NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	3.336
LogD:	3.22
LogS:	-4.343
# Rotatable Bonds:	3
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.932
Synthetic Accessibility Score:	2.591
Fsp3:	0.25
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:	-4.696
MDCK Permeability:	2.7777683499152772e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	95.20879364013672%
Volume Distribution (VD):	0.779
Pgp-substrate:	5.741398811340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.87
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.43
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.717

ADMET: Excretion

Clearance (CL):	13.174
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.8
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.904
Carcinogencity:	0.7
Eye Corrosion:	0.088
Eye Irritation:	0.871
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC134968

Natural Product ID:	NPC134968
*Common Name:**	Bauhibenzofurin A
IUPAC Name:	2-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-4,6-dimethoxyphenol
Synonyms:
Standard InCHIKey:	DGLCSBIQWVJZDY-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-18-11-8-12(16(17)15(9-11)19-2)14-7-10-5-3-4-6-13(10)20-14/h3-6,8-9,14,17H,7H2,1-2H3/t14-/m0/s1
SMILES:	COc1cc([C@@H]2Cc3ccccc3O2)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389399
PubChem CID:	44423123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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]
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]
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]

☑ 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	>	73500.0	nM	PMID[521905]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	367600.0	nM	PMID[521905]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	73500.0	nM	PMID[521905]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	130100.0	nM	PMID[521905]
NPT27	Others	Unspecified		IC50	>	73500.0	nM	PMID[521905]

☑ 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 NPC134968 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	412
0.1-0.2	1599
0.2-0.3	5142
0.3-0.4	12894
0.4-0.5	4894
0.5-0.6	4406
0.6-0.7	6807
0.7-0.8	4948
0.8-0.85	882
0.85-0.9	512
0.9-0.95	175
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC254759
0.9697	High Similarity	NPC160283
0.9621	High Similarity	NPC292882
0.9618	High Similarity	NPC472336
0.9618	High Similarity	NPC472334
0.9552	High Similarity	NPC107161
0.9545	High Similarity	NPC474282
0.9545	High Similarity	NPC326797
0.9545	High Similarity	NPC103976
0.9545	High Similarity	NPC107551
0.9545	High Similarity	NPC176051
0.9545	High Similarity	NPC102904
0.9542	High Similarity	NPC472337
0.9481	High Similarity	NPC477616
0.9478	High Similarity	NPC247291
0.9478	High Similarity	NPC311530
0.9457	High Similarity	NPC220935
0.9453	High Similarity	NPC266691
0.9453	High Similarity	NPC19694
0.9412	High Similarity	NPC93323
0.9412	High Similarity	NPC280092
0.9412	High Similarity	NPC45257
0.9412	High Similarity	NPC12641
0.9403	High Similarity	NPC184797
0.9403	High Similarity	NPC27495
0.9403	High Similarity	NPC309124
0.9398	High Similarity	NPC276490
0.9394	High Similarity	NPC201357
0.9394	High Similarity	NPC474206
0.9394	High Similarity	NPC94750
0.9394	High Similarity	NPC255147
0.9394	High Similarity	NPC121812
0.9394	High Similarity	NPC281521
0.9394	High Similarity	NPC112246
0.9394	High Similarity	NPC112939
0.9394	High Similarity	NPC470356
0.9389	High Similarity	NPC475840
0.9375	High Similarity	NPC216836
0.9338	High Similarity	NPC102044
0.9338	High Similarity	NPC85264
0.9338	High Similarity	NPC47633
0.9333	High Similarity	NPC471389
0.9333	High Similarity	NPC263261
0.9333	High Similarity	NPC87725
0.9328	High Similarity	NPC473739
0.9328	High Similarity	NPC236306
0.9328	High Similarity	NPC319647
0.9328	High Similarity	NPC25966
0.9328	High Similarity	NPC232164
0.9328	High Similarity	NPC245207
0.9328	High Similarity	NPC127218
0.9323	High Similarity	NPC227503
0.9323	High Similarity	NPC474639
0.9323	High Similarity	NPC230734
0.9323	High Similarity	NPC476698
0.9323	High Similarity	NPC306441
0.9323	High Similarity	NPC16435
0.9318	High Similarity	NPC310854
0.9318	High Similarity	NPC106215
