NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	3.709
LogD:	3.348
LogS:	-3.901
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.669
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.932
MDCK Permeability:	2.1011350327171385e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	99.8767318725586%
Volume Distribution (VD):	0.525
Pgp-substrate:	1.3647314310073853%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.605
CYP2C19-substrate:	0.561
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.608
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	9.11
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.684
AMES Toxicity:	0.44
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.956
Carcinogencity:	0.782
Eye Corrosion:	0.015
Eye Irritation:	0.933
Respiratory Toxicity:	0.834

Download Data

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

Natural Product: NPC152159

Natural Product ID:	NPC152159
*Common Name:**	Bauhinoxepin J
IUPAC Name:	3-methoxy-5,6-dihydrobenzo[b][1]benzoxepine-1,4-dione
Synonyms:	bauhinoxepin J
Standard InCHIKey:	LAAFMXBDDPXIKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-18-13-8-11(16)15-10(14(13)17)7-6-9-4-2-3-5-12(9)19-15/h2-5,8H,6-7H2,1H3
SMILES:	COC1=CC(=O)C2=C(C1=O)CCc1c(O2)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227903
PubChem CID:	16680047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids

*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
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11141127]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15595606]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562827]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17480099]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	roots	Phitsanulok Province, Thailand	2004-MAY	PMID[17480099]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6828	Purpura aperta	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9608	Lepraria citrina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8807	Laurentia longiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4382	Elmerrillia papuana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25475	Syphonota geographica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1490	Goldfussia yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9881	Petrosia hebes	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4628	Aloe deltoideodonta	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8977	0tholaena aschenborniana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3357	Alnus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2455	Thermopsis mollis	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
IC50	4
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10500.0	nM	PMID[533161]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	24400.0	nM	PMID[533161]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5800.0	nM	PMID[533161]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	195300.0	nM	PMID[533161]
NPT27	Others	Unspecified		IC50	=	12100.0	nM	PMID[533161]

☑ 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 NPC152159 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	322
0.1-0.2	1685
0.2-0.3	4551
0.3-0.4	10774
0.4-0.5	7356
0.5-0.6	6165
0.6-0.7	9865
0.7-0.8	1918
0.8-0.85	53
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8934	High Similarity	NPC201419
0.879	High Similarity	NPC146615
0.8504	High Similarity	NPC119985
0.8504	High Similarity	NPC280476
0.8417	Intermediate Similarity	NPC35744
0.8361	Intermediate Similarity	NPC314329
0.8347	Intermediate Similarity	NPC168050
0.8333	Intermediate Similarity	NPC32298
0.8306	Intermediate Similarity	NPC98509
0.8305	Intermediate Similarity	NPC114144
0.8304	Intermediate Similarity	NPC298224
0.8264	Intermediate Similarity	NPC54243
0.8264	Intermediate Similarity	NPC43435
0.8244	Intermediate Similarity	NPC266245
0.824	Intermediate Similarity	NPC224657
0.823	Intermediate Similarity	NPC38209
