NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.05
Volume:	177.592
LogP:	1.708
LogD:	1.492
LogS:	-2.261
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	2.121
Fsp3:	0.1
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:	-4.704
MDCK Permeability:	1.6431555195595138e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	91.70462036132812%
Volume Distribution (VD):	0.465
Pgp-substrate:	9.204383850097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.283
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	13.899
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.77
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.498
Carcinogencity:	0.805
Eye Corrosion:	0.485
Eye Irritation:	0.985
Respiratory Toxicity:	0.282

Download Data

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

Natural Product: NPC14177

Natural Product ID:	NPC14177
*Common Name:**	6-Hydroxy-7-Methylchromen-2-One
IUPAC Name:	6-hydroxy-7-methylchromen-2-one
Synonyms:
Standard InCHIKey:	JSKYRABEGKTTPD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O3/c1-6-4-9-7(5-8(6)11)2-3-10(12)13-9/h2-5,11H,1H3
SMILES:	O=c1ccc2c(o1)cc(c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457962
PubChem CID:	850207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins

*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
NPO31579	Artemisia capillaries	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	7

Activity Type	# Activity
NON-MOLECULAR	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	22.0	%	PMID[454110]
NPT1	Others	Radical scavenging activity		Activity	=	20.0	%	PMID[454110]
NPT1	Others	Radical scavenging activity		Activity	=	51.0	%	PMID[454110]
NPT35	Others	n.a.		Inhibition	=	24.0	%	PMID[454110]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	54.0	%	PMID[454110]
NPT2	Others	Unspecified		Inhibition	=	3.0	%	PMID[454110]

☑ 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 NPC14177 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	409
0.1-0.2	2001
0.2-0.3	5137
0.3-0.4	11468
0.4-0.5	6155
0.5-0.6	5206
0.6-0.7	7522
0.7-0.8	4621
0.8-0.85	158
0.85-0.9	14
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC163398
0.9292	High Similarity	NPC87563
0.9098	High Similarity	NPC81261
0.9	High Similarity	NPC248786
0.8862	High Similarity	NPC142087
0.8862	High Similarity	NPC95034
0.8833	High Similarity	NPC476165
0.8783	High Similarity	NPC474920
0.8772	High Similarity	NPC141068
0.875	High Similarity	NPC307253
0.8682	High Similarity	NPC115861
0.8661	High Similarity	NPC139891
0.8644	High Similarity	NPC33717
0.8607	High Similarity	NPC302211
0.8583	High Similarity	NPC471449
0.8583	High Similarity	NPC98748
0.8559	High Similarity	NPC473718
0.8516	High Similarity	NPC317601
0.8516	High Similarity	NPC329427
0.8496	Intermediate Similarity	NPC288760
0.8496	Intermediate Similarity	NPC227255
0.8492	Intermediate Similarity	NPC176590
0.8487	Intermediate Similarity	NPC290470
0.8487	Intermediate Similarity	NPC154256
0.8475	Intermediate Similarity	NPC41851
0.8462	Intermediate Similarity	NPC266116
0.8462	Intermediate Similarity	NPC280760
0.8443	Intermediate Similarity	NPC322569
0.8407	Intermediate Similarity	NPC93831
0.8374	Intermediate Similarity	NPC52247
0.8372	Intermediate Similarity	NPC137949
0.8362	Intermediate Similarity	NPC149545
0.8361	Intermediate Similarity	NPC474874
0.8361	Intermediate Similarity	NPC31314
0.8361	Intermediate Similarity	NPC193193
0.8361	Intermediate Similarity	NPC247553
0.8348	Intermediate Similarity	NPC233320
0.8333	Intermediate Similarity	NPC76336
0.8333	Intermediate Similarity	NPC95162
0.8333	Intermediate Similarity	NPC139548
0.8333	Intermediate Similarity	NPC52086
0.8333	Intermediate Similarity	NPC20511
