NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.06
Volume:	198.07
LogP:	3.198
LogD:	2.935
LogS:	-4.756
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	1.396
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.486
MDCK Permeability:	1.7640639271121472e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.255
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	97.98857879638672%
Volume Distribution (VD):	0.771
Pgp-substrate:	1.6999225616455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.638
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.481
CYP3A4-inhibitor:	0.186
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	3.177
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.121
Skin Sensitization:	0.233
Carcinogencity:	0.846
Eye Corrosion:	0.024
Eye Irritation:	0.992
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC113307

Natural Product ID:	NPC113307
*Common Name:**	Fluoren-9-One
IUPAC Name:	fluoren-9-one
Synonyms:
Standard InCHIKey:	YLQWCDOCJODRMT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
SMILES:	O=C1c2ccccc2c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL571655
PubChem CID:	10241
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	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	2
Others	6
Potency	3

Activity Type	# Activity
Individual Protein	2
Others	3
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	>	200000.0	nM	PMID[551070]
NPT2	Others	Unspecified		Potency	n.a.	55926.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15762.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	35287.2	nM	PubChem BioAssay data set
NPT614	Tissue	Plasma	Rattus norvegicus	Cmax	=	255.0	ng/g	PMID[551071]
NPT614	Tissue	Plasma	Rattus norvegicus	Tmax	=	1.2	hr	PMID[551071]
NPT614	Tissue	Plasma	Rattus norvegicus	AUCt	=	939.0	ng.hr/g	PMID[551071]
NPT632	Tissue	Brain	Rattus norvegicus	Cmax	=	971.0	ng/g	PMID[551071]
NPT632	Tissue	Brain	Rattus norvegicus	Tmax	=	0.8	hr	PMID[551071]
NPT632	Tissue	Brain	Rattus norvegicus	AUCt	=	2349.0	ng.hr/g	PMID[551071]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	IC50	>	1000.0	nM	PMID[551073]

☑ 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 NPC113307 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	622
0.1-0.2	2373
0.2-0.3	7144
0.3-0.4	15036
0.4-0.5	13203
0.5-0.6	3643
0.6-0.7	532
0.7-0.8	85
0.8-0.85	34
0.85-0.9	18
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.908	High Similarity	NPC418308
0.9036	High Similarity	NPC12936
0.9036	High Similarity	NPC273033
0.8977	High Similarity	NPC277277
0.8966	High Similarity	NPC267262
0.8925	High Similarity	NPC472879
0.8916	High Similarity	NPC71664
0.8824	High Similarity	NPC273758
0.8764	High Similarity	NPC19256
0.8652	High Similarity	NPC325709
0.8605	High Similarity	NPC215008
0.8587	High Similarity	NPC472880
0.8554	High Similarity	NPC245966
0.8539	High Similarity	NPC157778
0.8523	High Similarity	NPC160339
0.8523	High Similarity	NPC307
0.8478	Intermediate Similarity	NPC289883
0.8471	Intermediate Similarity	NPC95868
0.8471	Intermediate Similarity	NPC190567
0.8462	Intermediate Similarity	NPC103346
0.8452	Intermediate Similarity	NPC36342
0.8452	Intermediate Similarity	NPC285470
0.8452	Intermediate Similarity	NPC2785
0.8427	Intermediate Similarity	NPC43945
0.8427	Intermediate Similarity	NPC69057
0.8372	Intermediate Similarity	NPC145053
0.837	Intermediate Similarity	NPC59677
0.8353	Intermediate Similarity	NPC151405
0.8353	Intermediate Similarity	NPC300205
0.8353	Intermediate Similarity	NPC139901
0.8352	Intermediate Similarity	NPC173413
0.8316	Intermediate Similarity	NPC49994
0.8261	Intermediate Similarity	NPC133461
0.8261	Intermediate Similarity	NPC284475
0.8256	Intermediate Similarity	NPC164086
