NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	321.88
Volume:	210.056
LogP:	2.874
LogD:	2.53
LogS:	-3.251
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.93
Synthetic Accessibility Score:	2.068
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.594
MDCK Permeability:	1.7292633856413886e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	97.56412506103516%
Volume Distribution (VD):	0.221
Pgp-substrate:	2.941239595413208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.241
CYP1A2-substrate:	0.606
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	0.821
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.328
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.276
Carcinogencity:	0.397
Eye Corrosion:	0.09
Eye Irritation:	0.826
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC116562

Natural Product ID:	NPC116562
*Common Name:**	2-(3,5-Dibromo-4-Methoxyphenyl)Acetic Acid
IUPAC Name:	2-(3,5-dibromo-4-methoxyphenyl)acetic acid
Synonyms:
Standard InCHIKey:	PXJNCNLURDNKJO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8Br2O3/c1-14-9-6(10)2-5(3-7(9)11)4-8(12)13/h2-3H,4H2,1H3,(H,12,13)
SMILES:	COc1c(cc(cc1Br)CC(=O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL394119
PubChem CID:	10734734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5012	Lobelia hassleri	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5012	Lobelia hassleri	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12781	Schefflera heptaphylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11175	Chromolaena collina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27935	Setosphaeria rostrata	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7926	Ormosia macrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5012	Lobelia hassleri	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11700	Melicope subunifoliolata	Species	Rutaceae	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
Others	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3825	Individual Protein	Purinergic receptor P2Y1	Homo sapiens	Activity	<	37.5	%	PMID[519488]
NPT3826	Individual Protein	Purinergic receptor P2Y2	Homo sapiens	Activity	<	37.5	%	PMID[519488]
NPT3829	Individual Protein	Purinergic receptor P2Y11	Homo sapiens	Activity	<	37.5	%	PMID[519488]

☑ 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 NPC116562 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	325
0.1-0.2	2147
0.2-0.3	6126
0.3-0.4	13395
0.4-0.5	5191
0.5-0.6	12317
0.6-0.7	3046
0.7-0.8	130
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9076	High Similarity	NPC180207
0.8462	Intermediate Similarity	NPC234639
0.845	Intermediate Similarity	NPC11449
0.8244	Intermediate Similarity	NPC259017
0.8222	Intermediate Similarity	NPC81137
0.8217	Intermediate Similarity	NPC122359
0.8217	Intermediate Similarity	NPC78061
0.8217	Intermediate Similarity	NPC159987
0.8209	Intermediate Similarity	NPC177967
0.8209	Intermediate Similarity	NPC471237
0.8205	Intermediate Similarity	NPC1065
0.8182	Intermediate Similarity	NPC109241
0.8175	Intermediate Similarity	NPC184632
0.8148	Intermediate Similarity	NPC471236
0.8148	Intermediate Similarity	NPC197766
0.8099	Intermediate Similarity	NPC470710
0.8047	Intermediate Similarity	NPC105999
0.7984	Intermediate Similarity	NPC213414
0.7972	Intermediate Similarity	NPC471235
0.7972	Intermediate Similarity	NPC235033
0.7972	Intermediate Similarity	NPC73132
0.7883	Intermediate Similarity	NPC40321
0.7881	Intermediate Similarity	NPC38209
0.7829	Intermediate Similarity	NPC296202
0.7797	Intermediate Similarity	NPC298224
0.7795	Intermediate Similarity	NPC100395
0.7786	Intermediate Similarity	NPC147137
0.776	Intermediate Similarity	NPC322358
0.7752	Intermediate Similarity	NPC7830
