NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	419.8
Volume:	258.608
LogP:	5.377
LogD:	2.987
LogS:	-4.834
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	2.314
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741
MDCK Permeability:	1.3910324014432263e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.372
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.328
Plasma Protein Binding (PPB):	99.4050521850586%
Volume Distribution (VD):	2.053
Pgp-substrate:	2.7011969089508057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.646
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	0.791
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.565
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.312
Skin Sensitization:	0.907
Carcinogencity:	0.082
Eye Corrosion:	0.816
Eye Irritation:	0.965
Respiratory Toxicity:	0.252

Download Data

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

Natural Product: NPC94217

Natural Product ID:	NPC94217
*Common Name:**	4,4',6-Tribromo-2,2'-Biphenol
IUPAC Name:	2,4-dibromo-6-(5-bromo-2-hydroxyphenyl)phenol
Synonyms:
Standard InCHIKey:	KLKDPRUXCGOLFU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H7Br3O2/c13-6-1-2-11(16)8(3-6)9-4-7(14)5-10(15)12(9)17/h1-5,16-17H
SMILES:	Brc1ccc(c(c1)c1cc(Br)cc(c1O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641935
PubChem CID:	50899959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives [CHEMONTID:0000052] Brominated biphenyls [CHEMONTID:0003954] Polybrominated biphenyls

*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
NPO30945	Pseudoalteromonas	Genus	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2190.0	nM	PMID[570893]

☑ 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 NPC94217 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	630
0.1-0.2	3085
0.2-0.3	11653
0.3-0.4	8714
0.4-0.5	10096
0.5-0.6	7034
0.6-0.7	1286
0.7-0.8	189
0.8-0.85	1
0.85-0.9	2
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC33244
0.9182	High Similarity	NPC471488
0.9083	High Similarity	NPC473358
0.9083	High Similarity	NPC471487
0.8991	High Similarity	NPC473372
0.8899	High Similarity	NPC471495
0.8818	High Similarity	NPC54543
0.8559	High Similarity	NPC471486
0.8037	Intermediate Similarity	NPC271440
0.7934	Intermediate Similarity	NPC38483
0.784	Intermediate Similarity	NPC213414
0.7798	Intermediate Similarity	NPC128062
0.7795	Intermediate Similarity	NPC13004
0.7778	Intermediate Similarity	NPC220311
0.7769	Intermediate Similarity	NPC300678
0.7731	Intermediate Similarity	NPC76400
0.7719	Intermediate Similarity	NPC288411
0.7699	Intermediate Similarity	NPC12221
0.768	Intermediate Similarity	NPC296202
0.7652	Intermediate Similarity	NPC138942
0.7642	Intermediate Similarity	NPC252149
0.7632	Intermediate Similarity	NPC168829
0.7632	Intermediate Similarity	NPC233827
0.7619	Intermediate Similarity	NPC105999
0.7615	Intermediate Similarity	NPC45040
0.76	Intermediate Similarity	NPC7830
0.7589	Intermediate Similarity	NPC156313
0.7586	Intermediate Similarity	NPC54765
0.7576	Intermediate Similarity	NPC163560
0.7576	Intermediate Similarity	NPC244890
0.7557	Intermediate Similarity	NPC43613
0.7538	Intermediate Similarity	NPC478071
0.7538	Intermediate Similarity	NPC474614
0.7521	Intermediate Similarity	NPC115803
0.7519	Intermediate Similarity	NPC312155
0.7481	Intermediate Similarity	NPC475735
0.7481	Intermediate Similarity	NPC11449
0.7478	Intermediate Similarity	NPC168393
0.7477	Intermediate Similarity	NPC151715
0.7477	Intermediate Similarity	NPC155393
0.7458	Intermediate Similarity	NPC95344
0.7458	Intermediate Similarity	NPC262365
0.7455	Intermediate Similarity	NPC306074
0.7453	Intermediate Similarity	NPC319826