0.8182	Intermediate Similarity	NPC39600
0.8172	Intermediate Similarity	NPC323420
0.8172	Intermediate Similarity	NPC1682
0.8172	Intermediate Similarity	NPC155232
0.8172	Intermediate Similarity	NPC153885
0.8172	Intermediate Similarity	NPC188844
0.8118	Intermediate Similarity	NPC9796
0.8105	Intermediate Similarity	NPC219573
0.8105	Intermediate Similarity	NPC185208
0.8085	Intermediate Similarity	NPC238219
0.8021	Intermediate Similarity	NPC239185
0.8	Intermediate Similarity	NPC260233
0.7955	Intermediate Similarity	NPC73978
0.7938	Intermediate Similarity	NPC134882
0.7935	Intermediate Similarity	NPC153308
0.7931	Intermediate Similarity	NPC272260
0.7921	Intermediate Similarity	NPC472700
0.7921	Intermediate Similarity	NPC472699
0.7857	Intermediate Similarity	NPC285679
0.7843	Intermediate Similarity	NPC472683
0.7843	Intermediate Similarity	NPC472696
0.7843	Intermediate Similarity	NPC472695
0.7843	Intermediate Similarity	NPC472701
0.7841	Intermediate Similarity	NPC285716
0.7841	Intermediate Similarity	NPC17408
0.7835	Intermediate Similarity	NPC265220
0.7831	Intermediate Similarity	NPC263385
0.7822	Intermediate Similarity	NPC134120
0.7802	Intermediate Similarity	NPC252067
0.7778	Intermediate Similarity	NPC197581
0.7778	Intermediate Similarity	NPC109514
0.7778	Intermediate Similarity	NPC476993
0.7778	Intermediate Similarity	NPC324624
0.7766	Intermediate Similarity	NPC58872
0.7755	Intermediate Similarity	NPC75724
0.7738	Intermediate Similarity	NPC74458
0.7717	Intermediate Similarity	NPC164526
0.7701	Intermediate Similarity	NPC179726
0.767	Intermediate Similarity	NPC203732
0.7647	Intermediate Similarity	NPC1901
0.764	Intermediate Similarity	NPC477703
0.7614	Intermediate Similarity	NPC103488
0.7609	Intermediate Similarity	NPC123476
0.7586	Intermediate Similarity	NPC78500
0.7556	Intermediate Similarity	NPC100039
0.7525	Intermediate Similarity	NPC320891
0.75	Intermediate Similarity	NPC98880
0.7475	Intermediate Similarity	NPC156021
0.7474	Intermediate Similarity	NPC298115
0.7451	Intermediate Similarity	NPC471829
0.7451	Intermediate Similarity	NPC472691
0.7451	Intermediate Similarity	NPC247976
0.7451	Intermediate Similarity	NPC255676
0.7451	Intermediate Similarity	NPC474866
0.7451	Intermediate Similarity	NPC475939
0.7451	Intermediate Similarity	NPC274443
0.7451	Intermediate Similarity	NPC329556
0.7426	Intermediate Similarity	NPC112552
0.7416	Intermediate Similarity	NPC137847
0.7416	Intermediate Similarity	NPC76455
0.7412	Intermediate Similarity	NPC95289
0.7404	Intermediate Similarity	NPC37914
0.7404	Intermediate Similarity	NPC83409
0.7404	Intermediate Similarity	NPC185763
0.7396	Intermediate Similarity	NPC303967
0.7396	Intermediate Similarity	NPC67585
0.7396	Intermediate Similarity	NPC110420
0.7383	Intermediate Similarity	NPC186128
0.7381	Intermediate Similarity	NPC311343
0.7379	Intermediate Similarity	NPC329282
0.7368	Intermediate Similarity	NPC473345
0.7356	Intermediate Similarity	NPC208075
0.7353	Intermediate Similarity	NPC222390
0.7353	Intermediate Similarity	NPC244427
0.7333	Intermediate Similarity	NPC112903
0.7308	Intermediate Similarity	NPC474910
0.7308	Intermediate Similarity	NPC172483
0.7303	Intermediate Similarity	NPC298023
0.7303	Intermediate Similarity	NPC329318
0.7273	Intermediate Similarity	NPC172925
0.7264	Intermediate Similarity	NPC318327
0.7264	Intermediate Similarity	NPC470252
0.7248	Intermediate Similarity	NPC67377
0.7241	Intermediate Similarity	NPC271437
0.7238	Intermediate Similarity	NPC100767
0.7229	Intermediate Similarity	NPC291066
0.7222	Intermediate Similarity	NPC255345
0.7212	Intermediate Similarity	NPC249067
0.7209	Intermediate Similarity	NPC251490
0.7204	Intermediate Similarity	NPC149263
0.72	Intermediate Similarity	NPC12695
0.7172	Intermediate Similarity	NPC246757
