NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	251.09
Volume:	267.108
LogP:	2.778
LogD:	2.772
LogS:	-3.618
# Rotatable Bonds:	1
TPSA:	42.23
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.722
Synthetic Accessibility Score:	1.962
Fsp3:	0.062
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:	-4.743
MDCK Permeability:	2.375485928496346e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.663
Plasma Protein Binding (PPB):	95.13233947753906%
Volume Distribution (VD):	0.573
Pgp-substrate:	2.0829238891601562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.848
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.447
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	7.098
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.225
AMES Toxicity:	0.893
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.358
Skin Sensitization:	0.822
Carcinogencity:	0.854
Eye Corrosion:	0.006
Eye Irritation:	0.959
Respiratory Toxicity:	0.49

Download Data

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

Natural Product: NPC144691

Natural Product ID:	NPC144691
*Common Name:**	2-(4-Hydroxyphenyl)-1-Methylquinolin-4-One
IUPAC Name:	2-(4-hydroxyphenyl)-1-methylquinolin-4-one
Synonyms:
Standard InCHIKey:	IVVGAXUISDFFMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H13NO2/c1-17-14-5-3-2-4-13(14)16(19)10-15(17)11-6-8-12(18)9-7-11/h2-10,18H,1H3
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(n1C)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL276760
PubChem CID:	11043197
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
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23797	Skimmia reevesiana	Species	Rutaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	6
Individual Protein	2
Protein Complex	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[521732]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	5.71	ug.mL-1	PMID[521732]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[521732]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[521732]
NPT168	Cell Line	P388	Mus musculus	EC50	>	10.0	ug.mL-1	PMID[521732]
NPT1868	Cell Line	L1210 (1565)		EC50	>	10.0	ug.mL-1	PMID[521732]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	Inhibition	=	0.0	%	PMID[521733]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	Inhibition	=	0.0	%	PMID[521734]
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	>	40000.0	nM	PMID[521732]

☑ 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 NPC144691 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	477
0.1-0.2	3239
0.2-0.3	12866
0.3-0.4	4606
0.4-0.5	15081
0.5-0.6	3893
0.6-0.7	2036
0.7-0.8	474
0.8-0.85	21
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8701	High Similarity	NPC204867
0.8645	High Similarity	NPC299582
0.8344	Intermediate Similarity	NPC298320
0.8333	Intermediate Similarity	NPC93653
0.8129	Intermediate Similarity	NPC257490
0.8121	Intermediate Similarity	NPC5167
0.7904	Intermediate Similarity	NPC85613
0.7861	Intermediate Similarity	NPC114039
0.7861	Intermediate Similarity	NPC206109
0.7857	Intermediate Similarity	NPC177684
0.7857	Intermediate Similarity	NPC291962
0.7801	Intermediate Similarity	NPC112373
0.7801	Intermediate Similarity	NPC161956
0.7801	Intermediate Similarity	NPC258531
0.7778	Intermediate Similarity	NPC150308
0.7718	Intermediate Similarity	NPC253476
0.7716	Intermediate Similarity	NPC199737
0.7701	Intermediate Similarity	NPC1820
0.7667	Intermediate Similarity	NPC15987
0.7654	Intermediate Similarity	NPC27904
0.7635	Intermediate Similarity	NPC314098
0.7627	Intermediate Similarity	NPC170333
0.7569	Intermediate Similarity	NPC39818
0.75	Intermediate Similarity	NPC92803
0.7486	Intermediate Similarity	NPC18890