0.7444	Intermediate Similarity	NPC471328
0.744	Intermediate Similarity	NPC180207
0.7438	Intermediate Similarity	NPC59387
0.7436	Intermediate Similarity	NPC67250
0.7424	Intermediate Similarity	NPC259017
0.7411	Intermediate Similarity	NPC274678
0.7411	Intermediate Similarity	NPC26244
0.7407	Intermediate Similarity	NPC307235
0.7407	Intermediate Similarity	NPC407
0.7402	Intermediate Similarity	NPC219444
0.7368	Intermediate Similarity	NPC92730
0.7345	Intermediate Similarity	NPC473388
0.7345	Intermediate Similarity	NPC82664
0.7345	Intermediate Similarity	NPC132271
0.7345	Intermediate Similarity	NPC292730
0.7345	Intermediate Similarity	NPC216520
0.7344	Intermediate Similarity	NPC84606
0.7333	Intermediate Similarity	NPC296683
0.7321	Intermediate Similarity	NPC152415
0.7321	Intermediate Similarity	NPC76938
0.7299	Intermediate Similarity	NPC160932
0.7288	Intermediate Similarity	NPC248904
0.7287	Intermediate Similarity	NPC137117
0.7286	Intermediate Similarity	NPC109346
0.7281	Intermediate Similarity	NPC32674
0.7281	Intermediate Similarity	NPC225464
0.7279	Intermediate Similarity	NPC224663
0.7273	Intermediate Similarity	NPC474091
0.7273	Intermediate Similarity	NPC99280
0.7273	Intermediate Similarity	NPC308689
0.7266	Intermediate Similarity	NPC47790
0.7265	Intermediate Similarity	NPC238696
0.7265	Intermediate Similarity	NPC323810
0.7265	Intermediate Similarity	NPC102216
0.7265	Intermediate Similarity	NPC119860
0.7258	Intermediate Similarity	NPC79844
0.7257	Intermediate Similarity	NPC8392
0.7257	Intermediate Similarity	NPC32714
0.7252	Intermediate Similarity	NPC122359
0.7252	Intermediate Similarity	NPC78061
0.7252	Intermediate Similarity	NPC159987
0.7241	Intermediate Similarity	NPC51015
0.7227	Intermediate Similarity	NPC320439
0.7226	Intermediate Similarity	NPC156356
0.7222	Intermediate Similarity	NPC286904
0.7218	Intermediate Similarity	NPC473724
0.7217	Intermediate Similarity	NPC78119
0.7217	Intermediate Similarity	NPC132078
0.7217	Intermediate Similarity	NPC216468
0.7217	Intermediate Similarity	NPC51333
0.7213	Intermediate Similarity	NPC286222
0.7206	Intermediate Similarity	NPC309667
0.7203	Intermediate Similarity	NPC474839
0.7194	Intermediate Similarity	NPC89341
0.7194	Intermediate Similarity	NPC118794
0.7193	Intermediate Similarity	NPC259512
0.7193	Intermediate Similarity	NPC312132
0.719	Intermediate Similarity	NPC44732
0.7168	Intermediate Similarity	NPC245187
0.7168	Intermediate Similarity	NPC289769
0.7167	Intermediate Similarity	NPC233835
0.7155	Intermediate Similarity	NPC294741
0.7155	Intermediate Similarity	NPC248396
0.7155	Intermediate Similarity	NPC129373
0.7155	Intermediate Similarity	NPC213730
0.7155	Intermediate Similarity	NPC72729
0.7155	Intermediate Similarity	NPC48730
0.7155	Intermediate Similarity	NPC174911
0.7154	Intermediate Similarity	NPC236265
0.7143	Intermediate Similarity	NPC271274
0.7143	Intermediate Similarity	NPC304541
0.7143	Intermediate Similarity	NPC204210
0.7132	Intermediate Similarity	NPC245386
0.7131	Intermediate Similarity	NPC95716
0.713	Intermediate Similarity	NPC152097
0.713	Intermediate Similarity	NPC6597
0.713	Intermediate Similarity	NPC77492
0.713	Intermediate Similarity	NPC79241
0.7119	Intermediate Similarity	NPC254965
0.7119	Intermediate Similarity	NPC475580
0.7119	Intermediate Similarity	NPC475225
0.7119	Intermediate Similarity	NPC327811
0.7117	Intermediate Similarity	NPC318325
0.7117	Intermediate Similarity	NPC242240
0.7117	Intermediate Similarity	NPC123273
0.7117	Intermediate Similarity	NPC258219
0.7107	Intermediate Similarity	NPC58865
0.7107	Intermediate Similarity	NPC314187
0.7107	Intermediate Similarity	NPC202647
0.7101	Intermediate Similarity	NPC471236
