NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.1
Volume:	182.631
LogP:	1.517
LogD:	1.886
LogS:	-1.784
# Rotatable Bonds:	4
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	1.525
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.15
MDCK Permeability:	3.6652701965067536e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.563
Plasma Protein Binding (PPB):	26.690488815307617%
Volume Distribution (VD):	1.76
Pgp-substrate:	51.57347869873047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.252
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.667

ADMET: Excretion

Clearance (CL):	6.414
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.106
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.616
Carcinogencity:	0.627
Eye Corrosion:	0.018
Eye Irritation:	0.93
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC106313

Natural Product ID:	NPC106313
*Common Name:**	1,4-Bis(Methoxymethyl)Benzene
IUPAC Name:	1,4-bis(methoxymethyl)benzene
Synonyms:
Standard InCHIKey:	DAJPMKAQEUGECW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O2/c1-11-7-9-3-5-10(6-4-9)8-12-2/h3-6H,7-8H2,1-2H3
SMILES:	COCc1ccc(cc1)COC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3181980
PubChem CID:	81239
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
NPO15151	Syringa vulgaris	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15151	Syringa vulgaris	Species	Oleaceae	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
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2454.1	nM	PubChem BioAssay data set

☑ 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 NPC106313 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	237
0.1-0.2	2052
0.2-0.3	5648
0.3-0.4	14020
0.4-0.5	11322
0.5-0.6	7335
0.6-0.7	1836
0.7-0.8	231
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC58616
0.8875	High Similarity	NPC165212
0.869	High Similarity	NPC89377
0.8588	High Similarity	NPC304760
0.8488	Intermediate Similarity	NPC173443
0.8488	Intermediate Similarity	NPC220893
0.8353	Intermediate Similarity	NPC93843
0.8276	Intermediate Similarity	NPC1793
0.8172	Intermediate Similarity	NPC70624
0.8148	Intermediate Similarity	NPC66655
0.814	Intermediate Similarity	NPC474211
0.8118	Intermediate Similarity	NPC168855
0.8095	Intermediate Similarity	NPC99394
0.8095	Intermediate Similarity	NPC103326
0.8095	Intermediate Similarity	NPC329319
0.8095	Intermediate Similarity	NPC87299
0.809	Intermediate Similarity	NPC119631
0.8085	Intermediate Similarity	NPC154905
0.8085	Intermediate Similarity	NPC60373
0.8085	Intermediate Similarity	NPC188895
0.8072	Intermediate Similarity	NPC328178
0.8065	Intermediate Similarity	NPC203925
0.8023	Intermediate Similarity	NPC474354
0.8	Intermediate Similarity	NPC172984
0.7976	Intermediate Similarity	NPC117180
0.7952	Intermediate Similarity	NPC170484
0.7907	Intermediate Similarity	NPC304538
0.7889	Intermediate Similarity	NPC79917
0.7857	Intermediate Similarity	NPC121800
0.7849	Intermediate Similarity	NPC325499
0.7849	Intermediate Similarity	NPC276775
0.7849	Intermediate Similarity	NPC249912
0.7849	Intermediate Similarity	NPC92754
0.7826	Intermediate Similarity	NPC130398
0.7826	Intermediate Similarity	NPC5472
0.7805	Intermediate Similarity	NPC175393
0.7802	Intermediate Similarity	NPC321956
0.7789	Intermediate Similarity	NPC245927
0.7778	Intermediate Similarity	NPC108218
0.7778	Intermediate Similarity	NPC8002
0.7778	Intermediate Similarity	NPC177844
0.7778	Intermediate Similarity	NPC99886
0.7778	Intermediate Similarity	NPC259134
0.7766	Intermediate Similarity	NPC475954
0.7766	Intermediate Similarity	NPC225060
0.7766	Intermediate Similarity	NPC78701
0.7766	Intermediate Similarity	NPC35448
0.7765	Intermediate Similarity	NPC133050