0.7721	Intermediate Similarity	NPC471328
0.7717	Intermediate Similarity	NPC205502
0.7705	Intermediate Similarity	NPC54543
0.7705	Intermediate Similarity	NPC259554
0.7698	Intermediate Similarity	NPC470709
0.7687	Intermediate Similarity	NPC478071
0.7676	Intermediate Similarity	NPC272868
0.7676	Intermediate Similarity	NPC122599
0.7676	Intermediate Similarity	NPC270848
0.7656	Intermediate Similarity	NPC61779
0.7642	Intermediate Similarity	NPC473358
0.7639	Intermediate Similarity	NPC178097
0.7619	Intermediate Similarity	NPC51345
0.7584	Intermediate Similarity	NPC474535
0.7533	Intermediate Similarity	NPC475697
0.75	Intermediate Similarity	NPC240664
0.7481	Intermediate Similarity	NPC177291
0.7481	Intermediate Similarity	NPC194416
0.748	Intermediate Similarity	NPC220540
0.748	Intermediate Similarity	NPC471495
0.7479	Intermediate Similarity	NPC52472
0.7465	Intermediate Similarity	NPC250597
0.7444	Intermediate Similarity	NPC111088
0.7442	Intermediate Similarity	NPC293424
0.744	Intermediate Similarity	NPC23332
0.7438	Intermediate Similarity	NPC2518
0.7424	Intermediate Similarity	NPC69403
0.7424	Intermediate Similarity	NPC291189
0.7422	Intermediate Similarity	NPC19290
0.7395	Intermediate Similarity	NPC245561
0.7395	Intermediate Similarity	NPC100870
0.7391	Intermediate Similarity	NPC243404
0.7388	Intermediate Similarity	NPC110131
0.7381	Intermediate Similarity	NPC17693
0.7377	Intermediate Similarity	NPC473855
0.7377	Intermediate Similarity	NPC238115
0.7368	Intermediate Similarity	NPC473942
0.736	Intermediate Similarity	NPC183648
0.7339	Intermediate Similarity	NPC31274
0.7333	Intermediate Similarity	NPC474476
0.7313	Intermediate Similarity	NPC221798
0.7313	Intermediate Similarity	NPC272463
0.7313	Intermediate Similarity	NPC236265
0.7305	Intermediate Similarity	NPC474673
0.7287	Intermediate Similarity	NPC470860
0.7287	Intermediate Similarity	NPC131192
0.7279	Intermediate Similarity	NPC121104
0.7279	Intermediate Similarity	NPC281020
0.7273	Intermediate Similarity	NPC307425
0.7266	Intermediate Similarity	NPC235250
0.7259	Intermediate Similarity	NPC173608
0.7259	Intermediate Similarity	NPC280767
0.7252	Intermediate Similarity	NPC299406
0.7252	Intermediate Similarity	NPC264976
0.725	Intermediate Similarity	NPC280869
0.7244	Intermediate Similarity	NPC199462
0.7236	Intermediate Similarity	NPC227255
0.7236	Intermediate Similarity	NPC13495
0.723	Intermediate Similarity	NPC473608
0.7226	Intermediate Similarity	NPC2596
0.7213	Intermediate Similarity	NPC179686
0.7209	Intermediate Similarity	NPC188907
0.7209	Intermediate Similarity	NPC296526
0.7206	Intermediate Similarity	NPC475236
0.7197	Intermediate Similarity	NPC474874
0.7194	Intermediate Similarity	NPC474753
0.719	Intermediate Similarity	NPC107101
0.7188	Intermediate Similarity	NPC471488
0.7183	Intermediate Similarity	NPC213471
0.7179	Intermediate Similarity	NPC321956
0.7176	Intermediate Similarity	NPC94298
0.7176	Intermediate Similarity	NPC27633
0.7167	Intermediate Similarity	NPC260000
0.7165	Intermediate Similarity	NPC233238
0.7165	Intermediate Similarity	NPC57879
0.7164	Intermediate Similarity	NPC229213
0.7163	Intermediate Similarity	NPC470471
0.7154	Intermediate Similarity	NPC283546
0.7154	Intermediate Similarity	NPC128249
0.7154	Intermediate Similarity	NPC38079
0.7154	Intermediate Similarity	NPC108875
0.7154	Intermediate Similarity	NPC109637
0.7152	Intermediate Similarity	NPC135103
0.7132	Intermediate Similarity	NPC115803
0.7132	Intermediate Similarity	NPC81808
0.7111	Intermediate Similarity	NPC473572
0.7111	Intermediate Similarity	NPC474169
0.7109	Intermediate Similarity	NPC48525
0.7107	Intermediate Similarity	NPC171843
0.7101	Intermediate Similarity	NPC293453
0.7101	Intermediate Similarity	NPC196034
0.7099	Intermediate Similarity	NPC469954