0.7101	Intermediate Similarity	NPC271942
0.7101	Intermediate Similarity	NPC197766
0.7099	Intermediate Similarity	NPC142776
0.7097	Intermediate Similarity	NPC473137
0.7097	Intermediate Similarity	NPC12656
0.7094	Intermediate Similarity	NPC100340
0.7094	Intermediate Similarity	NPC143659
0.7094	Intermediate Similarity	NPC91461
0.7094	Intermediate Similarity	NPC7686
0.7094	Intermediate Similarity	NPC40258
0.7091	Intermediate Similarity	NPC23167
0.7087	Intermediate Similarity	NPC117759
0.7087	Intermediate Similarity	NPC100395
0.708	Intermediate Similarity	NPC55903
0.708	Intermediate Similarity	NPC29373
0.7073	Intermediate Similarity	NPC228988
0.7073	Intermediate Similarity	NPC46940
0.7071	Intermediate Similarity	NPC474851
0.7071	Intermediate Similarity	NPC474850
0.7069	Intermediate Similarity	NPC260775
0.7069	Intermediate Similarity	NPC128723
0.7069	Intermediate Similarity	NPC252821
0.7069	Intermediate Similarity	NPC299762
0.7069	Intermediate Similarity	NPC33675
0.7069	Intermediate Similarity	NPC122005
0.7068	Intermediate Similarity	NPC150929
0.7064	Intermediate Similarity	NPC175313
0.7063	Intermediate Similarity	NPC88896
0.7059	Intermediate Similarity	NPC239291
0.7059	Intermediate Similarity	NPC120114
0.7059	Intermediate Similarity	NPC99557
0.7059	Intermediate Similarity	NPC219286
0.7059	Intermediate Similarity	NPC47284
0.7059	Intermediate Similarity	NPC71888
0.7054	Intermediate Similarity	NPC47950
0.7054	Intermediate Similarity	NPC192
0.7054	Intermediate Similarity	NPC136543
0.7054	Intermediate Similarity	NPC300017
0.7034	Intermediate Similarity	NPC135784
0.7034	Intermediate Similarity	NPC108497
0.7034	Intermediate Similarity	NPC269212
0.7034	Intermediate Similarity	NPC471228
0.7034	Intermediate Similarity	NPC475432
0.7034	Intermediate Similarity	NPC235762
0.7034	Intermediate Similarity	NPC319933
0.7031	Intermediate Similarity	NPC474146
0.7027	Intermediate Similarity	NPC113460
0.7027	Intermediate Similarity	NPC27974
0.7027	Intermediate Similarity	NPC25493
0.7025	Intermediate Similarity	NPC61885
0.7025	Intermediate Similarity	NPC174981
0.7025	Intermediate Similarity	NPC63698
0.7018	Intermediate Similarity	NPC316301
0.7018	Intermediate Similarity	NPC27323
0.7016	Intermediate Similarity	NPC35344
0.7016	Intermediate Similarity	NPC141003
0.7015	Intermediate Similarity	NPC85049
0.7009	Intermediate Similarity	NPC225506
0.7009	Intermediate Similarity	NPC12931
0.7009	Intermediate Similarity	NPC130103
0.7009	Intermediate Similarity	NPC70677
0.7009	Intermediate Similarity	NPC130756
0.7	Intermediate Similarity	NPC53740
0.7	Intermediate Similarity	NPC197783
0.7	Intermediate Similarity	NPC155072
0.7	Intermediate Similarity	NPC229213

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 NPC94217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	561
0.1-0.2	1032
0.2-0.3	1988
0.3-0.4	3072
0.4-0.5	1724
0.5-0.6	686
0.6-0.7	74
0.7-0.8	13
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
0.7719	Intermediate Similarity	NPD9244	Approved
0.7411	Intermediate Similarity	NPD2860	Approved
0.7411	Intermediate Similarity	NPD2859	Approved
0.7407	Intermediate Similarity	NPD1169	Approved
0.7368	Intermediate Similarity	NPD3020	Approved
0.7321	Intermediate Similarity	NPD2933	Approved
0.7321	Intermediate Similarity	NPD2934	Approved
0.7304	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD845	Approved
0.7193	Intermediate Similarity	NPD288	Approved
0.7105	Intermediate Similarity	NPD844	Approved
0.7083	Intermediate Similarity	NPD2342	Discontinued
0.7073	Intermediate Similarity	NPD7635	Approved
0.7018	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1809	Phase 2
0.6949	Remote Similarity	NPD846	Approved
0.6949	Remote Similarity	NPD940	Approved
