NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	511.73
Volume:	295.188
LogP:	5.132
LogD:	2.845
LogS:	-5.186
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	2.394
Fsp3:	0.077
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	1.6191715985769406e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.708
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	100.69466400146484%
Volume Distribution (VD):	1.83
Pgp-substrate:	3.013420343399048%

ADMET: Metabolism

CYP1A2-inhibitor:	0.68
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.759
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	0.857
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.402
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.539
Skin Sensitization:	0.916
Carcinogencity:	0.072
Eye Corrosion:	0.009
Eye Irritation:	0.946
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC54543

Natural Product ID:	NPC54543
*Common Name:**	3,3',5,5'-Tetrabromo-4,4'-Dihydroxydiphenylmethane
IUPAC Name:	2,6-dibromo-4-[(3,5-dibromo-4-hydroxyphenyl)methyl]phenol
Synonyms:
Standard InCHIKey:	WPZJSWWEEJJSIZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8Br4O2/c14-8-2-6(3-9(15)12(8)18)1-7-4-10(16)13(19)11(17)5-7/h2-5,18-19H,1H2
SMILES:	Brc1cc(Cc2cc(Br)c(c(c2)Br)O)cc(c1O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253698
PubChem CID:	89069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	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
MIC	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[509000]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	>	100.0	ug.mL-1	PMID[509000]

☑ 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 NPC54543 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	590
0.1-0.2	3271
0.2-0.3	12169
0.3-0.4	8505
0.4-0.5	10558
0.5-0.6	6271
0.6-0.7	1125
0.7-0.8	191
0.8-0.85	9
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC473358
0.9515	High Similarity	NPC471495
0.9252	High Similarity	NPC471488
0.9074	High Similarity	NPC33244
0.8938	High Similarity	NPC471486
0.8818	High Similarity	NPC94217
0.8624	High Similarity	NPC471487
0.8596	High Similarity	NPC38483
0.8547	High Similarity	NPC105999
0.8532	High Similarity	NPC473372
0.8319	Intermediate Similarity	NPC213414
0.8319	Intermediate Similarity	NPC115803
0.8264	Intermediate Similarity	NPC13004
0.825	Intermediate Similarity	NPC220311
0.8205	Intermediate Similarity	NPC180207
0.8155	Intermediate Similarity	NPC45040
0.8151	Intermediate Similarity	NPC296202
0.8067	Intermediate Similarity	NPC7830
0.8	Intermediate Similarity	NPC128062
0.8	Intermediate Similarity	NPC151715
0.7984	Intermediate Similarity	NPC478071
0.7934	Intermediate Similarity	NPC84606
0.7925	Intermediate Similarity	NPC26244
0.7925	Intermediate Similarity	NPC274678
0.792	Intermediate Similarity	NPC475735
0.792	Intermediate Similarity	NPC11449
0.7913	Intermediate Similarity	NPC59387
0.7874	Intermediate Similarity	NPC471328
0.7851	Intermediate Similarity	NPC219444
0.785	Intermediate Similarity	NPC473388
0.7843	Intermediate Similarity	NPC252149
0.784	Intermediate Similarity	NPC474614
0.771	Intermediate Similarity	NPC81137
0.7706	Intermediate Similarity	NPC132078
0.7706	Intermediate Similarity	NPC92730
0.7706	Intermediate Similarity	NPC216468
0.7706	Intermediate Similarity	NPC51333
0.7706	Intermediate Similarity	NPC78119
0.7705	Intermediate Similarity	NPC116562
0.7698	Intermediate Similarity	NPC99280
0.7698	Intermediate Similarity	NPC474091
0.7692	Intermediate Similarity	NPC177967
0.7692	Intermediate Similarity	NPC471237
0.7685	Intermediate Similarity	NPC132271
0.7685	Intermediate Similarity	NPC82664
0.7685	Intermediate Similarity	NPC216520