0.8226	Intermediate Similarity	NPC11799
0.8226	Intermediate Similarity	NPC141252
0.8226	Intermediate Similarity	NPC93730
0.822	Intermediate Similarity	NPC279916
0.8205	Intermediate Similarity	NPC23332
0.8205	Intermediate Similarity	NPC233238
0.8197	Intermediate Similarity	NPC246214
0.8197	Intermediate Similarity	NPC230951
0.819	Intermediate Similarity	NPC259554
0.8182	Intermediate Similarity	NPC171023
0.816	Intermediate Similarity	NPC89630
0.812	Intermediate Similarity	NPC183648
0.8115	Intermediate Similarity	NPC201284
0.8099	Intermediate Similarity	NPC45104
0.8099	Intermediate Similarity	NPC469954
0.8095	Intermediate Similarity	NPC2771
0.8095	Intermediate Similarity	NPC470858
0.808	Intermediate Similarity	NPC472888
0.8067	Intermediate Similarity	NPC53953
0.8067	Intermediate Similarity	NPC90903
0.8053	Intermediate Similarity	NPC84325
0.8049	Intermediate Similarity	NPC474874
0.8047	Intermediate Similarity	NPC125887
0.8033	Intermediate Similarity	NPC206007
0.8033	Intermediate Similarity	NPC293424
0.8031	Intermediate Similarity	NPC237868
0.8017	Intermediate Similarity	NPC470860
0.8017	Intermediate Similarity	NPC19290
0.8017	Intermediate Similarity	NPC325646
0.8017	Intermediate Similarity	NPC28951
0.8016	Intermediate Similarity	NPC56332
0.8015	Intermediate Similarity	NPC470871
0.8	Intermediate Similarity	NPC324488
0.8	Intermediate Similarity	NPC139891
0.8	Intermediate Similarity	NPC252004
0.7984	Intermediate Similarity	NPC170546
0.7984	Intermediate Similarity	NPC473019
0.7984	Intermediate Similarity	NPC66246
0.797	Intermediate Similarity	NPC232996
0.797	Intermediate Similarity	NPC104796
0.7969	Intermediate Similarity	NPC298884
0.7967	Intermediate Similarity	NPC264976
0.7967	Intermediate Similarity	NPC98748
0.7955	Intermediate Similarity	NPC477210
0.7953	Intermediate Similarity	NPC165556
0.7951	Intermediate Similarity	NPC217423
0.7946	Intermediate Similarity	NPC175298
0.7937	Intermediate Similarity	NPC182646
0.7937	Intermediate Similarity	NPC473942
0.7934	Intermediate Similarity	NPC188907
0.7931	Intermediate Similarity	NPC1065
0.7923	Intermediate Similarity	NPC183348
0.7923	Intermediate Similarity	NPC172673
0.7923	Intermediate Similarity	NPC282230
0.791	Intermediate Similarity	NPC301341
0.791	Intermediate Similarity	NPC309452
0.791	Intermediate Similarity	NPC284184
0.7903	Intermediate Similarity	NPC470092
0.7895	Intermediate Similarity	NPC217914
0.7881	Intermediate Similarity	NPC149545
0.7879	Intermediate Similarity	NPC55147
0.7874	Intermediate Similarity	NPC193805
0.7874	Intermediate Similarity	NPC107846
0.7869	Intermediate Similarity	NPC316062
0.7863	Intermediate Similarity	NPC205360
0.7863	Intermediate Similarity	NPC301717
0.7863	Intermediate Similarity	NPC11173
0.7863	Intermediate Similarity	NPC15083
0.7863	Intermediate Similarity	NPC279596
0.7863	Intermediate Similarity	NPC470977
0.7863	Intermediate Similarity	NPC196979
0.7863	Intermediate Similarity	NPC470976
0.7857	Intermediate Similarity	NPC311219
0.7851	Intermediate Similarity	NPC87563
0.7846	Intermediate Similarity	NPC939
0.7845	Intermediate Similarity	NPC227255
0.7845	Intermediate Similarity	NPC128730
0.784	Intermediate Similarity	NPC322569
0.7833	Intermediate Similarity	NPC266116
0.7829	Intermediate Similarity	NPC475496
0.7829	Intermediate Similarity	NPC45537
0.7829	Intermediate Similarity	NPC41721
0.7829	Intermediate Similarity	NPC49852
0.7829	Intermediate Similarity	NPC37512
0.7826	Intermediate Similarity	NPC472840
0.7815	Intermediate Similarity	NPC473809
0.7805	Intermediate Similarity	NPC312525
0.7805	Intermediate Similarity	NPC217180
0.7803	Intermediate Similarity	NPC239302
0.7803	Intermediate Similarity	NPC175159
0.7803	Intermediate Similarity	NPC472882
0.7803	Intermediate Similarity	NPC153453
0.7795	Intermediate Similarity	NPC135062
0.7788	Intermediate Similarity	NPC95755
0.7787	Intermediate Similarity	NPC205523
0.7787	Intermediate Similarity	NPC51345
0.7786	Intermediate Similarity	NPC228184
0.7786	Intermediate Similarity	NPC2989
