NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	3.822
LogD:	3.146
LogS:	-3.605
# 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:	0.836
Synthetic Accessibility Score:	2.596
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	2.418281110294629e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	98.71617126464844%
Volume Distribution (VD):	0.813
Pgp-substrate:	1.1597386598587036%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.646
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.484
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	11.056
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.688
Skin Sensitization:	0.948
Carcinogencity:	0.303
Eye Corrosion:	0.005
Eye Irritation:	0.916
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC255147

Natural Product ID:	NPC255147
*Common Name:**	Bauhinoxepin C
IUPAC Name:	3-methoxy-2-methyl-5,6-dihydrobenzo[b][1]benzoxepine-1,7-diol
Synonyms:	bauhinoxepin C
Standard InCHIKey:	ZUEQCKLQPIWVQY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-9-14(19-2)8-10-6-7-11-12(17)4-3-5-13(11)20-16(10)15(9)18/h3-5,8,17-18H,6-7H2,1-2H3
SMILES:	COc1cc2CCc3c(Oc2c(c1C)O)cccc3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226611
PubChem CID:	16679963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines [CHEMONTID:0001988] Dibenzoxepines

*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]
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]
NPO5635	Bauhinia purpurea	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	=	44800.0	nM	PMID[572099]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	183800.0	nM	PMID[572099]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	73500.0	nM	PMID[572099]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	79400.0	nM	PMID[572099]
NPT27	Others	Unspecified		IC50	=	32300.0	nM	PMID[572099]

☑ 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 NPC255147 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	449
0.1-0.2	1818
0.2-0.3	5918
0.3-0.4	13200
0.4-0.5	3874
0.5-0.6	4469
0.6-0.7	7281
0.7-0.8	4462
0.8-0.85	697
0.85-0.9	383
0.9-0.95	132
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC281521
1.0	High Similarity	NPC201357
0.9844	High Similarity	NPC269528
0.969	High Similarity	NPC37196
0.969	High Similarity	NPC94236
0.9618	High Similarity	NPC476698
0.9612	High Similarity	NPC161203
0.9457	High Similarity	NPC229231
0.9453	High Similarity	NPC63179
0.9453	High Similarity	NPC266691
0.9394	High Similarity	NPC134968
0.9375	High Similarity	NPC236760
0.9375	High Similarity	NPC216836
0.9375	High Similarity	NPC50368
0.9323	High Similarity	NPC472334
0.9323	High Similarity	NPC472336
0.9308	High Similarity	NPC214860
0.9308	High Similarity	NPC299221
0.9308	High Similarity	NPC234488
0.9308	High Similarity	NPC51840
0.9308	High Similarity	NPC311680
0.9308	High Similarity	NPC220935
0.9254	High Similarity	NPC107551
0.9254	High Similarity	NPC102904
0.9254	High Similarity	NPC474282
0.9254	High Similarity	NPC176051
0.9254	High Similarity	NPC103976
0.9254	High Similarity	NPC276490
0.9254	High Similarity	NPC326797
0.9248	High Similarity	NPC261873
0.9248	High Similarity	NPC283009
0.9248	High Similarity	NPC472337
0.9237	High Similarity	NPC82503
0.9231	High Similarity	NPC58164
0.9231	High Similarity	NPC10225
0.9231	High Similarity	NPC45824
0.9197	High Similarity	NPC477616
0.9185	High Similarity	NPC319647
0.9185	High Similarity	NPC245207
0.9185	High Similarity	NPC25966
0.9185	High Similarity	NPC127218
0.9173	High Similarity	NPC106215
0.9173	High Similarity	NPC103967
0.9167	High Similarity	NPC86655
0.9167	High Similarity	NPC202762
0.9167	High Similarity	NPC6451
0.9167	High Similarity	NPC127624
0.9147	High Similarity	NPC112596
0.9118	High Similarity	NPC254759
0.9118	High Similarity	NPC160283
0.9111	High Similarity	NPC25111
0.9111	High Similarity	NPC6262
0.9111	High Similarity	NPC90615
0.9111	High Similarity	NPC73535
0.9111	High Similarity	NPC201145