0.7685	Intermediate Similarity	NPC292730
0.768	Intermediate Similarity	NPC122359
0.768	Intermediate Similarity	NPC159987
0.768	Intermediate Similarity	NPC78061
0.7667	Intermediate Similarity	NPC100395
0.7656	Intermediate Similarity	NPC300678
0.7638	Intermediate Similarity	NPC473724
0.7636	Intermediate Similarity	NPC213730
0.7623	Intermediate Similarity	NPC136543
0.7619	Intermediate Similarity	NPC123273
0.7619	Intermediate Similarity	NPC242240
0.7619	Intermediate Similarity	NPC318325
0.7619	Intermediate Similarity	NPC258219
0.7615	Intermediate Similarity	NPC309667
0.7615	Intermediate Similarity	NPC225464
0.7607	Intermediate Similarity	NPC76400
0.7597	Intermediate Similarity	NPC244890
0.7597	Intermediate Similarity	NPC163560
0.7596	Intermediate Similarity	NPC23167
0.7581	Intermediate Similarity	NPC137117
0.7581	Intermediate Similarity	NPC236265
0.7578	Intermediate Similarity	NPC43613
0.7573	Intermediate Similarity	NPC175313
0.757	Intermediate Similarity	NPC271440
0.7568	Intermediate Similarity	NPC40258
0.7568	Intermediate Similarity	NPC7686
0.7568	Intermediate Similarity	NPC91461
0.7563	Intermediate Similarity	NPC79844
0.7547	Intermediate Similarity	NPC300017
0.7538	Intermediate Similarity	NPC312155
0.7524	Intermediate Similarity	NPC113460
0.7524	Intermediate Similarity	NPC25493
0.7521	Intermediate Similarity	NPC117759
0.75	Intermediate Similarity	NPC197766
0.75	Intermediate Similarity	NPC135784
0.75	Intermediate Similarity	NPC471236
0.75	Intermediate Similarity	NPC197783
0.75	Intermediate Similarity	NPC168829
0.75	Intermediate Similarity	NPC76938
0.7477	Intermediate Similarity	NPC304541
0.7476	Intermediate Similarity	NPC265146
0.7462	Intermediate Similarity	NPC120114
0.7462	Intermediate Similarity	NPC71888
0.7459	Intermediate Similarity	NPC474146
0.7455	Intermediate Similarity	NPC32674
0.7453	Intermediate Similarity	NPC177420
0.7453	Intermediate Similarity	NPC70436
0.7453	Intermediate Similarity	NPC280347
0.7442	Intermediate Similarity	NPC259017
0.7434	Intermediate Similarity	NPC30506
0.7434	Intermediate Similarity	NPC8931
0.7434	Intermediate Similarity	NPC471511
0.7434	Intermediate Similarity	NPC288411
0.7434	Intermediate Similarity	NPC261573
0.7434	Intermediate Similarity	NPC119860
0.7434	Intermediate Similarity	NPC120693
0.7431	Intermediate Similarity	NPC32714
0.7424	Intermediate Similarity	NPC224663
0.7419	Intermediate Similarity	NPC229213
0.7407	Intermediate Similarity	NPC147137
0.7407	Intermediate Similarity	NPC325292
0.7407	Intermediate Similarity	NPC138117
0.7405	Intermediate Similarity	NPC245386
0.7404	Intermediate Similarity	NPC248817
0.7383	Intermediate Similarity	NPC55561
0.7368	Intermediate Similarity	NPC154899
0.7368	Intermediate Similarity	NPC271942
0.7368	Intermediate Similarity	NPC138942
0.7368	Intermediate Similarity	NPC99557
0.7368	Intermediate Similarity	NPC474839
0.7368	Intermediate Similarity	NPC233396
0.7368	Intermediate Similarity	NPC156356
0.7368	Intermediate Similarity	NPC239291
0.7368	Intermediate Similarity	NPC219286
0.736	Intermediate Similarity	NPC473572
0.736	Intermediate Similarity	NPC474169
0.7358	Intermediate Similarity	NPC104216
0.7344	Intermediate Similarity	NPC150929
0.7339	Intermediate Similarity	NPC316301
0.7339	Intermediate Similarity	NPC27323
0.7333	Intermediate Similarity	NPC118794
0.7333	Intermediate Similarity	NPC155393
0.7323	Intermediate Similarity	NPC43706
0.7321	Intermediate Similarity	NPC294741
0.7315	Intermediate Similarity	NPC204210
0.7315	Intermediate Similarity	NPC155908
0.7313	Intermediate Similarity	NPC160932
0.7308	Intermediate Similarity	NPC124436
0.7304	Intermediate Similarity	NPC92623
0.7304	Intermediate Similarity	NPC248904
0.7304	Intermediate Similarity	NPC188677
