NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.19
Volume:	245.61
LogP:	4.95
LogD:	4.542
LogS:	-5.287
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	4.172
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.576
MDCK Permeability:	1.9873332348652184e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.566
Plasma Protein Binding (PPB):	90.62560272216797%
Volume Distribution (VD):	2.19
Pgp-substrate:	13.224272727966309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.458
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.327
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.143
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	6.767
Half-life (T1/2):	0.259

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.523
Skin Sensitization:	0.517
Carcinogencity:	0.241
Eye Corrosion:	0.449
Eye Irritation:	0.855
Respiratory Toxicity:	0.485

Download Data

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

Natural Product: NPC60553

Natural Product ID:	NPC60553
*Common Name:**	1H-Quinolin-2-One
IUPAC Name:	1H-quinolin-2-one
Synonyms:	2-Hydroxyquinoline; Quinolin-2-ol
Standard InCHIKey:	LISFMEBWQUVKPJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)
SMILES:	Oc1ccc2c(n1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL186422
PubChem CID:	6038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	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
IC50	6
Ki	29
Others	20
Potency	4

Activity Type	# Activity
Cell Line	4
Individual Protein	42
Organism	5
Others	5
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	12589.3	nM	PMID[503999]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	15811.4	nM	PMID[503999]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	6309.6	nM	PMID[503999]
NPT569	Individual Protein	Matrix metalloproteinase 8	Homo sapiens	Inhibition	=	33.0	%	PMID[504000]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Inhibition	=	54.0	%	PMID[504000]
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	Inhibition	=	5.0	%	PMID[504000]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	Inhibition	=	5.0	%	PMID[504000]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Inhibition	=	36.0	%	PMID[504000]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	Inhibition	=	3.0	%	PMID[504000]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	5.0	%	PMID[504000]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	22.0	%	PMID[504000]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	8436.8	nM	PMID[503999]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	200000.0	nM	PMID[504001]
NPT1144	Individual Protein	Carbonic anhydrase VB	Homo sapiens	Ki	=	750.0	nM	PMID[504001]
NPT1146	Individual Protein	Carbonic anhydrase III	Homo sapiens	Ki	=	570.0	nM	PMID[504001]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	410.0	nM	PMID[504001]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	360.0	nM	PMID[504001]
NPT3101	Individual Protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	65.0	nM	PMID[504001]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	33.0	nM	PMID[504001]
NPT1182	Cell Line	J774.A1	Mus musculus	CC50	>	100000.0	nM	PMID[504002]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[504002]
NPT2563	Individual Protein	Tankyrase-2	Homo sapiens	IC50	>	20000.0	nM	PMID[504003]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	10000.0	nM	PMID[504005]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[504006]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	10000.0	nM	PMID[504007]
