NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	231.97
Volume:	176.113
LogP:	1.505
LogD:	1.605
LogS:	-1.686
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	2.288
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:	-4.463
MDCK Permeability:	1.6258323739748448e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	77.43569946289062%
Volume Distribution (VD):	0.781
Pgp-substrate:	22.16120719909668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.527
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	5.99
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.943
Carcinogencity:	0.386
Eye Corrosion:	0.355
Eye Irritation:	0.974
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: NPC229213

Natural Product ID:	NPC229213
*Common Name:**	3-Bromo-5-(Methoxymethyl)Benzene-1,2-Diol
IUPAC Name:	3-bromo-5-(methoxymethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	WNRMLKGLNSWHRX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9BrO3/c1-12-4-5-2-6(9)8(11)7(10)3-5/h2-3,10-11H,4H2,1H3
SMILES:	COCc1cc(c(c(c1)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448283
PubChem CID:	44584366
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
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]
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]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	35300.0	nM	PMID[464532]

☑ 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 NPC229213 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	461
0.1-0.2	2311
0.2-0.3	9052
0.3-0.4	11549
0.4-0.5	5446
0.5-0.6	9715
0.6-0.7	3697
0.7-0.8	434
0.8-0.85	12
0.85-0.9	10
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC474169
0.9914	High Similarity	NPC473572
0.95	High Similarity	NPC43706
0.9426	High Similarity	NPC85049
0.9421	High Similarity	NPC473708
0.9421	High Similarity	NPC474147
0.935	High Similarity	NPC160081
0.935	High Similarity	NPC226493
0.9224	High Similarity	NPC79844
0.8926	High Similarity	NPC136543
0.8906	High Similarity	NPC245386
0.8779	High Similarity	NPC160932
0.876	High Similarity	NPC474146
0.871	High Similarity	NPC137117
0.8702	High Similarity	NPC156356
0.8699	High Similarity	NPC47790
0.8647	High Similarity	NPC89341
0.8571	High Similarity	NPC134219
0.8561	High Similarity	NPC271942
0.8525	High Similarity	NPC117759
0.8525	High Similarity	NPC38483
0.8516	High Similarity	NPC474614
0.8456	Intermediate Similarity	NPC109346
0.8438	Intermediate Similarity	NPC150929
0.8321	Intermediate Similarity	NPC300678
0.8309	Intermediate Similarity	NPC184632
0.8258	Intermediate Similarity	NPC163560
0.8182	Intermediate Similarity	NPC303011
0.8156	Intermediate Similarity	NPC7398
0.8062	Intermediate Similarity	NPC220311
0.8062	Intermediate Similarity	NPC142776
0.8015	Intermediate Similarity	NPC168680
0.8014	Intermediate Similarity	NPC178097
0.7984	Intermediate Similarity	NPC221049
0.797	Intermediate Similarity	NPC43613
0.7953	Intermediate Similarity	NPC227976
0.7941	Intermediate Similarity	NPC224663
0.7937	Intermediate Similarity	NPC181969
0.7937	Intermediate Similarity	NPC477803
0.7937	Intermediate Similarity	NPC320987
0.7902	Intermediate Similarity	NPC152947
0.7881	Intermediate Similarity	NPC12278
0.7874	Intermediate Similarity	NPC148615
0.7874	Intermediate Similarity	NPC35071
0.7874	Intermediate Similarity	NPC177475
0.7857	Intermediate Similarity	NPC255675
0.7852	Intermediate Similarity	NPC244890
0.7842	Intermediate Similarity	NPC250597
0.782	Intermediate Similarity	NPC474536
0.7794	Intermediate Similarity	NPC312155
0.7752	Intermediate Similarity	NPC470804