0.7099	Intermediate Similarity	NPC217423
0.7099	Intermediate Similarity	NPC45104
0.7097	Intermediate Similarity	NPC288760
0.7097	Intermediate Similarity	NPC128730
0.7097	Intermediate Similarity	NPC470393
0.7094	Intermediate Similarity	NPC71853
0.709	Intermediate Similarity	NPC201777
0.7087	Intermediate Similarity	NPC473809
0.7087	Intermediate Similarity	NPC25067
0.7087	Intermediate Similarity	NPC88868
0.7087	Intermediate Similarity	NPC231251
0.708	Intermediate Similarity	NPC43706
0.7073	Intermediate Similarity	NPC305205
0.7073	Intermediate Similarity	NPC13426
0.7071	Intermediate Similarity	NPC125153
0.7063	Intermediate Similarity	NPC291837
0.7063	Intermediate Similarity	NPC470470
0.7059	Intermediate Similarity	NPC145134
0.7059	Intermediate Similarity	NPC6888
0.7059	Intermediate Similarity	NPC89630
0.7054	Intermediate Similarity	NPC148969
0.7054	Intermediate Similarity	NPC33244
0.7049	Intermediate Similarity	NPC253746
0.7045	Intermediate Similarity	NPC471033
0.7045	Intermediate Similarity	NPC311091
0.704	Intermediate Similarity	NPC326447
0.704	Intermediate Similarity	NPC176971
0.704	Intermediate Similarity	NPC113457
0.7037	Intermediate Similarity	NPC311219
0.7037	Intermediate Similarity	NPC67300
0.7037	Intermediate Similarity	NPC114298
0.7034	Intermediate Similarity	NPC474128
0.7029	Intermediate Similarity	NPC474147
0.7029	Intermediate Similarity	NPC473708
0.7025	Intermediate Similarity	NPC175298
0.7023	Intermediate Similarity	NPC128825
0.7015	Intermediate Similarity	NPC471486
0.7014	Intermediate Similarity	NPC128877
0.7009	Intermediate Similarity	NPC259134
0.7009	Intermediate Similarity	NPC99886
0.7009	Intermediate Similarity	NPC8002
0.7009	Intermediate Similarity	NPC177844
0.7008	Intermediate Similarity	NPC326187
0.7007	Intermediate Similarity	NPC4164
0.7	Intermediate Similarity	NPC307732
0.7	Intermediate Similarity	NPC327457
0.7	Intermediate Similarity	NPC42292
0.7	Intermediate Similarity	NPC114144
0.7	Intermediate Similarity	NPC285776
0.7	Intermediate Similarity	NPC252004
0.7	Intermediate Similarity	NPC86774
0.7	Intermediate Similarity	NPC94217
0.7	Intermediate Similarity	NPC109778
0.6985	Remote Similarity	NPC163083
0.6985	Remote Similarity	NPC4181
0.6985	Remote Similarity	NPC244876
0.6985	Remote Similarity	NPC257976
0.6985	Remote Similarity	NPC164778
0.6985	Remote Similarity	NPC242372
0.6984	Remote Similarity	NPC251306
0.6984	Remote Similarity	NPC151530
0.6984	Remote Similarity	NPC157473
0.6978	Remote Similarity	NPC2401
0.6972	Remote Similarity	NPC303993
0.6972	Remote Similarity	NPC307006
0.6972	Remote Similarity	NPC129889
0.6968	Remote Similarity	NPC305490
0.696	Remote Similarity	NPC127676
0.696	Remote Similarity	NPC473393
0.6954	Remote Similarity	NPC469711
0.695	Remote Similarity	NPC470392
0.694	Remote Similarity	NPC230951
0.694	Remote Similarity	NPC470092
0.6939	Remote Similarity	NPC78530
0.6939	Remote Similarity	NPC135349
0.6935	Remote Similarity	NPC304638
0.6934	Remote Similarity	NPC312404
0.6934	Remote Similarity	NPC184219
0.6934	Remote Similarity	NPC273686

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 NPC116562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1067
0.2-0.3	1833
0.3-0.4	2921
0.4-0.5	1787
0.5-0.6	1000
0.6-0.7	215
0.7-0.8	15
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
0.782	Intermediate Similarity	NPD9718	Approved
0.7578	Intermediate Similarity	NPD1894	Discontinued
0.7444	Intermediate Similarity	NPD1283	Approved
0.7351	Intermediate Similarity	NPD2296	Approved
0.7323	Intermediate Similarity	NPD1241	Discontinued
0.7293	Intermediate Similarity	NPD1481	Phase 2
0.7273	Intermediate Similarity	NPD3847	Discontinued
0.7237	Intermediate Similarity	NPD4288	Approved
0.7218	Intermediate Similarity	NPD1281	Approved