NPT69	Individual Protein	Matrix metalloproteinase-1	Homo sapiens	Inhibition	=	20.0	%	PMID[504000]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	6230.0	nM	PMID[504001]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	420.0	nM	PMID[504001]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	93.0	nM	PMID[504001]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	82.0	nM	PMID[504001]
NPT954	Individual Protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	36.0	nM	PMID[504001]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	50000.0	nM	PMID[504002]
NPT35	Others	n.a.		LogD7.4	n.a.	1.32	n.a.	PMID[504004]
NPT35	Others	n.a.		Activity	=	-1.86	V	PMID[504006]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	100000.0	nM	PMID[504006]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	50000.0	nM	PMID[504006]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	10000.0	nM	PMID[504007]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	82.0	nM	PMID[504007]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	93.0	nM	PMID[504007]
NPT26544	SINGLE PROTEIN	Neutrophil cytosol factor 1	Homo sapiens	Ki	>	2000000.0	nM	PMID[504008]
NPT26544	SINGLE PROTEIN	Neutrophil cytosol factor 1	Homo sapiens	Rmax	<	20.0	%	PMID[504008]
NPT2	Others	Unspecified		IC50	=	364000.0	nM	PMID[504009]
NPT2	Others	Unspecified		IC20	=	1.7	10'-4M	PMID[504009]
NPT2	Others	Unspecified		Activity	=	95.0	%	PMID[504009]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	2.62	%	PMID[504010]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.07	%	PMID[504011]

☑ 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 NPC60553 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	686
0.1-0.2	6758
0.2-0.3	10677
0.3-0.4	12104
0.4-0.5	7994
0.5-0.6	2846
0.6-0.7	1394
0.7-0.8	212
0.8-0.85	25
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC161292
0.8526	High Similarity	NPC303225
0.8389	Intermediate Similarity	NPC153769
0.8366	Intermediate Similarity	NPC315214
0.8366	Intermediate Similarity	NPC47298
0.8354	Intermediate Similarity	NPC288943
0.8333	Intermediate Similarity	NPC473764
0.8333	Intermediate Similarity	NPC314940
0.8333	Intermediate Similarity	NPC26872
0.8312	Intermediate Similarity	NPC159319
0.8312	Intermediate Similarity	NPC32028
0.8302	Intermediate Similarity	NPC283152
0.8269	Intermediate Similarity	NPC44161
0.8247	Intermediate Similarity	NPC224632
0.8228	Intermediate Similarity	NPC474409
0.8199	Intermediate Similarity	NPC478032
0.817	Intermediate Similarity	NPC26850
0.816	Intermediate Similarity	NPC62069
0.8153	Intermediate Similarity	NPC278874
0.8113	Intermediate Similarity	NPC208060
0.811	Intermediate Similarity	NPC42591
0.8101	Intermediate Similarity	NPC126481
0.8082	Intermediate Similarity	NPC280853
0.8061	Intermediate Similarity	NPC194040
0.805	Intermediate Similarity	NPC105758
0.805	Intermediate Similarity	NPC476688
0.805	Intermediate Similarity	NPC476686
0.8027	Intermediate Similarity	NPC285016
0.8027	Intermediate Similarity	NPC245657
0.8025	Intermediate Similarity	NPC88363
0.8025	Intermediate Similarity	NPC72980
0.8014	Intermediate Similarity	NPC471596
0.8013	Intermediate Similarity	NPC288445
0.8012	Intermediate Similarity	NPC66083
0.8	Intermediate Similarity	NPC259545
0.8	Intermediate Similarity	NPC84508
0.8	Intermediate Similarity	NPC471294
0.7987	Intermediate Similarity	NPC141353
0.7987	Intermediate Similarity	NPC164664
0.7962	Intermediate Similarity	NPC118511
0.7937	Intermediate Similarity	NPC252590
0.7927	Intermediate Similarity	NPC144114
0.7898	Intermediate Similarity	NPC177404
0.7879	Intermediate Similarity	NPC212535
0.7867	Intermediate Similarity	NPC471598