0.9308	High Similarity	NPC214860
0.9308	High Similarity	NPC299221
0.9308	High Similarity	NPC234488
0.9308	High Similarity	NPC311680
0.9308	High Similarity	NPC51840
0.927	High Similarity	NPC63879
0.9254	High Similarity	NPC211549
0.9248	High Similarity	NPC195022
0.9248	High Similarity	NPC151224
0.9248	High Similarity	NPC234333
0.9248	High Similarity	NPC260898
0.9248	High Similarity	NPC47398
0.9248	High Similarity	NPC61946
0.9242	High Similarity	NPC269528
0.9242	High Similarity	NPC11060
0.9242	High Similarity	NPC37196
0.9242	High Similarity	NPC229442
0.9242	High Similarity	NPC168059
0.9242	High Similarity	NPC158331
0.9242	High Similarity	NPC94236
0.9237	High Similarity	NPC472597
0.9231	High Similarity	NPC10225
0.9231	High Similarity	NPC45824
0.9231	High Similarity	NPC58164
0.9209	High Similarity	NPC21776
0.9209	High Similarity	NPC16269
0.9197	High Similarity	NPC81638
0.9185	High Similarity	NPC471388
0.9179	High Similarity	NPC265433
0.9179	High Similarity	NPC270456
0.9179	High Similarity	NPC162659
0.9179	High Similarity	NPC302701
0.9179	High Similarity	NPC248727
0.9179	High Similarity	NPC269091
0.9179	High Similarity	NPC173660
0.9173	High Similarity	NPC287745
0.9173	High Similarity	NPC317380
0.9167	High Similarity	NPC7903
0.9167	High Similarity	NPC470752
0.9167	High Similarity	NPC127624
0.9167	High Similarity	NPC86655
0.9167	High Similarity	NPC35932
0.9167	High Similarity	NPC204215
0.9167	High Similarity	NPC161203
0.9167	High Similarity	NPC202762
0.9167	High Similarity	NPC6451
0.9167	High Similarity	NPC160991
0.9167	High Similarity	NPC16208
0.9167	High Similarity	NPC175067
0.9167	High Similarity	NPC184447
0.916	High Similarity	NPC472338
0.9154	High Similarity	NPC63179
0.9147	High Similarity	NPC112596
0.913	High Similarity	NPC50250
0.9118	High Similarity	NPC259519
0.9118	High Similarity	NPC22317
0.9111	High Similarity	NPC477938
0.9104	High Similarity	NPC164787
0.9104	High Similarity	NPC473413
0.9104	High Similarity	NPC126409
0.9104	High Similarity	NPC99572
0.9098	High Similarity	NPC263064
0.9091	High Similarity	NPC232275
0.9091	High Similarity	NPC45715
0.9091	High Similarity	NPC12275
0.9091	High Similarity	NPC309787
0.9091	High Similarity	NPC474356
0.9084	High Similarity	NPC273295
0.9084	High Similarity	NPC218856
0.9084	High Similarity	NPC3439
0.9084	High Similarity	NPC158477
0.9084	High Similarity	NPC476968
0.9084	High Similarity	NPC212015
0.9084	High Similarity	NPC222004
0.9084	High Similarity	NPC470258
0.9084	High Similarity	NPC285339
0.9084	High Similarity	NPC202582
0.9084	High Similarity	NPC170844
0.9084	High Similarity	NPC226788
0.9084	High Similarity	NPC190629
0.9084	High Similarity	NPC210623
0.9077	High Similarity	NPC159968
0.9077	High Similarity	NPC324112
0.9077	High Similarity	NPC82679
0.9077	High Similarity	NPC74817
0.9077	High Similarity	NPC210355
0.9077	High Similarity	NPC236760
0.9077	High Similarity	NPC293054
0.9077	High Similarity	NPC169474
0.9077	High Similarity	NPC246620
0.9077	High Similarity	NPC282000
0.9077	High Similarity	NPC50368
0.9077	High Similarity	NPC124452
0.9077	High Similarity	NPC236791
0.9071	High Similarity	NPC101376
0.9065	High Similarity	NPC307466
0.9062	High Similarity	NPC95168
0.9062	High Similarity	NPC121115
0.9044	High Similarity	NPC19869
0.9044	High Similarity	NPC70682
0.9044	High Similarity	NPC260741
0.9037	High Similarity	NPC209985
0.9037	High Similarity	NPC29799
0.9037	High Similarity	NPC477939
0.9037	High Similarity	NPC470802
0.9037	High Similarity	NPC10737
0.9037	High Similarity	NPC177160
0.9037	High Similarity	NPC234952
0.9037	High Similarity	NPC54743
0.9037	High Similarity	NPC156502
0.9037	High Similarity	NPC263367
0.903	High Similarity	NPC326095
0.903	High Similarity	NPC474478
0.903	High Similarity	NPC244983
0.903	High Similarity	NPC49603
0.903	High Similarity	NPC193026
0.903	High Similarity	NPC170694
0.903	High Similarity	NPC187616
0.9023	High Similarity	NPC253105
0.9023	High Similarity	NPC185604
0.9023	High Similarity	NPC219876
0.9023	High Similarity	NPC261619
0.9023	High Similarity	NPC201587
0.9023	High Similarity	NPC61477
0.9023	High Similarity	NPC126029
0.9023	High Similarity	NPC15658
0.9023	High Similarity	NPC78770
