-4.741
MDCK Permeability:	2.6571937269181944e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.576
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.822
Plasma Protein Binding (PPB):	95.94647979736328%
Volume Distribution (VD):	0.56
Pgp-substrate:	2.2543587684631348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.553
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	5.419
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.354
AMES Toxicity:	0.91
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.39
Skin Sensitization:	0.611
Carcinogencity:	0.839
Eye Corrosion:	0.01
Eye Irritation:	0.967
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC257490

Natural Product ID:	NPC257490
*Common Name:**	1-Methyl-2-Phenylquinolin-4-One
IUPAC Name:	1-methyl-2-phenylquinolin-4-one
Synonyms:
Standard InCHIKey:	AFKNCQDBTBDPOQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H13NO/c1-17-14-10-6-5-9-13(14)16(18)11-15(17)12-7-3-2-4-8-12/h2-11H,1H3
SMILES:	O=c1cc(c2ccccc2)n(c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL277048
PubChem CID:	776143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	PMID[10075120]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473429]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17228877]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7931371]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868168]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24396	Grosvenoria rimbachii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11475	Vernonia chloropappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15572	Espeletiopsis purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14640	Uresiphita reversalis	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23398	Caralluma russeliana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18014	Gracilaria eucheumoides	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17231	Pycnarrhena australiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17624	Spatoglossum pacificum	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23822	Polypodium aureum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24280	Helianthus californicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16936	Evea brasiliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12658	Melipotis perpendicularis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11784	Sickingia rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9814	Lactarius fuliginosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23490	Dalbergia monetaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17492	Amomum reticulatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	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
EC50	6
IC50	2
Kd	1
Potency	6

Activity Type	# Activity
Cell Line	6
Individual Protein	7
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[451285]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[451285]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[451285]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[451285]
NPT168	Cell Line	P388	Mus musculus	EC50	>	10.0	ug.mL-1	PMID[451285]
NPT1868	Cell Line	L1210 (1565)		EC50	>	10.0	ug.mL-1	PMID[451285]
NPT3597	Individual Protein	Tubulin beta chain	Bos taurus	IC50	>	40000.0	nM	PMID[451285]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	25118.9	nM	PMID[451286]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[451286]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	891.3	nM	PMID[451286]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	6309.6	nM	PMID[451286]
NPT781	Individual Protein	Tubulin alpha chain	Sus scrofa	IC50	>	40000.0	nM	PMID[451284]
NPT2	Others	Unspecified		Kd	=	1000000.0	nM	PMID[451287]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4653.5	nM	PMID[451286]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[451286]

☑ 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 NPC257490 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	670
0.1-0.2	5678
0.2-0.3	12766