0.7853	Intermediate Similarity	NPC184964
0.7853	Intermediate Similarity	NPC96890
0.7834	Intermediate Similarity	NPC322644
0.7818	Intermediate Similarity	NPC477891
0.7805	Intermediate Similarity	NPC232340
0.7794	Intermediate Similarity	NPC148140
0.7784	Intermediate Similarity	NPC94943
0.777	Intermediate Similarity	NPC471594
0.7742	Intermediate Similarity	NPC36168
0.7738	Intermediate Similarity	NPC314573
0.7737	Intermediate Similarity	NPC81561
0.7736	Intermediate Similarity	NPC97367
0.7725	Intermediate Similarity	NPC190007
0.7688	Intermediate Similarity	NPC471178
0.7682	Intermediate Similarity	NPC470404
0.7682	Intermediate Similarity	NPC470403
0.7682	Intermediate Similarity	NPC470394
0.7681	Intermediate Similarity	NPC54102
0.7681	Intermediate Similarity	NPC162689
0.7673	Intermediate Similarity	NPC471177
0.7673	Intermediate Similarity	NPC124542
0.7673	Intermediate Similarity	NPC59779
0.7665	Intermediate Similarity	NPC133306
0.7665	Intermediate Similarity	NPC220765
0.7647	Intermediate Similarity	NPC128751
0.7647	Intermediate Similarity	NPC246700
0.7625	Intermediate Similarity	NPC473057
0.7622	Intermediate Similarity	NPC312872
0.7619	Intermediate Similarity	NPC204717
0.7607	Intermediate Similarity	NPC158129
0.7602	Intermediate Similarity	NPC469497
0.7602	Intermediate Similarity	NPC106833
0.7602	Intermediate Similarity	NPC144381
0.7588	Intermediate Similarity	NPC46580
0.7582	Intermediate Similarity	NPC470395
0.7574	Intermediate Similarity	NPC314002
0.7571	Intermediate Similarity	NPC215519
0.7557	Intermediate Similarity	NPC280714
0.7552	Intermediate Similarity	NPC151489
0.7529	Intermediate Similarity	NPC171171
0.7515	Intermediate Similarity	NPC320394
0.7514	Intermediate Similarity	NPC324149
0.75	Intermediate Similarity	NPC120798
0.75	Intermediate Similarity	NPC131718
0.75	Intermediate Similarity	NPC25899
0.75	Intermediate Similarity	NPC192315
0.7485	Intermediate Similarity	NPC206186
0.7484	Intermediate Similarity	NPC257142
0.7471	Intermediate Similarity	NPC329541
0.7471	Intermediate Similarity	NPC230403
0.7458	Intermediate Similarity	NPC476167
0.7453	Intermediate Similarity	NPC48192
0.7453	Intermediate Similarity	NPC79911
0.7448	Intermediate Similarity	NPC278451
0.7442	Intermediate Similarity	NPC183805
0.7429	Intermediate Similarity	NPC276517
0.7416	Intermediate Similarity	NPC249040
0.7414	Intermediate Similarity	NPC99666
0.7413	Intermediate Similarity	NPC46358
0.7407	Intermediate Similarity	NPC102423
0.7396	Intermediate Similarity	NPC206201
0.7396	Intermediate Similarity	NPC314394
0.7386	Intermediate Similarity	NPC242209
0.7375	Intermediate Similarity	NPC116573
0.7371	Intermediate Similarity	NPC279401
0.7371	Intermediate Similarity	NPC79293
0.7365	Intermediate Similarity	NPC150048
0.7365	Intermediate Similarity	NPC134586
0.7365	Intermediate Similarity	NPC203754
0.7365	Intermediate Similarity	NPC256893
0.7361	Intermediate Similarity	NPC122718
0.7353	Intermediate Similarity	NPC176127
0.7345	Intermediate Similarity	NPC70956
0.7345	Intermediate Similarity	NPC90229
0.7345	Intermediate Similarity	NPC243834
0.7345	Intermediate Similarity	NPC474188
0.7345	Intermediate Similarity	NPC153042
0.7342	Intermediate Similarity	NPC284348
0.7341	Intermediate Similarity	NPC472289
0.7341	Intermediate Similarity	NPC230805
0.7337	Intermediate Similarity	NPC222592
0.7337	Intermediate Similarity	NPC168486
0.7333	Intermediate Similarity	NPC211813
0.733	Intermediate Similarity	NPC326634
0.7326	Intermediate Similarity	NPC61350
0.7321	Intermediate Similarity	NPC211997
0.7312	Intermediate Similarity	NPC477889
0.731	Intermediate Similarity	NPC84478
