NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	217.96
Volume:	158.817
LogP:	0.998
LogD:	0.923
LogS:	-1.162
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	2.326
Fsp3:	0.143
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:	-4.547
MDCK Permeability:	1.3057383512204979e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	76.23088073730469%
Volume Distribution (VD):	0.564
Pgp-substrate:	25.424665451049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.587
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.368
CYP2D6-inhibitor:	0.206
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	9.827
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.231
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.936
Carcinogencity:	0.225
Eye Corrosion:	0.075
Eye Irritation:	0.972
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC79844

Natural Product ID:	NPC79844
*Common Name:**	3-Bromo-4,5-Dihydroxybenzyl Alcohol
IUPAC Name:	3-bromo-5-(hydroxymethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	VKMNUQABTPJNTP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H7BrO3/c8-5-1-4(3-9)2-6(10)7(5)11/h1-2,9-11H,3H2
SMILES:	c1c(cc(c(c1Br)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451595
PubChem CID:	13887341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0031-9422(98)00251-9]
NPO32930	polysiphonia lanosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387639]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180830]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668556]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3778	Perityle emoryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15014	Senecio linearifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22076	Laurus novocanariensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19169	Helichrysum caespititium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	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	1
Others	13

Activity Type	# Activity
Cell Line	2
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ID50	=	8.9	ug ml-1	PMID[548099]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	51500.0	nM	PMID[548100]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[548099]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[548099]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[548099]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[548099]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[548099]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	13.0	mm	PMID[548099]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	8.0	mm	PMID[548099]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	9.0	mm	PMID[548099]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.0	mm	PMID[548099]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	IZ	=	9.0	mm	PMID[548099]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	IZ	=	13.0	mm	PMID[548099]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	8.0	mm	PMID[548099]

☑ 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 NPC79844 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	595
0.1-0.2	2609
0.2-0.3	11852
0.3-0.4	9151
0.4-0.5	8032
0.5-0.6	7903
0.6-0.7	2380
0.7-0.8	137
0.8-0.85	16
0.85-0.9	14
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9469	High Similarity	NPC474146
0.9391	High Similarity	NPC47790
0.9224	High Similarity	NPC229213
0.9145	High Similarity	NPC473572
0.9145	High Similarity	NPC474169
0.9138	High Similarity	NPC136543
0.9068	High Similarity	NPC137117
0.8852	High Similarity	NPC474614
0.876	High Similarity	NPC43706
0.8718	High Similarity	NPC38483
0.8699	High Similarity	NPC85049
0.8689	High Similarity	NPC473708
0.8689	High Similarity	NPC474147
0.864	High Similarity	NPC300678
0.8629	High Similarity	NPC226493
0.8629	High Similarity	NPC160081
0.8618	High Similarity	NPC150929
0.8571	High Similarity	NPC227976