0.7744	Intermediate Similarity	NPC214553
0.7742	Intermediate Similarity	NPC264558
0.7742	Intermediate Similarity	NPC76400
0.7724	Intermediate Similarity	NPC139617
0.7724	Intermediate Similarity	NPC78918
0.7724	Intermediate Similarity	NPC8547
0.7724	Intermediate Similarity	NPC156840
0.7724	Intermediate Similarity	NPC173746
0.7724	Intermediate Similarity	NPC257124
0.7712	Intermediate Similarity	NPC110764
0.7705	Intermediate Similarity	NPC246358
0.7705	Intermediate Similarity	NPC7097
0.7705	Intermediate Similarity	NPC36108
0.7705	Intermediate Similarity	NPC233731
0.7698	Intermediate Similarity	NPC193067
0.7692	Intermediate Similarity	NPC209567
0.7692	Intermediate Similarity	NPC131587
0.7674	Intermediate Similarity	NPC470414
0.7669	Intermediate Similarity	NPC13004
0.7656	Intermediate Similarity	NPC135961
0.7656	Intermediate Similarity	NPC20674
0.7638	Intermediate Similarity	NPC259638
0.7634	Intermediate Similarity	NPC220598
0.7634	Intermediate Similarity	NPC165375
0.7623	Intermediate Similarity	NPC471495
0.7619	Intermediate Similarity	NPC50782
0.7615	Intermediate Similarity	NPC476343
0.7615	Intermediate Similarity	NPC49341
0.7607	Intermediate Similarity	NPC109955
0.76	Intermediate Similarity	NPC38980
0.7597	Intermediate Similarity	NPC229401
0.7591	Intermediate Similarity	NPC471328
0.7586	Intermediate Similarity	NPC107522
0.7574	Intermediate Similarity	NPC158078
0.7569	Intermediate Similarity	NPC88896
0.7533	Intermediate Similarity	NPC475697
0.7519	Intermediate Similarity	NPC226629
0.75	Intermediate Similarity	NPC164386
0.75	Intermediate Similarity	NPC471693
0.75	Intermediate Similarity	NPC473451
0.75	Intermediate Similarity	NPC196479
0.75	Intermediate Similarity	NPC473358
0.7467	Intermediate Similarity	NPC474535
0.7466	Intermediate Similarity	NPC473608
0.7465	Intermediate Similarity	NPC118794
0.7463	Intermediate Similarity	NPC191037
0.7463	Intermediate Similarity	NPC178284
0.7463	Intermediate Similarity	NPC58607
0.746	Intermediate Similarity	NPC95381
0.746	Intermediate Similarity	NPC471485
0.745	Intermediate Similarity	NPC294870
0.7444	Intermediate Similarity	NPC131747
0.7444	Intermediate Similarity	NPC257682
0.7444	Intermediate Similarity	NPC146355
0.7444	Intermediate Similarity	NPC183446
0.744	Intermediate Similarity	NPC195873
0.744	Intermediate Similarity	NPC226250
0.7438	Intermediate Similarity	NPC120719
0.7419	Intermediate Similarity	NPC54543
0.7417	Intermediate Similarity	NPC305490
0.7407	Intermediate Similarity	NPC41706
0.7407	Intermediate Similarity	NPC5428
0.7407	Intermediate Similarity	NPC319625
0.7407	Intermediate Similarity	NPC147821
0.7407	Intermediate Similarity	NPC292056
0.7407	Intermediate Similarity	NPC118787
0.7407	Intermediate Similarity	NPC183181
0.7407	Intermediate Similarity	NPC111247
0.7407	Intermediate Similarity	NPC118533
0.7407	Intermediate Similarity	NPC165045
0.7407	Intermediate Similarity	NPC163332
0.7402	Intermediate Similarity	NPC328593
0.7402	Intermediate Similarity	NPC261453
0.7402	Intermediate Similarity	NPC33749
0.7398	Intermediate Similarity	NPC227894
0.7398	Intermediate Similarity	NPC251306
0.7391	Intermediate Similarity	NPC474135
0.7388	Intermediate Similarity	NPC148627
0.7388	Intermediate Similarity	NPC194519
0.7385	Intermediate Similarity	NPC311595
0.7385	Intermediate Similarity	NPC24474
0.7368	Intermediate Similarity	NPC84086
0.7368	Intermediate Similarity	NPC136319
0.7368	Intermediate Similarity	NPC84606
0.7364	Intermediate Similarity	NPC39793
0.7364	Intermediate Similarity	NPC293619
