NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.11
Volume:	240.856
LogP:	3.208
LogD:	3.396
LogS:	-3.857
# Rotatable Bonds:	1
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	3.89
Fsp3:	0.5
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:	-4.64
MDCK Permeability:	2.8867372748209164e-05
Pgp-inhibitor:	0.185
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	94.88724517822266%
Volume Distribution (VD):	2.519
Pgp-substrate:	5.766786575317383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.768
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.361
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	13.588
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.099
Carcinogencity:	0.807
Eye Corrosion:	0.044
Eye Irritation:	0.841
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC319140

Natural Product ID:	NPC319140
*Common Name:**	3-(Furan-3-Yl)-3A,7-Dimethyl-3,4,5,6-Tetrahydro-2-Benzofuran-1-One
IUPAC Name:	3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	XYYAFLHHHZVPRN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3
SMILES:	CC1=C2C(=O)OC(C2(CCC1)C)c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1595442
PubChem CID:	500095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11473427]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18198838]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10830	Dictamnus dasycarpus	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
Potency	11

Activity Type	# Activity
Individual Protein	8
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	25118.9	nM	PMID[511829]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	31622.8	nM	PMID[511829]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	5623.4	nM	PMID[511829]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	35481.3	nM	PMID[511829]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	25118.9	nM	PMID[511829]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[511829]
NPT2	Others	Unspecified		Potency	=	651.3	nM	PMID[511829]
NPT2	Others	Unspecified		Potency	n.a.	20596.2	nM	PMID[511829]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	928.5	nM	PMID[511829]

☑ 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 NPC319140 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	283
0.1-0.2	1411
0.2-0.3	3620
0.3-0.4	9048
0.4-0.5	11824
0.5-0.6	9853
0.6-0.7	5895
0.7-0.8	653
0.8-0.85	77
0.85-0.9	21
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95567
0.9593	High Similarity	NPC21460
0.937	High Similarity	NPC92941
0.9225	High Similarity	NPC186626
0.9225	High Similarity	NPC470742
0.8931	High Similarity	NPC310830
0.8906	High Similarity	NPC298190
0.8864	High Similarity	NPC220094
0.8855	High Similarity	NPC146872
0.8815	High Similarity	NPC470741
0.8815	High Similarity	NPC223415
0.88	High Similarity	NPC188377
0.88	High Similarity	NPC65735
0.8722	High Similarity	NPC476943
0.8722	High Similarity	NPC236532
0.871	High Similarity	NPC1848
0.8676	High Similarity	NPC267632
0.8667	High Similarity	NPC20500
0.8623	High Similarity	NPC346
0.8571	High Similarity	NPC16922
0.8561	High Similarity	NPC476938
0.8561	High Similarity	NPC250228
0.8561	High Similarity	NPC476937
0.8525	High Similarity	NPC150895
0.8519	High Similarity	NPC90953
0.85	High Similarity	NPC7388
0.85	High Similarity	NPC476941
0.85	High Similarity	NPC476942
0.8485	Intermediate Similarity	NPC470740
0.8478	Intermediate Similarity	NPC137295
0.8478	Intermediate Similarity	NPC86935
0.8478	Intermediate Similarity	NPC142113
0.8468	Intermediate Similarity	NPC243704
0.845	Intermediate Similarity	NPC83178
0.8444	Intermediate Similarity	NPC472376
