NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	146.04
Volume:	151.506
LogP:	1.683
LogD:	1.538
LogS:	-2.07
# Rotatable Bonds:	0
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	1.888
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.365
MDCK Permeability:	2.9263048418215476e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.204
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.807
30% Bioavailability (F30%):	0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	88.43299102783203%
Volume Distribution (VD):	1.213
Pgp-substrate:	17.010297775268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.646
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.839
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	4.739
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.302
Carcinogencity:	0.843
Eye Corrosion:	0.747
Eye Irritation:	0.994
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC279916

Natural Product ID:	NPC279916
*Common Name:**	Chromone
IUPAC Name:	chromen-4-one
Synonyms:	Chromen-4-One; Chromone
Standard InCHIKey:	OTAFHZMPRISVEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
SMILES:	O=c1ccoc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL13311
PubChem CID:	10286
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17703773]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19355	Natrii sulfas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8445	Radix polygoni aubertii	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15542	Herba nerviliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO1483	Herba gynurae bicoloris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25159	Radix ilicis asprellae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11856	Natrii sulfas exsiccatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19355	Natrii sulfas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25746	Radix semiaquilegiae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	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	1
ED50	1
IC50	7
MIC	1
Others	11

Activity Type	# Activity
Cell Line	5
Individual Protein	3
NON-MOLECULAR	2
Organism	5
Others	4
SINGLE PROTEIN	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	=	95.0	%	PMID[551043]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	47.55	%	PMID[551043]
NPT113	Cell Line	RAW264.7	Mus musculus	CC50	>	150000.0	nM	PMID[551046]
NPT113	Cell Line	RAW264.7	Mus musculus	MNTD70	>	150.0	uM	PMID[551046]
NPT113	Cell Line	RAW264.7	Mus musculus	MNTD90	=	37.5	uM	PMID[551046]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	54900.0	nM	PMID[551047]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	39900.0	nM	PMID[551047]
NPT496	Individual Protein	Alpha-L-fucosidase 1	Bos taurus	IC50	=	54000.0	nM	PMID[551051]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	>	20.0	ug.mL-1	PMID[551042]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	Inhibition	=	25.4	%	PMID[551043]
NPT2557	Organism	Dermatophagoides pteronyssinus	Dermatophagoides pteronyssinus	EC50	=	0.037	g/m2	PMID[551045]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[551046]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.9	%	PMID[551046]
NPT2	Others	Unspecified		Ratio IC50	=	1.0	n.a.	PMID[551047]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	log10LT50	=	1.744	n.a.	PMID[551048]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LT50	=	55.42	hr	PMID[551048]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	0.168	umol/cm2	PMID[551049]
NPT35	Others	n.a.		LogD7.4	n.a.	1.4	n.a.	PMID[551050]
NPT2	Others	Unspecified		IC50	=	14000.0	nM	PMID[551051]
NPT2	Others	Unspecified		IC50	=	81030.0	nM	PMID[551051]
NPT24816	SINGLE PROTEIN	Alpha-mannosidase	Canavalia ensiformis	IC50	=	49000.0	nM	PMID[551051]

☑ 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 NPC279916 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	575
0.1-0.2	2706
0.2-0.3	6985
0.3-0.4	11450
0.4-0.5	4510
0.5-0.6	7193
0.6-0.7	6646