0.736	Intermediate Similarity	NPC137685
0.7357	Intermediate Similarity	NPC199089
0.7355	Intermediate Similarity	NPC477801
0.7355	Intermediate Similarity	NPC477802
0.7355	Intermediate Similarity	NPC305205
0.7353	Intermediate Similarity	NPC21867
0.7353	Intermediate Similarity	NPC184733
0.7353	Intermediate Similarity	NPC11258
0.7353	Intermediate Similarity	NPC282703
0.7353	Intermediate Similarity	NPC252307
0.7353	Intermediate Similarity	NPC45774
0.7353	Intermediate Similarity	NPC129570
0.7353	Intermediate Similarity	NPC474178
0.7353	Intermediate Similarity	NPC472968
0.7353	Intermediate Similarity	NPC128208
0.7353	Intermediate Similarity	NPC245826
0.7348	Intermediate Similarity	NPC147654
0.7348	Intermediate Similarity	NPC285289
0.7344	Intermediate Similarity	NPC474967
0.7344	Intermediate Similarity	NPC233669
0.7333	Intermediate Similarity	NPC223393
0.7328	Intermediate Similarity	NPC10932
0.7328	Intermediate Similarity	NPC61516
0.7328	Intermediate Similarity	NPC247364
0.7328	Intermediate Similarity	NPC232084
0.7328	Intermediate Similarity	NPC180207
0.7317	Intermediate Similarity	NPC477814
0.7317	Intermediate Similarity	NPC19149
0.7313	Intermediate Similarity	NPC5796
0.7313	Intermediate Similarity	NPC109822
0.7313	Intermediate Similarity	NPC206487
0.7313	Intermediate Similarity	NPC94276
0.7308	Intermediate Similarity	NPC203124
0.7308	Intermediate Similarity	NPC63083
0.7308	Intermediate Similarity	NPC275519
0.7308	Intermediate Similarity	NPC470626
0.7308	Intermediate Similarity	NPC309434
0.7299	Intermediate Similarity	NPC476968
0.7299	Intermediate Similarity	NPC226855
0.7299	Intermediate Similarity	NPC170844
0.7299	Intermediate Similarity	NPC5851
0.7299	Intermediate Similarity	NPC86030
0.7295	Intermediate Similarity	NPC79672
0.7295	Intermediate Similarity	NPC52087
0.7295	Intermediate Similarity	NPC130817
0.7295	Intermediate Similarity	NPC471511
0.7293	Intermediate Similarity	NPC474864
0.7293	Intermediate Similarity	NPC41562
0.7293	Intermediate Similarity	NPC85488
0.7293	Intermediate Similarity	NPC219444
0.7293	Intermediate Similarity	NPC71579
0.7293	Intermediate Similarity	NPC473411
0.7293	Intermediate Similarity	NPC262253
0.7287	Intermediate Similarity	NPC281277
0.728	Intermediate Similarity	NPC55617
0.728	Intermediate Similarity	NPC473372
0.728	Intermediate Similarity	NPC62258
0.7279	Intermediate Similarity	NPC159987
0.7279	Intermediate Similarity	NPC78061
0.7279	Intermediate Similarity	NPC21563
0.7279	Intermediate Similarity	NPC122359
0.7279	Intermediate Similarity	NPC158654
0.7279	Intermediate Similarity	NPC106511

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 NPC229213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	423
0.1-0.2	1103
0.2-0.3	2567
0.3-0.4	2748
0.4-0.5	1364
0.5-0.6	811
0.6-0.7	128
0.7-0.8	6
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
0.7724	Intermediate Similarity	NPD228	Approved
0.7299	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7092	Intermediate Similarity	NPD230	Phase 1
0.7087	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9381	Approved
0.7068	Intermediate Similarity	NPD9384	Approved
0.7029	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1613	Approved
0.7016	Intermediate Similarity	NPD9244	Approved
0.6985	Remote Similarity	NPD9622	Approved
0.6978	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1357	Approved
0.6861	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9377	Approved
0.6846	Remote Similarity	NPD9379	Approved
0.6838	Remote Similarity	NPD3705	Approved
0.6835	Remote Similarity	NPD9619	Approved