0.9015	High Similarity	NPC91291
0.9015	High Similarity	NPC224157
0.9015	High Similarity	NPC192687
0.9015	High Similarity	NPC229231
0.9008	High Similarity	NPC206615
0.9008	High Similarity	NPC186843
0.9008	High Similarity	NPC98631
0.9008	High Similarity	NPC470213
0.9007	High Similarity	NPC301961
0.9007	High Similarity	NPC166584
0.9	High Similarity	NPC103823
0.9	High Similarity	NPC317053
0.9	High Similarity	NPC214406
0.9	High Similarity	NPC324492

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 NPC134968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	886
0.2-0.3	1920
0.3-0.4	2750
0.4-0.5	1565
0.5-0.6	921
0.6-0.7	623
0.7-0.8	122
0.8-0.85	8
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9084	High Similarity	NPD3027	Phase 3
0.9023	High Similarity	NPD1612	Clinical (unspecified phase)
0.9023	High Similarity	NPD1613	Approved
0.8864	High Similarity	NPD1529	Clinical (unspecified phase)
0.8788	High Similarity	NPD1530	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2861	Phase 2
0.82	Intermediate Similarity	NPD1934	Approved
0.8175	Intermediate Similarity	NPD4908	Phase 1
0.8146	Intermediate Similarity	NPD2801	Approved
0.806	Intermediate Similarity	NPD1610	Phase 2
0.8058	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1653	Approved
0.8039	Intermediate Similarity	NPD3882	Suspended
0.803	Intermediate Similarity	NPD1548	Phase 1
0.8026	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4625	Phase 3
0.7971	Intermediate Similarity	NPD3018	Phase 2
0.7941	Intermediate Similarity	NPD4749	Approved
0.7939	Intermediate Similarity	NPD6671	Approved
0.7821	Intermediate Similarity	NPD6234	Discontinued
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.781	Intermediate Similarity	NPD2983	Phase 2
0.781	Intermediate Similarity	NPD2982	Phase 2
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6166	Phase 2
0.7799	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1091	Approved
0.7769	Intermediate Similarity	NPD228	Approved
0.7737	Intermediate Similarity	NPD2981	Phase 2
0.7667	Intermediate Similarity	NPD1511	Approved
0.7658	Intermediate Similarity	NPD5494	Approved
0.7656	Intermediate Similarity	NPD968	Approved
0.7652	Intermediate Similarity	NPD5283	Phase 1
0.7626	Intermediate Similarity	NPD6696	Suspended
0.7613	Intermediate Similarity	NPD37	Approved
0.761	Intermediate Similarity	NPD7199	Phase 2
0.7607	Intermediate Similarity	NPD7074	Phase 3
0.7597	Intermediate Similarity	NPD290	Approved
0.758	Intermediate Similarity	NPD4967	Phase 2
0.758	Intermediate Similarity	NPD4966	Approved
0.758	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD1558	Phase 1
0.7569	Intermediate Similarity	NPD4060	Phase 1
0.7566	Intermediate Similarity	NPD1512	Approved
0.7554	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7546	Intermediate Similarity	NPD7054	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7532	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD4678	Approved
0.7484	Intermediate Similarity	NPD4675	Approved
0.747	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3892	Phase 2
0.7464	Intermediate Similarity	NPD3496	Discontinued
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3620	Phase 2
0.7417	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD422	Phase 1
0.7405	Intermediate Similarity	NPD2684	Approved
0.7405	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD5177	Phase 3
0.74	Intermediate Similarity	NPD6674	Discontinued
0.7383	Intermediate Similarity	NPD5763	Approved
0.7383	Intermediate Similarity	NPD5762	Approved
0.7383	Intermediate Similarity	NPD3540	Phase 1
0.7365	Intermediate Similarity	NPD5588	Approved
0.7349	Intermediate Similarity	NPD6797	Phase 2
0.7348	Intermediate Similarity	NPD3021	Approved
0.7348	Intermediate Similarity	NPD3022	Approved
0.732	Intermediate Similarity	NPD7213	Phase 3
0.732	Intermediate Similarity	NPD7212	Phase 2
0.7319	Intermediate Similarity	NPD1357	Approved
0.7315	Intermediate Similarity	NPD6100	Approved
0.7315	Intermediate Similarity	NPD6099	Approved
0.7315	Intermediate Similarity	NPD3539	Phase 1
0.7313	Intermediate Similarity	NPD7843	Approved
0.7312	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.7303	Intermediate Similarity	NPD2677	Approved