0.7303	Intermediate Similarity	NPC306376
0.7293	Intermediate Similarity	NPC200836
0.7293	Intermediate Similarity	NPC53144
0.7293	Intermediate Similarity	NPC476098
0.7293	Intermediate Similarity	NPC223427
0.7278	Intermediate Similarity	NPC42979
0.7273	Intermediate Similarity	NPC317430
0.7273	Intermediate Similarity	NPC45850
0.7267	Intermediate Similarity	NPC129721
0.7262	Intermediate Similarity	NPC224764
0.726	Intermediate Similarity	NPC476140
0.7253	Intermediate Similarity	NPC475070
0.7247	Intermediate Similarity	NPC77555
0.7225	Intermediate Similarity	NPC204385
0.7222	Intermediate Similarity	NPC230869
0.7216	Intermediate Similarity	NPC141915
0.7216	Intermediate Similarity	NPC114335
0.7216	Intermediate Similarity	NPC280964
0.7213	Intermediate Similarity	NPC474145
0.7213	Intermediate Similarity	NPC475841
0.7212	Intermediate Similarity	NPC108469
0.7205	Intermediate Similarity	NPC285469
0.7191	Intermediate Similarity	NPC222018
0.7184	Intermediate Similarity	NPC254762
0.7179	Intermediate Similarity	NPC242556
0.7174	Intermediate Similarity	NPC53344
0.7174	Intermediate Similarity	NPC270918
0.7167	Intermediate Similarity	NPC128823
0.716	Intermediate Similarity	NPC84347
0.7159	Intermediate Similarity	NPC469390
0.7151	Intermediate Similarity	NPC156704
0.7151	Intermediate Similarity	NPC48938
0.7143	Intermediate Similarity	NPC135887
0.7143	Intermediate Similarity	NPC199277
0.7143	Intermediate Similarity	NPC66815
0.7143	Intermediate Similarity	NPC247980
0.7143	Intermediate Similarity	NPC475112
0.7143	Intermediate Similarity	NPC475085
0.7143	Intermediate Similarity	NPC313791
0.7143	Intermediate Similarity	NPC242928
0.7143	Intermediate Similarity	NPC291535
0.7135	Intermediate Similarity	NPC249662
0.7135	Intermediate Similarity	NPC470931
0.7127	Intermediate Similarity	NPC213308
0.712	Intermediate Similarity	NPC476121
0.712	Intermediate Similarity	NPC476124
0.712	Intermediate Similarity	NPC477113
0.7118	Intermediate Similarity	NPC219848
0.7107	Intermediate Similarity	NPC37548
0.7103	Intermediate Similarity	NPC41174
0.7101	Intermediate Similarity	NPC95898
0.7097	Intermediate Similarity	NPC476116
0.7095	Intermediate Similarity	NPC251090
0.7095	Intermediate Similarity	NPC165370
0.7095	Intermediate Similarity	NPC212125
0.7095	Intermediate Similarity	NPC306397
0.7095	Intermediate Similarity	NPC472193
0.7093	Intermediate Similarity	NPC474798
0.7091	Intermediate Similarity	NPC476118
0.7089	Intermediate Similarity	NPC220523
0.7086	Intermediate Similarity	NPC184437
0.7076	Intermediate Similarity	NPC256268
0.7069	Intermediate Similarity	NPC241025
0.7065	Intermediate Similarity	NPC470500
0.7059	Intermediate Similarity	NPC85273
0.7059	Intermediate Similarity	NPC5145
0.7059	Intermediate Similarity	NPC309845

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 NPC60553 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	796
0.2-0.3	717
0.3-0.4	1315
0.4-0.5	2998
0.5-0.6	2250
0.6-0.7	579
0.7-0.8	80
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8366	Intermediate Similarity	NPD1685	Approved
0.8366	Intermediate Similarity	NPD1684	Approved
0.825	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6158	Phase 2
0.8146	Intermediate Similarity	NPD2882	Phase 1
0.8146	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD9705	Discontinued
0.8065	Intermediate Similarity	NPD112	Approved
0.8063	Intermediate Similarity	NPD9690	Approved
0.8037	Intermediate Similarity	NPD4204	Approved
0.8037	Intermediate Similarity	NPD4203	Approved
0.8025	Intermediate Similarity	NPD926	Approved
0.8025	Intermediate Similarity	NPD925	Approved