0.8333	Intermediate Similarity	NPC148835
0.832	Intermediate Similarity	NPC147896
0.832	Intermediate Similarity	NPC474237
0.8308	Intermediate Similarity	NPC277021
0.8293	Intermediate Similarity	NPC302107
0.8279	Intermediate Similarity	NPC51341
0.8271	Intermediate Similarity	NPC13067
0.8264	Intermediate Similarity	NPC183154
0.8264	Intermediate Similarity	NPC263754
0.8258	Intermediate Similarity	NPC126682
0.8258	Intermediate Similarity	NPC82271
0.8254	Intermediate Similarity	NPC244495
0.8254	Intermediate Similarity	NPC93219
0.825	Intermediate Similarity	NPC301321
0.823	Intermediate Similarity	NPC94343
0.8226	Intermediate Similarity	NPC187868
0.8214	Intermediate Similarity	NPC307039
0.8197	Intermediate Similarity	NPC124916
0.8195	Intermediate Similarity	NPC476171
0.8182	Intermediate Similarity	NPC128633
0.8182	Intermediate Similarity	NPC51087
0.8182	Intermediate Similarity	NPC281169
0.8182	Intermediate Similarity	NPC161856
0.8182	Intermediate Similarity	NPC291119
0.8182	Intermediate Similarity	NPC69539
0.8175	Intermediate Similarity	NPC276962
0.8175	Intermediate Similarity	NPC190086
0.816	Intermediate Similarity	NPC473464
0.816	Intermediate Similarity	NPC46634
0.816	Intermediate Similarity	NPC476332
0.8151	Intermediate Similarity	NPC26615
0.8145	Intermediate Similarity	NPC45663
0.8134	Intermediate Similarity	NPC43500
0.8134	Intermediate Similarity	NPC164148
0.813	Intermediate Similarity	NPC137294
0.813	Intermediate Similarity	NPC85895
0.8125	Intermediate Similarity	NPC243688
0.8125	Intermediate Similarity	NPC71525
0.812	Intermediate Similarity	NPC241549
0.8115	Intermediate Similarity	NPC240664
0.8115	Intermediate Similarity	NPC187993
0.8115	Intermediate Similarity	NPC238176
0.8106	Intermediate Similarity	NPC92830
0.8092	Intermediate Similarity	NPC194277
0.8087	Intermediate Similarity	NPC2518
0.8083	Intermediate Similarity	NPC190212
0.808	Intermediate Similarity	NPC168707
0.808	Intermediate Similarity	NPC48623
0.8077	Intermediate Similarity	NPC240722
0.8077	Intermediate Similarity	NPC244799
0.8077	Intermediate Similarity	NPC7569
0.8067	Intermediate Similarity	NPC228609
0.8067	Intermediate Similarity	NPC275627
0.8065	Intermediate Similarity	NPC2058
0.8062	Intermediate Similarity	NPC201419
0.806	Intermediate Similarity	NPC130976
0.806	Intermediate Similarity	NPC38874
0.8049	Intermediate Similarity	NPC265547
0.8049	Intermediate Similarity	NPC152306
0.8049	Intermediate Similarity	NPC283616
0.8047	Intermediate Similarity	NPC329272
0.8031	Intermediate Similarity	NPC61685
0.803	Intermediate Similarity	NPC26673
0.803	Intermediate Similarity	NPC163557
0.8029	Intermediate Similarity	NPC236419
0.8017	Intermediate Similarity	NPC127676
0.8017	Intermediate Similarity	NPC128730
0.8016	Intermediate Similarity	NPC132518
0.8016	Intermediate Similarity	NPC311219
0.8016	Intermediate Similarity	NPC325301
0.8016	Intermediate Similarity	NPC477151
0.8015	Intermediate Similarity	NPC142530
0.8015	Intermediate Similarity	NPC73738
0.8	Intermediate Similarity	NPC474289
0.8	Intermediate Similarity	NPC271832
0.8	Intermediate Similarity	NPC199462
0.8	Intermediate Similarity	NPC218753
0.8	Intermediate Similarity	NPC123127
0.8	Intermediate Similarity	NPC96423
0.8	Intermediate Similarity	NPC27239
0.8	Intermediate Similarity	NPC473875
0.7984	Intermediate Similarity	NPC37858
0.7984	Intermediate Similarity	NPC298796
0.7984	Intermediate Similarity	NPC258567
0.7984	Intermediate Similarity	NPC224774
0.7984	Intermediate Similarity	NPC281356
0.7984	Intermediate Similarity	NPC121740
0.7984	Intermediate Similarity	NPC32152
0.7982	Intermediate Similarity	NPC107101
0.797	Intermediate Similarity	NPC473054