0.7172	Intermediate Similarity	NPC34243
0.7172	Intermediate Similarity	NPC261181
0.7172	Intermediate Similarity	NPC291070
0.717	Intermediate Similarity	NPC211439
0.7143	Intermediate Similarity	NPC475023
0.7143	Intermediate Similarity	NPC475059
0.7143	Intermediate Similarity	NPC110704
0.7143	Intermediate Similarity	NPC167336
0.7143	Intermediate Similarity	NPC105899
0.713	Intermediate Similarity	NPC265513
0.7129	Intermediate Similarity	NPC240042
0.7113	Intermediate Similarity	NPC231591
0.7108	Intermediate Similarity	NPC113670
0.7108	Intermediate Similarity	NPC21211
0.7103	Intermediate Similarity	NPC192577
0.7093	Intermediate Similarity	NPC213570
0.7093	Intermediate Similarity	NPC246822
0.7093	Intermediate Similarity	NPC139416
0.7091	Intermediate Similarity	NPC196673
0.708	Intermediate Similarity	NPC472697
0.708	Intermediate Similarity	NPC472698
0.7071	Intermediate Similarity	NPC475057
0.7065	Intermediate Similarity	NPC157055
0.7064	Intermediate Similarity	NPC280789
0.7064	Intermediate Similarity	NPC79496
0.7064	Intermediate Similarity	NPC66208
0.7059	Intermediate Similarity	NPC229242
0.7048	Intermediate Similarity	NPC114594
0.7027	Intermediate Similarity	NPC274839
0.7027	Intermediate Similarity	NPC476357
0.7011	Intermediate Similarity	NPC72670
0.701	Intermediate Similarity	NPC477704
0.701	Intermediate Similarity	NPC477693
0.7009	Intermediate Similarity	NPC470391
0.7	Intermediate Similarity	NPC93287
0.7	Intermediate Similarity	NPC470253
0.6988	Remote Similarity	NPC71009
0.6981	Remote Similarity	NPC209632
0.6972	Remote Similarity	NPC137315
0.6972	Remote Similarity	NPC474057
0.6972	Remote Similarity	NPC210089
0.697	Remote Similarity	NPC187725
0.697	Remote Similarity	NPC476484
0.697	Remote Similarity	NPC141607
0.697	Remote Similarity	NPC125226
0.6961	Remote Similarity	NPC289201
0.6961	Remote Similarity	NPC103048
0.6957	Remote Similarity	NPC232958
0.6944	Remote Similarity	NPC265407
0.6944	Remote Similarity	NPC83628
0.6937	Remote Similarity	NPC326664
0.6937	Remote Similarity	NPC471721
0.6937	Remote Similarity	NPC241851
0.6937	Remote Similarity	NPC477411
0.6932	Remote Similarity	NPC326200
0.6932	Remote Similarity	NPC87099
0.6932	Remote Similarity	NPC280135
0.6932	Remote Similarity	NPC39799
0.6932	Remote Similarity	NPC193578
0.6932	Remote Similarity	NPC226999
0.6932	Remote Similarity	NPC135433
0.6932	Remote Similarity	NPC1008
0.6932	Remote Similarity	NPC158028
0.693	Remote Similarity	NPC318173
0.6923	Remote Similarity	NPC42211
0.6923	Remote Similarity	NPC473325
0.6916	Remote Similarity	NPC37622
0.6916	Remote Similarity	NPC30594
0.6915	Remote Similarity	NPC230068
0.6909	Remote Similarity	NPC292834
0.6909	Remote Similarity	NPC218855
0.6909	Remote Similarity	NPC212415
0.6907	Remote Similarity	NPC194326

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 NPC113307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	541
0.1-0.2	981
0.2-0.3	1637
0.3-0.4	3467
0.4-0.5	1845
0.5-0.6	566
0.6-0.7	93
0.7-0.8	13
0.8-0.85	1
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9425	High Similarity	NPD1508	Approved
0.9111	High Similarity	NPD1843	Approved
0.9036	High Similarity	NPD942	Approved
0.8471	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.8427	Intermediate Similarity	NPD650	Approved
0.8261	Intermediate Similarity	NPD7609	Phase 3
0.8172	Intermediate Similarity	NPD7631	Approved
0.8021	Intermediate Similarity	NPD3495	Discontinued
0.77	Intermediate Similarity	NPD1932	Approved
0.7634	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1930	Approved
0.7451	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1929	Approved
0.7273	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2329	Discontinued
0.7212	Intermediate Similarity	NPD1237	Approved