0.3-0.4	16322
0.4-0.5	3343
0.5-0.6	2295
0.6-0.7	1349
0.7-0.8	244
0.8-0.85	15
0.85-0.9	7
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC177684
0.9649	High Similarity	NPC291962
0.9565	High Similarity	NPC258531
0.9565	High Similarity	NPC112373
0.9565	High Similarity	NPC161956
0.9068	High Similarity	NPC279385
0.9068	High Similarity	NPC179605
0.8992	High Similarity	NPC103292
0.8917	High Similarity	NPC39818
0.876	High Similarity	NPC268534
0.8672	High Similarity	NPC300299
0.8667	High Similarity	NPC226143
0.8485	Intermediate Similarity	NPC471574
0.8346	Intermediate Similarity	NPC209389
0.8296	Intermediate Similarity	NPC136002
0.8276	Intermediate Similarity	NPC172170
0.8175	Intermediate Similarity	NPC192533
0.8134	Intermediate Similarity	NPC207554
0.8129	Intermediate Similarity	NPC144691
0.806	Intermediate Similarity	NPC83214
0.8017	Intermediate Similarity	NPC57051
0.8	Intermediate Similarity	NPC194562
0.7953	Intermediate Similarity	NPC254698
0.7941	Intermediate Similarity	NPC471164
0.7941	Intermediate Similarity	NPC2823
0.7829	Intermediate Similarity	NPC472244
0.7829	Intermediate Similarity	NPC470343
0.7687	Intermediate Similarity	NPC93653
0.7652	Intermediate Similarity	NPC150863
0.7639	Intermediate Similarity	NPC117032
0.763	Intermediate Similarity	NPC316104
0.763	Intermediate Similarity	NPC162417
0.7612	Intermediate Similarity	NPC207428
0.7594	Intermediate Similarity	NPC314431
0.7594	Intermediate Similarity	NPC472245
0.7594	Intermediate Similarity	NPC280807
0.7586	Intermediate Similarity	NPC295021
0.7537	Intermediate Similarity	NPC316746
0.7533	Intermediate Similarity	NPC299582
0.75	Intermediate Similarity	NPC167336
0.7372	Intermediate Similarity	NPC253476
0.7353	Intermediate Similarity	NPC53044
0.7338	Intermediate Similarity	NPC318183
0.7333	Intermediate Similarity	NPC27904
0.7319	Intermediate Similarity	NPC173295
0.731	Intermediate Similarity	NPC300596
0.731	Intermediate Similarity	NPC237649
0.7273	Intermediate Similarity	NPC130797
0.7273	Intermediate Similarity	NPC470822
0.725	Intermediate Similarity	NPC291610
0.7237	Intermediate Similarity	NPC204867
0.7234	Intermediate Similarity	NPC315051
0.7203	Intermediate Similarity	NPC308197
0.7188	Intermediate Similarity	NPC288232
0.7165	Intermediate Similarity	NPC296163
0.7165	Intermediate Similarity	NPC187036
0.7113	Intermediate Similarity	NPC472243
0.708	Intermediate Similarity	NPC187231
0.7078	Intermediate Similarity	NPC471130
0.7077	Intermediate Similarity	NPC313449
0.7077	Intermediate Similarity	NPC192209
0.7075	Intermediate Similarity	NPC242000
0.7063	Intermediate Similarity	NPC85613
0.7063	Intermediate Similarity	NPC43477
0.7063	Intermediate Similarity	NPC5167
0.7059	Intermediate Similarity	NPC88970
0.7059	Intermediate Similarity	NPC307437
0.7059	Intermediate Similarity	NPC72473
0.7059	Intermediate Similarity	NPC58827
0.7055	Intermediate Similarity	NPC324445
0.7051	Intermediate Similarity	NPC471943
0.7042	Intermediate Similarity	NPC469560
0.7029	Intermediate Similarity	NPC231382
0.7029	Intermediate Similarity	NPC314098
0.7025	Intermediate Similarity	NPC475594
0.6993	Remote Similarity	NPC130251
0.6985	Remote Similarity	NPC250476
0.6981	Remote Similarity	NPC471743
0.6981	Remote Similarity	NPC475607
0.6978	Remote Similarity	NPC40364
0.6972	Remote Similarity	NPC122553
0.6966	Remote Similarity	NPC478040
0.6957	Remote Similarity	NPC477432
0.6944	Remote Similarity	NPC301760
0.6943	Remote Similarity	NPC472118
0.6942	Remote Similarity	NPC75496
0.6937	Remote Similarity	NPC474081
0.6928	Remote Similarity	NPC154478
0.6918	Remote Similarity	NPC314186
0.6918	Remote Similarity	NPC469529
0.6908	Remote Similarity	NPC84317
0.6903	Remote Similarity	NPC138293
0.6903	Remote Similarity	NPC113056
0.6901	Remote Similarity	NPC471123
0.6897	Remote Similarity	NPC472241
0.6884	Remote Similarity	NPC122235
0.6855	Remote Similarity	NPC38262
0.6852	Remote Similarity	NPC475685
0.6839	Remote Similarity	NPC469741
0.6839	Remote Similarity	NPC293458
0.6838	Remote Similarity	NPC226794
0.6828	Remote Similarity	NPC316202