0.797	Intermediate Similarity	NPC211164
0.7969	Intermediate Similarity	NPC168259
0.7969	Intermediate Similarity	NPC252962
0.7956	Intermediate Similarity	NPC469564
0.7955	Intermediate Similarity	NPC137669
0.7953	Intermediate Similarity	NPC477152
0.7951	Intermediate Similarity	NPC296526
0.7949	Intermediate Similarity	NPC176971
0.7946	Intermediate Similarity	NPC257182
0.7946	Intermediate Similarity	NPC246679
0.7939	Intermediate Similarity	NPC196621
0.7939	Intermediate Similarity	NPC278787
0.7937	Intermediate Similarity	NPC212965
0.7931	Intermediate Similarity	NPC130817
0.7931	Intermediate Similarity	NPC109637
0.7923	Intermediate Similarity	NPC469453
0.7923	Intermediate Similarity	NPC185066
0.792	Intermediate Similarity	NPC232295
0.792	Intermediate Similarity	NPC202474
0.792	Intermediate Similarity	NPC474131
0.7913	Intermediate Similarity	NPC307425
0.791	Intermediate Similarity	NPC252095
0.7907	Intermediate Similarity	NPC128321
0.7903	Intermediate Similarity	NPC96705
0.7903	Intermediate Similarity	NPC272471
0.7903	Intermediate Similarity	NPC107588
0.7903	Intermediate Similarity	NPC139047
0.7903	Intermediate Similarity	NPC212743
0.7903	Intermediate Similarity	NPC164706
0.7903	Intermediate Similarity	NPC70744
0.7903	Intermediate Similarity	NPC137537
0.7899	Intermediate Similarity	NPC34245
0.7899	Intermediate Similarity	NPC110067
0.7899	Intermediate Similarity	NPC256555
0.7899	Intermediate Similarity	NPC91492
0.7899	Intermediate Similarity	NPC230157
0.7899	Intermediate Similarity	NPC7439
0.7895	Intermediate Similarity	NPC36437
0.7895	Intermediate Similarity	NPC233018
0.7895	Intermediate Similarity	NPC31849
0.7895	Intermediate Similarity	NPC474810
0.7895	Intermediate Similarity	NPC241341
0.7891	Intermediate Similarity	NPC229113
0.7891	Intermediate Similarity	NPC248557
0.7891	Intermediate Similarity	NPC140521
0.7891	Intermediate Similarity	NPC89630
0.7891	Intermediate Similarity	NPC4012
0.7883	Intermediate Similarity	NPC300611
0.7881	Intermediate Similarity	NPC151530
0.7881	Intermediate Similarity	NPC157473
0.7879	Intermediate Similarity	NPC147317
0.7879	Intermediate Similarity	NPC141549
0.7874	Intermediate Similarity	NPC327070
0.7874	Intermediate Similarity	NPC120638
0.7869	Intermediate Similarity	NPC197513
0.7869	Intermediate Similarity	NPC294941
0.7869	Intermediate Similarity	NPC81808
0.7869	Intermediate Similarity	NPC235250
0.7863	Intermediate Similarity	NPC59654
0.7863	Intermediate Similarity	NPC238309
0.7857	Intermediate Similarity	NPC475529
0.7857	Intermediate Similarity	NPC204466
0.7857	Intermediate Similarity	NPC235190
0.7857	Intermediate Similarity	NPC129176
0.7857	Intermediate Similarity	NPC163200
0.7857	Intermediate Similarity	NPC100108
0.7857	Intermediate Similarity	NPC180006
0.7857	Intermediate Similarity	NPC277798

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 NPC14177 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	992
0.2-0.3	1611
0.3-0.4	2660
0.4-0.5	1885
0.5-0.6	1074
0.6-0.7	394
0.7-0.8	112
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD9697	Approved
0.8595	High Similarity	NPD3496	Discontinued
0.8403	Intermediate Similarity	NPD6671	Approved
0.8374	Intermediate Similarity	NPD1611	Approved
0.8374	Intermediate Similarity	NPD422	Phase 1
0.8211	Intermediate Similarity	NPD1778	Approved
0.8103	Intermediate Similarity	NPD968	Approved
0.8077	Intermediate Similarity	NPD411	Approved
0.8065	Intermediate Similarity	NPD4626	Approved
0.8016	Intermediate Similarity	NPD9717	Approved
0.7969	Intermediate Similarity	NPD2797	Approved
0.7969	Intermediate Similarity	NPD1203	Approved
0.7895	Intermediate Similarity	NPD447	Suspended
0.7891	Intermediate Similarity	NPD3225	Approved
0.7852	Intermediate Similarity	NPD4308	Phase 3