0.7485	Intermediate Similarity	NPC283810
0.744	Intermediate Similarity	NPC112336
0.744	Intermediate Similarity	NPC474814
0.7436	Intermediate Similarity	NPC308197
0.7432	Intermediate Similarity	NPC305717
0.7431	Intermediate Similarity	NPC279385
0.7431	Intermediate Similarity	NPC179605
0.7427	Intermediate Similarity	NPC474815
0.7421	Intermediate Similarity	NPC237649
0.7421	Intermediate Similarity	NPC300596
0.7419	Intermediate Similarity	NPC43477
0.741	Intermediate Similarity	NPC471130
0.7405	Intermediate Similarity	NPC198160
0.7394	Intermediate Similarity	NPC88970
0.7391	Intermediate Similarity	NPC133156
0.7379	Intermediate Similarity	NPC103292
0.7377	Intermediate Similarity	NPC288759
0.7353	Intermediate Similarity	NPC475594
0.7348	Intermediate Similarity	NPC234933
0.7337	Intermediate Similarity	NPC318183
0.7333	Intermediate Similarity	NPC194562
0.7312	Intermediate Similarity	NPC242000
0.731	Intermediate Similarity	NPC475607
0.731	Intermediate Similarity	NPC471743
0.7303	Intermediate Similarity	NPC203628
0.7296	Intermediate Similarity	NPC146370
0.7267	Intermediate Similarity	NPC474081
0.7249	Intermediate Similarity	NPC220241
0.7249	Intermediate Similarity	NPC295479
0.7244	Intermediate Similarity	NPC472243
0.7219	Intermediate Similarity	NPC212123
0.7211	Intermediate Similarity	NPC268534
0.7211	Intermediate Similarity	NPC116178
0.7208	Intermediate Similarity	NPC173295
0.7208	Intermediate Similarity	NPC300299
0.7204	Intermediate Similarity	NPC313112
0.7204	Intermediate Similarity	NPC301292
0.7184	Intermediate Similarity	NPC475685
0.7181	Intermediate Similarity	NPC470343
0.7181	Intermediate Similarity	NPC472244
0.7176	Intermediate Similarity	NPC471778
0.7173	Intermediate Similarity	NPC217903
0.7173	Intermediate Similarity	NPC321166
0.7171	Intermediate Similarity	NPC316746
0.7171	Intermediate Similarity	NPC120251
0.717	Intermediate Similarity	NPC297322
0.717	Intermediate Similarity	NPC473804
0.7169	Intermediate Similarity	NPC103250
0.7168	Intermediate Similarity	NPC9475
0.716	Intermediate Similarity	NPC241392
0.7151	Intermediate Similarity	NPC5630
0.7151	Intermediate Similarity	NPC470548
0.7143	Intermediate Similarity	NPC303214
0.7143	Intermediate Similarity	NPC266425
0.7135	Intermediate Similarity	NPC469671
0.7135	Intermediate Similarity	NPC206186
0.7135	Intermediate Similarity	NPC126676
0.7134	Intermediate Similarity	NPC204156
0.7126	Intermediate Similarity	NPC474041
0.7126	Intermediate Similarity	NPC475761
0.7125	Intermediate Similarity	NPC119569
0.7123	Intermediate Similarity	NPC226143
0.712	Intermediate Similarity	NPC305542
0.7115	Intermediate Similarity	NPC43218
0.7102	Intermediate Similarity	NPC470317
0.7089	Intermediate Similarity	NPC471574
0.7083	Intermediate Similarity	NPC289776
0.7083	Intermediate Similarity	NPC30749
0.7083	Intermediate Similarity	NPC133470
0.7083	Intermediate Similarity	NPC191863
0.7075	Intermediate Similarity	NPC130931
0.7059	Intermediate Similarity	NPC231382
0.7044	Intermediate Similarity	NPC472241
0.7039	Intermediate Similarity	NPC150863
0.7039	Intermediate Similarity	NPC473815
0.7039	Intermediate Similarity	NPC209389
0.7032	Intermediate Similarity	NPC184437
0.7027	Intermediate Similarity	NPC241263
0.7026	Intermediate Similarity	NPC182853
0.7026	Intermediate Similarity	NPC134702
0.7025	Intermediate Similarity	NPC242933
0.7025	Intermediate Similarity	NPC315051
0.702	Intermediate Similarity	NPC250476
0.7	Intermediate Similarity	NPC100573
0.7	Intermediate Similarity	NPC207873
0.6995	Remote Similarity	NPC198401
0.6994	Remote Similarity	NPC73280
0.6993	Remote Similarity	NPC280807
0.6993	Remote Similarity	NPC472245
0.6993	Remote Similarity	NPC314431
0.6987	Remote Similarity	NPC473360
0.6982	Remote Similarity	NPC476231
