NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	309.88
Volume:	195.396
LogP:	2.529
LogD:	2.173
LogS:	-2.897
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	2.724
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	1.5024986169009935e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.383
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	96.57247924804688%
Volume Distribution (VD):	0.892
Pgp-substrate:	8.101404190063477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.729
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.301
CYP2D6-inhibitor:	0.229
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	2.854
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.422
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.073
Skin Sensitization:	0.946
Carcinogencity:	0.187
Eye Corrosion:	0.285
Eye Irritation:	0.963
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC85049

Natural Product ID:	NPC85049
*Common Name:**	2,3-Dibromo-4,5-Dihydroxybenzylmethyl Ether
IUPAC Name:	3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	SOPOZEAOODNSCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8Br2O3/c1-13-3-4-2-5(11)8(12)7(10)6(4)9/h2,11-12H,3H2,1H3
SMILES:	COCc1cc(c(c(c1Br)Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402381
PubChem CID:	316020
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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]
NPO32930	polysiphonia lanosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387639]
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
IC50	2
MIC	10

Activity Type	# Activity
Cell Line	2
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	14600.0	nM	PMID[456017]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	14100.0	nM	PMID[456017]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	100.0	ug.mL-1	PMID[456016]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[456016]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	12.5	ug.mL-1	PMID[456016]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	=	12.5	ug.mL-1	PMID[456016]

☑ 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 NPC85049 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	531
0.1-0.2	2662
0.2-0.3	11257
0.3-0.4	9568
0.4-0.5	6777
0.5-0.6	9261
0.6-0.7	2510
0.7-0.8	95
0.8-0.85	12
0.85-0.9	8
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC226493
0.9919	High Similarity	NPC160081
0.9453	High Similarity	NPC245386
0.9435	High Similarity	NPC43706
0.9426	High Similarity	NPC229213
0.936	High Similarity	NPC473708
0.936	High Similarity	NPC474147
0.935	High Similarity	NPC474169
0.935	High Similarity	NPC473572
0.9313	High Similarity	NPC160932
0.9274	High Similarity	NPC137117
0.9268	High Similarity	NPC47790
0.9173	High Similarity	NPC89341
0.9127	High Similarity	NPC134219
0.9091	High Similarity	NPC271942
0.8984	High Similarity	NPC150929
0.8971	High Similarity	NPC109346
0.8788	High Similarity	NPC163560
0.872	High Similarity	NPC474146
0.8712	High Similarity	NPC303011
0.8699	High Similarity	NPC79844
0.8667	High Similarity	NPC156356
0.8605	High Similarity	NPC220311
0.8605	High Similarity	NPC142776
0.8529	High Similarity	NPC168680
0.8504	High Similarity	NPC227976
0.8485	Intermediate Similarity	NPC474614
0.8456	Intermediate Similarity	NPC224663
0.8438	Intermediate Similarity	NPC136543
0.837	Intermediate Similarity	NPC244890
0.8346	Intermediate Similarity	NPC474536
0.8203	Intermediate Similarity	NPC38483
0.8195	Intermediate Similarity	NPC13004
0.8175	Intermediate Similarity	NPC50782
0.8138	Intermediate Similarity	NPC152947
0.8062	Intermediate Similarity	NPC117759
0.8029	Intermediate Similarity	NPC300678
0.8	Intermediate Similarity	NPC475697
0.7958	Intermediate Similarity	NPC118794