0.784	Intermediate Similarity	NPD5691	Approved
0.7795	Intermediate Similarity	NPD1535	Discovery
0.7787	Intermediate Similarity	NPD1398	Phase 1
0.7734	Intermediate Similarity	NPD1481	Phase 2
0.771	Intermediate Similarity	NPD2237	Approved
0.768	Intermediate Similarity	NPD7644	Approved
0.7669	Intermediate Similarity	NPD3268	Approved
0.7664	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD3134	Approved
0.7615	Intermediate Similarity	NPD6696	Suspended
0.7609	Intermediate Similarity	NPD2346	Discontinued
0.76	Intermediate Similarity	NPD7340	Approved
0.7597	Intermediate Similarity	NPD1608	Approved
0.7583	Intermediate Similarity	NPD290	Approved
0.7583	Intermediate Similarity	NPD1358	Approved
0.7571	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD5535	Approved
0.7559	Intermediate Similarity	NPD5585	Approved
0.7556	Intermediate Similarity	NPD4060	Phase 1
0.7556	Intermediate Similarity	NPD4307	Phase 2
0.7538	Intermediate Similarity	NPD4749	Approved
0.7537	Intermediate Similarity	NPD2313	Discontinued
0.7536	Intermediate Similarity	NPD1551	Phase 2
0.7521	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD844	Approved
0.746	Intermediate Similarity	NPD9493	Approved
0.7444	Intermediate Similarity	NPD2861	Phase 2
0.7424	Intermediate Similarity	NPD3267	Approved
0.7424	Intermediate Similarity	NPD3266	Approved
0.7414	Intermediate Similarity	NPD288	Approved
0.7397	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD1019	Discontinued
0.7364	Intermediate Similarity	NPD17	Approved
0.7361	Intermediate Similarity	NPD1578	Phase 2
0.736	Intermediate Similarity	NPD1241	Discontinued
0.7348	Intermediate Similarity	NPD1283	Approved
0.7344	Intermediate Similarity	NPD1548	Phase 1
0.7339	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7299	Intermediate Similarity	NPD4140	Approved
0.7273	Intermediate Similarity	NPD4359	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6832	Phase 2
0.7259	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9295	Approved
0.7244	Intermediate Similarity	NPD709	Approved
0.7214	Intermediate Similarity	NPD2799	Discontinued
0.7209	Intermediate Similarity	NPD1894	Discontinued
0.7209	Intermediate Similarity	NPD9545	Approved
0.7206	Intermediate Similarity	NPD7095	Approved
0.7203	Intermediate Similarity	NPD3750	Approved
0.7183	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6032	Approved
0.7153	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD7635	Approved
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7132	Intermediate Similarity	NPD2614	Approved
0.7132	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5124	Phase 1
0.7121	Intermediate Similarity	NPD1281	Approved
0.7121	Intermediate Similarity	NPD1091	Approved
0.7121	Intermediate Similarity	NPD1610	Phase 2
0.7113	Intermediate Similarity	NPD5762	Approved
0.7113	Intermediate Similarity	NPD5763	Approved
0.7113	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2798	Approved
0.7101	Intermediate Similarity	NPD6233	Phase 2
0.7097	Intermediate Similarity	NPD2684	Approved
0.7095	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7071	Intermediate Similarity	NPD6653	Approved
0.7068	Intermediate Similarity	NPD2235	Phase 2
0.7068	Intermediate Similarity	NPD2231	Phase 2
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6099	Approved
0.7042	Intermediate Similarity	NPD6100	Approved
0.7037	Intermediate Similarity	NPD987	Approved
0.7029	Intermediate Similarity	NPD1048	Approved
0.7029	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6798	Discontinued
0.7029	Intermediate Similarity	NPD1296	Phase 2
0.7015	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD5536	Phase 2
0.6993	Remote Similarity	NPD2344	Approved