0.7701	Intermediate Similarity	NPC95429
0.7692	Intermediate Similarity	NPC71853
0.7684	Intermediate Similarity	NPC100870
0.7684	Intermediate Similarity	NPC146351
0.7674	Intermediate Similarity	NPC323103
0.7674	Intermediate Similarity	NPC103387
0.7629	Intermediate Similarity	NPC234305
0.7629	Intermediate Similarity	NPC24327
0.7629	Intermediate Similarity	NPC12870
0.7619	Intermediate Similarity	NPC224544
0.7609	Intermediate Similarity	NPC128645
0.7586	Intermediate Similarity	NPC270507
0.7582	Intermediate Similarity	NPC185501
0.7582	Intermediate Similarity	NPC213156
0.7582	Intermediate Similarity	NPC240108
0.7579	Intermediate Similarity	NPC470161
0.7551	Intermediate Similarity	NPC85977
0.7551	Intermediate Similarity	NPC130817
0.7531	Intermediate Similarity	NPC208302
0.7529	Intermediate Similarity	NPC167577
0.7529	Intermediate Similarity	NPC78517
0.7526	Intermediate Similarity	NPC300166
0.7526	Intermediate Similarity	NPC84325
0.75	Intermediate Similarity	NPC287790
0.75	Intermediate Similarity	NPC3672
0.75	Intermediate Similarity	NPC472318
0.75	Intermediate Similarity	NPC118343
0.75	Intermediate Similarity	NPC98911
0.747	Intermediate Similarity	NPC189371
0.7449	Intermediate Similarity	NPC301943
0.7449	Intermediate Similarity	NPC305205
0.7449	Intermediate Similarity	NPC474365
0.7447	Intermediate Similarity	NPC471581
0.7444	Intermediate Similarity	NPC96625
0.7423	Intermediate Similarity	NPC316797
0.7423	Intermediate Similarity	NPC289117
0.7423	Intermediate Similarity	NPC13755
0.7423	Intermediate Similarity	NPC42211
0.7423	Intermediate Similarity	NPC174911
0.7419	Intermediate Similarity	NPC231150
0.7416	Intermediate Similarity	NPC294134
0.7412	Intermediate Similarity	NPC176228
0.74	Intermediate Similarity	NPC30416
0.7396	Intermediate Similarity	NPC95755
0.7396	Intermediate Similarity	NPC175298
0.7386	Intermediate Similarity	NPC288903
0.7375	Intermediate Similarity	NPC239931
0.7375	Intermediate Similarity	NPC78954
0.7375	Intermediate Similarity	NPC82770
0.7374	Intermediate Similarity	NPC292792
0.7374	Intermediate Similarity	NPC108875
0.7374	Intermediate Similarity	NPC38079
0.7356	Intermediate Similarity	NPC303245
0.7356	Intermediate Similarity	NPC89950
0.7347	Intermediate Similarity	NPC12714
0.7347	Intermediate Similarity	NPC310905
0.7347	Intermediate Similarity	NPC51633
0.734	Intermediate Similarity	NPC23453
0.734	Intermediate Similarity	NPC138117
0.734	Intermediate Similarity	NPC325292
0.732	Intermediate Similarity	NPC471576
0.732	Intermediate Similarity	NPC171843
0.732	Intermediate Similarity	NPC325497
0.7312	Intermediate Similarity	NPC300017
0.7312	Intermediate Similarity	NPC312304
0.7308	Intermediate Similarity	NPC228452
0.73	Intermediate Similarity	NPC473855
0.73	Intermediate Similarity	NPC238115
0.73	Intermediate Similarity	NPC470393
0.7292	Intermediate Similarity	NPC253423
0.7283	Intermediate Similarity	NPC199567
0.7283	Intermediate Similarity	NPC27974
0.7283	Intermediate Similarity	NPC104216
0.7273	Intermediate Similarity	NPC471228
0.7273	Intermediate Similarity	NPC179686
0.7273	Intermediate Similarity	NPC19856
0.7273	Intermediate Similarity	NPC298224
0.7273	Intermediate Similarity	NPC192596
0.7273	Intermediate Similarity	NPC235762
0.7255	Intermediate Similarity	NPC241549
0.7253	Intermediate Similarity	NPC286608
0.7253	Intermediate Similarity	NPC169050
0.7253	Intermediate Similarity	NPC198747
0.7253	Intermediate Similarity	NPC211237
0.7245	Intermediate Similarity	NPC469481
0.7241	Intermediate Similarity	NPC309279
0.7238	Intermediate Similarity	NPC169616
0.7237	Intermediate Similarity	NPC8235
0.7234	Intermediate Similarity	NPC314690
0.7234	Intermediate Similarity	NPC265521
0.7228	Intermediate Similarity	NPC475203