0.6889	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD9718	Approved
0.6867	Remote Similarity	NPD2296	Approved
0.6829	Remote Similarity	NPD3022	Approved
0.6829	Remote Similarity	NPD3021	Approved
0.6825	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD111	Approved
0.6723	Remote Similarity	NPD1242	Phase 1
0.6721	Remote Similarity	NPD968	Approved
0.6695	Remote Similarity	NPD9273	Approved
0.6694	Remote Similarity	NPD4750	Phase 3
0.6562	Remote Similarity	NPD497	Approved
0.656	Remote Similarity	NPD1792	Phase 2
0.6536	Remote Similarity	NPD4288	Approved
0.6512	Remote Similarity	NPD6671	Approved
0.6489	Remote Similarity	NPD5304	Approved
0.6489	Remote Similarity	NPD5303	Approved
0.6484	Remote Similarity	NPD2229	Approved
0.6484	Remote Similarity	NPD498	Approved
0.6484	Remote Similarity	NPD496	Approved
0.6484	Remote Similarity	NPD2228	Approved
0.6484	Remote Similarity	NPD2234	Approved
0.6484	Remote Similarity	NPD495	Approved
0.6481	Remote Similarity	NPD9088	Approved
0.6452	Remote Similarity	NPD1445	Approved
0.6452	Remote Similarity	NPD1444	Approved
0.6446	Remote Similarity	NPD3028	Approved
0.6418	Remote Similarity	NPD1201	Approved
0.6418	Remote Similarity	NPD1610	Phase 2
0.6415	Remote Similarity	NPD9087	Approved
0.6391	Remote Similarity	NPD4589	Approved
0.6391	Remote Similarity	NPD2286	Discontinued
0.6385	Remote Similarity	NPD709	Approved
0.6364	Remote Similarity	NPD1548	Phase 1
0.6364	Remote Similarity	NPD7330	Discontinued
0.635	Remote Similarity	NPD1164	Approved
0.6336	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.629	Remote Similarity	NPD9608	Approved
0.629	Remote Similarity	NPD9610	Approved
0.6289	Remote Similarity	NPD1161	Approved
0.6259	Remote Similarity	NPD2861	Phase 2
0.6241	Remote Similarity	NPD3091	Approved
0.6241	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD1470	Approved
0.6231	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.622	Remote Similarity	NPD9266	Approved
0.622	Remote Similarity	NPD74	Approved
0.6194	Remote Similarity	NPD4093	Discontinued
0.6179	Remote Similarity	NPD1616	Discontinued
0.6172	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4625	Phase 3
0.6148	Remote Similarity	NPD4059	Approved
0.6148	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD3019	Approved
0.6148	Remote Similarity	NPD2932	Approved
0.6142	Remote Similarity	NPD9264	Approved
0.6142	Remote Similarity	NPD290	Approved
0.6142	Remote Similarity	NPD9267	Approved
0.6142	Remote Similarity	NPD9263	Approved
0.6131	Remote Similarity	NPD2230	Approved
0.6131	Remote Similarity	NPD2232	Approved
0.6131	Remote Similarity	NPD2233	Approved
0.6118	Remote Similarity	NPD2184	Approved
0.6118	Remote Similarity	NPD2183	Approved
0.6118	Remote Similarity	NPD4287	Approved
0.6115	Remote Similarity	NPD2797	Approved
0.6106	Remote Similarity	NPD9089	Approved
0.6101	Remote Similarity	NPD1168	Approved
0.6099	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD4908	Phase 1
0.6091	Remote Similarity	NPD9294	Approved
0.608	Remote Similarity	NPD9500	Approved
0.608	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD228	Approved
0.6061	Remote Similarity	NPD1793	Approved
0.6061	Remote Similarity	NPD1791	Approved
0.6061	Remote Similarity	NPD9618	Approved
0.6061	Remote Similarity	NPD9614	Approved
0.6058	Remote Similarity	NPD1611	Approved
0.6058	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3092	Approved
0.6058	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD1535	Discovery
0.6048	Remote Similarity	NPD2802	Phase 3
0.6047	Remote Similarity	NPD5451	Approved
0.6031	Remote Similarity	NPD9379	Approved
0.6031	Remote Similarity	NPD2497	Approved
0.6031	Remote Similarity	NPD9377	Approved