0.6993	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6584	Phase 3
0.6978	Remote Similarity	NPD8032	Phase 2
0.6972	Remote Similarity	NPD7033	Discontinued
0.697	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7003	Approved
0.696	Remote Similarity	NPD9266	Approved
0.696	Remote Similarity	NPD74	Approved
0.6959	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD2676	Approved
0.6959	Remote Similarity	NPD2675	Approved
0.695	Remote Similarity	NPD1607	Approved
0.6947	Remote Similarity	NPD1182	Approved
0.694	Remote Similarity	NPD2232	Approved
0.694	Remote Similarity	NPD2233	Approved
0.694	Remote Similarity	NPD2230	Approved
0.6939	Remote Similarity	NPD1511	Approved
0.6934	Remote Similarity	NPD9494	Approved
0.6929	Remote Similarity	NPD1613	Approved
0.6929	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5402	Approved
0.6923	Remote Similarity	NPD1519	Approved
0.6923	Remote Similarity	NPD1537	Approved
0.6923	Remote Similarity	NPD1538	Phase 1
0.6917	Remote Similarity	NPD3847	Discontinued
0.6905	Remote Similarity	NPD4750	Phase 3
0.6894	Remote Similarity	NPD1651	Approved
0.6892	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD600	Approved
0.6884	Remote Similarity	NPD596	Approved
0.6884	Remote Similarity	NPD4908	Phase 1
0.688	Remote Similarity	NPD9264	Approved
0.688	Remote Similarity	NPD9263	Approved
0.688	Remote Similarity	NPD9267	Approved
0.6879	Remote Similarity	NPD1933	Approved
0.6879	Remote Similarity	NPD4340	Discontinued
0.6879	Remote Similarity	NPD1184	Approved
0.6875	Remote Similarity	NPD7843	Approved
0.6875	Remote Similarity	NPD5844	Phase 1
0.6863	Remote Similarity	NPD2801	Approved
0.6861	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4870	Approved
0.6853	Remote Similarity	NPD3748	Approved
0.6849	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7157	Approved
0.6846	Remote Similarity	NPD1512	Approved
0.6835	Remote Similarity	NPD5163	Phase 2
0.6812	Remote Similarity	NPD1712	Approved
0.6809	Remote Similarity	NPD1240	Approved
0.6809	Remote Similarity	NPD2979	Phase 3
0.6807	Remote Similarity	NPD2933	Approved
0.6807	Remote Similarity	NPD2934	Approved
0.6806	Remote Similarity	NPD1523	Approved
0.6806	Remote Similarity	NPD4477	Approved
0.6806	Remote Similarity	NPD1522	Approved
0.6806	Remote Similarity	NPD4476	Approved
0.6803	Remote Similarity	NPD2309	Approved
0.6797	Remote Similarity	NPD6844	Discontinued
0.6794	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6362	Approved
0.6786	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7097	Phase 1
0.6783	Remote Similarity	NPD1536	Approved
0.6781	Remote Similarity	NPD1243	Approved
0.6779	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1357	Approved
0.6765	Remote Similarity	NPD6583	Phase 3
0.6765	Remote Similarity	NPD6582	Phase 2
0.6761	Remote Similarity	NPD230	Phase 1
0.6761	Remote Similarity	NPD9694	Discovery
0.6759	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6004	Phase 3
0.6759	Remote Similarity	NPD6002	Phase 3
0.6759	Remote Similarity	NPD6005	Phase 3
0.6757	Remote Similarity	NPD6667	Approved
0.6757	Remote Similarity	NPD6666	Approved
0.6754	Remote Similarity	NPD111	Approved
0.675	Remote Similarity	NPD2859	Approved
0.675	Remote Similarity	NPD2860	Approved
0.6746	Remote Similarity	NPD2342	Discontinued
0.6746	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4062	Phase 3
0.6738	Remote Similarity	NPD839	Approved
0.6738	Remote Similarity	NPD840	Approved
0.6736	Remote Similarity	NPD1510	Phase 2
0.6735	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4110	Phase 3
0.6733	Remote Similarity	NPD6090	Discontinued
0.6731	Remote Similarity	NPD3453	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