0.8438	Intermediate Similarity	NPC179354
0.8429	Intermediate Similarity	NPC221809
0.8385	Intermediate Similarity	NPC112706
0.8385	Intermediate Similarity	NPC207294
0.8374	Intermediate Similarity	NPC28054
0.8372	Intermediate Similarity	NPC138139
0.8372	Intermediate Similarity	NPC216810
0.8372	Intermediate Similarity	NPC74612
0.8372	Intermediate Similarity	NPC46536
0.8347	Intermediate Similarity	NPC105249
0.8345	Intermediate Similarity	NPC84479
0.8345	Intermediate Similarity	NPC476944
0.8333	Intermediate Similarity	NPC136340
0.831	Intermediate Similarity	NPC195325
0.831	Intermediate Similarity	NPC329180
0.8308	Intermediate Similarity	NPC137570
0.8306	Intermediate Similarity	NPC45536
0.8298	Intermediate Similarity	NPC10088
0.8271	Intermediate Similarity	NPC471817
0.8268	Intermediate Similarity	NPC79557
0.8264	Intermediate Similarity	NPC476939
0.8264	Intermediate Similarity	NPC476940
0.8261	Intermediate Similarity	NPC205765
0.8254	Intermediate Similarity	NPC473969
0.8252	Intermediate Similarity	NPC476936
0.824	Intermediate Similarity	NPC208906
0.824	Intermediate Similarity	NPC144745
0.8235	Intermediate Similarity	NPC42400
0.8227	Intermediate Similarity	NPC262198
0.8227	Intermediate Similarity	NPC276676
0.8217	Intermediate Similarity	NPC243269
0.8209	Intermediate Similarity	NPC474425
0.8209	Intermediate Similarity	NPC471006
0.8209	Intermediate Similarity	NPC474407
0.8209	Intermediate Similarity	NPC474426
0.8207	Intermediate Similarity	NPC57998
0.8203	Intermediate Similarity	NPC477967
0.8203	Intermediate Similarity	NPC317217
0.8203	Intermediate Similarity	NPC263870
0.8201	Intermediate Similarity	NPC473152
0.8195	Intermediate Similarity	NPC61788
0.8194	Intermediate Similarity	NPC18135
0.8169	Intermediate Similarity	NPC470941
0.8168	Intermediate Similarity	NPC476016
0.8154	Intermediate Similarity	NPC471074
0.8154	Intermediate Similarity	NPC473885
0.8151	Intermediate Similarity	NPC214541
0.8151	Intermediate Similarity	NPC44675
0.8138	Intermediate Similarity	NPC75906
0.8125	Intermediate Similarity	NPC469335
0.8125	Intermediate Similarity	NPC159927
0.8125	Intermediate Similarity	NPC46551
0.8116	Intermediate Similarity	NPC474722
0.8099	Intermediate Similarity	NPC473356
0.8099	Intermediate Similarity	NPC471521
0.8095	Intermediate Similarity	NPC131801
0.8092	Intermediate Similarity	NPC474260
0.8092	Intermediate Similarity	NPC329694
0.8092	Intermediate Similarity	NPC329922
0.8092	Intermediate Similarity	NPC81912
0.8092	Intermediate Similarity	NPC23086
0.8088	Intermediate Similarity	NPC159786
0.8085	Intermediate Similarity	NPC251865
0.8077	Intermediate Similarity	NPC477965
0.8077	Intermediate Similarity	NPC477038
0.806	Intermediate Similarity	NPC89133
0.806	Intermediate Similarity	NPC17681
0.8058	Intermediate Similarity	NPC56197
0.8056	Intermediate Similarity	NPC472654
0.8041	Intermediate Similarity	NPC472776
0.8041	Intermediate Similarity	NPC261597
0.8041	Intermediate Similarity	NPC36655
0.8041	Intermediate Similarity	NPC472778
0.8041	Intermediate Similarity	NPC472777
0.8041	Intermediate Similarity	NPC187149
0.8015	Intermediate Similarity	NPC75557
0.8015	Intermediate Similarity	NPC71274
0.8015	Intermediate Similarity	NPC474829
0.8015	Intermediate Similarity	NPC471559
0.8014	Intermediate Similarity	NPC205071
0.8014	Intermediate Similarity	NPC80635
0.8014	Intermediate Similarity	NPC469503
0.8014	Intermediate Similarity	NPC476946
0.8014	Intermediate Similarity	NPC44577
0.8	Intermediate Similarity	NPC156189
0.8	Intermediate Similarity	NPC45358
0.8	Intermediate Similarity	NPC477404
0.8	Intermediate Similarity	NPC97740
0.8	Intermediate Similarity	NPC196864
0.8	Intermediate Similarity	NPC476122