0.8571	High Similarity	NPC163560
0.8559	High Similarity	NPC117759
0.8359	Intermediate Similarity	NPC245386
0.8226	Intermediate Similarity	NPC220311
0.8214	Intermediate Similarity	NPC12278
0.8175	Intermediate Similarity	NPC214553
0.8168	Intermediate Similarity	NPC156356
0.8125	Intermediate Similarity	NPC43613
0.8106	Intermediate Similarity	NPC160932
0.8092	Intermediate Similarity	NPC224663
0.808	Intermediate Similarity	NPC142776
0.8036	Intermediate Similarity	NPC110764
0.803	Intermediate Similarity	NPC271942
0.8018	Intermediate Similarity	NPC131587
0.8016	Intermediate Similarity	NPC134219
0.8	Intermediate Similarity	NPC244890
0.7985	Intermediate Similarity	NPC89341
0.7953	Intermediate Similarity	NPC13004
0.7939	Intermediate Similarity	NPC312155
0.7917	Intermediate Similarity	NPC50782
0.7829	Intermediate Similarity	NPC474536
0.7826	Intermediate Similarity	NPC88896
0.781	Intermediate Similarity	NPC109346
0.7786	Intermediate Similarity	NPC474135
0.7778	Intermediate Similarity	NPC471495
0.7768	Intermediate Similarity	NPC109955
0.775	Intermediate Similarity	NPC471485
0.775	Intermediate Similarity	NPC76400
0.7748	Intermediate Similarity	NPC107522
0.7744	Intermediate Similarity	NPC199089
0.7727	Intermediate Similarity	NPC471328
0.7664	Intermediate Similarity	NPC184632
0.7652	Intermediate Similarity	NPC477802
0.7652	Intermediate Similarity	NPC477801
0.7652	Intermediate Similarity	NPC303011
0.7647	Intermediate Similarity	NPC473358
0.7591	Intermediate Similarity	NPC118794
0.7563	Intermediate Similarity	NPC62258
0.7563	Intermediate Similarity	NPC54543
0.7563	Intermediate Similarity	NPC55617
0.7563	Intermediate Similarity	NPC71266
0.7559	Intermediate Similarity	NPC219444
0.7545	Intermediate Similarity	NPC300478
0.7545	Intermediate Similarity	NPC312304
0.7541	Intermediate Similarity	NPC120280
0.7535	Intermediate Similarity	NPC152947
0.7535	Intermediate Similarity	NPC7398
0.7518	Intermediate Similarity	NPC178097
0.75	Intermediate Similarity	NPC120982
0.75	Intermediate Similarity	NPC174096
0.75	Intermediate Similarity	NPC196479
0.75	Intermediate Similarity	NPC79793
0.75	Intermediate Similarity	NPC226401
0.75	Intermediate Similarity	NPC147634
0.75	Intermediate Similarity	NPC84606
0.7478	Intermediate Similarity	NPC223393
0.7464	Intermediate Similarity	NPC250597
0.7459	Intermediate Similarity	NPC264558
0.7458	Intermediate Similarity	NPC19149
0.744	Intermediate Similarity	NPC15350
0.7438	Intermediate Similarity	NPC257430
0.7438	Intermediate Similarity	NPC187583
0.7438	Intermediate Similarity	NPC179002
0.7436	Intermediate Similarity	NPC120719
0.7436	Intermediate Similarity	NPC471511
0.7419	Intermediate Similarity	NPC221049
0.7417	Intermediate Similarity	NPC473372
0.7395	Intermediate Similarity	NPC176527
0.7381	Intermediate Similarity	NPC181969
0.7381	Intermediate Similarity	NPC320987
0.7373	Intermediate Similarity	NPC239291
0.7372	Intermediate Similarity	NPC168680
0.7355	Intermediate Similarity	NPC471487
0.7333	Intermediate Similarity	NPC58427
0.7333	Intermediate Similarity	NPC114392
0.7333	Intermediate Similarity	NPC105727
0.7333	Intermediate Similarity	NPC34864
0.7328	Intermediate Similarity	NPC130103
0.7323	Intermediate Similarity	NPC115627
0.7323	Intermediate Similarity	NPC118522
0.7323	Intermediate Similarity	NPC148615
0.7323	Intermediate Similarity	NPC169207
0.7323	Intermediate Similarity	NPC177475
0.7323	Intermediate Similarity	NPC35071
0.7323	Intermediate Similarity	NPC472071
0.7317	Intermediate Similarity	NPC471488
0.7311	Intermediate Similarity	NPC477814
0.7302	Intermediate Similarity	NPC63126
0.7302	Intermediate Similarity	NPC255675
0.7295	Intermediate Similarity	NPC268032
0.7295	Intermediate Similarity	NPC139617
0.7295	Intermediate Similarity	NPC78918
0.7288	Intermediate Similarity	NPC52087
0.7288	Intermediate Similarity	NPC79672
0.7281	Intermediate Similarity	NPC313650