0.7297	Intermediate Similarity	NPD4536	Approved
0.7297	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4538	Approved
0.7285	Intermediate Similarity	NPD4236	Phase 3
0.7285	Intermediate Similarity	NPD1652	Phase 2
0.7285	Intermediate Similarity	NPD4237	Approved
0.7279	Intermediate Similarity	NPD7157	Approved
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD7447	Phase 1
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7262	Intermediate Similarity	NPD7808	Phase 3
0.7262	Intermediate Similarity	NPD7549	Discontinued
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.726	Intermediate Similarity	NPD6233	Phase 2
0.7255	Intermediate Similarity	NPD5058	Phase 3
0.7254	Intermediate Similarity	NPD8651	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7209	Intermediate Similarity	NPD291	Approved
0.7208	Intermediate Similarity	NPD4357	Discontinued
0.7208	Intermediate Similarity	NPD1774	Approved
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7075	Discontinued
0.7202	Intermediate Similarity	NPD6559	Discontinued
0.72	Intermediate Similarity	NPD6032	Approved
0.7192	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD2560	Approved
0.7188	Intermediate Similarity	NPD2563	Approved
0.7183	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1247	Approved
0.7171	Intermediate Similarity	NPD3060	Approved
0.7162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5124	Phase 1
0.7161	Intermediate Similarity	NPD4123	Phase 3
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7151	Intermediate Similarity	NPD7906	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7125	Intermediate Similarity	NPD2977	Approved
0.7125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2978	Approved
0.7124	Intermediate Similarity	NPD6331	Phase 2
0.7124	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7114	Intermediate Similarity	NPD6653	Approved
0.7113	Intermediate Similarity	NPD2235	Phase 2
0.7113	Intermediate Similarity	NPD2231	Phase 2
0.7105	Intermediate Similarity	NPD2424	Discontinued
0.7097	Intermediate Similarity	NPD6799	Approved
0.7095	Intermediate Similarity	NPD2238	Phase 2
0.7093	Intermediate Similarity	NPD4663	Approved
0.7089	Intermediate Similarity	NPD4005	Discontinued
0.7086	Intermediate Similarity	NPD1551	Phase 2
0.7086	Intermediate Similarity	NPD2796	Approved
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7078	Intermediate Similarity	NPD6190	Approved
0.7077	Intermediate Similarity	NPD940	Approved
0.7077	Intermediate Similarity	NPD846	Approved
0.7076	Intermediate Similarity	NPD8054	Approved
0.7076	Intermediate Similarity	NPD8053	Approved
0.707	Intermediate Similarity	NPD5976	Discontinued
0.707	Intermediate Similarity	NPD5403	Approved
0.707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3384	Approved
0.7063	Intermediate Similarity	NPD3383	Approved
0.7063	Intermediate Similarity	NPD3382	Approved
0.7059	Intermediate Similarity	NPD4162	Approved
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7048	Intermediate Similarity	NPD2489	Approved
0.7048	Intermediate Similarity	NPD27	Approved
0.7047	Intermediate Similarity	NPD447	Suspended
0.7047	Intermediate Similarity	NPD5735	Approved
0.7047	Intermediate Similarity	NPD230	Phase 1
0.7042	Intermediate Similarity	NPD1611	Approved
0.7039	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6002	Phase 3
0.7039	Intermediate Similarity	NPD6005	Phase 3
0.7039	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6004	Phase 3
0.7035	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7124	Phase 2
0.703	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6516	Phase 2
0.7021	Intermediate Similarity	NPD5846	Approved
0.7021	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1510	Phase 2
0.702	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5773	Approved
0.7019	Intermediate Similarity	NPD5772	Approved
0.7018	Intermediate Similarity	NPD7312	Approved
0.7018	Intermediate Similarity	NPD4577	Approved
0.7018	Intermediate Similarity	NPD7313	Approved
0.7018	Intermediate Similarity	NPD7310	Approved
0.7018	Intermediate Similarity	NPD4578	Approved
0.7018	Intermediate Similarity	NPD7311	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