0.7972	Intermediate Similarity	NPC471292
0.7971	Intermediate Similarity	NPC286130
0.797	Intermediate Similarity	NPC477966
0.797	Intermediate Similarity	NPC474438
0.797	Intermediate Similarity	NPC477123
0.797	Intermediate Similarity	NPC477039
0.797	Intermediate Similarity	NPC474279
0.7969	Intermediate Similarity	NPC4898
0.7959	Intermediate Similarity	NPC30222
0.7959	Intermediate Similarity	NPC178932
0.7958	Intermediate Similarity	NPC199044
0.7958	Intermediate Similarity	NPC238843
0.7956	Intermediate Similarity	NPC158525
0.7941	Intermediate Similarity	NPC218838
0.7937	Intermediate Similarity	NPC205523
0.7931	Intermediate Similarity	NPC470791
0.7931	Intermediate Similarity	NPC470790
0.7923	Intermediate Similarity	NPC473379
0.7923	Intermediate Similarity	NPC471549
0.7923	Intermediate Similarity	NPC36255
0.7919	Intermediate Similarity	NPC299038
0.791	Intermediate Similarity	NPC59502
0.791	Intermediate Similarity	NPC198904
0.791	Intermediate Similarity	NPC208389
0.7905	Intermediate Similarity	NPC264943
0.7905	Intermediate Similarity	NPC469850
0.7905	Intermediate Similarity	NPC281258
0.7905	Intermediate Similarity	NPC35000
0.7905	Intermediate Similarity	NPC469336
0.7895	Intermediate Similarity	NPC474830
0.7891	Intermediate Similarity	NPC476201
0.7883	Intermediate Similarity	NPC106247
0.7883	Intermediate Similarity	NPC471998
0.7877	Intermediate Similarity	NPC470997
0.7867	Intermediate Similarity	NPC475967
0.7863	Intermediate Similarity	NPC476351
0.7863	Intermediate Similarity	NPC475818
0.7857	Intermediate Similarity	NPC474615
0.7852	Intermediate Similarity	NPC204663
0.7852	Intermediate Similarity	NPC209364
0.7852	Intermediate Similarity	NPC60973
0.7847	Intermediate Similarity	NPC62799
0.7842	Intermediate Similarity	NPC170604
0.7842	Intermediate Similarity	NPC215109
0.7842	Intermediate Similarity	NPC307401
0.784	Intermediate Similarity	NPC26157
0.784	Intermediate Similarity	NPC1811
0.7838	Intermediate Similarity	NPC282445
0.7836	Intermediate Similarity	NPC327527
0.7836	Intermediate Similarity	NPC476917
0.7836	Intermediate Similarity	NPC477040
0.7829	Intermediate Similarity	NPC67345
0.7829	Intermediate Similarity	NPC244862
0.7823	Intermediate Similarity	NPC240214
0.7823	Intermediate Similarity	NPC116717
0.7817	Intermediate Similarity	NPC121158
0.7815	Intermediate Similarity	NPC305016
0.7815	Intermediate Similarity	NPC191828
0.7812	Intermediate Similarity	NPC312525
0.7812	Intermediate Similarity	NPC217180
0.781	Intermediate Similarity	NPC214097
0.7808	Intermediate Similarity	NPC471001
0.7803	Intermediate Similarity	NPC130275
0.7803	Intermediate Similarity	NPC83115
0.78	Intermediate Similarity	NPC472283
0.78	Intermediate Similarity	NPC286722
0.78	Intermediate Similarity	NPC195131
0.7793	Intermediate Similarity	NPC224418
0.7793	Intermediate Similarity	NPC308799
0.7786	Intermediate Similarity	NPC289911
0.7786	Intermediate Similarity	NPC283284
0.7785	Intermediate Similarity	NPC476262
0.7778	Intermediate Similarity	NPC56731
0.777	Intermediate Similarity	NPC33938
0.777	Intermediate Similarity	NPC46896

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 NPC319140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	1010
0.2-0.3	2119
0.3-0.4	2738
0.4-0.5	1991
0.5-0.6	823
0.6-0.7	203
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.755	Intermediate Similarity	NPD5761	Phase 2
0.755	Intermediate Similarity	NPD5760	Phase 2
0.7391	Intermediate Similarity	NPD6832	Phase 2
0.7383	Intermediate Similarity	NPD920	Approved
0.7372	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9717	Approved
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1241	Discontinued