0.7-0.8	2499
0.8-0.85	110
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC201284
0.9266	High Similarity	NPC53953
0.9196	High Similarity	NPC32298
0.9115	High Similarity	NPC54243
0.9043	High Similarity	NPC314329
0.9035	High Similarity	NPC470092
0.9027	High Similarity	NPC171023
0.8947	High Similarity	NPC35744
0.8938	High Similarity	NPC217423
0.8929	High Similarity	NPC188907
0.8824	High Similarity	NPC474264
0.8739	High Similarity	NPC23332
0.8739	High Similarity	NPC2771
0.8729	High Similarity	NPC472888
0.8729	High Similarity	NPC93730
0.8729	High Similarity	NPC182646
0.8655	High Similarity	NPC56332
0.8655	High Similarity	NPC193805
0.8649	High Similarity	NPC183648
0.8609	High Similarity	NPC45104
0.8607	High Similarity	NPC60558
0.8595	High Similarity	NPC298884
0.8583	High Similarity	NPC224657
0.8547	High Similarity	NPC230951
0.8537	High Similarity	NPC185497
0.8534	High Similarity	NPC206007
0.8525	High Similarity	NPC125887
0.8448	Intermediate Similarity	NPC469954
0.8443	Intermediate Similarity	NPC41721
0.8443	Intermediate Similarity	NPC22783
0.8443	Intermediate Similarity	NPC470841
0.8443	Intermediate Similarity	NPC45537
0.844	Intermediate Similarity	NPC38209
0.843	Intermediate Similarity	NPC4164
0.843	Intermediate Similarity	NPC65041
0.8407	Intermediate Similarity	NPC57879
0.8407	Intermediate Similarity	NPC54626
0.84	Intermediate Similarity	NPC474340
0.8374	Intermediate Similarity	NPC196034
0.8361	Intermediate Similarity	NPC237868
0.8349	Intermediate Similarity	NPC298224
0.8347	Intermediate Similarity	NPC255073
0.8347	Intermediate Similarity	NPC4012
0.8333	Intermediate Similarity	NPC182428
0.832	Intermediate Similarity	NPC301717
0.8306	Intermediate Similarity	NPC211120
0.8304	Intermediate Similarity	NPC224584
0.8293	Intermediate Similarity	NPC293387
0.8293	Intermediate Similarity	NPC49852
0.8293	Intermediate Similarity	NPC475496
0.8268	Intermediate Similarity	NPC223354
0.8264	Intermediate Similarity	NPC11799
0.8264	Intermediate Similarity	NPC141252
0.8257	Intermediate Similarity	NPC84325
0.8254	Intermediate Similarity	NPC472882
0.8254	Intermediate Similarity	NPC65060
0.8254	Intermediate Similarity	NPC284424
0.824	Intermediate Similarity	NPC7569
0.824	Intermediate Similarity	NPC228184
0.8235	Intermediate Similarity	NPC233282
0.8235	Intermediate Similarity	NPC246214
0.8226	Intermediate Similarity	NPC80694
0.8226	Intermediate Similarity	NPC186098
0.8226	Intermediate Similarity	NPC473907
0.8226	Intermediate Similarity	NPC475017
0.822	Intermediate Similarity	NPC152159
0.822	Intermediate Similarity	NPC94637
0.8214	Intermediate Similarity	NPC303264
0.8205	Intermediate Similarity	NPC316062
0.8205	Intermediate Similarity	NPC128825
0.8197	Intermediate Similarity	NPC470162
0.8197	Intermediate Similarity	NPC470163
0.819	Intermediate Similarity	NPC114144
0.819	Intermediate Similarity	NPC252004
0.8189	Intermediate Similarity	NPC229646
0.8182	Intermediate Similarity	NPC311219
0.8175	Intermediate Similarity	NPC477412
0.8175	Intermediate Similarity	NPC205360
0.816	Intermediate Similarity	NPC473019
0.816	Intermediate Similarity	NPC473894
0.816	Intermediate Similarity	NPC197425
0.816	Intermediate Similarity	NPC57552
0.816	Intermediate Similarity	NPC187907
0.8151	Intermediate Similarity	NPC328459
0.8151	Intermediate Similarity	NPC90522
0.8145	Intermediate Similarity	NPC264428
0.814	Intermediate Similarity	NPC324929
0.814	Intermediate Similarity	NPC234560
0.814	Intermediate Similarity	NPC39426
0.813	Intermediate Similarity	NPC470858
0.8125	Intermediate Similarity	NPC292998
0.8125	Intermediate Similarity	NPC1065
0.812	Intermediate Similarity	NPC220540
0.811	Intermediate Similarity	NPC308037
0.811	Intermediate Similarity	NPC313618
0.811	Intermediate Similarity	NPC278556
0.811	Intermediate Similarity	NPC262359
0.811	Intermediate Similarity	NPC64359
0.8095	Intermediate Similarity	NPC39753
0.8095	Intermediate Similarity	NPC278787
0.8095	Intermediate Similarity	NPC115998
0.8095	Intermediate Similarity	NPC473271