0.7228	Intermediate Similarity	NPC119271
0.7228	Intermediate Similarity	NPC472315
0.7228	Intermediate Similarity	NPC472316
0.7228	Intermediate Similarity	NPC474376
0.7216	Intermediate Similarity	NPC474073
0.72	Intermediate Similarity	NPC241224
0.72	Intermediate Similarity	NPC38209
0.72	Intermediate Similarity	NPC148060
0.72	Intermediate Similarity	NPC474603
0.72	Intermediate Similarity	NPC31786
0.72	Intermediate Similarity	NPC283546
0.72	Intermediate Similarity	NPC475225
0.72	Intermediate Similarity	NPC12987
0.72	Intermediate Similarity	NPC315794
0.7191	Intermediate Similarity	NPC127491
0.7191	Intermediate Similarity	NPC308619
0.7191	Intermediate Similarity	NPC324835
0.7188	Intermediate Similarity	NPC313650
0.7184	Intermediate Similarity	NPC273837
0.7174	Intermediate Similarity	NPC407
0.7174	Intermediate Similarity	NPC307235
0.7174	Intermediate Similarity	NPC23167
0.7172	Intermediate Similarity	NPC94343
0.7157	Intermediate Similarity	NPC258171
0.7157	Intermediate Similarity	NPC251306
0.7157	Intermediate Similarity	NPC227894
0.7157	Intermediate Similarity	NPC194034
0.7157	Intermediate Similarity	NPC233320
0.7157	Intermediate Similarity	NPC277788
0.7157	Intermediate Similarity	NPC56493
0.7143	Intermediate Similarity	NPC150837
0.7143	Intermediate Similarity	NPC248817
0.7143	Intermediate Similarity	NPC286904
0.7143	Intermediate Similarity	NPC217621
0.7143	Intermediate Similarity	NPC26615
0.7143	Intermediate Similarity	NPC128368
0.7143	Intermediate Similarity	NPC13784
0.7129	Intermediate Similarity	NPC288760
0.7129	Intermediate Similarity	NPC37714
0.7129	Intermediate Similarity	NPC152384
0.7129	Intermediate Similarity	NPC227255
0.7129	Intermediate Similarity	NPC8302
0.7129	Intermediate Similarity	NPC154899
0.7129	Intermediate Similarity	NPC233396
0.7129	Intermediate Similarity	NPC128730
0.7129	Intermediate Similarity	NPC269457
0.7129	Intermediate Similarity	NPC471133
0.7129	Intermediate Similarity	NPC472919
0.7128	Intermediate Similarity	NPC300478
0.7128	Intermediate Similarity	NPC47950
0.7126	Intermediate Similarity	NPC469894
0.7115	Intermediate Similarity	NPC137685
0.7113	Intermediate Similarity	NPC312132
0.7113	Intermediate Similarity	NPC259512
0.7113	Intermediate Similarity	NPC270654
0.7103	Intermediate Similarity	NPC232165
0.7103	Intermediate Similarity	NPC135730
0.71	Intermediate Similarity	NPC91820
0.71	Intermediate Similarity	NPC89886
0.71	Intermediate Similarity	NPC304638
0.71	Intermediate Similarity	NPC82426

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 NPC106313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1137
0.2-0.3	1357
0.3-0.4	3134
0.4-0.5	1974
0.5-0.6	1032
0.6-0.7	269
0.7-0.8	23
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
0.8148	Intermediate Similarity	NPD9294	Approved
0.7765	Intermediate Similarity	NPD9250	Approved
0.75	Intermediate Similarity	NPD1238	Approved
0.7423	Intermediate Similarity	NPD2558	Approved
0.7423	Intermediate Similarity	NPD2549	Approved
0.7423	Intermediate Similarity	NPD2553	Approved
0.7423	Intermediate Similarity	NPD2555	Approved
0.7423	Intermediate Similarity	NPD2552	Approved
0.7423	Intermediate Similarity	NPD2550	Approved
0.7347	Intermediate Similarity	NPD4189	Approved
0.7347	Intermediate Similarity	NPD4188	Approved
0.7253	Intermediate Similarity	NPD1282	Approved
0.72	Intermediate Similarity	NPD3046	Approved
0.72	Intermediate Similarity	NPD164	Approved
0.72	Intermediate Similarity	NPD3048	Approved
0.72	Intermediate Similarity	NPD3047	Approved
0.7188	Intermediate Similarity	NPD844	Approved
0.7157	Intermediate Similarity	NPD290	Approved
0.7129	Intermediate Similarity	NPD794	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD288	Approved