0.7258	Intermediate Similarity	NPC94217
0.7244	Intermediate Similarity	NPC477803
0.7232	Intermediate Similarity	NPC300017
0.7209	Intermediate Similarity	NPC266045
0.7209	Intermediate Similarity	NPC476343
0.7209	Intermediate Similarity	NPC470804
0.7207	Intermediate Similarity	NPC104216
0.719	Intermediate Similarity	NPC233835
0.7188	Intermediate Similarity	NPC180207
0.7177	Intermediate Similarity	NPC59387
0.7177	Intermediate Similarity	NPC33244
0.7167	Intermediate Similarity	NPC1075
0.7167	Intermediate Similarity	NPC1786
0.7167	Intermediate Similarity	NPC294902
0.7164	Intermediate Similarity	NPC105702
0.7155	Intermediate Similarity	NPC474073
0.7155	Intermediate Similarity	NPC88420
0.7154	Intermediate Similarity	NPC8547
0.7154	Intermediate Similarity	NPC257124
0.7154	Intermediate Similarity	NPC209567
0.7154	Intermediate Similarity	NPC173746
0.7154	Intermediate Similarity	NPC156840
0.7132	Intermediate Similarity	NPC471486
0.7132	Intermediate Similarity	NPC470414
0.7131	Intermediate Similarity	NPC246358
0.7131	Intermediate Similarity	NPC7097
0.7131	Intermediate Similarity	NPC473524
0.7131	Intermediate Similarity	NPC36108
0.7131	Intermediate Similarity	NPC233731
0.7131	Intermediate Similarity	NPC228343
0.7131	Intermediate Similarity	NPC254833
0.712	Intermediate Similarity	NPC217472
0.7111	Intermediate Similarity	NPC473724
0.7109	Intermediate Similarity	NPC100395
0.7109	Intermediate Similarity	NPC135961
0.7105	Intermediate Similarity	NPC325292
0.7105	Intermediate Similarity	NPC138117
0.7103	Intermediate Similarity	NPC473608
0.7099	Intermediate Similarity	NPC473451
0.7099	Intermediate Similarity	NPC165375
0.7099	Intermediate Similarity	NPC220598
0.709	Intermediate Similarity	NPC55113
0.7087	Intermediate Similarity	NPC164386
0.7077	Intermediate Similarity	NPC49341
0.7073	Intermediate Similarity	NPC222084
0.7063	Intermediate Similarity	NPC4665
0.7063	Intermediate Similarity	NPC472893
0.7059	Intermediate Similarity	NPC110800
0.7054	Intermediate Similarity	NPC229401
0.704	Intermediate Similarity	NPC148969
0.704	Intermediate Similarity	NPC95381
0.7034	Intermediate Similarity	NPC174911
0.702	Intermediate Similarity	NPC38980
0.7016	Intermediate Similarity	NPC297657
0.7016	Intermediate Similarity	NPC226250
0.7008	Intermediate Similarity	NPC193067
0.7	Intermediate Similarity	NPC474535
0.6992	Remote Similarity	NPC90318
0.6984	Remote Similarity	NPC33749
0.6984	Remote Similarity	NPC261453
0.6984	Remote Similarity	NPC115803
0.6984	Remote Similarity	NPC328593
0.6983	Remote Similarity	NPC274678
0.698	Remote Similarity	NPC294870
0.6977	Remote Similarity	NPC156654
0.6977	Remote Similarity	NPC470215
0.6977	Remote Similarity	NPC311595
0.6977	Remote Similarity	NPC24474
0.6977	Remote Similarity	NPC470214
0.6977	Remote Similarity	NPC20674
0.6977	Remote Similarity	NPC109371
0.6975	Remote Similarity	NPC471578
0.6975	Remote Similarity	NPC101025
0.697	Remote Similarity	NPC471693
0.6967	Remote Similarity	NPC227894
0.696	Remote Similarity	NPC146422
0.6957	Remote Similarity	NPC29373
0.6957	Remote Similarity	NPC295295
0.6954	Remote Similarity	NPC475697
0.6953	Remote Similarity	NPC610
0.6953	Remote Similarity	NPC259638
0.6953	Remote Similarity	NPC277588
0.6953	Remote Similarity	NPC200988
0.6953	Remote Similarity	NPC145023
0.6953	Remote Similarity	NPC175799
0.6947	Remote Similarity	NPC322332
0.6947	Remote Similarity	NPC472271

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 NPC79844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	521
0.1-0.2	1065
0.2-0.3	2857
0.3-0.4	2703
0.4-0.5	1380
0.5-0.6	510
0.6-0.7	107
0.7-0.8	7
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
0.75	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD9381	Approved
0.7323	Intermediate Similarity	NPD9384	Approved
0.7288	Intermediate Similarity	NPD9244	Approved
0.7154	Intermediate Similarity	NPD228	Approved
0.7131	Intermediate Similarity	NPD3021	Approved