0.6825	Remote Similarity	NPC79618
0.6824	Remote Similarity	NPC478039
0.6824	Remote Similarity	NPC470579
0.6813	Remote Similarity	NPC470548
0.68	Remote Similarity	NPC13526
0.6792	Remote Similarity	NPC292265
0.6792	Remote Similarity	NPC355
0.679	Remote Similarity	NPC474041
0.679	Remote Similarity	NPC475761
0.679	Remote Similarity	NPC475094
0.6772	Remote Similarity	NPC70949
0.6768	Remote Similarity	NPC470317
0.6757	Remote Similarity	NPC472242
0.675	Remote Similarity	NPC256452
0.6748	Remote Similarity	NPC73994
0.6748	Remote Similarity	NPC298320
0.6739	Remote Similarity	NPC322433
0.6735	Remote Similarity	NPC314287
0.6714	Remote Similarity	NPC179224
0.6693	Remote Similarity	NPC55529
0.6691	Remote Similarity	NPC476950
0.6688	Remote Similarity	NPC265100
0.6686	Remote Similarity	NPC1820
0.6667	Remote Similarity	NPC291070
0.6667	Remote Similarity	NPC130931
0.6667	Remote Similarity	NPC238499
0.6667	Remote Similarity	NPC475248
0.6667	Remote Similarity	NPC246757
0.6667	Remote Similarity	NPC63047
0.6646	Remote Similarity	NPC115232
0.6646	Remote Similarity	NPC283810
0.6645	Remote Similarity	NPC123241
0.6643	Remote Similarity	NPC184437
0.6642	Remote Similarity	NPC228515
0.6641	Remote Similarity	NPC302790
0.6627	Remote Similarity	NPC21429
0.6626	Remote Similarity	NPC284775
0.6624	Remote Similarity	NPC476231
0.6624	Remote Similarity	NPC242116
0.6622	Remote Similarity	NPC469537
0.6613	Remote Similarity	NPC326792
0.6604	Remote Similarity	NPC114637
0.6604	Remote Similarity	NPC279527
0.6604	Remote Similarity	NPC214960
0.6599	Remote Similarity	NPC470301
0.6582	Remote Similarity	NPC189116
0.6579	Remote Similarity	NPC473329
0.6562	Remote Similarity	NPC434
0.6558	Remote Similarity	NPC281094
0.6555	Remote Similarity	NPC78154
0.6549	Remote Similarity	NPC71664
0.6547	Remote Similarity	NPC79698
0.6543	Remote Similarity	NPC252572
0.6543	Remote Similarity	NPC177261
0.6538	Remote Similarity	NPC113946
0.6538	Remote Similarity	NPC477887
0.6536	Remote Similarity	NPC154602
0.6536	Remote Similarity	NPC243756
0.6529	Remote Similarity	NPC313293
0.6519	Remote Similarity	NPC199737
0.6519	Remote Similarity	NPC472117
0.6519	Remote Similarity	NPC214106
0.6516	Remote Similarity	NPC114808
0.6509	Remote Similarity	NPC473815
0.65	Remote Similarity	NPC182131
0.6496	Remote Similarity	NPC475915
0.6494	Remote Similarity	NPC285381
0.6494	Remote Similarity	NPC122106
0.6491	Remote Similarity	NPC273033
0.6491	Remote Similarity	NPC12936
0.6488	Remote Similarity	NPC49184
0.6488	Remote Similarity	NPC133003
0.6488	Remote Similarity	NPC476341
0.6486	Remote Similarity	NPC22082
0.6486	Remote Similarity	NPC186284
0.6484	Remote Similarity	NPC473498
0.6479	Remote Similarity	NPC9856
0.6475	Remote Similarity	NPC285394
0.646	Remote Similarity	NPC223595
0.646	Remote Similarity	NPC167724
0.646	Remote Similarity	NPC224970
0.6456	Remote Similarity	NPC315368
0.6452	Remote Similarity	NPC200743
0.645	Remote Similarity	NPC150308
0.645	Remote Similarity	NPC141612
0.645	Remote Similarity	NPC135601
0.645	Remote Similarity	NPC17273
0.6446	Remote Similarity	NPC88110
0.6442	Remote Similarity	NPC307640
0.6441	Remote Similarity	NPC69057
0.6438	Remote Similarity	NPC325599
0.6437	Remote Similarity	NPC472539
0.6437	Remote Similarity	NPC472540
0.6437	Remote Similarity	NPC470787
0.6434	Remote Similarity	NPC20322
0.6433	Remote Similarity	NPC104345
0.6433	Remote Similarity	NPC324091
0.6433	Remote Similarity	NPC61013

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 NPC257490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	713
0.2-0.3	871
0.3-0.4	1873
0.4-0.5	2477
0.5-0.6	2010
0.6-0.7	721
0.7-0.8	93
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD1527	Phase 2
0.8504	High Similarity	NPD486	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1919	Approved
0.8438	Intermediate Similarity	NPD1920	Approved
0.8372	Intermediate Similarity	NPD441	Approved
0.8279	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6017	Discontinued
0.8231	Intermediate Similarity	NPD2949	Approved
0.8231	Intermediate Similarity	NPD2950	Approved