0.7778	Intermediate Similarity	NPC72452
0.7778	Intermediate Similarity	NPC61546
0.7778	Intermediate Similarity	NPC176971
0.7778	Intermediate Similarity	NPC477534
0.7769	Intermediate Similarity	NPC473907
0.7761	Intermediate Similarity	NPC22644
0.776	Intermediate Similarity	NPC31314
0.776	Intermediate Similarity	NPC193193
0.7759	Intermediate Similarity	NPC109637
0.7752	Intermediate Similarity	NPC474264
0.775	Intermediate Similarity	NPC57879
0.775	Intermediate Similarity	NPC54626
0.7744	Intermediate Similarity	NPC54503
0.7744	Intermediate Similarity	NPC477536
0.7744	Intermediate Similarity	NPC229646
0.7737	Intermediate Similarity	NPC477537
0.7731	Intermediate Similarity	NPC234639
0.7727	Intermediate Similarity	NPC474246
0.7727	Intermediate Similarity	NPC477412
0.7727	Intermediate Similarity	NPC472517
0.7727	Intermediate Similarity	NPC474143
0.7727	Intermediate Similarity	NPC141549
0.7724	Intermediate Similarity	NPC33717
0.7724	Intermediate Similarity	NPC128633
0.7721	Intermediate Similarity	NPC221046
0.7717	Intermediate Similarity	NPC49441
0.7712	Intermediate Similarity	NPC157473
0.7712	Intermediate Similarity	NPC151530
0.771	Intermediate Similarity	NPC59654
0.771	Intermediate Similarity	NPC271832
0.771	Intermediate Similarity	NPC473894
0.771	Intermediate Similarity	NPC238309
0.7704	Intermediate Similarity	NPC21797
0.7704	Intermediate Similarity	NPC194847
0.7698	Intermediate Similarity	NPC316691
0.7692	Intermediate Similarity	NPC22783
0.7692	Intermediate Similarity	NPC473855
0.7692	Intermediate Similarity	NPC161322
0.7692	Intermediate Similarity	NPC477214
0.7692	Intermediate Similarity	NPC477211
0.7692	Intermediate Similarity	NPC293387
0.7692	Intermediate Similarity	NPC477212
0.7692	Intermediate Similarity	NPC319422
0.7687	Intermediate Similarity	NPC292998
0.7686	Intermediate Similarity	NPC199462
0.7686	Intermediate Similarity	NPC161611
0.768	Intermediate Similarity	NPC137710
0.768	Intermediate Similarity	NPC298796
0.7674	Intermediate Similarity	NPC65041
0.7674	Intermediate Similarity	NPC88403
0.7674	Intermediate Similarity	NPC4164
0.7672	Intermediate Similarity	NPC179686
0.7669	Intermediate Similarity	NPC284424
0.7669	Intermediate Similarity	NPC278556
0.7669	Intermediate Similarity	NPC470859
0.7664	Intermediate Similarity	NPC477408
0.7661	Intermediate Similarity	NPC183154
0.7661	Intermediate Similarity	NPC263754
0.7656	Intermediate Similarity	NPC472518
0.7652	Intermediate Similarity	NPC475880
0.7652	Intermediate Similarity	NPC109778
0.7652	Intermediate Similarity	NPC278787
0.7652	Intermediate Similarity	NPC13755
0.7647	Intermediate Similarity	NPC254741
0.7647	Intermediate Similarity	NPC290601
0.7647	Intermediate Similarity	NPC186647
0.7647	Intermediate Similarity	NPC472516
0.7643	Intermediate Similarity	NPC471600
0.7643	Intermediate Similarity	NPC232883
0.7642	Intermediate Similarity	NPC220540
0.7638	Intermediate Similarity	NPC144418
0.7634	Intermediate Similarity	NPC50583
0.7634	Intermediate Similarity	NPC181675
0.7634	Intermediate Similarity	NPC2401
0.7634	Intermediate Similarity	NPC59502
0.7634	Intermediate Similarity	NPC475017
0.7634	Intermediate Similarity	NPC196034
0.763	Intermediate Similarity	NPC125269
0.763	Intermediate Similarity	NPC66705
0.7627	Intermediate Similarity	NPC326801
0.7626	Intermediate Similarity	NPC229916
0.7626	Intermediate Similarity	NPC136840
0.7623	Intermediate Similarity	NPC109241
0.7615	Intermediate Similarity	NPC474737
0.7615	Intermediate Similarity	NPC141059
0.7612	Intermediate Similarity	NPC101294

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 NPC152159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	1005
0.2-0.3	1316
0.3-0.4	2563
0.4-0.5	2056
0.5-0.6	1257
0.6-0.7	536
0.7-0.8	100
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.886	High Similarity	NPD1241	Discontinued
0.8361	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3267	Approved
0.8095	Intermediate Similarity	NPD3266	Approved
0.8	Intermediate Similarity	NPD9697	Approved