0.9111	High Similarity	NPC272157
0.9104	High Similarity	NPC470356
0.9104	High Similarity	NPC94750
0.9104	High Similarity	NPC121812
0.9104	High Similarity	NPC195022
0.9104	High Similarity	NPC112246
0.9104	High Similarity	NPC112939
0.9104	High Similarity	NPC474206
0.9098	High Similarity	NPC168059
0.9098	High Similarity	NPC36661
0.9098	High Similarity	NPC475840
0.9098	High Similarity	NPC229442
0.9091	High Similarity	NPC232275
0.9091	High Similarity	NPC474356
0.9091	High Similarity	NPC45715
0.9091	High Similarity	NPC12275
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	NPC246620
0.9077	High Similarity	NPC293054
0.9077	High Similarity	NPC169474
0.9077	High Similarity	NPC282000
0.9077	High Similarity	NPC124452
0.9077	High Similarity	NPC236791
0.9062	High Similarity	NPC95168
0.9062	High Similarity	NPC121115
0.9051	High Similarity	NPC471389
0.9044	High Similarity	NPC292882
0.9044	High Similarity	NPC19869
0.9037	High Similarity	NPC173660
0.9037	High Similarity	NPC306441
0.9037	High Similarity	NPC270456
0.9037	High Similarity	NPC16435
0.9037	High Similarity	NPC162659
0.9037	High Similarity	NPC114155
0.9037	High Similarity	NPC227503
0.9037	High Similarity	NPC474639
0.9037	High Similarity	NPC230734
0.9037	High Similarity	NPC265433
0.9037	High Similarity	NPC476639
0.9037	High Similarity	NPC248727
0.9037	High Similarity	NPC300846
0.903	High Similarity	NPC310854
0.903	High Similarity	NPC317380
0.9023	High Similarity	NPC218884
0.9015	High Similarity	NPC224157
0.9015	High Similarity	NPC192687
0.9	High Similarity	NPC245060
0.9	High Similarity	NPC103823
0.9	High Similarity	NPC214406
0.9	High Similarity	NPC44748
0.9	High Similarity	NPC112251
0.9	High Similarity	NPC223136
0.9	High Similarity	NPC18924
0.9	High Similarity	NPC28730
0.9	High Similarity	NPC78974
0.8986	High Similarity	NPC107161
0.8986	High Similarity	NPC472332
0.8986	High Similarity	NPC472335
0.8984	High Similarity	NPC135414
0.8978	High Similarity	NPC259519
0.8978	High Similarity	NPC295719
0.8978	High Similarity	NPC34431
0.8978	High Similarity	NPC165026
0.8978	High Similarity	NPC73505
0.8971	High Similarity	NPC211549
0.8963	High Similarity	NPC111655
0.8963	High Similarity	NPC47398
0.8963	High Similarity	NPC252095
0.8963	High Similarity	NPC151224
0.8963	High Similarity	NPC61946
0.8963	High Similarity	NPC260898
0.8963	High Similarity	NPC234333
0.8955	High Similarity	NPC11060
0.8947	High Similarity	NPC472597
0.8939	High Similarity	NPC190144
0.8931	High Similarity	NPC470699
0.8923	High Similarity	NPC298757
0.8923	High Similarity	NPC116907
0.8923	High Similarity	NPC233410
0.8923	High Similarity	NPC117214
0.8923	High Similarity	NPC57490
0.8923	High Similarity	NPC193544
0.8923	High Similarity	NPC251855
0.8923	High Similarity	NPC203133
0.8923	High Similarity	NPC472093
0.8923	High Similarity	NPC221077
0.8923	High Similarity	NPC17943
0.8923	High Similarity	NPC265483
0.8923	High Similarity	NPC208950
0.8923	High Similarity	NPC299584
0.8923	High Similarity	NPC475169
0.8923	High Similarity	NPC82483
0.8923	High Similarity	NPC105925
0.8923	High Similarity	NPC234400
0.8923	High Similarity	NPC60885
0.8913	High Similarity	NPC247291
0.8913	High Similarity	NPC311530
0.8906	High Similarity	NPC75713
0.8905	High Similarity	NPC212942
0.8905	High Similarity	NPC260741
0.8905	High Similarity	NPC79622
0.8905	High Similarity	NPC29868
0.8905	High Similarity	NPC70682
0.8905	High Similarity	NPC471388
0.8897	High Similarity	NPC302701
0.8897	High Similarity	NPC269091
0.8881	High Similarity	NPC184447
0.8881	High Similarity	NPC7903
0.8881	High Similarity	NPC35932
0.8881	High Similarity	NPC160991
0.8881	High Similarity	NPC16208
0.8881	High Similarity	NPC470752
0.8872	High Similarity	NPC91291
0.8872	High Similarity	NPC474481
0.8872	High Similarity	NPC126836
0.8872	High Similarity	NPC472338
0.8864	High Similarity	NPC226331
0.8864	High Similarity	NPC154866
0.8864	High Similarity	NPC19694
0.8864	High Similarity	NPC28765