0.6835	Remote Similarity	NPD9621	Approved
0.6835	Remote Similarity	NPD9620	Approved
0.6786	Remote Similarity	NPD9494	Approved
0.6783	Remote Similarity	NPD1558	Phase 1
0.6774	Remote Similarity	NPD1242	Phase 1
0.6735	Remote Similarity	NPD7266	Discontinued
0.6735	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD9545	Approved
0.6643	Remote Similarity	NPD598	Approved
0.6643	Remote Similarity	NPD597	Approved
0.6643	Remote Similarity	NPD601	Approved
0.6641	Remote Similarity	NPD968	Approved
0.664	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2934	Approved
0.6639	Remote Similarity	NPD2933	Approved
0.6639	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD9296	Approved
0.6597	Remote Similarity	NPD2674	Phase 3
0.6597	Remote Similarity	NPD1136	Approved
0.6597	Remote Similarity	NPD1130	Approved
0.6597	Remote Similarity	NPD1132	Approved
0.6589	Remote Similarity	NPD290	Approved
0.6587	Remote Similarity	NPD846	Approved
0.6587	Remote Similarity	NPD940	Approved
0.6585	Remote Similarity	NPD844	Approved
0.6585	Remote Similarity	NPD2859	Approved
0.6585	Remote Similarity	NPD2860	Approved
0.656	Remote Similarity	NPD3020	Approved
0.6549	Remote Similarity	NPD2861	Phase 2
0.6544	Remote Similarity	NPD1548	Phase 1
0.6543	Remote Similarity	NPD4010	Discontinued
0.6532	Remote Similarity	NPD288	Approved
0.6528	Remote Similarity	NPD3144	Approved
0.6528	Remote Similarity	NPD3145	Approved
0.65	Remote Similarity	NPD2982	Phase 2
0.65	Remote Similarity	NPD2983	Phase 2
0.6475	Remote Similarity	NPD1610	Phase 2
0.6466	Remote Similarity	NPD7843	Approved
0.6447	Remote Similarity	NPD6190	Approved
0.6444	Remote Similarity	NPD7157	Approved
0.6444	Remote Similarity	NPD6671	Approved
0.6438	Remote Similarity	NPD3062	Approved
0.6438	Remote Similarity	NPD3061	Approved
0.6438	Remote Similarity	NPD3059	Approved
0.6434	Remote Similarity	NPD3018	Phase 2
0.6429	Remote Similarity	NPD2981	Phase 2
0.6429	Remote Similarity	NPD9269	Phase 2
0.6429	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4750	Phase 3
0.6357	Remote Similarity	NPD1091	Approved
0.6357	Remote Similarity	NPD3092	Approved
0.6351	Remote Similarity	NPD5314	Approved
0.6351	Remote Similarity	NPD817	Approved
0.6351	Remote Similarity	NPD823	Approved
0.635	Remote Similarity	NPD5536	Phase 2
0.6345	Remote Similarity	NPD9718	Approved
0.6343	Remote Similarity	NPD821	Approved
0.6338	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1778	Approved
0.6327	Remote Similarity	NPD826	Approved
0.6327	Remote Similarity	NPD825	Approved
0.632	Remote Similarity	NPD1809	Phase 2
0.6316	Remote Similarity	NPD3060	Approved
0.6306	Remote Similarity	NPD1653	Approved
0.6294	Remote Similarity	NPD3053	Approved
0.6294	Remote Similarity	NPD3055	Approved
0.6294	Remote Similarity	NPD3094	Phase 2
0.6291	Remote Similarity	NPD1375	Discontinued
0.6284	Remote Similarity	NPD555	Phase 2
0.6282	Remote Similarity	NPD2183	Approved
0.6282	Remote Similarity	NPD2184	Approved
0.6281	Remote Similarity	NPD9094	Approved
0.6276	Remote Similarity	NPD4908	Phase 1
0.6268	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD4749	Approved
0.6259	Remote Similarity	NPD259	Phase 1
0.6258	Remote Similarity	NPD1511	Approved
0.625	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.625	Remote Similarity	NPD258	Approved
0.625	Remote Similarity	NPD9614	Approved
0.625	Remote Similarity	NPD6584	Phase 3
0.625	Remote Similarity	NPD257	Approved
0.625	Remote Similarity	NPD1934	Approved
0.625	Remote Similarity	NPD9618	Approved
0.6241	Remote Similarity	NPD422	Phase 1
0.6234	Remote Similarity	NPD2219	Phase 1
