NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.08
Volume:	174.125
LogP:	1.595
LogD:	1.765
LogS:	-1.957
# Rotatable Bonds:	2
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	1.672
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.459
MDCK Permeability:	1.7775024389266036e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.287
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	86.28199768066406%
Volume Distribution (VD):	0.638
Pgp-substrate:	12.468611717224121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.893
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.741
CYP2D6-inhibitor:	0.072
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	12.384
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.911
Carcinogencity:	0.115
Eye Corrosion:	0.945
Eye Irritation:	0.983
Respiratory Toxicity:	0.314

Download Data

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

Natural Product: NPC193067

Natural Product ID:	NPC193067
*Common Name:**	2,6-Dimethoxy-4-Methylphenol
IUPAC Name:	2,6-dimethoxy-4-methylphenol
Synonyms:
Standard InCHIKey:	ZFBNNSOJNZBLLS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O3/c1-6-4-7(11-2)9(10)8(5-6)12-3/h4-5,10H,1-3H3
SMILES:	COc1cc(C)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205268
PubChem CID:	240925
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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	8

Activity Type	# Activity
Cell Line	2
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	2.4	n.a.	PMID[496604]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	2.89	n.a.	PMID[496604]
NPT1	Others	Radical scavenging activity		IC50	=	18000.0	nM	PMID[496603]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	11.48	%	PMID[496605]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	15.78	%	PMID[496605]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	-54.62	%	PMID[496605]
NPT2	Others	Unspecified		Percent Effect	=	-22.31	%	PMID[496606]
NPT2	Others	Unspecified		Percent Effect	=	1.579	%	PMID[496606]
NPT2	Others	Unspecified		Percent Effect	=	13.03	%	PMID[496606]