0.8864	High Similarity	NPC46274
0.8857	High Similarity	NPC280092
0.8857	High Similarity	NPC93323
0.8857	High Similarity	NPC12641
0.8857	High Similarity	NPC469795
0.8857	High Similarity	NPC45257
0.8857	High Similarity	NPC50250
0.8855	High Similarity	NPC181361
0.8855	High Similarity	NPC476006
0.8849	High Similarity	NPC175838
0.8846	High Similarity	NPC183446
0.8846	High Similarity	NPC122792
0.8846	High Similarity	NPC228972
0.8841	High Similarity	NPC309124
0.8841	High Similarity	NPC22317
0.8841	High Similarity	NPC27495
0.8841	High Similarity	NPC184797
0.8837	High Similarity	NPC246967
0.8837	High Similarity	NPC474864
0.8832	High Similarity	NPC476171
0.8824	High Similarity	NPC327382

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 NPC255147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	944
0.2-0.3	1942
0.3-0.4	2767
0.4-0.5	1541
0.5-0.6	877
0.6-0.7	574
0.7-0.8	93
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD1529	Clinical (unspecified phase)
0.8797	High Similarity	NPD3027	Phase 3
0.8788	High Similarity	NPD1530	Clinical (unspecified phase)
0.8741	High Similarity	NPD1613	Approved
0.8741	High Similarity	NPD1612	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD4625	Phase 3
0.8209	Intermediate Similarity	NPD4749	Approved
0.8146	Intermediate Similarity	NPD2801	Approved
0.8043	Intermediate Similarity	NPD4908	Phase 1
0.7971	Intermediate Similarity	NPD3018	Phase 2
0.7961	Intermediate Similarity	NPD1934	Approved
0.7939	Intermediate Similarity	NPD6671	Approved
0.7929	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1610	Phase 2
0.7895	Intermediate Similarity	NPD1548	Phase 1
0.7842	Intermediate Similarity	NPD2861	Phase 2
0.7815	Intermediate Similarity	NPD1653	Approved
0.781	Intermediate Similarity	NPD2983	Phase 2
0.781	Intermediate Similarity	NPD2982	Phase 2
0.7792	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD228	Approved
0.7737	Intermediate Similarity	NPD2981	Phase 2
0.7692	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD1511	Approved
0.7652	Intermediate Similarity	NPD5283	Phase 1
0.7643	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6696	Suspended
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1558	Phase 1
0.7566	Intermediate Similarity	NPD1512	Approved
0.7554	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7536	Intermediate Similarity	NPD1091	Approved
0.7519	Intermediate Similarity	NPD968	Approved
0.7517	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7481	Intermediate Similarity	NPD4750	Phase 3
0.7464	Intermediate Similarity	NPD3496	Discontinued
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD422	Phase 1
0.7405	Intermediate Similarity	NPD3817	Phase 2
0.74	Intermediate Similarity	NPD6674	Discontinued
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7383	Intermediate Similarity	NPD3540	Phase 1
0.7378	Intermediate Similarity	NPD3818	Discontinued
0.7372	Intermediate Similarity	NPD4678	Approved
0.7372	Intermediate Similarity	NPD4675	Approved
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3021	Approved
0.7348	Intermediate Similarity	NPD3022	Approved
0.7346	Intermediate Similarity	NPD6232	Discontinued
0.7333	Intermediate Similarity	NPD7054	Approved
0.7328	Intermediate Similarity	NPD290	Approved
0.7315	Intermediate Similarity	NPD3539	Phase 1
0.7303	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7472	Approved
0.7286	Intermediate Similarity	NPD1611	Approved
0.7284	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1398	Phase 1
0.725	Intermediate Similarity	NPD4967	Phase 2
0.725	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD3892	Phase 2
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.7226	Intermediate Similarity	NPD7340	Approved
0.7222	Intermediate Similarity	NPD5494	Approved
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1551	Phase 2
0.7195	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5402	Approved
0.7185	Intermediate Similarity	NPD7843	Approved