0.8083	Intermediate Similarity	NPC72977
0.8077	Intermediate Similarity	NPC235428
0.8077	Intermediate Similarity	NPC87545
0.8077	Intermediate Similarity	NPC254741
0.8067	Intermediate Similarity	NPC166591
0.8062	Intermediate Similarity	NPC217914
0.8062	Intermediate Similarity	NPC125269
0.8053	Intermediate Similarity	NPC141523
0.8051	Intermediate Similarity	NPC19290
0.8051	Intermediate Similarity	NPC470860
0.8049	Intermediate Similarity	NPC6888
0.8047	Intermediate Similarity	NPC101294
0.8047	Intermediate Similarity	NPC87231
0.8047	Intermediate Similarity	NPC257756
0.8047	Intermediate Similarity	NPC473655
0.8047	Intermediate Similarity	NPC212631
0.8047	Intermediate Similarity	NPC129132
0.8047	Intermediate Similarity	NPC205468
0.8036	Intermediate Similarity	NPC139891
0.8031	Intermediate Similarity	NPC141549
0.8031	Intermediate Similarity	NPC137264
0.8031	Intermediate Similarity	NPC11173
0.8018	Intermediate Similarity	NPC60679
0.8017	Intermediate Similarity	NPC225245
0.8016	Intermediate Similarity	NPC78662
0.8016	Intermediate Similarity	NPC8005
0.8016	Intermediate Similarity	NPC261759
0.8015	Intermediate Similarity	NPC162680
0.8015	Intermediate Similarity	NPC212767
0.8015	Intermediate Similarity	NPC294409
0.8015	Intermediate Similarity	NPC209560
0.8015	Intermediate Similarity	NPC116632
0.8015	Intermediate Similarity	NPC7013
0.8015	Intermediate Similarity	NPC303644
0.8015	Intermediate Similarity	NPC181124
0.8	Intermediate Similarity	NPC128428
0.8	Intermediate Similarity	NPC232996
0.8	Intermediate Similarity	NPC71525
0.8	Intermediate Similarity	NPC43435
0.8	Intermediate Similarity	NPC305518
0.8	Intermediate Similarity	NPC77955
0.7984	Intermediate Similarity	NPC472365
0.7984	Intermediate Similarity	NPC56031
0.7984	Intermediate Similarity	NPC175098
0.7984	Intermediate Similarity	NPC1249
0.7984	Intermediate Similarity	NPC223457
0.7984	Intermediate Similarity	NPC139813
0.7984	Intermediate Similarity	NPC165556
0.7984	Intermediate Similarity	NPC192304
0.7984	Intermediate Similarity	NPC312318
0.7984	Intermediate Similarity	NPC242294
0.7984	Intermediate Similarity	NPC337373
0.7984	Intermediate Similarity	NPC188646
0.7984	Intermediate Similarity	NPC57601
0.7984	Intermediate Similarity	NPC263670
0.7983	Intermediate Similarity	NPC240664
0.7982	Intermediate Similarity	NPC175298
0.7969	Intermediate Similarity	NPC113006
0.7969	Intermediate Similarity	NPC473584
0.7969	Intermediate Similarity	NPC475008
0.7969	Intermediate Similarity	NPC186097
0.7969	Intermediate Similarity	NPC475009
0.7969	Intermediate Similarity	NPC475589
0.7969	Intermediate Similarity	NPC31872
0.7955	Intermediate Similarity	NPC90665
0.7955	Intermediate Similarity	NPC279668
0.7955	Intermediate Similarity	NPC278323
0.7955	Intermediate Similarity	NPC309154
0.7955	Intermediate Similarity	NPC55162
0.7955	Intermediate Similarity	NPC12175
0.7953	Intermediate Similarity	NPC12694
0.7939	Intermediate Similarity	NPC284184
0.7939	Intermediate Similarity	NPC301341
0.7939	Intermediate Similarity	NPC240593
0.7939	Intermediate Similarity	NPC193792
0.7939	Intermediate Similarity	NPC472883
0.7939	Intermediate Similarity	NPC472516
0.7937	Intermediate Similarity	NPC50583
0.7931	Intermediate Similarity	NPC114682
0.7931	Intermediate Similarity	NPC233238
0.7923	Intermediate Similarity	NPC286336
0.7923	Intermediate Similarity	NPC164136
0.7923	Intermediate Similarity	NPC66705
0.7923	Intermediate Similarity	NPC172262
0.7923	Intermediate Similarity	NPC22222
0.7923	Intermediate Similarity	NPC281513
0.792	Intermediate Similarity	NPC474737
0.7917	Intermediate Similarity	NPC41567
0.7917	Intermediate Similarity	NPC184527
0.7913	Intermediate Similarity	NPC149545
0.7913	Intermediate Similarity	NPC234639
0.7907	Intermediate Similarity	NPC25937
0.7907	Intermediate Similarity	NPC128216
0.7907	Intermediate Similarity	NPC287533
0.7903	Intermediate Similarity	NPC107846
0.7903	Intermediate Similarity	NPC265910
0.7903	Intermediate Similarity	NPC91475