0.6031	Remote Similarity	NPD2496	Approved
0.6029	Remote Similarity	NPD1751	Approved
0.6028	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD9093	Approved
0.6016	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD6387	Discontinued
0.6015	Remote Similarity	NPD255	Approved
0.6015	Remote Similarity	NPD256	Approved
0.6014	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1481	Phase 2
0.6	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4103	Phase 2
0.6	Remote Similarity	NPD3094	Phase 2
0.6	Remote Similarity	NPD1759	Phase 1
0.6	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD1980	Approved
0.5985	Remote Similarity	NPD1981	Approved
0.5985	Remote Similarity	NPD1983	Approved
0.5985	Remote Similarity	NPD5283	Phase 1
0.5984	Remote Similarity	NPD9697	Approved
0.5971	Remote Similarity	NPD6582	Phase 2
0.5971	Remote Similarity	NPD4659	Approved
0.5971	Remote Similarity	NPD4749	Approved
0.5971	Remote Similarity	NPD6583	Phase 3
0.597	Remote Similarity	NPD9493	Approved
0.597	Remote Similarity	NPD7636	Approved
0.5969	Remote Similarity	NPD2684	Approved
0.5956	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4658	Approved
0.5952	Remote Similarity	NPD4656	Approved
0.5944	Remote Similarity	NPD2372	Approved
0.5942	Remote Similarity	NPD422	Phase 1
0.594	Remote Similarity	NPD475	Phase 2
0.5931	Remote Similarity	NPD4060	Phase 1
0.5931	Remote Similarity	NPD1613	Approved
0.5931	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD1283	Approved
0.5926	Remote Similarity	NPD9615	Approved
0.5926	Remote Similarity	NPD9616	Approved
0.5926	Remote Similarity	NPD9613	Approved
0.5926	Remote Similarity	NPD1758	Phase 1
0.5917	Remote Similarity	NPD1239	Approved
0.5912	Remote Similarity	NPD2668	Approved
0.5912	Remote Similarity	NPD4626	Approved
0.5912	Remote Similarity	NPD3095	Discontinued
0.5912	Remote Similarity	NPD2667	Approved
0.5909	Remote Similarity	NPD1138	Approved
0.5909	Remote Similarity	NPD5535	Approved
0.5906	Remote Similarity	NPD1237	Approved
0.5903	Remote Similarity	NPD3268	Approved
0.5899	Remote Similarity	NPD1157	Approved
0.5899	Remote Similarity	NPD2562	Approved
0.5899	Remote Similarity	NPD1608	Approved
0.5899	Remote Similarity	NPD2561	Approved
0.5896	Remote Similarity	NPD2557	Approved
0.5887	Remote Similarity	NPD1203	Approved
0.5882	Remote Similarity	NPD316	Approved
0.5882	Remote Similarity	NPD9295	Approved
0.5873	Remote Similarity	NPD4817	Approved
0.5873	Remote Similarity	NPD4818	Approved
0.587	Remote Similarity	NPD3847	Discontinued
0.587	Remote Similarity	NPD3143	Discontinued
0.587	Remote Similarity	NPD3421	Phase 3
0.5865	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1398	Phase 1
0.5862	Remote Similarity	NPD6407	Approved
0.5862	Remote Similarity	NPD6405	Approved
0.5857	Remote Similarity	NPD1669	Approved
0.5857	Remote Similarity	NPD1755	Approved
0.5852	Remote Similarity	NPD9568	Approved
0.5845	Remote Similarity	NPD6584	Phase 3
0.5845	Remote Similarity	NPD2798	Approved
0.5839	Remote Similarity	NPD3443	Approved
0.5839	Remote Similarity	NPD1651	Approved
0.5839	Remote Similarity	NPD3444	Approved
0.5839	Remote Similarity	NPD3445	Approved
0.5833	Remote Similarity	NPD3027	Phase 3
0.5833	Remote Similarity	NPD1139	Approved
0.5833	Remote Similarity	NPD1137	Approved
0.5827	Remote Similarity	NPD3680	Approved
0.5827	Remote Similarity	NPD4229	Approved
0.5827	Remote Similarity	NPD4231	Approved
0.5827	Remote Similarity	NPD3682	Approved
0.5827	Remote Similarity	NPD9261	Approved
0.5827	Remote Similarity	NPD1091	Approved
0.5822	Remote Similarity	NPD943	Approved
0.5822	Remote Similarity	NPD4445	Approved
0.5822	Remote Similarity	NPD1240	Approved
0.5821	Remote Similarity	NPD9281	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