0.6972	Remote Similarity	NPC116842
0.6966	Remote Similarity	NPC160179
0.6962	Remote Similarity	NPC238412
0.6961	Remote Similarity	NPC45389
0.6959	Remote Similarity	NPC148391
0.6957	Remote Similarity	NPC323798
0.6957	Remote Similarity	NPC136002
0.6952	Remote Similarity	NPC232600
0.695	Remote Similarity	NPC17525
0.6949	Remote Similarity	NPC472163
0.6947	Remote Similarity	NPC16249
0.6947	Remote Similarity	NPC478075
0.6941	Remote Similarity	NPC189116
0.694	Remote Similarity	NPC254957
0.6936	Remote Similarity	NPC471604
0.6933	Remote Similarity	NPC2672
0.6933	Remote Similarity	NPC315829
0.6927	Remote Similarity	NPC241025
0.6919	Remote Similarity	NPC329830
0.6919	Remote Similarity	NPC473814
0.6919	Remote Similarity	NPC78767
0.6918	Remote Similarity	NPC207554
0.6918	Remote Similarity	NPC314252
0.6914	Remote Similarity	NPC472242
0.6907	Remote Similarity	NPC114468
0.6903	Remote Similarity	NPC257390
0.6902	Remote Similarity	NPC93390
0.6893	Remote Similarity	NPC39822
0.6891	Remote Similarity	NPC218303
0.6887	Remote Similarity	NPC285394
0.6887	Remote Similarity	NPC192533
0.6885	Remote Similarity	NPC56170
0.6884	Remote Similarity	NPC220851
0.6882	Remote Similarity	NPC71124
0.6878	Remote Similarity	NPC41216
0.6872	Remote Similarity	NPC2905
0.6868	Remote Similarity	NPC313293
0.6864	Remote Similarity	NPC301163
0.686	Remote Similarity	NPC182131
0.6857	Remote Similarity	NPC303225
0.6842	Remote Similarity	NPC205946
0.6842	Remote Similarity	NPC313757
0.6839	Remote Similarity	NPC474366
0.6839	Remote Similarity	NPC25961
0.6839	Remote Similarity	NPC292265
0.6837	Remote Similarity	NPC322064
0.6834	Remote Similarity	NPC118189
0.6831	Remote Similarity	NPC22476
0.6818	Remote Similarity	NPC122235
0.6809	Remote Similarity	NPC69332
0.6809	Remote Similarity	NPC29989
0.6809	Remote Similarity	NPC6984
0.6809	Remote Similarity	NPC95178
0.6806	Remote Similarity	NPC268388
0.68	Remote Similarity	NPC307640
0.6792	Remote Similarity	NPC316574
0.6791	Remote Similarity	NPC17677
0.6789	Remote Similarity	NPC134848
0.6786	Remote Similarity	NPC176113
0.6784	Remote Similarity	NPC257763
0.6782	Remote Similarity	NPC472118
0.6778	Remote Similarity	NPC471742
0.6776	Remote Similarity	NPC226794
0.6774	Remote Similarity	NPC472539
0.6774	Remote Similarity	NPC472540
0.6774	Remote Similarity	NPC470787
0.6772	Remote Similarity	NPC470441
0.677	Remote Similarity	NPC471164
0.6761	Remote Similarity	NPC226699
0.6761	Remote Similarity	NPC172170
0.6761	Remote Similarity	NPC141523
0.676	Remote Similarity	NPC270301
0.6757	Remote Similarity	NPC473821
0.6757	Remote Similarity	NPC471825
0.6755	Remote Similarity	NPC5374
0.6755	Remote Similarity	NPC268348
0.6754	Remote Similarity	NPC268077
0.6753	Remote Similarity	NPC218323
0.675	Remote Similarity	NPC83214
0.675	Remote Similarity	NPC7560
0.675	Remote Similarity	NPC76478
0.6748	Remote Similarity	NPC130797
0.674	Remote Similarity	NPC49184

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 NPC144691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	652
0.2-0.3	865
0.3-0.4	1044
0.4-0.5	2757
0.5-0.6	2386
0.6-0.7	975
0.7-0.8	139
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD3229	Phase 2
0.7965	Intermediate Similarity	NPD5937	Approved
0.7805	Intermediate Similarity	NPD5183	Approved
0.7805	Intermediate Similarity	NPD5186	Approved
0.7785	Intermediate Similarity	NPD2791	Discontinued
0.7662	Intermediate Similarity	NPD1625	Approved
0.7643	Intermediate Similarity	NPD4888	Discontinued
0.7576	Intermediate Similarity	NPD5823	Approved
0.7564	Intermediate Similarity	NPD6017	Discontinued
0.756	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4430	Phase 2
0.7485	Intermediate Similarity	NPD5445	Approved
0.7484	Intermediate Similarity	NPD1189	Approved