0.7923	Intermediate Similarity	NPD6798	Discontinued
0.7907	Intermediate Similarity	NPD6832	Phase 2
0.7857	Intermediate Similarity	NPD9717	Approved
0.7812	Intermediate Similarity	NPD2797	Approved
0.7786	Intermediate Similarity	NPD3268	Approved
0.7752	Intermediate Similarity	NPD1019	Discontinued
0.7744	Intermediate Similarity	NPD6355	Discontinued
0.7717	Intermediate Similarity	NPD3972	Approved
0.7704	Intermediate Similarity	NPD2799	Discontinued
0.7698	Intermediate Similarity	NPD3496	Discontinued
0.7674	Intermediate Similarity	NPD1203	Approved
0.7669	Intermediate Similarity	NPD4307	Phase 2
0.7652	Intermediate Similarity	NPD1296	Phase 2
0.7652	Intermediate Similarity	NPD2313	Discontinued
0.7619	Intermediate Similarity	NPD17	Approved
0.7615	Intermediate Similarity	NPD2798	Approved
0.7597	Intermediate Similarity	NPD1876	Approved
0.7591	Intermediate Similarity	NPD1471	Phase 3
0.7591	Intermediate Similarity	NPD2353	Approved
0.7591	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3748	Approved
0.7563	Intermediate Similarity	NPD1358	Approved
0.7541	Intermediate Similarity	NPD5535	Approved
0.754	Intermediate Similarity	NPD1651	Approved
0.7518	Intermediate Similarity	NPD6799	Approved
0.7518	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.7482	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1933	Approved
0.7481	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD3134	Approved
0.7463	Intermediate Similarity	NPD4062	Phase 3
0.7463	Intermediate Similarity	NPD6233	Phase 2
0.746	Intermediate Similarity	NPD1894	Discontinued
0.7445	Intermediate Similarity	NPD4308	Phase 3
0.7442	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD290	Approved
0.741	Intermediate Similarity	NPD1549	Phase 2
0.7407	Intermediate Similarity	NPD1240	Approved
0.7407	Intermediate Similarity	NPD3140	Approved
0.7407	Intermediate Similarity	NPD3142	Approved
0.7388	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5536	Phase 2
0.7376	Intermediate Similarity	NPD2354	Approved
0.7364	Intermediate Similarity	NPD1535	Discovery
0.7355	Intermediate Similarity	NPD2684	Approved
0.7344	Intermediate Similarity	NPD1778	Approved
0.7343	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5401	Approved
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6599	Discontinued
0.7328	Intermediate Similarity	NPD3225	Approved
0.7317	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1481	Phase 2
0.7305	Intermediate Similarity	NPD3750	Approved
0.7302	Intermediate Similarity	NPD9493	Approved
0.7299	Intermediate Similarity	NPD1607	Approved
0.7292	Intermediate Similarity	NPD5049	Phase 3
0.7286	Intermediate Similarity	NPD2897	Discontinued
0.7266	Intermediate Similarity	NPD5585	Approved
0.7266	Intermediate Similarity	NPD5691	Approved
0.7259	Intermediate Similarity	NPD411	Approved
0.7258	Intermediate Similarity	NPD7843	Approved
0.7241	Intermediate Similarity	NPD5403	Approved
0.7231	Intermediate Similarity	NPD1281	Approved
0.7231	Intermediate Similarity	NPD1611	Approved
0.7231	Intermediate Similarity	NPD422	Phase 1
0.7226	Intermediate Similarity	NPD4622	Approved
0.7226	Intermediate Similarity	NPD4618	Approved
0.7226	Intermediate Similarity	NPD447	Suspended
0.7222	Intermediate Similarity	NPD2557	Approved
0.7222	Intermediate Similarity	NPD6671	Approved
0.7194	Intermediate Similarity	NPD1510	Phase 2
0.719	Intermediate Similarity	NPD968	Approved
0.7185	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7095	Approved
0.7183	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3847	Discontinued
0.7154	Intermediate Similarity	NPD2067	Discontinued
0.7153	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7133	Intermediate Similarity	NPD2309	Approved
0.7132	Intermediate Similarity	NPD3444	Approved
0.7132	Intermediate Similarity	NPD3443	Approved
0.7132	Intermediate Similarity	NPD3445	Approved
0.7122	Intermediate Similarity	NPD5688	Approved
0.7122	Intermediate Similarity	NPD5689	Approved
0.7114	Intermediate Similarity	NPD6801	Discontinued