0.7131	Intermediate Similarity	NPD3022	Approved
0.7099	Intermediate Similarity	NPD9622	Approved
0.696	Remote Similarity	NPD9377	Approved
0.696	Remote Similarity	NPD9379	Approved
0.694	Remote Similarity	NPD9621	Approved
0.694	Remote Similarity	NPD9619	Approved
0.694	Remote Similarity	NPD9620	Approved
0.6891	Remote Similarity	NPD1242	Phase 1
0.6847	Remote Similarity	NPD111	Approved
0.6788	Remote Similarity	NPD3027	Phase 3
0.6767	Remote Similarity	NPD9269	Phase 2
0.6739	Remote Similarity	NPD601	Approved
0.6739	Remote Similarity	NPD598	Approved
0.6739	Remote Similarity	NPD597	Approved
0.6691	Remote Similarity	NPD1136	Approved
0.6691	Remote Similarity	NPD1132	Approved
0.6691	Remote Similarity	NPD1130	Approved
0.6667	Remote Similarity	NPD9094	Approved
0.6643	Remote Similarity	NPD3059	Approved
0.6643	Remote Similarity	NPD1613	Approved
0.6643	Remote Similarity	NPD3062	Approved
0.6643	Remote Similarity	NPD3061	Approved
0.6643	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD289	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2934	Approved
0.661	Remote Similarity	NPD2933	Approved
0.6587	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD846	Approved
0.6557	Remote Similarity	NPD940	Approved
0.6555	Remote Similarity	NPD2860	Approved
0.6555	Remote Similarity	NPD844	Approved
0.6555	Remote Similarity	NPD2859	Approved
0.6549	Remote Similarity	NPD5314	Approved
0.6549	Remote Similarity	NPD823	Approved
0.6549	Remote Similarity	NPD817	Approved
0.6529	Remote Similarity	NPD3020	Approved
0.6522	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.65	Remote Similarity	NPD288	Approved
0.6479	Remote Similarity	NPD230	Phase 1
0.6475	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1357	Approved
0.6466	Remote Similarity	NPD9268	Approved
0.6444	Remote Similarity	NPD3092	Approved
0.6429	Remote Similarity	NPD9718	Approved
0.6414	Remote Similarity	NPD9570	Approved
0.6377	Remote Similarity	NPD3094	Phase 2
0.637	Remote Similarity	NPD7266	Discontinued
0.635	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD9614	Approved
0.6336	Remote Similarity	NPD9618	Approved
0.6328	Remote Similarity	NPD4750	Phase 3
0.6312	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5311	Approved
0.6304	Remote Similarity	NPD5310	Approved
0.6304	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3620	Phase 2
0.6286	Remote Similarity	NPD9494	Approved
0.6281	Remote Similarity	NPD1809	Phase 2
0.6277	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD9294	Approved
0.6269	Remote Similarity	NPD3091	Approved
0.6259	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD3053	Approved
0.6259	Remote Similarity	NPD3055	Approved
0.625	Remote Similarity	NPD2684	Approved
0.622	Remote Similarity	NPD968	Approved
0.6216	Remote Similarity	NPD9088	Approved
0.6214	Remote Similarity	NPD257	Approved
0.6214	Remote Similarity	NPD258	Approved
0.6204	Remote Similarity	NPD3705	Approved
0.62	Remote Similarity	NPD6190	Approved
0.6198	Remote Similarity	NPD9296	Approved
0.6195	Remote Similarity	NPD9093	Approved
0.6194	Remote Similarity	NPD317	Approved
0.6194	Remote Similarity	NPD318	Approved
0.6194	Remote Similarity	NPD856	Approved
0.6194	Remote Similarity	NPD9616	Approved
0.6194	Remote Similarity	NPD9613	Approved
0.6194	Remote Similarity	NPD9615	Approved
0.6194	Remote Similarity	NPD16	Approved
0.6181	Remote Similarity	NPD826	Approved
0.6181	Remote Similarity	NPD943	Approved
0.6181	Remote Similarity	NPD1558	Phase 1
0.6181	Remote Similarity	NPD825	Approved
0.6179	Remote Similarity	NPD9273	Approved
0.6172	Remote Similarity	NPD290	Approved
0.617	Remote Similarity	NPD9569	Approved
0.6148	Remote Similarity	NPD316	Approved
0.6147	Remote Similarity	NPD9087	Approved
0.614	Remote Similarity	NPD9089	Approved
0.6138	Remote Similarity	NPD555	Phase 2
0.6136	Remote Similarity	NPD5283	Phase 1
0.6122	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD845	Approved