0.7172	Intermediate Similarity	NPD1202	Approved
0.7157	Intermediate Similarity	NPD2066	Phase 3
0.7143	Intermediate Similarity	NPD7610	Discontinued
0.7143	Intermediate Similarity	NPD1239	Approved
0.7108	Intermediate Similarity	NPD675	Discontinued
0.71	Intermediate Similarity	NPD4094	Approved
0.708	Intermediate Similarity	NPD7009	Phase 2
0.7019	Intermediate Similarity	NPD2648	Phase 3
0.7019	Intermediate Similarity	NPD2196	Discontinued
0.7019	Intermediate Similarity	NPD2193	Phase 2
0.7	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1563	Approved
0.6972	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4657	Approved
0.6961	Remote Similarity	NPD1099	Approved
0.6961	Remote Similarity	NPD4655	Approved
0.6961	Remote Similarity	NPD1100	Approved
0.6952	Remote Similarity	NPD3357	Discontinued
0.6949	Remote Similarity	NPD1876	Approved
0.6931	Remote Similarity	NPD1693	Approved
0.6909	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD664	Approved
0.6863	Remote Similarity	NPD1989	Approved
0.6857	Remote Similarity	NPD2171	Approved
0.6848	Remote Similarity	NPD225	Approved
0.6848	Remote Similarity	NPD227	Approved
0.6842	Remote Similarity	NPD3971	Phase 1
0.6827	Remote Similarity	NPD1238	Approved
0.6822	Remote Similarity	NPD2197	Approved
0.6822	Remote Similarity	NPD1677	Discontinued
0.6822	Remote Similarity	NPD2192	Approved
0.6818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5836	Discontinued
0.6804	Remote Similarity	NPD9259	Approved
0.6804	Remote Similarity	NPD9257	Approved
0.6796	Remote Similarity	NPD1566	Phase 3
0.6796	Remote Similarity	NPD1564	Approved
0.6796	Remote Similarity	NPD1565	Approved
0.6774	Remote Similarity	NPD9490	Approved
0.6735	Remote Similarity	NPD1087	Approved
0.6729	Remote Similarity	NPD164	Approved
0.6726	Remote Similarity	NPD5951	Approved
0.6705	Remote Similarity	NPD1673	Approved
0.6698	Remote Similarity	NPD6024	Approved
0.6698	Remote Similarity	NPD6027	Approved
0.6696	Remote Similarity	NPD7094	Approved
0.6696	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9491	Approved
0.6632	Remote Similarity	NPD226	Approved
0.661	Remote Similarity	NPD4879	Approved
0.661	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5909	Discontinued
0.6535	Remote Similarity	NPD9256	Approved
0.6535	Remote Similarity	NPD1089	Approved
0.6535	Remote Similarity	NPD1086	Approved
0.6535	Remote Similarity	NPD9258	Approved
0.6535	Remote Similarity	NPD1090	Approved
0.6522	Remote Similarity	NPD9716	Approved
0.65	Remote Similarity	NPD4878	Approved
0.6491	Remote Similarity	NPD7077	Approved
0.6491	Remote Similarity	NPD7076	Approved
0.6486	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2182	Approved
0.6436	Remote Similarity	NPD800	Approved
0.6435	Remote Similarity	NPD1246	Approved
0.6429	Remote Similarity	NPD1317	Discontinued
0.6417	Remote Similarity	NPD1201	Approved
0.6408	Remote Similarity	NPD1088	Approved
0.64	Remote Similarity	NPD4793	Discontinued
0.6389	Remote Similarity	NPD813	Approved
0.6387	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2345	Approved
0.6387	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3673	Approved
0.6373	Remote Similarity	NPD3672	Approved
0.6364	Remote Similarity	NPD3356	Approved
0.6364	Remote Similarity	NPD3355	Approved
0.6341	Remote Similarity	NPD1470	Approved
0.6333	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1245	Approved
0.6299	Remote Similarity	NPD7961	Discontinued
0.6286	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6049	Phase 2
0.6286	Remote Similarity	NPD9260	Approved
0.6275	Remote Similarity	NPD5346	Phase 2
0.6275	Remote Similarity	NPD5347	Phase 2
0.6271	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD466	Approved
0.626	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3972	Approved