0.7304	Intermediate Similarity	NPC54765
0.7304	Intermediate Similarity	NPC135464
0.7304	Intermediate Similarity	NPC113457
0.7299	Intermediate Similarity	NPC272868
0.7299	Intermediate Similarity	NPC122599
0.7299	Intermediate Similarity	NPC270848
0.7297	Intermediate Similarity	NPC201967
0.7293	Intermediate Similarity	NPC213471
0.7287	Intermediate Similarity	NPC105702
0.7281	Intermediate Similarity	NPC254965
0.7281	Intermediate Similarity	NPC327811
0.728	Intermediate Similarity	NPC47790
0.7273	Intermediate Similarity	NPC313650
0.7273	Intermediate Similarity	NPC144682
0.7273	Intermediate Similarity	NPC8392
0.7266	Intermediate Similarity	NPC474147
0.7266	Intermediate Similarity	NPC473708
0.7266	Intermediate Similarity	NPC202776
0.7264	Intermediate Similarity	NPC407
0.7264	Intermediate Similarity	NPC184169
0.7264	Intermediate Similarity	NPC307235
0.7257	Intermediate Similarity	NPC100340
0.7257	Intermediate Similarity	NPC12221
0.7257	Intermediate Similarity	NPC143659
0.7244	Intermediate Similarity	NPC142776
0.7232	Intermediate Similarity	NPC275104
0.7232	Intermediate Similarity	NPC130193
0.7232	Intermediate Similarity	NPC128723
0.7222	Intermediate Similarity	NPC192
0.7222	Intermediate Similarity	NPC300478
0.7206	Intermediate Similarity	NPC89341
0.7196	Intermediate Similarity	NPC27974
0.719	Intermediate Similarity	NPC50782
0.7179	Intermediate Similarity	NPC11554
0.7179	Intermediate Similarity	NPC61885
0.7179	Intermediate Similarity	NPC75440
0.7179	Intermediate Similarity	NPC262365
0.7179	Intermediate Similarity	NPC95344
0.7179	Intermediate Similarity	NPC63698
0.7174	Intermediate Similarity	NPC109346
0.7168	Intermediate Similarity	NPC223393
0.7168	Intermediate Similarity	NPC275053
0.7168	Intermediate Similarity	NPC161571
0.7168	Intermediate Similarity	NPC248573
0.7156	Intermediate Similarity	NPC270547
0.7156	Intermediate Similarity	NPC306074
0.7155	Intermediate Similarity	NPC69332
0.7155	Intermediate Similarity	NPC29989
0.7155	Intermediate Similarity	NPC271274
0.7155	Intermediate Similarity	NPC70843
0.7155	Intermediate Similarity	NPC95178
0.7154	Intermediate Similarity	NPC85049
0.7143	Intermediate Similarity	NPC260000
0.7143	Intermediate Similarity	NPC77492
0.7143	Intermediate Similarity	NPC109955
0.7143	Intermediate Similarity	NPC319826
0.7143	Intermediate Similarity	NPC107619
0.7143	Intermediate Similarity	NPC156313
0.7132	Intermediate Similarity	NPC474128
0.713	Intermediate Similarity	NPC102216
0.713	Intermediate Similarity	NPC241891
0.713	Intermediate Similarity	NPC323810
0.713	Intermediate Similarity	NPC98772

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 NPC54543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	538
0.1-0.2	1057
0.2-0.3	2076
0.3-0.4	3110
0.4-0.5	1652
0.5-0.6	627
0.6-0.7	79
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7925	Intermediate Similarity	NPD2859	Approved
0.7925	Intermediate Similarity	NPD2860	Approved
0.783	Intermediate Similarity	NPD2934	Approved
0.783	Intermediate Similarity	NPD2933	Approved
0.7748	Intermediate Similarity	NPD9244	Approved
0.7706	Intermediate Similarity	NPD3020	Approved
0.7559	Intermediate Similarity	NPD9718	Approved
0.7339	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD111	Approved
0.7273	Intermediate Similarity	NPD1809	Phase 2
0.7168	Intermediate Similarity	NPD1242	Phase 1
0.7164	Intermediate Similarity	NPD1169	Approved
0.7119	Intermediate Similarity	NPD3022	Approved
0.7119	Intermediate Similarity	NPD3021	Approved
0.7105	Intermediate Similarity	NPD940	Approved
0.7105	Intermediate Similarity	NPD846	Approved
0.7091	Intermediate Similarity	NPD845	Approved
0.7023	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD288	Approved