0.7113	Intermediate Similarity	NPD1243	Approved
0.7111	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4661	Approved
0.7103	Intermediate Similarity	NPD4662	Approved
0.7087	Intermediate Similarity	NPD7157	Approved
0.708	Intermediate Similarity	NPD8032	Phase 2
0.7077	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD7033	Discontinued
0.7068	Intermediate Similarity	NPD1283	Approved
0.7063	Intermediate Similarity	NPD4628	Phase 3
0.7054	Intermediate Similarity	NPD9545	Approved
0.7042	Intermediate Similarity	NPD2424	Discontinued
0.7042	Intermediate Similarity	NPD4534	Discontinued
0.704	Intermediate Similarity	NPD1137	Approved
0.704	Intermediate Similarity	NPD1139	Approved
0.7039	Intermediate Similarity	NPD7075	Discontinued
0.7016	Intermediate Similarity	NPD5451	Approved
0.7015	Intermediate Similarity	NPD987	Approved
0.7007	Intermediate Similarity	NPD920	Approved
0.7	Intermediate Similarity	NPD3049	Approved
0.6993	Remote Similarity	NPD919	Approved
0.6992	Remote Similarity	NPD4359	Approved
0.6992	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2614	Approved
0.6984	Remote Similarity	NPD821	Approved
0.6984	Remote Similarity	NPD1138	Approved
0.6975	Remote Similarity	NPD1238	Approved
0.6974	Remote Similarity	NPD3882	Suspended
0.6966	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5647	Approved
0.6959	Remote Similarity	NPD957	Approved
0.6942	Remote Similarity	NPD9261	Approved
0.6939	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD7411	Suspended
0.6929	Remote Similarity	NPD594	Approved
0.6929	Remote Similarity	NPD592	Approved
0.6929	Remote Similarity	NPD5283	Phase 1
0.6923	Remote Similarity	NPD5958	Discontinued
0.6923	Remote Similarity	NPD1548	Phase 1
0.6913	Remote Similarity	NPD3226	Approved
0.6912	Remote Similarity	NPD454	Approved
0.6908	Remote Similarity	NPD3817	Phase 2
0.6908	Remote Similarity	NPD5402	Approved
0.6906	Remote Similarity	NPD2979	Phase 3
0.6903	Remote Similarity	NPD1247	Approved
0.6901	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6099	Approved
0.6901	Remote Similarity	NPD6100	Approved
0.6899	Remote Similarity	NPD3596	Phase 2
0.6899	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3294	Phase 2
0.6885	Remote Similarity	NPD1237	Approved
0.6885	Remote Similarity	NPD164	Approved
0.6884	Remote Similarity	NPD1048	Approved
0.6871	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1184	Approved
0.6857	Remote Similarity	NPD4340	Discontinued
0.6853	Remote Similarity	NPD6005	Phase 3
0.6853	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5762	Approved
0.6853	Remote Similarity	NPD6002	Phase 3
0.6853	Remote Similarity	NPD6004	Phase 3
0.6853	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5763	Approved
0.6849	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD1610	Phase 2
0.6828	Remote Similarity	NPD7003	Approved
0.6825	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6387	Discontinued
0.6821	Remote Similarity	NPD958	Approved
0.6821	Remote Similarity	NPD5889	Approved
0.6821	Remote Similarity	NPD5890	Approved
0.6818	Remote Similarity	NPD2554	Approved
0.6818	Remote Similarity	NPD2556	Approved
0.6815	Remote Similarity	NPD8651	Approved
0.6806	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1511	Approved
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2182	Approved
0.68	Remote Similarity	NPD2649	Approved
0.68	Remote Similarity	NPD2651	Approved
0.6794	Remote Similarity	NPD2486	Discontinued
0.6794	Remote Similarity	NPD6580	Approved
0.6794	Remote Similarity	NPD6581	Approved
0.6788	Remote Similarity	NPD9494	Approved
0.6783	Remote Similarity	NPD6032	Approved
0.6781	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3873	Phase 3
0.6779	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3869	Phase 3
0.6776	Remote Similarity	NPD7317	Phase 3
0.6776	Remote Similarity	NPD1934	Approved
0.6776	Remote Similarity	NPD6844	Discontinued
0.6776	Remote Similarity	NPD6280	Approved

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