0.7103	Intermediate Similarity	NPD4198	Discontinued
0.71	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9249	Phase 1
0.7087	Intermediate Similarity	NPD2182	Approved
0.7087	Intermediate Similarity	NPD2684	Approved
0.7065	Intermediate Similarity	NPD1087	Approved
0.7059	Intermediate Similarity	NPD2559	Approved
0.7059	Intermediate Similarity	NPD810	Approved
0.7059	Intermediate Similarity	NPD3134	Approved
0.7059	Intermediate Similarity	NPD3526	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7059	Intermediate Similarity	NPD3524	Approved
0.7059	Intermediate Similarity	NPD811	Approved
0.7059	Intermediate Similarity	NPD812	Approved
0.7059	Intermediate Similarity	NPD2551	Approved
0.7033	Intermediate Similarity	NPD111	Approved
0.7011	Intermediate Similarity	NPD227	Approved
0.7011	Intermediate Similarity	NPD225	Approved
0.701	Intermediate Similarity	NPD1989	Approved
0.699	Remote Similarity	NPD1358	Approved
0.6989	Remote Similarity	NPD1101	Approved
0.6989	Remote Similarity	NPD531	Approved
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD9259	Approved
0.6952	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD9490	Approved
0.6915	Remote Similarity	NPD800	Approved
0.6907	Remote Similarity	NPD2934	Approved
0.6907	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2933	Approved
0.69	Remote Similarity	NPD1616	Discontinued
0.6887	Remote Similarity	NPD228	Approved
0.6875	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9609	Approved
0.6869	Remote Similarity	NPD9612	Approved
0.6869	Remote Similarity	NPD9611	Approved
0.6869	Remote Similarity	NPD9495	Approved
0.6857	Remote Similarity	NPD9713	Approved
0.6857	Remote Similarity	NPD5451	Approved
0.6857	Remote Similarity	NPD550	Approved
0.6857	Remote Similarity	NPD551	Approved
0.6847	Remote Similarity	NPD5691	Approved
0.6842	Remote Similarity	NPD1090	Approved
0.6842	Remote Similarity	NPD1086	Approved
0.6842	Remote Similarity	NPD1089	Approved
0.6837	Remote Similarity	NPD2859	Approved
0.6837	Remote Similarity	NPD2860	Approved
0.6822	Remote Similarity	NPD821	Approved
0.6822	Remote Similarity	NPD7843	Approved
0.6813	Remote Similarity	NPD9491	Approved
0.6804	Remote Similarity	NPD3719	Approved
0.6804	Remote Similarity	NPD3718	Approved
0.6804	Remote Similarity	NPD845	Approved
0.6804	Remote Similarity	NPD1202	Approved
0.68	Remote Similarity	NPD3020	Approved
0.6789	Remote Similarity	NPD7157	Approved
0.6786	Remote Similarity	NPD5126	Approved
0.6786	Remote Similarity	NPD5125	Phase 3
0.6786	Remote Similarity	NPD1778	Approved
0.6778	Remote Similarity	NPD226	Approved
0.6759	Remote Similarity	NPD5283	Phase 1
0.6759	Remote Similarity	NPD1241	Discontinued
0.6737	Remote Similarity	NPD689	Discontinued
0.6733	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD969	Suspended
0.6729	Remote Similarity	NPD4572	Approved
0.6729	Remote Similarity	NPD4573	Approved
0.6729	Remote Similarity	NPD4571	Approved
0.6729	Remote Similarity	NPD1139	Approved
0.6729	Remote Similarity	NPD1137	Approved
0.6729	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1088	Approved
0.6701	Remote Similarity	NPD9251	Approved
0.67	Remote Similarity	NPD5926	Approved
0.6698	Remote Similarity	NPD5237	Approved
0.6698	Remote Similarity	NPD5235	Approved
0.6698	Remote Similarity	NPD5236	Approved
0.6698	Remote Similarity	NPD5239	Approved
0.6698	Remote Similarity	NPD5240	Approved
0.6696	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2496	Approved
0.6667	Remote Similarity	NPD855	Approved
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD2497	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD854	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD9716	Approved
0.6637	Remote Similarity	NPD4626	Approved