0.7429	Intermediate Similarity	NPD4515	Suspended
0.7417	Intermediate Similarity	NPD1527	Phase 2
0.7403	Intermediate Similarity	NPD1626	Approved
0.7386	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1913	Phase 1
0.7246	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5637	Discontinued
0.7229	Intermediate Similarity	NPD2506	Approved
0.7222	Intermediate Similarity	NPD1230	Approved
0.7219	Intermediate Similarity	NPD2821	Approved
0.7196	Intermediate Similarity	NPD5860	Discontinued
0.7188	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1839	Phase 1
0.7171	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3793	Phase 3
0.7158	Intermediate Similarity	NPD5194	Approved
0.7158	Intermediate Similarity	NPD5197	Approved
0.7158	Intermediate Similarity	NPD5196	Approved
0.7152	Intermediate Similarity	NPD2672	Discontinued
0.7134	Intermediate Similarity	NPD3391	Approved
0.7126	Intermediate Similarity	NPD3782	Discontinued
0.7117	Intermediate Similarity	NPD3277	Phase 3
0.7115	Intermediate Similarity	NPD6636	Phase 3
0.7104	Intermediate Similarity	NPD5195	Discontinued
0.7104	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1168	Approved
0.7099	Intermediate Similarity	NPD4161	Discontinued
0.7097	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4330	Approved
0.7086	Intermediate Similarity	NPD4329	Approved
0.7078	Intermediate Similarity	NPD441	Approved
0.7078	Intermediate Similarity	NPD1541	Approved
0.7077	Intermediate Similarity	NPD5496	Approved
0.7069	Intermediate Similarity	NPD3792	Approved
0.7067	Intermediate Similarity	NPD6320	Approved
0.7066	Intermediate Similarity	NPD2427	Approved
0.7063	Intermediate Similarity	NPD1196	Approved
0.7056	Intermediate Similarity	NPD5928	Phase 1
0.7044	Intermediate Similarity	NPD2365	Approved
0.7037	Intermediate Similarity	NPD1543	Discontinued
0.7018	Intermediate Similarity	NPD2037	Approved
0.7013	Intermediate Similarity	NPD1920	Approved
0.7013	Intermediate Similarity	NPD1919	Approved
0.7011	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1544	Phase 1
0.7006	Intermediate Similarity	NPD2670	Approved
0.7006	Intermediate Similarity	NPD3253	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1195	Approved
0.7	Intermediate Similarity	NPD2820	Phase 3
0.6989	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD313	Approved
0.6972	Remote Similarity	NPD9376	Approved
0.6968	Remote Similarity	NPD3802	Phase 3
0.6966	Remote Similarity	NPD5923	Phase 1
0.6961	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1574	Approved
0.6954	Remote Similarity	NPD5466	Approved
0.694	Remote Similarity	NPD5610	Approved
0.6931	Remote Similarity	NPD3298	Approved
0.6928	Remote Similarity	NPD5086	Approved
0.6919	Remote Similarity	NPD6457	Approved
0.6919	Remote Similarity	NPD5515	Phase 2
0.6919	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2361	Approved
0.6911	Remote Similarity	NPD4082	Approved
0.6908	Remote Similarity	NPD1593	Approved
0.6887	Remote Similarity	NPD5157	Phase 1
0.6887	Remote Similarity	NPD5159	Phase 2
0.6887	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1210	Approved
0.6882	Remote Similarity	NPD5071	Phase 2
0.6879	Remote Similarity	NPD1161	Approved
0.6879	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7546	Discontinued
0.6871	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3141	Discontinued
0.6859	Remote Similarity	NPD2950	Approved
0.6859	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2949	Approved
0.6857	Remote Similarity	NPD2359	Approved
0.6856	Remote Similarity	NPD7225	Discontinued
0.6848	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4539	Phase 1
0.6845	Remote Similarity	NPD6874	Approved
0.6845	Remote Similarity	NPD3297	Approved
0.6845	Remote Similarity	NPD2836	Approved