0.8092	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1541	Approved
0.8017	Intermediate Similarity	NPD1175	Approved
0.7985	Intermediate Similarity	NPD6342	Discontinued
0.7883	Intermediate Similarity	NPD6512	Approved
0.7883	Intermediate Similarity	NPD6513	Approved
0.7752	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD1065	Approved
0.7731	Intermediate Similarity	NPD1064	Approved
0.7714	Intermediate Similarity	NPD5931	Phase 3
0.7714	Intermediate Similarity	NPD5932	Phase 3
0.7714	Intermediate Similarity	NPD5933	Phase 3
0.7676	Intermediate Similarity	NPD4942	Approved
0.7655	Intermediate Similarity	NPD4045	Phase 2
0.7655	Intermediate Similarity	NPD4042	Phase 2
0.7643	Intermediate Similarity	NPD5918	Discontinued
0.7639	Intermediate Similarity	NPD3248	Phase 1
0.7634	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3482	Approved
0.7626	Intermediate Similarity	NPD6768	Approved
0.7597	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5181	Approved
0.7581	Intermediate Similarity	NPD5180	Approved
0.7581	Intermediate Similarity	NPD5179	Approved
0.7556	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1626	Approved
0.7518	Intermediate Similarity	NPD4043	Approved
0.7518	Intermediate Similarity	NPD4046	Approved
0.7518	Intermediate Similarity	NPD3481	Approved
0.75	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6566	Discontinued
0.7463	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2331	Discontinued
0.7431	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD708	Approved
0.7388	Intermediate Similarity	NPD4549	Discontinued
0.7364	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2790	Discontinued
0.7333	Intermediate Similarity	NPD5131	Approved
0.7324	Intermediate Similarity	NPD1625	Approved
0.7319	Intermediate Similarity	NPD2791	Discontinued
0.731	Intermediate Similarity	NPD4888	Discontinued
0.7295	Intermediate Similarity	NPD3546	Approved
0.7295	Intermediate Similarity	NPD3545	Approved
0.7258	Intermediate Similarity	NPD4116	Approved
0.7255	Intermediate Similarity	NPD4645	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2365	Approved
0.7252	Intermediate Similarity	NPD1123	Approved
0.7252	Intermediate Similarity	NPD1124	Approved
0.7236	Intermediate Similarity	NPD4114	Approved
0.7236	Intermediate Similarity	NPD4115	Approved
0.7219	Intermediate Similarity	NPD2506	Approved
0.7203	Intermediate Similarity	NPD1100	Approved
0.7203	Intermediate Similarity	NPD2820	Phase 3
0.7203	Intermediate Similarity	NPD1099	Approved
0.7183	Intermediate Similarity	NPD4461	Discontinued
0.7183	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1574	Approved
0.7163	Intermediate Similarity	NPD7254	Discontinued
0.7163	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1854	Approved
0.7153	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1619	Phase 3
0.7152	Intermediate Similarity	NPD33	Approved
0.7152	Intermediate Similarity	NPD4393	Approved
0.7143	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1189	Approved
0.7111	Intermediate Similarity	NPD1593	Approved
0.7107	Intermediate Similarity	NPD2648	Phase 3
0.7107	Intermediate Similarity	NPD3782	Discontinued
0.7107	Intermediate Similarity	NPD2193	Phase 2
0.7107	Intermediate Similarity	NPD4734	Approved
0.7107	Intermediate Similarity	NPD4735	Approved
0.7083	Intermediate Similarity	NPD4430	Phase 2
0.7077	Intermediate Similarity	NPD7481	Approved
0.7077	Intermediate Similarity	NPD7480	Approved
0.7071	Intermediate Similarity	NPD1410	Phase 1
0.7063	Intermediate Similarity	NPD4329	Approved
0.7063	Intermediate Similarity	NPD2010	Phase 3
0.7063	Intermediate Similarity	NPD1222	Discontinued
0.7063	Intermediate Similarity	NPD4330	Approved
0.7055	Intermediate Similarity	NPD1524	Phase 1
0.7044	Intermediate Similarity	NPD3792	Approved
0.7039	Intermediate Similarity	NPD2427	Approved
0.7031	Intermediate Similarity	NPD2914	Approved
0.7031	Intermediate Similarity	NPD2913	Approved
0.7029	Intermediate Similarity	NPD2754	Discontinued
0.7029	Intermediate Similarity	NPD1190	Approved
0.702	Intermediate Similarity	NPD2351	Discontinued