0.6637	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2201	Approved
0.6635	Remote Similarity	NPD9697	Approved
0.6633	Remote Similarity	NPD1563	Approved
0.6633	Remote Similarity	NPD1409	Phase 3
0.6607	Remote Similarity	NPD7741	Discontinued
0.6607	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2991	Approved
0.6606	Remote Similarity	NPD594	Approved
0.6606	Remote Similarity	NPD592	Approved
0.6606	Remote Similarity	NPD2988	Approved
0.6598	Remote Similarity	NPD1239	Approved
0.6598	Remote Similarity	NPD9365	Approved
0.6579	Remote Similarity	NPD3897	Approved
0.6579	Remote Similarity	NPD3895	Approved
0.6579	Remote Similarity	NPD3898	Approved
0.6579	Remote Similarity	NPD3896	Approved
0.6569	Remote Similarity	NPD3028	Approved
0.6566	Remote Similarity	NPD1693	Approved
0.6566	Remote Similarity	NPD4814	Discontinued
0.6562	Remote Similarity	NPD9295	Approved
0.6549	Remote Similarity	NPD5585	Approved
0.6542	Remote Similarity	NPD2067	Discontinued
0.6538	Remote Similarity	NPD314	Approved
0.6538	Remote Similarity	NPD10	Approved
0.6538	Remote Similarity	NPD315	Approved
0.6538	Remote Similarity	NPD311	Approved
0.6538	Remote Similarity	NPD310	Approved
0.6538	Remote Similarity	NPD309	Approved
0.6538	Remote Similarity	NPD1237	Approved
0.6526	Remote Similarity	NPD9538	Approved
0.6522	Remote Similarity	NPD6287	Discontinued
0.6522	Remote Similarity	NPD1281	Approved
0.6514	Remote Similarity	NPD5535	Approved
0.6509	Remote Similarity	NPD9532	Phase 3
0.6505	Remote Similarity	NPD846	Approved
0.6505	Remote Similarity	NPD940	Approved
0.65	Remote Similarity	NPD1809	Phase 2
0.6486	Remote Similarity	NPD6671	Approved
0.6486	Remote Similarity	NPD709	Approved
0.6486	Remote Similarity	NPD2557	Approved
0.6471	Remote Similarity	NPD9712	Approved
0.646	Remote Similarity	NPD1182	Approved
0.646	Remote Similarity	NPD9545	Approved
0.6455	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1566	Phase 3
0.6436	Remote Similarity	NPD1564	Approved
0.6436	Remote Similarity	NPD1565	Approved
0.6435	Remote Similarity	NPD3496	Discontinued
0.6429	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5291	Approved
0.6429	Remote Similarity	NPD3596	Phase 2
0.6429	Remote Similarity	NPD9493	Approved
0.6429	Remote Similarity	NPD530	Approved
0.6429	Remote Similarity	NPD5292	Approved
0.641	Remote Similarity	NPD5327	Phase 3
0.6408	Remote Similarity	NPD1242	Phase 1
0.6404	Remote Similarity	NPD3444	Approved
0.6404	Remote Similarity	NPD1357	Approved
0.6404	Remote Similarity	NPD3445	Approved
0.6404	Remote Similarity	NPD3443	Approved
0.64	Remote Similarity	NPD9260	Approved
0.6396	Remote Similarity	NPD593	Approved
0.6396	Remote Similarity	NPD595	Approved
0.6396	Remote Similarity	NPD2629	Approved
0.6396	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4750	Phase 3
0.6379	Remote Similarity	NPD1611	Approved
0.6373	Remote Similarity	NPD9710	Approved
0.6373	Remote Similarity	NPD9711	Approved
0.6372	Remote Similarity	NPD2484	Approved
0.6372	Remote Similarity	NPD5536	Phase 2
0.6372	Remote Similarity	NPD2485	Approved
0.6364	Remote Similarity	NPD7635	Approved
0.6364	Remote Similarity	NPD752	Approved
0.6356	Remote Similarity	NPD1283	Approved
0.6355	Remote Similarity	NPD2342	Discontinued
0.6348	Remote Similarity	NPD5723	Approved
0.6348	Remote Similarity	NPD2667	Approved
0.6348	Remote Similarity	NPD2668	Approved
0.6346	Remote Similarity	NPD1735	Approved
0.6346	Remote Similarity	NPD1736	Approved
0.6346	Remote Similarity	NPD4818	Approved
0.6346	Remote Similarity	NPD1737	Approved
0.6346	Remote Similarity	NPD4817	Approved
0.6339	Remote Similarity	NPD6387	Discontinued
0.6325	Remote Similarity	NPD3972	Approved
0.6316	Remote Similarity	NPD6581	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