0.6839	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2431	Approved
0.6839	Remote Similarity	NPD2432	Approved
0.6836	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2454	Approved
0.6821	Remote Similarity	NPD2455	Approved
0.6818	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3784	Discontinued
0.6798	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD9279	Approved
0.6788	Remote Similarity	NPD4942	Approved
0.6784	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2369	Discontinued
0.678	Remote Similarity	NPD1170	Approved
0.678	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4393	Approved
0.6765	Remote Similarity	NPD33	Approved
0.6761	Remote Similarity	NPD7324	Discontinued
0.6754	Remote Similarity	NPD4465	Phase 2
0.6754	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4467	Phase 2
0.6742	Remote Similarity	NPD7479	Phase 2
0.6742	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5504	Discontinued
0.6734	Remote Similarity	NPD2899	Discontinued
0.6728	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD9277	Approved
0.6728	Remote Similarity	NPD75	Approved
0.6725	Remote Similarity	NPD4311	Approved
0.6718	Remote Similarity	NPD4493	Discontinued
0.6705	Remote Similarity	NPD3377	Discontinued
0.6705	Remote Similarity	NPD1220	Phase 1
0.6705	Remote Similarity	NPD3252	Approved
0.6702	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.669	Remote Similarity	NPD308	Approved
0.6687	Remote Similarity	NPD6342	Discontinued
0.6687	Remote Similarity	NPD743	Approved
0.6686	Remote Similarity	NPD3684	Discontinued
0.6685	Remote Similarity	NPD3965	Phase 1
0.6685	Remote Similarity	NPD1221	Approved
0.6684	Remote Similarity	NPD4596	Phase 1
0.6667	Remote Similarity	NPD3423	Phase 2
0.6667	Remote Similarity	NPD3471	Approved
0.6667	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3422	Phase 3
0.6667	Remote Similarity	NPD6283	Phase 2
0.6667	Remote Similarity	NPD9274	Approved
0.6667	Remote Similarity	NPD5609	Approved
0.6667	Remote Similarity	NPD9276	Approved
0.6667	Remote Similarity	NPD5608	Approved
0.6667	Remote Similarity	NPD4845	Discontinued
0.6667	Remote Similarity	NPD9275	Approved
0.6667	Remote Similarity	NPD9278	Suspended
0.6667	Remote Similarity	NPD3470	Approved
0.6649	Remote Similarity	NPD7316	Discontinued
0.6649	Remote Similarity	NPD5871	Discontinued
0.6649	Remote Similarity	NPD2906	Approved
0.6649	Remote Similarity	NPD3472	Approved
0.6649	Remote Similarity	NPD2336	Approved
0.6649	Remote Similarity	NPD2907	Approved
0.6649	Remote Similarity	NPD4022	Approved
0.6648	Remote Similarity	NPD3975	Discontinued
0.6647	Remote Similarity	NPD2469	Approved
0.6647	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2366	Approved
0.6647	Remote Similarity	NPD1208	Approved
0.6647	Remote Similarity	NPD2468	Approved
0.6646	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD9723	Approved
0.6633	Remote Similarity	NPD683	Approved
0.6632	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2404	Discontinued
0.6628	Remote Similarity	NPD5992	Approved
0.6627	Remote Similarity	NPD824	Approved
0.6627	Remote Similarity	NPD6357	Discontinued
0.6627	Remote Similarity	NPD1801	Approved
0.6627	Remote Similarity	NPD1802	Approved
0.6626	Remote Similarity	NPD6512	Approved
0.6626	Remote Similarity	NPD6513	Approved
0.6625	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD9272	Approved
0.6618	Remote Similarity	NPD7186	Phase 3
0.6617	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4668	Phase 2
0.6609	Remote Similarity	NPD5430	Discontinued
0.6607	Remote Similarity	NPD1670	Discontinued
0.6606	Remote Similarity	NPD3301	Approved
0.6604	Remote Similarity	NPD3140	Approved

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