0.7183	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7169	Intermediate Similarity	NPD7228	Approved
0.7163	Intermediate Similarity	NPD3705	Approved
0.7161	Intermediate Similarity	NPD7447	Phase 1
0.716	Intermediate Similarity	NPD7549	Discontinued
0.7153	Intermediate Similarity	NPD7157	Approved
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD1778	Approved
0.7133	Intermediate Similarity	NPD8651	Approved
0.7115	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1607	Approved
0.7101	Intermediate Similarity	NPD7251	Discontinued
0.7099	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4357	Discontinued
0.7097	Intermediate Similarity	NPD7212	Phase 2
0.7097	Intermediate Similarity	NPD7213	Phase 3
0.7089	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2677	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
0.7067	Intermediate Similarity	NPD4538	Approved
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4536	Approved
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD7635	Approved
0.7059	Intermediate Similarity	NPD7808	Phase 3
0.7051	Intermediate Similarity	NPD4123	Phase 3
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7047	Intermediate Similarity	NPD447	Suspended
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7044	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6584	Phase 3
0.7032	Intermediate Similarity	NPD7124	Phase 2
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.7014	Intermediate Similarity	NPD2922	Phase 1
0.7013	Intermediate Similarity	NPD3750	Approved
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD1242	Phase 1
0.6994	Remote Similarity	NPD7075	Discontinued
0.6994	Remote Similarity	NPD4055	Discovery
0.6994	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD1549	Phase 2
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6799	Approved
0.6987	Remote Similarity	NPD1774	Approved
0.6981	Remote Similarity	NPD4005	Discontinued
0.698	Remote Similarity	NPD1240	Approved
0.6975	Remote Similarity	NPD2563	Approved
0.6975	Remote Similarity	NPD2560	Approved
0.6974	Remote Similarity	NPD6032	Approved
0.6968	Remote Similarity	NPD2219	Phase 1
0.6966	Remote Similarity	NPD2797	Approved
0.6959	Remote Similarity	NPD6798	Discontinued
0.6953	Remote Similarity	NPD844	Approved
0.695	Remote Similarity	NPD3443	Approved
0.695	Remote Similarity	NPD3445	Approved
0.695	Remote Similarity	NPD3444	Approved
0.6948	Remote Similarity	NPD3060	Approved
0.6947	Remote Similarity	NPD291	Approved
0.6943	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD5124	Phase 1
0.6933	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD1375	Discontinued
0.6914	Remote Similarity	NPD5929	Approved
0.6914	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2674	Phase 3
0.6908	Remote Similarity	NPD5960	Phase 3
0.6908	Remote Similarity	NPD7033	Discontinued
0.6908	Remote Similarity	NPD5588	Approved
0.6908	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1510	Phase 2
0.6908	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD6516	Phase 2
0.6901	Remote Similarity	NPD4626	Approved
0.6901	Remote Similarity	NPD5846	Approved
0.6899	Remote Similarity	NPD6090	Discontinued
0.6897	Remote Similarity	NPD3225	Approved
0.6875	Remote Similarity	NPD2233	Approved
0.6875	Remote Similarity	NPD2232	Approved
0.6875	Remote Similarity	NPD9296	Approved
0.6875	Remote Similarity	NPD2230	Approved
0.6875	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD2235	Phase 2
0.687	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2238	Phase 2
0.6867	Remote Similarity	NPD6959	Discontinued
0.6867	Remote Similarity	NPD943	Approved
0.6867	Remote Similarity	NPD1247	Approved
0.6863	Remote Similarity	NPD2796	Approved
0.6859	Remote Similarity	NPD6190	Approved
0.6857	Remote Similarity	NPD7906	Approved
0.6855	Remote Similarity	NPD5403	Approved
0.6855	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3268	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