0.7027	Intermediate Similarity	NPD1243	Approved
0.7014	Intermediate Similarity	NPD447	Suspended
0.6939	Remote Similarity	NPD1551	Phase 2
0.6939	Remote Similarity	NPD2796	Approved
0.6929	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6892	Remote Similarity	NPD1471	Phase 3
0.6871	Remote Similarity	NPD2799	Discontinued
0.6867	Remote Similarity	NPD4628	Phase 3
0.6864	Remote Similarity	NPD8434	Phase 2
0.6863	Remote Similarity	NPD6273	Approved
0.6828	Remote Similarity	NPD4307	Phase 2
0.6824	Remote Similarity	NPD2935	Discontinued
0.6815	Remote Similarity	NPD9493	Approved
0.6813	Remote Similarity	NPD919	Approved
0.6806	Remote Similarity	NPD411	Approved
0.6788	Remote Similarity	NPD5585	Approved
0.6781	Remote Similarity	NPD1933	Approved
0.6779	Remote Similarity	NPD2346	Discontinued
0.6779	Remote Similarity	NPD2344	Approved
0.6757	Remote Similarity	NPD3748	Approved
0.6718	Remote Similarity	NPD2182	Approved
0.6714	Remote Similarity	NPD3972	Approved
0.669	Remote Similarity	NPD2797	Approved
0.6688	Remote Similarity	NPD6599	Discontinued
0.6687	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD6765	Approved
0.6644	Remote Similarity	NPD4308	Phase 3
0.6643	Remote Similarity	NPD2798	Approved
0.6626	Remote Similarity	NPD1247	Approved
0.6623	Remote Similarity	NPD6799	Approved
0.662	Remote Similarity	NPD1876	Approved
0.6619	Remote Similarity	NPD17	Approved
0.6619	Remote Similarity	NPD1778	Approved
0.6601	Remote Similarity	NPD2309	Approved
0.6581	Remote Similarity	NPD2534	Approved
0.6581	Remote Similarity	NPD2533	Approved
0.6581	Remote Similarity	NPD2532	Approved
0.6573	Remote Similarity	NPD3266	Approved
0.6573	Remote Similarity	NPD3267	Approved
0.6571	Remote Similarity	NPD3496	Discontinued
0.6568	Remote Similarity	NPD6559	Discontinued
0.6565	Remote Similarity	NPD3134	Approved
0.6562	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7819	Suspended
0.6556	Remote Similarity	NPD6005	Phase 3
0.6556	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6004	Phase 3
0.6556	Remote Similarity	NPD6002	Phase 3
0.6556	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4359	Approved
0.6543	Remote Similarity	NPD3749	Approved
0.6538	Remote Similarity	NPD164	Approved
0.6536	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3750	Approved
0.6531	Remote Similarity	NPD8032	Phase 2
0.6528	Remote Similarity	NPD5647	Approved
0.6522	Remote Similarity	NPD5402	Approved
0.6519	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD1358	Approved
0.6513	Remote Similarity	NPD1549	Phase 2
0.6512	Remote Similarity	NPD6784	Approved
0.6512	Remote Similarity	NPD6785	Approved
0.65	Remote Similarity	NPD6279	Approved
0.65	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6280	Approved
0.6497	Remote Similarity	NPD5403	Approved
0.6494	Remote Similarity	NPD3887	Approved
0.6479	Remote Similarity	NPD1608	Approved
0.6475	Remote Similarity	NPD9545	Approved
0.6474	Remote Similarity	NPD5401	Approved
0.6471	Remote Similarity	NPD2800	Approved
0.6471	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5494	Approved
0.6463	Remote Similarity	NPD3268	Approved
0.6463	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD9261	Approved
0.6447	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4618	Approved
0.6443	Remote Similarity	NPD6355	Discontinued
0.6443	Remote Similarity	NPD4622	Approved
0.6442	Remote Similarity	NPD7075	Discontinued
0.6438	Remote Similarity	NPD7411	Suspended
0.6429	Remote Similarity	NPD5691	Approved
0.6429	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7003	Approved
0.6429	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6233	Phase 2
0.6419	Remote Similarity	NPD4870	Approved