0.6233	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.623	Remote Similarity	NPD9295	Approved
0.6225	Remote Similarity	NPD9570	Approved
0.6224	Remote Similarity	NPD5310	Approved
0.6224	Remote Similarity	NPD5311	Approved
0.6224	Remote Similarity	NPD6696	Suspended
0.6218	Remote Similarity	NPD4123	Phase 3
0.6216	Remote Similarity	NPD4060	Phase 1
0.6214	Remote Similarity	NPD4626	Approved
0.6212	Remote Similarity	NPD1358	Approved
0.6211	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4237	Approved
0.6209	Remote Similarity	NPD4236	Phase 3
0.6202	Remote Similarity	NPD291	Approved
0.6197	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD3091	Approved
0.6187	Remote Similarity	NPD1182	Approved
0.6178	Remote Similarity	NPD1512	Approved
0.617	Remote Similarity	NPD3496	Discontinued
0.6169	Remote Similarity	NPD8166	Discontinued
0.616	Remote Similarity	NPD845	Approved
0.6154	Remote Similarity	NPD9500	Approved
0.6149	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD9268	Approved
0.6136	Remote Similarity	NPD1444	Approved
0.6136	Remote Similarity	NPD3134	Approved
0.6136	Remote Similarity	NPD1445	Approved
0.6115	Remote Similarity	NPD16	Approved
0.6115	Remote Similarity	NPD856	Approved
0.6115	Remote Similarity	NPD317	Approved
0.6115	Remote Similarity	NPD318	Approved
0.6115	Remote Similarity	NPD9615	Approved
0.6115	Remote Similarity	NPD9613	Approved
0.6115	Remote Similarity	NPD9616	Approved
0.6111	Remote Similarity	NPD2977	Approved
0.6111	Remote Similarity	NPD2801	Approved
0.6111	Remote Similarity	NPD2978	Approved
0.6111	Remote Similarity	NPD8651	Approved
0.6107	Remote Similarity	NPD2238	Phase 2
0.6107	Remote Similarity	NPD9610	Approved
0.6107	Remote Similarity	NPD9608	Approved
0.6107	Remote Similarity	NPD943	Approved
0.6104	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD3687	Approved
0.6101	Remote Similarity	NPD3686	Approved
0.6096	Remote Similarity	NPD9569	Approved
0.6084	Remote Similarity	NPD2235	Phase 2
0.6084	Remote Similarity	NPD2230	Approved
0.6084	Remote Similarity	NPD2232	Approved
0.6084	Remote Similarity	NPD2231	Phase 2
0.6084	Remote Similarity	NPD1608	Approved
0.6084	Remote Similarity	NPD2233	Approved
0.6074	Remote Similarity	NPD4288	Approved
0.6074	Remote Similarity	NPD2296	Approved
0.6071	Remote Similarity	NPD316	Approved
0.6067	Remote Similarity	NPD5735	Approved
0.6061	Remote Similarity	NPD6234	Discontinued
0.6054	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD9493	Approved
0.6042	Remote Similarity	NPD6583	Phase 3
0.6042	Remote Similarity	NPD6582	Phase 2
0.6038	Remote Similarity	NPD2122	Discontinued
0.6037	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD3882	Suspended
0.6029	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD5691	Approved
0.6026	Remote Similarity	NPD2677	Approved
0.6025	Remote Similarity	NPD4678	Approved
0.6025	Remote Similarity	NPD4675	Approved
0.6014	Remote Similarity	NPD3180	Approved
0.6014	Remote Similarity	NPD9536	Phase 1
0.6014	Remote Similarity	NPD4625	Phase 3
0.6014	Remote Similarity	NPD3179	Approved
0.6014	Remote Similarity	NPD9537	Phase 1
0.6013	Remote Similarity	NPD2161	Phase 2
0.6	Remote Similarity	NPD1283	Approved
0.6	Remote Similarity	NPD9365	Approved
0.6	Remote Similarity	NPD6674	Discontinued
0.6	Remote Similarity	NPD1792	Phase 2
0.6	Remote Similarity	NPD5451	Approved
0.5987	Remote Similarity	NPD4538	Approved
0.5987	Remote Similarity	NPD6111	Discontinued
0.5987	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD4536	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