0.7945	Intermediate Similarity	NPC473608
0.7933	Intermediate Similarity	NPC474535
0.7902	Intermediate Similarity	NPC184632
0.7895	Intermediate Similarity	NPC84606
0.7891	Intermediate Similarity	NPC7398
0.7857	Intermediate Similarity	NPC199089
0.782	Intermediate Similarity	NPC219444
0.7786	Intermediate Similarity	NPC312155
0.7635	Intermediate Similarity	NPC178097
0.7571	Intermediate Similarity	NPC43613
0.7568	Intermediate Similarity	NPC88896
0.7557	Intermediate Similarity	NPC221049
0.7554	Intermediate Similarity	NPC105702
0.7519	Intermediate Similarity	NPC181969
0.7519	Intermediate Similarity	NPC320987
0.7519	Intermediate Similarity	NPC477803
0.7482	Intermediate Similarity	NPC55113
0.7466	Intermediate Similarity	NPC250597
0.7463	Intermediate Similarity	NPC35071
0.7463	Intermediate Similarity	NPC148615
0.7463	Intermediate Similarity	NPC177475
0.7447	Intermediate Similarity	NPC158078
0.7444	Intermediate Similarity	NPC255675
0.744	Intermediate Similarity	NPC12278
0.7394	Intermediate Similarity	NPC474135
0.7372	Intermediate Similarity	NPC38980
0.7357	Intermediate Similarity	NPC214553
0.7353	Intermediate Similarity	NPC470804
0.7344	Intermediate Similarity	NPC471495
0.7343	Intermediate Similarity	NPC471328
0.7338	Intermediate Similarity	NPC294870
0.7328	Intermediate Similarity	NPC76400
0.7328	Intermediate Similarity	NPC264558
0.7308	Intermediate Similarity	NPC305490
0.7308	Intermediate Similarity	NPC257124
0.7308	Intermediate Similarity	NPC156840
0.7308	Intermediate Similarity	NPC139617
0.7308	Intermediate Similarity	NPC8547
0.7308	Intermediate Similarity	NPC173746
0.7308	Intermediate Similarity	NPC78918
0.7299	Intermediate Similarity	NPC209567
0.7293	Intermediate Similarity	NPC193067
0.7287	Intermediate Similarity	NPC36108
0.7287	Intermediate Similarity	NPC233731
0.7287	Intermediate Similarity	NPC246358
0.7287	Intermediate Similarity	NPC7097
0.728	Intermediate Similarity	NPC110764
0.7279	Intermediate Similarity	NPC470414
0.7259	Intermediate Similarity	NPC135961
0.7259	Intermediate Similarity	NPC20674
0.7258	Intermediate Similarity	NPC131587
0.7246	Intermediate Similarity	NPC220598
0.7246	Intermediate Similarity	NPC165375
0.7239	Intermediate Similarity	NPC259638
0.7231	Intermediate Similarity	NPC473358
0.7231	Intermediate Similarity	NPC471487
0.7226	Intermediate Similarity	NPC476343
0.7226	Intermediate Similarity	NPC49341
0.7226	Intermediate Similarity	NPC173511
0.7226	Intermediate Similarity	NPC88733
0.7219	Intermediate Similarity	NPC113862
0.7206	Intermediate Similarity	NPC229401
0.7203	Intermediate Similarity	NPC110800
0.7197	Intermediate Similarity	NPC471488
0.7185	Intermediate Similarity	NPC191194
0.7177	Intermediate Similarity	NPC109955
0.7154	Intermediate Similarity	NPC107522
0.7154	Intermediate Similarity	NPC473372
0.7154	Intermediate Similarity	NPC54543
0.7153	Intermediate Similarity	NPC170824
0.7133	Intermediate Similarity	NPC178301
0.7132	Intermediate Similarity	NPC226629
0.7122	Intermediate Similarity	NPC473451
0.7122	Intermediate Similarity	NPC230013
0.7122	Intermediate Similarity	NPC81149
0.7122	Intermediate Similarity	NPC471693
0.7122	Intermediate Similarity	NPC131940
0.7122	Intermediate Similarity	NPC197576
0.7122	Intermediate Similarity	NPC68350
0.7111	Intermediate Similarity	NPC164386
0.7092	Intermediate Similarity	NPC178284
0.7092	Intermediate Similarity	NPC58607
0.7092	Intermediate Similarity	NPC191037
0.7087	Intermediate Similarity	NPC196479
0.708	Intermediate Similarity	NPC41232
0.708	Intermediate Similarity	NPC180207
0.708	Intermediate Similarity	NPC63317
0.7071	Intermediate Similarity	NPC183446
0.7071	Intermediate Similarity	NPC131747
0.7071	Intermediate Similarity	NPC146355