0.7218	Intermediate Similarity	NPD1535	Discovery
0.7185	Intermediate Similarity	NPD196	Phase 1
0.7176	Intermediate Similarity	NPD9545	Approved
0.7164	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD454	Approved
0.704	Intermediate Similarity	NPD3134	Approved
0.7037	Intermediate Similarity	NPD9717	Approved
0.7023	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6984	Remote Similarity	NPD1358	Approved
0.695	Remote Similarity	NPD4062	Phase 3
0.695	Remote Similarity	NPD6233	Phase 2
0.694	Remote Similarity	NPD17	Approved
0.694	Remote Similarity	NPD1778	Approved
0.6884	Remote Similarity	NPD2797	Approved
0.6866	Remote Similarity	NPD1651	Approved
0.6857	Remote Similarity	NPD2614	Approved
0.6853	Remote Similarity	NPD6355	Discontinued
0.6846	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD4626	Approved
0.6797	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD3972	Approved
0.6781	Remote Similarity	NPD4477	Approved
0.6781	Remote Similarity	NPD4476	Approved
0.6781	Remote Similarity	NPD2935	Discontinued
0.6769	Remote Similarity	NPD228	Approved
0.6763	Remote Similarity	NPD1203	Approved
0.6746	Remote Similarity	NPD9244	Approved
0.6719	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD821	Approved
0.6715	Remote Similarity	NPD422	Phase 1
0.6712	Remote Similarity	NPD2799	Discontinued
0.6692	Remote Similarity	NPD255	Approved
0.6692	Remote Similarity	NPD256	Approved
0.6691	Remote Similarity	NPD1876	Approved
0.6689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6647	Remote Similarity	NPD4287	Approved
0.6644	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD2313	Discontinued
0.6643	Remote Similarity	NPD987	Approved
0.662	Remote Similarity	NPD6832	Phase 2
0.6618	Remote Similarity	NPD5585	Approved
0.6618	Remote Similarity	NPD5691	Approved
0.6613	Remote Similarity	NPD9495	Approved
0.66	Remote Similarity	NPD4628	Phase 3
0.66	Remote Similarity	NPD7003	Approved
0.6597	Remote Similarity	NPD4870	Approved
0.6596	Remote Similarity	NPD5647	Approved
0.6596	Remote Similarity	NPD1019	Discontinued
0.6596	Remote Similarity	NPD2798	Approved
0.6591	Remote Similarity	NPD7843	Approved
0.6589	Remote Similarity	NPD290	Approved
0.6577	Remote Similarity	NPD4534	Discontinued
0.6575	Remote Similarity	NPD1607	Approved
0.6573	Remote Similarity	NPD5163	Phase 2
0.6573	Remote Similarity	NPD7095	Approved
0.6562	Remote Similarity	NPD9697	Approved
0.6554	Remote Similarity	NPD2239	Approved
0.6554	Remote Similarity	NPD2240	Approved
0.6552	Remote Similarity	NPD9491	Approved
0.6533	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1520	Approved
0.6531	Remote Similarity	NPD1521	Approved
0.6531	Remote Similarity	NPD1536	Approved
0.6528	Remote Similarity	NPD411	Approved
0.6525	Remote Similarity	NPD3266	Approved
0.6525	Remote Similarity	NPD3267	Approved
0.6525	Remote Similarity	NPD6362	Approved
0.6522	Remote Similarity	NPD3496	Discontinued
0.6519	Remote Similarity	NPD9568	Approved
0.6512	Remote Similarity	NPD968	Approved
0.651	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD447	Suspended
0.6507	Remote Similarity	NPD1184	Approved
0.6493	Remote Similarity	NPD690	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4110	Phase 3
0.649	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5451	Approved
0.6486	Remote Similarity	NPD4308	Phase 3
0.6484	Remote Similarity	NPD164	Approved
0.6483	Remote Similarity	NPD8032	Phase 2
0.6475	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5958	Discontinued
0.6462	Remote Similarity	NPD9267	Approved
0.6462	Remote Similarity	NPD9264	Approved
0.6462	Remote Similarity	NPD9263	Approved
0.6454	Remote Similarity	NPD3225	Approved
0.6447	Remote Similarity	NPD2354	Approved
0.6444	Remote Similarity	NPD7157	Approved
0.6443	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2531	Phase 2