0.6111	Remote Similarity	NPD259	Phase 1
0.6111	Remote Similarity	NPD4010	Discontinued
0.6111	Remote Similarity	NPD2674	Phase 3
0.6111	Remote Similarity	NPD9500	Approved
0.6094	Remote Similarity	NPD1445	Approved
0.6094	Remote Similarity	NPD1444	Approved
0.6093	Remote Similarity	NPD302	Approved
0.6084	Remote Similarity	NPD9537	Phase 1
0.6084	Remote Similarity	NPD9536	Phase 1
0.6063	Remote Similarity	NPD9610	Approved
0.6063	Remote Similarity	NPD9608	Approved
0.6061	Remote Similarity	NPD7843	Approved
0.6058	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2861	Phase 2
0.6045	Remote Similarity	NPD7157	Approved
0.6042	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3144	Approved
0.6042	Remote Similarity	NPD3145	Approved
0.6029	Remote Similarity	NPD9545	Approved
0.6029	Remote Similarity	NPD1548	Phase 1
0.5986	Remote Similarity	NPD859	Approved
0.5986	Remote Similarity	NPD602	Approved
0.5986	Remote Similarity	NPD858	Approved
0.5986	Remote Similarity	NPD599	Approved
0.5985	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1610	Phase 2
0.5971	Remote Similarity	NPD1091	Approved
0.5962	Remote Similarity	NPD1653	Approved
0.596	Remote Similarity	NPD3060	Approved
0.5954	Remote Similarity	NPD1792	Phase 2
0.5942	Remote Similarity	NPD3095	Discontinued
0.594	Remote Similarity	NPD7635	Approved
0.5929	Remote Similarity	NPD2561	Approved
0.5929	Remote Similarity	NPD2562	Approved
0.5926	Remote Similarity	NPD6671	Approved
0.5923	Remote Similarity	NPD2342	Discontinued
0.5918	Remote Similarity	NPD275	Approved
0.5918	Remote Similarity	NPD274	Approved
0.5906	Remote Similarity	NPD1169	Approved
0.5896	Remote Similarity	NPD2234	Approved
0.5896	Remote Similarity	NPD2229	Approved
0.5896	Remote Similarity	NPD2228	Approved
0.5896	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD2983	Phase 2
0.5887	Remote Similarity	NPD4659	Approved
0.5887	Remote Similarity	NPD2982	Phase 2
0.5878	Remote Similarity	NPD2568	Approved
0.5871	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD5536	Phase 2
0.5833	Remote Similarity	NPD3018	Phase 2
0.5827	Remote Similarity	NPD2286	Discontinued
0.5827	Remote Similarity	NPD3019	Approved
0.5827	Remote Similarity	NPD3028	Approved
0.5827	Remote Similarity	NPD2932	Approved
0.5827	Remote Similarity	NPD4059	Approved
0.5821	Remote Similarity	NPD821	Approved
0.5817	Remote Similarity	NPD8166	Discontinued
0.5816	Remote Similarity	NPD2981	Phase 2
0.5816	Remote Similarity	NPD2235	Phase 2
0.5816	Remote Similarity	NPD2231	Phase 2
0.5806	Remote Similarity	NPD1511	Approved
0.5804	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD1133	Approved
0.5804	Remote Similarity	NPD1134	Approved
0.5804	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD1129	Approved
0.5804	Remote Similarity	NPD4103	Phase 2
0.5804	Remote Similarity	NPD1131	Approved
0.5804	Remote Similarity	NPD1135	Approved
0.5797	Remote Similarity	NPD1182	Approved
0.5794	Remote Similarity	NPD9495	Approved
0.5785	Remote Similarity	NPD9295	Approved
0.5781	Remote Similarity	NPD291	Approved
0.5776	Remote Similarity	NPD2978	Approved
0.5776	Remote Similarity	NPD2977	Approved
0.5775	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3645	Discontinued
0.5766	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD6584	Phase 3
0.5764	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD74	Approved
0.5758	Remote Similarity	NPD9266	Approved
0.5755	Remote Similarity	NPD4093	Discontinued
0.5752	Remote Similarity	NPD4236	Phase 3
0.5752	Remote Similarity	NPD4237	Approved
0.5745	Remote Similarity	NPD1201	Approved
0.5743	Remote Similarity	NPD4060	Phase 1
0.5743	Remote Similarity	NPD2238	Phase 2
0.5735	Remote Similarity	NPD1791	Approved
0.5735	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD1793	Approved
0.5732	Remote Similarity	NPD2184	Approved
0.5732	Remote Similarity	NPD1512	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