0.7071	Intermediate Similarity	NPC257682
0.7068	Intermediate Similarity	NPC471485
0.7068	Intermediate Similarity	NPC95381
0.7045	Intermediate Similarity	NPC226250
0.7045	Intermediate Similarity	NPC195873
0.7042	Intermediate Similarity	NPC41706
0.7042	Intermediate Similarity	NPC118533
0.7042	Intermediate Similarity	NPC165045
0.7042	Intermediate Similarity	NPC111247
0.7042	Intermediate Similarity	NPC118787
0.7042	Intermediate Similarity	NPC163332
0.7042	Intermediate Similarity	NPC292056
0.7042	Intermediate Similarity	NPC147821
0.7042	Intermediate Similarity	NPC319625
0.7042	Intermediate Similarity	NPC5428
0.7042	Intermediate Similarity	NPC183181
0.7031	Intermediate Similarity	NPC120719
0.7029	Intermediate Similarity	NPC153580
0.7029	Intermediate Similarity	NPC471486
0.7029	Intermediate Similarity	NPC226737
0.7029	Intermediate Similarity	NPC299939
0.7021	Intermediate Similarity	NPC194519
0.7021	Intermediate Similarity	NPC148627
0.7015	Intermediate Similarity	NPC328593
0.7015	Intermediate Similarity	NPC261453
0.7015	Intermediate Similarity	NPC33749
0.7015	Intermediate Similarity	NPC94217
0.7007	Intermediate Similarity	NPC24474
0.7007	Intermediate Similarity	NPC311595
0.7	Intermediate Similarity	NPC251306
0.7	Intermediate Similarity	NPC84086
0.7	Intermediate Similarity	NPC227894
0.7	Intermediate Similarity	NPC125861
0.7	Intermediate Similarity	NPC136319
0.6993	Remote Similarity	NPC45774
0.6993	Remote Similarity	NPC474178
0.6993	Remote Similarity	NPC11258
0.6993	Remote Similarity	NPC472968
0.6993	Remote Similarity	NPC184733
0.6993	Remote Similarity	NPC282703
0.6993	Remote Similarity	NPC21867
0.6993	Remote Similarity	NPC245826
0.6993	Remote Similarity	NPC129570
0.6993	Remote Similarity	NPC128208
0.6993	Remote Similarity	NPC252307
0.6985	Remote Similarity	NPC293619
0.6985	Remote Similarity	NPC39793
0.6978	Remote Similarity	NPC147654
0.6978	Remote Similarity	NPC285289
0.6978	Remote Similarity	NPC40302
0.6978	Remote Similarity	NPC137922
0.697	Remote Similarity	NPC137685
0.6966	Remote Similarity	NPC259017
0.6963	Remote Similarity	NPC233669
0.6963	Remote Similarity	NPC474967
0.6957	Remote Similarity	NPC247364
0.6957	Remote Similarity	NPC10932
0.6957	Remote Similarity	NPC232084
0.6957	Remote Similarity	NPC61516
0.6953	Remote Similarity	NPC477802
0.6953	Remote Similarity	NPC305205
0.6953	Remote Similarity	NPC477801
0.695	Remote Similarity	NPC5796
0.695	Remote Similarity	NPC109822
0.695	Remote Similarity	NPC94276
0.695	Remote Similarity	NPC206487
0.6944	Remote Similarity	NPC206183
0.6944	Remote Similarity	NPC5851
0.6944	Remote Similarity	NPC226855
0.6944	Remote Similarity	NPC476968
0.6944	Remote Similarity	NPC170844

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 NPC85049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	1141
0.2-0.3	2822
0.3-0.4	2687
0.4-0.5	1334
0.5-0.6	620
0.6-0.7	65
0.7-0.8	2
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
0.7308	Intermediate Similarity	NPD228	Approved
0.7302	Intermediate Similarity	NPD9244	Approved
0.6944	Remote Similarity	NPD3027	Phase 3
0.6767	Remote Similarity	NPD3022	Approved
0.6767	Remote Similarity	NPD3021	Approved
0.6757	Remote Similarity	NPD230	Phase 1
0.6716	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD9381	Approved
0.6714	Remote Similarity	NPD9384	Approved
0.669	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1613	Approved
0.6689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4010	Discontinued
0.6644	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD9622	Approved
0.6528	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1357	Approved
0.6507	Remote Similarity	NPD9619	Approved
0.6507	Remote Similarity	NPD9621	Approved