0.7899	Intermediate Similarity	NPC108288

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 NPC279916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	530
0.1-0.2	997
0.2-0.3	1550
0.3-0.4	2738
0.4-0.5	1894
0.5-0.6	1035
0.6-0.7	307
0.7-0.8	90
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9043	High Similarity	NPD1547	Clinical (unspecified phase)
0.8584	High Similarity	NPD1241	Discontinued
0.8512	High Similarity	NPD2798	Approved
0.8374	Intermediate Similarity	NPD6832	Phase 2
0.8211	Intermediate Similarity	NPD1019	Discontinued
0.8205	Intermediate Similarity	NPD9493	Approved
0.8182	Intermediate Similarity	NPD9717	Approved
0.8182	Intermediate Similarity	NPD9261	Approved
0.814	Intermediate Similarity	NPD1510	Phase 2
0.813	Intermediate Similarity	NPD1203	Approved
0.811	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD2313	Discontinued
0.8077	Intermediate Similarity	NPD2796	Approved
0.8036	Intermediate Similarity	NPD9697	Approved
0.8033	Intermediate Similarity	NPD3972	Approved
0.7984	Intermediate Similarity	NPD1607	Approved
0.7907	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD1876	Approved
0.7899	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD9267	Approved
0.7895	Intermediate Similarity	NPD9263	Approved
0.7895	Intermediate Similarity	NPD9264	Approved
0.7836	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD74	Approved
0.7826	Intermediate Similarity	NPD9266	Approved
0.782	Intermediate Similarity	NPD1549	Phase 2
0.7769	Intermediate Similarity	NPD1933	Approved
0.7744	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7721	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD411	Approved
0.7669	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD2344	Approved
0.7609	Intermediate Similarity	NPD5401	Approved
0.7609	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1238	Approved
0.7559	Intermediate Similarity	NPD3266	Approved
0.7559	Intermediate Similarity	NPD3267	Approved
0.7557	Intermediate Similarity	NPD3142	Approved
0.7557	Intermediate Similarity	NPD4307	Phase 2
0.7557	Intermediate Similarity	NPD3140	Approved
0.7536	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7482	Intermediate Similarity	NPD4661	Approved
0.7482	Intermediate Similarity	NPD4662	Approved
0.7481	Intermediate Similarity	NPD2346	Discontinued
0.748	Intermediate Similarity	NPD9545	Approved
0.7479	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD9281	Approved
0.7436	Intermediate Similarity	NPD1358	Approved
0.7426	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2797	Approved
0.7419	Intermediate Similarity	NPD1651	Approved
0.7391	Intermediate Similarity	NPD2309	Approved
0.7381	Intermediate Similarity	NPD1201	Approved
0.7376	Intermediate Similarity	NPD920	Approved
0.7372	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1471	Phase 3
0.7343	Intermediate Similarity	NPD4380	Phase 2
0.7339	Intermediate Similarity	NPD1894	Discontinued
0.7338	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD9494	Approved
0.7287	Intermediate Similarity	NPD1470	Approved
0.7286	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD5536	Phase 2
0.7246	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD1281	Approved
0.7241	Intermediate Similarity	NPD6844	Discontinued
0.7234	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7194	Intermediate Similarity	NPD3750	Approved
0.7183	Intermediate Similarity	NPD1512	Approved
0.7179	Intermediate Similarity	NPD164	Approved
0.7179	Intermediate Similarity	NPD1237	Approved
0.7172	Intermediate Similarity	NPD5890	Approved
0.7172	Intermediate Similarity	NPD7411	Suspended
0.7172	Intermediate Similarity	NPD5889	Approved
0.7154	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9259	Approved
0.713	Intermediate Similarity	NPD9257	Approved
0.7123	Intermediate Similarity	NPD6280	Approved
0.7123	Intermediate Similarity	NPD6279	Approved
0.7123	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD520	Approved
0.7087	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD2182	Approved