0.8012	Intermediate Similarity	NPD2383	Phase 1
0.7963	Intermediate Similarity	NPD6159	Phase 2
0.7879	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD424	Approved
0.775	Intermediate Similarity	NPD425	Approved
0.7733	Intermediate Similarity	NPD1592	Phase 3
0.7725	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3525	Discontinued
0.7677	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2727	Phase 2
0.7557	Intermediate Similarity	NPD2177	Approved
0.7557	Intermediate Similarity	NPD2176	Approved
0.7557	Intermediate Similarity	NPD2175	Phase 3
0.7546	Intermediate Similarity	NPD1325	Approved
0.7546	Intermediate Similarity	NPD1326	Approved
0.7544	Intermediate Similarity	NPD408	Approved
0.7516	Intermediate Similarity	NPD444	Approved
0.7471	Intermediate Similarity	NPD2762	Phase 2
0.7471	Intermediate Similarity	NPD9695	Approved
0.7414	Intermediate Similarity	NPD9689	Approved
0.741	Intermediate Similarity	NPD6492	Phase 2
0.741	Intermediate Similarity	NPD5065	Approved
0.7403	Intermediate Similarity	NPD3813	Approved
0.7401	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2781	Approved
0.7371	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2382	Approved
0.7365	Intermediate Similarity	NPD5100	Phase 3
0.7365	Intermediate Similarity	NPD2381	Approved
0.7365	Intermediate Similarity	NPD2380	Approved
0.7362	Intermediate Similarity	NPD2782	Approved
0.7362	Intermediate Similarity	NPD2780	Approved
0.7349	Intermediate Similarity	NPD3224	Phase 2
0.7341	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5255	Approved
0.7308	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3920	Phase 2
0.7273	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6290	Phase 2
0.7247	Intermediate Similarity	NPD7948	Phase 1
0.7235	Intermediate Similarity	NPD6452	Discontinued
0.7232	Intermediate Similarity	NPD6590	Discontinued
0.7213	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5512	Phase 3
0.719	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7222	Phase 2
0.7167	Intermediate Similarity	NPD9688	Approved
0.7167	Intermediate Similarity	NPD9687	Approved
0.7152	Intermediate Similarity	NPD4703	Approved
0.7152	Intermediate Similarity	NPD1661	Suspended
0.7152	Intermediate Similarity	NPD4702	Approved
0.7143	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3928	Approved
0.7143	Intermediate Similarity	NPD3931	Approved
0.7135	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2916	Discontinued
0.7126	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5530	Phase 1
0.7118	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD947	Approved
0.7112	Intermediate Similarity	NPD5936	Approved
0.7112	Intermediate Similarity	NPD5939	Approved
0.7112	Intermediate Similarity	NPD4502	Phase 2
0.7104	Intermediate Similarity	NPD6991	Approved
0.7095	Intermediate Similarity	NPD9080	Approved
0.7095	Intermediate Similarity	NPD9284	Approved
0.7091	Intermediate Similarity	NPD863	Approved
0.7091	Intermediate Similarity	NPD861	Approved
0.7091	Intermediate Similarity	NPD5140	Approved
0.7091	Intermediate Similarity	NPD5138	Approved
0.7091	Intermediate Similarity	NPD862	Approved
0.7078	Intermediate Similarity	NPD852	Discontinued
0.7072	Intermediate Similarity	NPD3814	Phase 1
0.7072	Intermediate Similarity	NPD8396	Approved
0.7072	Intermediate Similarity	NPD8395	Approved
0.7069	Intermediate Similarity	NPD6227	Discontinued
0.7059	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6988	Phase 1
0.7041	Intermediate Similarity	NPD7418	Discontinued
0.7037	Intermediate Similarity	NPD3243	Approved
0.7033	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD484	Approved