0.687	Remote Similarity	NPD3028	Approved
0.687	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2342	Discontinued
0.6757	Remote Similarity	NPD2296	Approved
0.6748	Remote Similarity	NPD2228	Approved
0.6748	Remote Similarity	NPD2229	Approved
0.6748	Remote Similarity	NPD2234	Approved
0.6723	Remote Similarity	NPD968	Approved
0.6695	Remote Similarity	NPD9608	Approved
0.6695	Remote Similarity	NPD9610	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6585	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1792	Phase 2
0.6557	Remote Similarity	NPD4750	Phase 3
0.6512	Remote Similarity	NPD2286	Discontinued
0.6512	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5304	Approved
0.6484	Remote Similarity	NPD3091	Approved
0.6484	Remote Similarity	NPD1548	Phase 1
0.6484	Remote Similarity	NPD5303	Approved
0.648	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD228	Approved
0.6446	Remote Similarity	NPD1444	Approved
0.6446	Remote Similarity	NPD1445	Approved
0.6434	Remote Similarity	NPD4093	Discontinued
0.6423	Remote Similarity	NPD5451	Approved
0.6412	Remote Similarity	NPD1610	Phase 2
0.641	Remote Similarity	NPD9273	Approved
0.6408	Remote Similarity	NPD9087	Approved
0.64	Remote Similarity	NPD9379	Approved
0.64	Remote Similarity	NPD9377	Approved
0.6385	Remote Similarity	NPD2932	Approved
0.6385	Remote Similarity	NPD4059	Approved
0.6385	Remote Similarity	NPD3019	Approved
0.6385	Remote Similarity	NPD4589	Approved
0.6381	Remote Similarity	NPD9294	Approved
0.6378	Remote Similarity	NPD256	Approved
0.6378	Remote Similarity	NPD255	Approved
0.6357	Remote Similarity	NPD7330	Discontinued
0.6341	Remote Similarity	NPD2684	Approved
0.6333	Remote Similarity	NPD9500	Approved
0.6321	Remote Similarity	NPD9088	Approved
0.6316	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4288	Approved
0.6316	Remote Similarity	NPD4659	Approved
0.6316	Remote Similarity	NPD6583	Phase 3
0.6316	Remote Similarity	NPD6582	Phase 2
0.6288	Remote Similarity	NPD1535	Discovery
0.6288	Remote Similarity	NPD3092	Approved
0.627	Remote Similarity	NPD2496	Approved
0.627	Remote Similarity	NPD2497	Approved
0.627	Remote Similarity	NPD5535	Approved
0.626	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.626	Remote Similarity	NPD1751	Approved
0.625	Remote Similarity	NPD6671	Approved
0.6241	Remote Similarity	NPD2562	Approved
0.6241	Remote Similarity	NPD1481	Phase 2
0.6241	Remote Similarity	NPD2561	Approved
0.6231	Remote Similarity	NPD1894	Discontinued
0.6222	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1164	Approved
0.6222	Remote Similarity	NPD4103	Phase 2
0.6222	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5283	Phase 1
0.6212	Remote Similarity	NPD3847	Discontinued
0.6212	Remote Similarity	NPD3421	Phase 3
0.6202	Remote Similarity	NPD9568	Approved
0.6202	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6584	Phase 3
0.6172	Remote Similarity	NPD475	Phase 2
0.6167	Remote Similarity	NPD1616	Discontinued
0.6165	Remote Similarity	NPD1201	Approved
0.6154	Remote Similarity	NPD317	Approved
0.6154	Remote Similarity	NPD856	Approved
0.6154	Remote Similarity	NPD318	Approved
0.6154	Remote Similarity	NPD16	Approved
0.6148	Remote Similarity	NPD5310	Approved
0.6148	Remote Similarity	NPD5311	Approved
0.6148	Remote Similarity	NPD1237	Approved
0.6147	Remote Similarity	NPD9093	Approved
0.6142	Remote Similarity	NPD821	Approved
0.6142	Remote Similarity	NPD7843	Approved
0.6136	Remote Similarity	NPD6516	Phase 2
0.6136	Remote Similarity	NPD2667	Approved
0.6136	Remote Similarity	NPD2668	Approved
0.6136	Remote Similarity	NPD5846	Approved
0.6136	Remote Similarity	NPD3095	Discontinued
0.6131	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD2861	Phase 2