0.6507	Remote Similarity	NPD9620	Approved
0.6503	Remote Similarity	NPD3705	Approved
0.6496	Remote Similarity	NPD9379	Approved
0.6496	Remote Similarity	NPD9377	Approved
0.6467	Remote Similarity	NPD1558	Phase 1
0.6463	Remote Similarity	NPD9494	Approved
0.6429	Remote Similarity	NPD7266	Discontinued
0.6429	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1242	Phase 1
0.6358	Remote Similarity	NPD3620	Phase 2
0.6358	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD111	Approved
0.6338	Remote Similarity	NPD9545	Approved
0.6333	Remote Similarity	NPD597	Approved
0.6333	Remote Similarity	NPD601	Approved
0.6333	Remote Similarity	NPD598	Approved
0.6331	Remote Similarity	NPD5283	Phase 1
0.6324	Remote Similarity	NPD2684	Approved
0.6296	Remote Similarity	NPD968	Approved
0.6291	Remote Similarity	NPD2674	Phase 3
0.6291	Remote Similarity	NPD1136	Approved
0.6291	Remote Similarity	NPD1132	Approved
0.6291	Remote Similarity	NPD1130	Approved
0.6288	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2933	Approved
0.6279	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD9296	Approved
0.6279	Remote Similarity	NPD2934	Approved
0.625	Remote Similarity	NPD290	Approved
0.6242	Remote Similarity	NPD2861	Phase 2
0.6241	Remote Similarity	NPD846	Approved
0.6241	Remote Similarity	NPD940	Approved
0.6231	Remote Similarity	NPD844	Approved
0.6231	Remote Similarity	NPD2859	Approved
0.6231	Remote Similarity	NPD2860	Approved
0.6225	Remote Similarity	NPD3145	Approved
0.6225	Remote Similarity	NPD3144	Approved
0.6224	Remote Similarity	NPD1548	Phase 1
0.6212	Remote Similarity	NPD3020	Approved
0.6211	Remote Similarity	NPD2183	Approved
0.6211	Remote Similarity	NPD2184	Approved
0.619	Remote Similarity	NPD2983	Phase 2
0.619	Remote Similarity	NPD2982	Phase 2
0.6183	Remote Similarity	NPD288	Approved
0.6164	Remote Similarity	NPD1610	Phase 2
0.6164	Remote Similarity	NPD6190	Approved
0.6159	Remote Similarity	NPD9718	Approved
0.6149	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD3059	Approved
0.6144	Remote Similarity	NPD3061	Approved
0.6144	Remote Similarity	NPD3062	Approved
0.6143	Remote Similarity	NPD7843	Approved
0.6133	Remote Similarity	NPD3018	Phase 2
0.6127	Remote Similarity	NPD6671	Approved
0.6127	Remote Similarity	NPD7157	Approved
0.6122	Remote Similarity	NPD2981	Phase 2
0.6122	Remote Similarity	NPD9269	Phase 2
0.6108	Remote Similarity	NPD4288	Approved
0.6065	Remote Similarity	NPD5314	Approved
0.6065	Remote Similarity	NPD823	Approved
0.6065	Remote Similarity	NPD817	Approved
0.6054	Remote Similarity	NPD1091	Approved
0.6054	Remote Similarity	NPD3092	Approved
0.6047	Remote Similarity	NPD6687	Approved
0.6047	Remote Similarity	NPD6688	Approved
0.6043	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD4750	Phase 3
0.6042	Remote Similarity	NPD5536	Phase 2
0.604	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD826	Approved
0.6039	Remote Similarity	NPD825	Approved
0.6038	Remote Similarity	NPD3060	Approved
0.6037	Remote Similarity	NPD1653	Approved
0.6028	Remote Similarity	NPD821	Approved
0.6027	Remote Similarity	NPD1778	Approved
0.6013	Remote Similarity	NPD1375	Discontinued
0.6	Remote Similarity	NPD3055	Approved
0.6	Remote Similarity	NPD3053	Approved
0.6	Remote Similarity	NPD555	Phase 2
0.6	Remote Similarity	NPD3094	Phase 2
0.5988	Remote Similarity	NPD1934	Approved
0.5988	Remote Similarity	NPD1511	Approved
0.5987	Remote Similarity	NPD4908	Phase 1
0.5985	Remote Similarity	NPD1809	Phase 2
0.5974	Remote Similarity	NPD259	Phase 1
0.5973	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD4749	Approved
0.5963	Remote Similarity	NPD2219	Phase 1
0.596	Remote Similarity	NPD258	Approved
0.596	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.596	Remote Similarity	NPD257	Approved