0.7077	Intermediate Similarity	NPD3225	Approved
0.7077	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7819	Suspended
0.7071	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7054	Intermediate Similarity	NPD1481	Phase 2
0.7054	Intermediate Similarity	NPD1608	Approved
0.7047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3226	Approved
0.7031	Intermediate Similarity	NPD3496	Discontinued
0.7027	Intermediate Similarity	NPD3817	Phase 2
0.7021	Intermediate Similarity	NPD3887	Approved
0.7015	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6798	Discontinued
0.7008	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD1934	Approved
0.7007	Intermediate Similarity	NPD7317	Phase 3
0.7	Intermediate Similarity	NPD919	Approved
0.6991	Remote Similarity	NPD1202	Approved
0.6986	Remote Similarity	NPD6585	Discontinued
0.6985	Remote Similarity	NPD4622	Approved
0.6985	Remote Similarity	NPD4618	Approved
0.698	Remote Similarity	NPD3882	Suspended
0.6978	Remote Similarity	NPD2353	Approved
0.6978	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1535	Discovery
0.6977	Remote Similarity	NPD422	Phase 1
0.6959	Remote Similarity	NPD2801	Approved
0.6959	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7033	Discontinued
0.6953	Remote Similarity	NPD4626	Approved
0.695	Remote Similarity	NPD4628	Phase 3
0.6942	Remote Similarity	NPD2684	Approved
0.6934	Remote Similarity	NPD6651	Approved
0.6933	Remote Similarity	NPD7075	Discontinued
0.6929	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD2651	Approved
0.6918	Remote Similarity	NPD2649	Approved
0.6918	Remote Similarity	NPD7458	Discontinued
0.6917	Remote Similarity	NPD454	Approved
0.6913	Remote Similarity	NPD7318	Phase 3
0.6913	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD943	Approved
0.6908	Remote Similarity	NPD1247	Approved
0.6899	Remote Similarity	NPD3847	Discontinued
0.6885	Remote Similarity	NPD5451	Approved
0.6884	Remote Similarity	NPD5689	Approved
0.6884	Remote Similarity	NPD5688	Approved
0.6875	Remote Similarity	NPD9258	Approved
0.6875	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9256	Approved
0.687	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7768	Phase 2
0.6861	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD5535	Approved
0.6853	Remote Similarity	NPD7440	Discontinued
0.6842	Remote Similarity	NPD5647	Approved
0.6842	Remote Similarity	NPD5494	Approved
0.6825	Remote Similarity	NPD2557	Approved
0.6822	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD196	Phase 1
0.6803	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2296	Approved
0.6788	Remote Similarity	NPD2979	Phase 3
0.6786	Remote Similarity	NPD4477	Approved
0.6786	Remote Similarity	NPD4476	Approved
0.6783	Remote Similarity	NPD2354	Approved
0.6781	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3252	Approved
0.6774	Remote Similarity	NPD1137	Approved
0.6774	Remote Similarity	NPD1139	Approved
0.6774	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3764	Approved
0.6763	Remote Similarity	NPD743	Approved
0.6761	Remote Similarity	NPD2800	Approved
0.6753	Remote Similarity	NPD6808	Phase 2
0.6746	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4359	Approved
0.6741	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1184	Approved
0.6736	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.672	Remote Similarity	NPD821	Approved
0.672	Remote Similarity	NPD7843	Approved
0.672	Remote Similarity	NPD1138	Approved
0.6715	Remote Similarity	NPD4062	Phase 3
0.6715	Remote Similarity	NPD6233	Phase 2
0.6712	Remote Similarity	NPD5049	Phase 3
0.6712	Remote Similarity	NPD6273	Approved
0.6711	Remote Similarity	NPD2366	Approved
0.6711	Remote Similarity	NPD3749	Approved
0.6693	Remote Similarity	NPD6671	Approved
0.6693	Remote Similarity	NPD709	Approved
0.669	Remote Similarity	NPD2897	Discontinued
0.6689	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3818	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