0.703	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7474	Suspended
0.702	Intermediate Similarity	NPD1251	Discontinued
0.7006	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4511	Phase 1
0.6994	Remote Similarity	NPD7867	Phase 1
0.6994	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7453	Approved
0.6989	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7452	Approved
0.6987	Remote Similarity	NPD1649	Discontinued
0.6983	Remote Similarity	NPD802	Phase 2
0.6983	Remote Similarity	NPD1038	Approved
0.6978	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4035	Approved
0.6973	Remote Similarity	NPD4039	Approved
0.6973	Remote Similarity	NPD4037	Approved
0.6973	Remote Similarity	NPD31	Approved
0.6973	Remote Similarity	NPD4034	Approved
0.6973	Remote Similarity	NPD4033	Approved
0.6973	Remote Similarity	NPD32	Approved
0.6973	Remote Similarity	NPD4122	Approved
0.6973	Remote Similarity	NPD4036	Approved
0.6973	Remote Similarity	NPD4038	Approved
0.6964	Remote Similarity	NPD2844	Phase 3
0.6957	Remote Similarity	NPD6975	Discontinued
0.6957	Remote Similarity	NPD4462	Approved
0.6957	Remote Similarity	NPD4463	Approved
0.6952	Remote Similarity	NPD7672	Approved
0.6952	Remote Similarity	NPD7671	Approved
0.6951	Remote Similarity	NPD2582	Approved
0.6951	Remote Similarity	NPD2581	Approved
0.6951	Remote Similarity	NPD9382	Approved
0.6951	Remote Similarity	NPD9383	Approved
0.6944	Remote Similarity	NPD6251	Discontinued
0.6944	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4418	Discontinued
0.6943	Remote Similarity	NPD5020	Approved
0.6941	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD43	Approved
0.6941	Remote Similarity	NPD6182	Approved
0.694	Remote Similarity	NPD1740	Approved
0.694	Remote Similarity	NPD1739	Approved
0.6928	Remote Similarity	NPD3385	Approved
0.6927	Remote Similarity	NPD6569	Phase 2
0.6927	Remote Similarity	NPD3404	Approved
0.691	Remote Similarity	NPD1213	Phase 3
0.691	Remote Similarity	NPD2410	Phase 2
0.6906	Remote Similarity	NPD6550	Discontinued
0.6897	Remote Similarity	NPD3037	Phase 1
0.6891	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1768	Approved
0.6882	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7112	Discontinued
0.6867	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5596	Phase 2
0.6857	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1254	Approved
0.6839	Remote Similarity	NPD1255	Approved
0.6839	Remote Similarity	NPD1256	Approved
0.6839	Remote Similarity	NPD1253	Approved
0.6833	Remote Similarity	NPD3924	Approved
0.6833	Remote Similarity	NPD3922	Approved
0.6833	Remote Similarity	NPD3923	Approved
0.6833	Remote Similarity	NPD3921	Approved
0.6823	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6642	Approved
0.6821	Remote Similarity	NPD6641	Approved
0.6813	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5429	Discontinued
0.6806	Remote Similarity	NPD3330	Phase 1
0.6795	Remote Similarity	NPD9506	Approved
0.6795	Remote Similarity	NPD45	Approved
0.6795	Remote Similarity	NPD6554	Approved
0.6792	Remote Similarity	NPD3717	Discontinued
0.6791	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4795	Phase 2
0.6788	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3417	Phase 1
0.678	Remote Similarity	NPD4889	Approved
0.6776	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1218	Approved
0.6776	Remote Similarity	NPD1219	Approved
0.6776	Remote Similarity	NPD3654	Approved
0.677	Remote Similarity	NPD7469	Discontinued
0.6768	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5862	Discovery

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