0.6418	Remote Similarity	NPD2067	Discontinued
0.6415	Remote Similarity	NPD3226	Approved
0.6408	Remote Similarity	NPD1281	Approved
0.6405	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6801	Discontinued
0.638	Remote Similarity	NPD7768	Phase 2
0.6376	Remote Similarity	NPD1240	Approved
0.6376	Remote Similarity	NPD3142	Approved
0.6376	Remote Similarity	NPD3140	Approved
0.6376	Remote Similarity	NPD2979	Phase 3
0.637	Remote Similarity	NPD9494	Approved
0.6369	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9697	Approved
0.6358	Remote Similarity	NPD5689	Approved
0.6358	Remote Similarity	NPD5688	Approved
0.6357	Remote Similarity	NPD1894	Discontinued
0.6357	Remote Similarity	NPD1238	Approved
0.6351	Remote Similarity	NPD3764	Approved
0.6351	Remote Similarity	NPD6798	Discontinued
0.6351	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD6362	Approved
0.6335	Remote Similarity	NPD5890	Approved
0.6335	Remote Similarity	NPD5889	Approved
0.6324	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4110	Phase 3
0.6319	Remote Similarity	NPD3817	Phase 2
0.6316	Remote Similarity	NPD1510	Phase 2
0.6299	Remote Similarity	NPD4534	Discontinued
0.6299	Remote Similarity	NPD2897	Discontinued
0.6291	Remote Similarity	NPD1607	Approved
0.6291	Remote Similarity	NPD6653	Approved
0.6289	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3873	Phase 3
0.6289	Remote Similarity	NPD3869	Phase 3
0.6287	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.628	Remote Similarity	NPD3882	Suspended
0.6277	Remote Similarity	NPD5535	Approved
0.6276	Remote Similarity	NPD1283	Approved
0.6275	Remote Similarity	NPD4476	Approved
0.6275	Remote Similarity	NPD2438	Suspended
0.6275	Remote Similarity	NPD4477	Approved
0.6269	Remote Similarity	NPD9264	Approved
0.6269	Remote Similarity	NPD9267	Approved
0.6269	Remote Similarity	NPD9263	Approved
0.6267	Remote Similarity	NPD4140	Approved
0.6266	Remote Similarity	NPD4661	Approved
0.6266	Remote Similarity	NPD4662	Approved
0.6258	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1481	Phase 2
0.625	Remote Similarity	NPD3926	Phase 2
0.6242	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1296	Phase 2
0.6242	Remote Similarity	NPD7440	Discontinued
0.6235	Remote Similarity	NPD3818	Discontinued
0.6234	Remote Similarity	NPD2353	Approved
0.6234	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD230	Phase 1
0.6222	Remote Similarity	NPD9266	Approved
0.6222	Remote Similarity	NPD74	Approved
0.62	Remote Similarity	NPD4062	Phase 3
0.6197	Remote Similarity	NPD1651	Approved
0.6196	Remote Similarity	NPD1934	Approved
0.6196	Remote Similarity	NPD6844	Discontinued
0.6194	Remote Similarity	NPD2424	Discontinued
0.619	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6287	Discontinued
0.6181	Remote Similarity	NPD1535	Discovery
0.6173	Remote Similarity	NPD6585	Discontinued
0.6173	Remote Similarity	NPD4380	Phase 2
0.6164	Remote Similarity	NPD1578	Phase 2
0.6154	Remote Similarity	NPD4626	Approved
0.6149	Remote Similarity	NPD454	Approved
0.6143	Remote Similarity	NPD7157	Approved
0.6131	Remote Similarity	NPD8127	Discontinued
0.6121	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2296	Approved
0.6118	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2649	Approved
0.6111	Remote Similarity	NPD7458	Discontinued
0.6111	Remote Similarity	NPD2651	Approved
0.6105	Remote Similarity	NPD5844	Phase 1
0.6105	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD2684	Approved
0.6103	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5327	Phase 3
0.609	Remote Similarity	NPD5958	Discontinued

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