0.6226	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1175	Approved
0.6204	Remote Similarity	NPD7798	Approved
0.6204	Remote Similarity	NPD742	Approved
0.62	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3903	Approved
0.6186	Remote Similarity	NPD3979	Approved
0.6186	Remote Similarity	NPD3981	Approved
0.6186	Remote Similarity	NPD3904	Approved
0.6182	Remote Similarity	NPD6647	Phase 2
0.6167	Remote Similarity	NPD3024	Approved
0.6167	Remote Similarity	NPD3025	Approved
0.616	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1007	Discontinued
0.6154	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2508	Discontinued
0.6148	Remote Similarity	NPD6287	Discontinued
0.6148	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5630	Phase 1
0.6142	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7008	Discontinued
0.6134	Remote Similarity	NPD6065	Approved
0.6116	Remote Similarity	NPD3019	Approved
0.6116	Remote Similarity	NPD2932	Approved
0.6094	Remote Similarity	NPD3764	Approved
0.6091	Remote Similarity	NPD4803	Discontinued
0.6083	Remote Similarity	NPD4479	Discontinued
0.608	Remote Similarity	NPD1164	Approved
0.6066	Remote Similarity	NPD3023	Approved
0.6066	Remote Similarity	NPD3026	Approved
0.6064	Remote Similarity	NPD4058	Approved
0.6058	Remote Similarity	NPD3346	Approved
0.6058	Remote Similarity	NPD3344	Approved
0.605	Remote Similarity	NPD3797	Approved
0.6048	Remote Similarity	NPD3549	Approved
0.6048	Remote Similarity	NPD3547	Approved
0.6048	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5157	Phase 1
0.6048	Remote Similarity	NPD5159	Phase 2
0.6047	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5765	Approved
0.6036	Remote Similarity	NPD9261	Approved
0.6033	Remote Similarity	NPD1651	Approved
0.6033	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD2798	Approved
0.6032	Remote Similarity	NPD4980	Approved
0.6017	Remote Similarity	NPD1073	Approved
0.6017	Remote Similarity	NPD4766	Approved
0.6017	Remote Similarity	NPD1075	Approved
0.6017	Remote Similarity	NPD1074	Approved
0.6	Remote Similarity	NPD1574	Approved
0.6	Remote Similarity	NPD4635	Approved
0.6	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6	Remote Similarity	NPD423	Phase 3
0.5984	Remote Similarity	NPD1727	Approved
0.5984	Remote Similarity	NPD7084	Phase 3
0.5969	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD3317	Approved
0.5963	Remote Similarity	NPD5926	Approved
0.5963	Remote Similarity	NPD253	Approved
0.5963	Remote Similarity	NPD9495	Approved
0.5952	Remote Similarity	NPD1593	Approved
0.595	Remote Similarity	NPD3798	Phase 3
0.5941	Remote Similarity	NPD3429	Approved
0.5941	Remote Similarity	NPD3427	Approved
0.5941	Remote Similarity	NPD4544	Approved
0.5938	Remote Similarity	NPD7055	Discontinued
0.5932	Remote Similarity	NPD1241	Discontinued
0.5929	Remote Similarity	NPD5048	Discontinued
0.5929	Remote Similarity	NPD1018	Approved
0.5922	Remote Similarity	NPD1282	Approved
0.5918	Remote Similarity	NPD1475	Approved
0.5902	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4687	Approved
0.5893	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD2754	Discontinued
0.5889	Remote Similarity	NPD173	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5618	Discontinued
0.5887	Remote Similarity	NPD1281	Approved
0.5882	Remote Similarity	NPD1023	Approved
0.5882	Remote Similarity	NPD2319	Discontinued
0.5882	Remote Similarity	NPD1021	Approved
0.5882	Remote Similarity	NPD1022	Approved
0.5882	Remote Similarity	NPD1020	Approved
0.5878	Remote Similarity	NPD1588	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6685	Approved
0.5873	Remote Similarity	NPD2056	Discontinued
0.5872	Remote Similarity	NPD2487	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data