0.6111	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD3055	Approved
0.6103	Remote Similarity	NPD3094	Phase 2
0.6103	Remote Similarity	NPD3053	Approved
0.6091	Remote Similarity	NPD9089	Approved
0.609	Remote Similarity	NPD3143	Discontinued
0.6087	Remote Similarity	NPD4908	Phase 1
0.6087	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD1161	Approved
0.6066	Remote Similarity	NPD4656	Approved
0.6066	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4658	Approved
0.6058	Remote Similarity	NPD7451	Discontinued
0.6047	Remote Similarity	NPD497	Approved
0.6047	Remote Similarity	NPD1793	Approved
0.6047	Remote Similarity	NPD1791	Approved
0.6047	Remote Similarity	NPD9618	Approved
0.6047	Remote Similarity	NPD9614	Approved
0.6045	Remote Similarity	NPD422	Phase 1
0.6045	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3027	Phase 3
0.6029	Remote Similarity	NPD1283	Approved
0.6015	Remote Similarity	NPD9384	Approved
0.6015	Remote Similarity	NPD9381	Approved
0.6014	Remote Similarity	NPD5736	Approved
0.6012	Remote Similarity	NPD4287	Approved
0.6	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6	Remote Similarity	NPD709	Approved
0.6	Remote Similarity	NPD7157	Approved
0.6	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6	Remote Similarity	NPD290	Approved
0.6	Remote Similarity	NPD3764	Approved
0.6	Remote Similarity	NPD3070	Discontinued
0.6	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD1470	Approved
0.5985	Remote Similarity	NPD9545	Approved
0.5985	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4817	Approved
0.5984	Remote Similarity	NPD4818	Approved
0.5983	Remote Similarity	NPD159	Clinical (unspecified phase)
0.597	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD498	Approved
0.5969	Remote Similarity	NPD495	Approved
0.5969	Remote Similarity	NPD496	Approved
0.5957	Remote Similarity	NPD6405	Approved
0.5957	Remote Similarity	NPD6407	Approved
0.5956	Remote Similarity	NPD1669	Approved
0.5956	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD3596	Phase 2
0.5954	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7636	Approved
0.5952	Remote Similarity	NPD74	Approved
0.5952	Remote Similarity	NPD9266	Approved
0.5942	Remote Similarity	NPD2194	Approved
0.5942	Remote Similarity	NPD2195	Approved
0.594	Remote Similarity	NPD1651	Approved
0.5935	Remote Similarity	NPD3680	Approved
0.5935	Remote Similarity	NPD4229	Approved
0.5935	Remote Similarity	NPD4231	Approved
0.5935	Remote Similarity	NPD3682	Approved
0.5929	Remote Similarity	NPD5156	Approved
0.5929	Remote Similarity	NPD5155	Approved
0.5915	Remote Similarity	NPD1613	Approved
0.5915	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD4060	Phase 1
0.5915	Remote Similarity	NPD4445	Approved
0.5915	Remote Similarity	NPD1240	Approved
0.5915	Remote Similarity	NPD943	Approved
0.5909	Remote Similarity	NPD9613	Approved
0.5909	Remote Similarity	NPD9616	Approved
0.5909	Remote Similarity	NPD9615	Approved
0.5899	Remote Similarity	NPD3637	Approved
0.5899	Remote Similarity	NPD3636	Approved
0.5899	Remote Similarity	NPD4208	Discontinued
0.5899	Remote Similarity	NPD3635	Approved
0.5897	Remote Similarity	NPD1239	Approved
0.5896	Remote Similarity	NPD4626	Approved
0.5882	Remote Similarity	NPD1608	Approved
0.5882	Remote Similarity	NPD2232	Approved
0.5882	Remote Similarity	NPD1157	Approved
0.5882	Remote Similarity	NPD2233	Approved
0.5882	Remote Similarity	NPD2230	Approved
0.5878	Remote Similarity	NPD6387	Discontinued
0.5873	Remote Similarity	NPD9267	Approved
0.5873	Remote Similarity	NPD9264	Approved
0.5873	Remote Similarity	NPD4095	Clinical (unspecified phase)

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