0.596	Remote Similarity	NPD6584	Phase 3
0.5952	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD4123	Phase 3
0.5949	Remote Similarity	NPD9570	Approved
0.5948	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD422	Phase 1
0.5944	Remote Similarity	NPD9614	Approved
0.5944	Remote Similarity	NPD9618	Approved
0.5938	Remote Similarity	NPD9094	Approved
0.5938	Remote Similarity	NPD4237	Approved
0.5938	Remote Similarity	NPD4236	Phase 3
0.5935	Remote Similarity	NPD4060	Phase 1
0.5933	Remote Similarity	NPD5310	Approved
0.5933	Remote Similarity	NPD6696	Suspended
0.5933	Remote Similarity	NPD5311	Approved
0.5918	Remote Similarity	NPD4626	Approved
0.5917	Remote Similarity	NPD2296	Approved
0.5915	Remote Similarity	NPD1512	Approved
0.5909	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD8166	Discontinued
0.5899	Remote Similarity	NPD1358	Approved
0.5891	Remote Similarity	NPD9295	Approved
0.589	Remote Similarity	NPD3091	Approved
0.589	Remote Similarity	NPD1182	Approved
0.5886	Remote Similarity	NPD1169	Approved
0.5882	Remote Similarity	NPD291	Approved
0.5878	Remote Similarity	NPD3496	Discontinued
0.5871	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD2977	Approved
0.5858	Remote Similarity	NPD2801	Approved
0.5858	Remote Similarity	NPD2978	Approved
0.5851	Remote Similarity	NPD8095	Phase 1
0.585	Remote Similarity	NPD9268	Approved
0.5843	Remote Similarity	NPD3687	Approved
0.5843	Remote Similarity	NPD3686	Approved
0.5839	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD9500	Approved
0.5833	Remote Similarity	NPD845	Approved
0.5833	Remote Similarity	NPD2238	Phase 2
0.5833	Remote Similarity	NPD943	Approved
0.5828	Remote Similarity	NPD8651	Approved
0.5827	Remote Similarity	NPD3134	Approved
0.5827	Remote Similarity	NPD1445	Approved
0.5827	Remote Similarity	NPD1444	Approved
0.5822	Remote Similarity	NPD9613	Approved
0.5822	Remote Similarity	NPD317	Approved
0.5822	Remote Similarity	NPD9616	Approved
0.5822	Remote Similarity	NPD318	Approved
0.5822	Remote Similarity	NPD16	Approved
0.5822	Remote Similarity	NPD9615	Approved
0.5822	Remote Similarity	NPD856	Approved
0.5817	Remote Similarity	NPD9569	Approved
0.5814	Remote Similarity	NPD6234	Discontinued
0.58	Remote Similarity	NPD2231	Phase 2
0.58	Remote Similarity	NPD2233	Approved
0.58	Remote Similarity	NPD1608	Approved
0.58	Remote Similarity	NPD2230	Approved
0.58	Remote Similarity	NPD2235	Phase 2
0.58	Remote Similarity	NPD2232	Approved
0.5797	Remote Similarity	NPD9610	Approved
0.5797	Remote Similarity	NPD9608	Approved
0.5796	Remote Similarity	NPD5735	Approved
0.5793	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3882	Suspended
0.5789	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD651	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD2122	Discontinued
0.5782	Remote Similarity	NPD316	Approved
0.5779	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD4678	Approved
0.5774	Remote Similarity	NPD4675	Approved
0.5767	Remote Similarity	NPD2677	Approved
0.5762	Remote Similarity	NPD6583	Phase 3
0.5762	Remote Similarity	NPD6582	Phase 2
0.5753	Remote Similarity	NPD9493	Approved
0.575	Remote Similarity	NPD2161	Phase 2
0.5743	Remote Similarity	NPD5691	Approved
0.5742	Remote Similarity	NPD4625	Phase 3
0.5742	Remote Similarity	NPD9537	Phase 1
0.5742	Remote Similarity	NPD3180	Approved
0.5742	Remote Similarity	NPD9536	Phase 1
0.5742	Remote Similarity	NPD3179	Approved
0.5741	Remote Similarity	NPD6674	Discontinued
0.5734	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD1283	Approved
0.5723	Remote Similarity	NPD4536	Approved
0.5723	Remote Similarity	NPD6111	Discontinued
0.5723	Remote Similarity	NPD4538	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