0.7008	Intermediate Similarity	NPD2999	Approved
0.7008	Intermediate Similarity	NPD3001	Approved
0.7007	Intermediate Similarity	NPD7088	Discontinued
0.6987	Remote Similarity	NPD2037	Approved
0.6985	Remote Similarity	NPD2840	Approved
0.6984	Remote Similarity	NPD7633	Discontinued
0.6974	Remote Similarity	NPD5660	Approved
0.6974	Remote Similarity	NPD6019	Approved
0.6974	Remote Similarity	NPD5659	Approved
0.6974	Remote Similarity	NPD6018	Approved
0.6972	Remote Similarity	NPD6358	Phase 2
0.6967	Remote Similarity	NPD2171	Approved
0.6967	Remote Similarity	NPD813	Approved
0.6967	Remote Similarity	NPD2196	Discontinued
0.6966	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5253	Approved
0.696	Remote Similarity	NPD6300	Approved
0.696	Remote Similarity	NPD6299	Approved
0.6954	Remote Similarity	NPD7072	Phase 2
0.6943	Remote Similarity	NPD2369	Discontinued
0.6935	Remote Similarity	NPD2192	Approved
0.6935	Remote Similarity	NPD2197	Approved
0.6934	Remote Similarity	NPD5993	Phase 1
0.6933	Remote Similarity	NPD8241	Phase 2
0.6923	Remote Similarity	NPD7142	Discontinued
0.6908	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1342	Approved
0.6903	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3387	Approved
0.6894	Remote Similarity	NPD5657	Phase 3
0.6887	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1781	Discontinued
0.6883	Remote Similarity	NPD5992	Approved
0.6867	Remote Similarity	NPD1230	Approved
0.6866	Remote Similarity	NPD678	Discontinued
0.6866	Remote Similarity	NPD1079	Discontinued
0.6853	Remote Similarity	NPD2670	Approved
0.6853	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7082	Approved
0.6846	Remote Similarity	NPD5631	Phase 3
0.6842	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9539	Approved
0.6838	Remote Similarity	NPD9541	Approved
0.6835	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6027	Approved
0.6829	Remote Similarity	NPD6024	Approved
0.6824	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6629	Discontinued
0.6803	Remote Similarity	NPD7487	Discontinued
0.6803	Remote Similarity	NPD7259	Approved
0.68	Remote Similarity	NPD5748	Phase 2
0.6792	Remote Similarity	NPD2432	Approved
0.6792	Remote Similarity	NPD2431	Approved
0.6788	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4655	Approved
0.6777	Remote Similarity	NPD4657	Approved
0.6772	Remote Similarity	NPD2454	Approved
0.6772	Remote Similarity	NPD2455	Approved
0.677	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1360	Approved
0.6761	Remote Similarity	NPD1531	Approved
0.6757	Remote Similarity	NPD7295	Approved
0.675	Remote Similarity	NPD4094	Approved
0.6746	Remote Similarity	NPD993	Approved
0.6746	Remote Similarity	NPD990	Approved
0.6744	Remote Similarity	NPD2039	Approved
0.6744	Remote Similarity	NPD3865	Approved
0.6744	Remote Similarity	NPD2038	Approved
0.6742	Remote Similarity	NPD6070	Approved
0.6742	Remote Similarity	NPD6069	Approved
0.6741	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD9540	Approved
0.673	Remote Similarity	NPD5186	Approved
0.673	Remote Similarity	NPD5183	Approved
0.672	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1539	Approved
0.6719	Remote Similarity	NPD3548	Approved
0.6713	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4988	Discontinued
0.6689	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD951	Approved
0.6688	Remote Similarity	NPD2836	Approved
0.6688	Remote Similarity	NPD1208	Approved
0.6688	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5504	Discontinued
0.6667	Remote Similarity	NPD1677	Discontinued
0.6667	Remote Similarity	NPD7478	Approved
0.6667	Remote Similarity	NPD3747	Discontinued
0.6667	Remote Similarity	NPD6489	Phase 3
0.6646	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3377	Discontinued
0.6645	Remote Similarity	NPD3277	Phase 3
0.6643	Remote Similarity	NPD5182	Approved
0.6643	Remote Similarity	NPD5184	Approved
0.6643	Remote Similarity	NPD5185	Approved
0.6641	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5923	Phase 1

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