0.6443	Remote Similarity	NPD1523	Approved
0.6443	Remote Similarity	NPD1537	Approved
0.6443	Remote Similarity	NPD1538	Phase 1
0.6443	Remote Similarity	NPD1519	Approved
0.6443	Remote Similarity	NPD1522	Approved
0.6443	Remote Similarity	NPD2438	Suspended
0.6429	Remote Similarity	NPD1238	Approved
0.6419	Remote Similarity	NPD7097	Phase 1
0.6414	Remote Similarity	NPD1296	Phase 2
0.6414	Remote Similarity	NPD3764	Approved
0.6412	Remote Similarity	NPD74	Approved
0.6412	Remote Similarity	NPD9266	Approved
0.6405	Remote Similarity	NPD7440	Discontinued
0.64	Remote Similarity	NPD6005	Phase 3
0.64	Remote Similarity	NPD6002	Phase 3
0.64	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2346	Discontinued
0.64	Remote Similarity	NPD6004	Phase 3
0.64	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4618	Approved
0.6395	Remote Similarity	NPD230	Phase 1
0.6395	Remote Similarity	NPD4622	Approved
0.6387	Remote Similarity	NPD6273	Approved
0.6383	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4359	Approved
0.6382	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3750	Approved
0.6379	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1510	Phase 2
0.6376	Remote Similarity	NPD7033	Discontinued
0.6371	Remote Similarity	NPD2933	Approved
0.6371	Remote Similarity	NPD2934	Approved
0.6364	Remote Similarity	NPD800	Approved
0.6364	Remote Similarity	NPD6799	Approved
0.6351	Remote Similarity	NPD6653	Approved
0.635	Remote Similarity	NPD5536	Phase 2
0.6343	Remote Similarity	NPD1138	Approved
0.6333	Remote Similarity	NPD1551	Phase 2
0.6331	Remote Similarity	NPD2668	Approved
0.6331	Remote Similarity	NPD2667	Approved
0.6327	Remote Similarity	NPD4140	Approved
0.6327	Remote Similarity	NPD4307	Phase 2
0.6327	Remote Similarity	NPD4060	Phase 1
0.6327	Remote Similarity	NPD3142	Approved
0.6327	Remote Similarity	NPD3140	Approved
0.632	Remote Similarity	NPD2859	Approved
0.632	Remote Similarity	NPD2860	Approved
0.6316	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1086	Approved
0.6311	Remote Similarity	NPD1089	Approved
0.6311	Remote Similarity	NPD9258	Approved
0.6311	Remote Similarity	NPD9256	Approved
0.6311	Remote Similarity	NPD1090	Approved
0.6309	Remote Similarity	NPD5688	Approved
0.6309	Remote Similarity	NPD5689	Approved
0.6304	Remote Similarity	NPD1548	Phase 1
0.6303	Remote Similarity	NPD111	Approved
0.6296	Remote Similarity	NPD5283	Phase 1
0.6291	Remote Similarity	NPD2353	Approved
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2344	Approved
0.6291	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD2182	Approved
0.6284	Remote Similarity	NPD1933	Approved
0.6284	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6390	Discontinued
0.6282	Remote Similarity	NPD5049	Phase 3
0.6279	Remote Similarity	NPD9261	Approved
0.6269	Remote Similarity	NPD1139	Approved
0.6269	Remote Similarity	NPD1137	Approved
0.6268	Remote Similarity	NPD3685	Discontinued
0.6267	Remote Similarity	NPD3748	Approved
0.6266	Remote Similarity	NPD7458	Discontinued
0.6259	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1357	Approved
0.6259	Remote Similarity	NPD5745	Approved
0.625	Remote Similarity	NPD1549	Phase 2
0.6242	Remote Similarity	NPD1670	Discontinued
0.6242	Remote Similarity	NPD7427	Discontinued
0.624	Remote Similarity	NPD1693	Approved
0.624	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD226	Approved
0.6234	Remote Similarity	NPD3887	Approved
0.6232	Remote Similarity	NPD1758	Phase 1
0.6231	Remote Similarity	NPD5909	Discontinued
0.623	Remote Similarity	NPD9295	Approved
0.6218	Remote Similarity	NPD2533	Approved
0.6218	Remote Similarity	NPD2534	Approved
0.6218	Remote Similarity	NPD2532	Approved
0.6216	Remote Similarity	NPD2203	Discontinued

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