☑ 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 NPC193067 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	427
0.1-0.2	2344
0.2-0.3	8701
0.3-0.4	11236
0.4-0.5	3705
0.5-0.6	5371
0.6-0.7	7534
0.7-0.8	2586
0.8-0.85	517
0.85-0.9	189
0.9-0.95	83
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC259638
0.973	High Similarity	NPC20674
0.9643	High Similarity	NPC229401
0.9474	High Similarity	NPC49341
0.9469	High Similarity	NPC61516
0.9469	High Similarity	NPC232084
0.9469	High Similarity	NPC10932
0.9469	High Similarity	NPC247364
0.9391	High Similarity	NPC262253
0.9391	High Similarity	NPC71579
0.9391	High Similarity	NPC473411
0.9381	High Similarity	NPC226629
0.9352	High Similarity	NPC165386
0.931	High Similarity	NPC238810
0.931	High Similarity	NPC165375
0.931	High Similarity	NPC220598
0.9304	High Similarity	NPC145780
0.9231	High Similarity	NPC206487
0.9231	High Similarity	NPC183446
0.9231	High Similarity	NPC5796
0.9224	High Similarity	NPC41562
0.9217	High Similarity	NPC166759
0.9182	High Similarity	NPC203924
0.9174	High Similarity	NPC246358
0.9174	High Similarity	NPC7097
0.9174	High Similarity	NPC36108
0.9174	High Similarity	NPC233731
0.9153	High Similarity	NPC203133
0.9153	High Similarity	NPC234400
0.9153	High Similarity	NPC298757
0.9153	High Similarity	NPC251855
0.9153	High Similarity	NPC117214
0.9153	High Similarity	NPC58279
0.9153	High Similarity	NPC472093
0.9153	High Similarity	NPC299584
0.9153	High Similarity	NPC57490
0.9153	High Similarity	NPC116907
0.9153	High Similarity	NPC300326
0.9153	High Similarity	NPC193544
0.9153	High Similarity	NPC221077
0.9153	High Similarity	NPC17943
0.9153	High Similarity	NPC208950
0.9153	High Similarity	NPC271985
0.9153	High Similarity	NPC60885
0.9153	High Similarity	NPC475169
0.9153	High Similarity	NPC82483
0.9153	High Similarity	NPC265483
0.9153	High Similarity	NPC233410
0.9145	High Similarity	NPC228922
0.9145	High Similarity	NPC197757
0.9138	High Similarity	NPC285289
0.913	High Similarity	NPC474565
0.9123	High Similarity	NPC63083
0.9115	High Similarity	NPC221049
0.9076	High Similarity	NPC28730
0.9076	High Similarity	NPC78974
0.9076	High Similarity	NPC223136
0.9076	High Similarity	NPC18924
0.9076	High Similarity	NPC214406
0.9076	High Similarity	NPC44748
0.9076	High Similarity	NPC76451
0.9076	High Similarity	NPC103823
0.9074	High Similarity	NPC164576
0.9018	High Similarity	NPC204120
0.9009	High Similarity	NPC8547
0.9009	High Similarity	NPC78918
0.9009	High Similarity	NPC156840
0.9009	High Similarity	NPC139617
0.9009	High Similarity	NPC257124
0.9009	High Similarity	NPC173746
0.9	High Similarity	NPC246620
0.9	High Similarity	NPC324112
0.9	High Similarity	NPC159968
0.9	High Similarity	NPC210355
0.9	High Similarity	NPC124452
0.9	High Similarity	NPC236791
0.9	High Similarity	NPC293054
0.9	High Similarity	NPC74817
0.9	High Similarity	NPC282000
0.9	High Similarity	NPC266555
0.9	High Similarity	NPC82679
0.9	High Similarity	NPC169474
0.9	High Similarity	NPC127587
0.8983	High Similarity	NPC95168
0.8983	High Similarity	NPC136319
0.8983	High Similarity	NPC84086
0.8983	High Similarity	NPC282496
0.8983	High Similarity	NPC233526
0.8966	High Similarity	NPC35071
0.8966	High Similarity	NPC148615
0.8966	High Similarity	NPC177475
0.8957	High Similarity	NPC255675
0.8929	High Similarity	NPC280606
0.8926	High Similarity	NPC154866
0.8926	High Similarity	NPC28765
0.8926	High Similarity	NPC109275
0.8926	High Similarity	NPC470213
0.8926	High Similarity	NPC98631
0.8926	High Similarity	NPC206615
0.8926	High Similarity	NPC186843
0.8908	High Similarity	NPC228972
0.8908	High Similarity	NPC122792
0.8898	High Similarity	NPC246967
0.8898	High Similarity	NPC135414
0.8889	High Similarity	NPC199023
0.8879	High Similarity	NPC181969
0.8879	High Similarity	NPC320987
0.8852	High Similarity	NPC10225
0.8852	High Similarity	NPC228769
0.8852	High Similarity	NPC470633
0.8852	High Similarity	NPC170844
0.8852	High Similarity	NPC58164
0.8852	High Similarity	NPC48315
0.8852	High Similarity	NPC476968
0.8852	High Similarity	NPC45824
0.8843	High Similarity	NPC252131
0.8839	High Similarity	NPC90520
0.8839	High Similarity	NPC296920
0.8833	High Similarity	NPC105925
0.8824	High Similarity	NPC121115
0.8814	High Similarity	NPC310373
0.8814	High Similarity	NPC75713
0.8814	High Similarity	NPC470804
0.8807	High Similarity	NPC307875
0.8783	High Similarity	NPC123948
0.878	High Similarity	NPC51840
0.878	High Similarity	NPC299221
0.878	High Similarity	NPC472338
0.878	High Similarity	NPC126836
0.878	High Similarity	NPC311680
0.878	High Similarity	NPC214860
0.878	High Similarity	NPC234488
0.8772	High Similarity	NPC228287
0.8772	High Similarity	NPC180508
0.876	High Similarity	NPC181361
0.876	High Similarity	NPC223953
0.876	High Similarity	NPC245060
0.876	High Similarity	NPC112596
0.875	High Similarity	NPC94045
0.875	High Similarity	NPC168657
0.8739	High Similarity	NPC209567
0.8739	High Similarity	NPC474864
0.8739	High Similarity	NPC270326
0.8718	High Similarity	NPC135961
0.871	High Similarity	NPC472597
0.871	High Similarity	NPC474017
0.871	High Similarity	NPC474356
0.871	High Similarity	NPC470095
0.871	High Similarity	NPC12275
0.871	High Similarity	NPC45715
0.871	High Similarity	NPC470096
0.8707	High Similarity	NPC33271
0.8707	High Similarity	NPC304208
0.8707	High Similarity	NPC52464
0.8699	High Similarity	NPC212015
0.8689	High Similarity	NPC470699
0.8689	High Similarity	NPC236760
0.8689	High Similarity	NPC216836
0.8673	High Similarity	NPC195873
0.8655	High Similarity	NPC476343
0.8649	High Similarity	NPC227894
0.864	High Similarity	NPC470270
0.864	High Similarity	NPC16208
0.864	High Similarity	NPC86655
0.864	High Similarity	NPC204215
0.864	High Similarity	NPC6451
0.864	High Similarity	NPC202762
0.864	High Similarity	NPC127624
0.864	High Similarity	NPC35932
0.864	High Similarity	NPC7903
0.864	High Similarity	NPC161958
0.864	High Similarity	NPC160991
0.864	High Similarity	NPC201587
0.864	High Similarity	NPC175067
0.864	High Similarity	NPC253105
0.864	High Similarity	NPC184447
0.864	High Similarity	NPC14224
0.8629	High Similarity	NPC91291
0.8621	High Similarity	NPC141090
0.8621	High Similarity	NPC203113
0.8618	High Similarity	NPC266691
0.8618	High Similarity	NPC19694
0.8607	High Similarity	NPC473960
0.8571	High Similarity	NPC229442
0.8571	High Similarity	NPC132895
0.8571	High Similarity	NPC471391
0.8571	High Similarity	NPC158331
0.8571	High Similarity	NPC471390
0.8571	High Similarity	NPC168059
0.8571	High Similarity	NPC36661
0.8571	High Similarity	NPC475840
0.8571	High Similarity	NPC32778
0.856	High Similarity	NPC309787
0.856	High Similarity	NPC469907
0.856	High Similarity	NPC232275
0.8559	High Similarity	NPC254625
0.8559	High Similarity	NPC119949
0.8559	High Similarity	NPC311595
0.8559	High Similarity	NPC475961
0.8559	High Similarity	NPC24474

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 NPC193067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1070
0.2-0.3	2414
0.3-0.4	2561
0.4-0.5	1385
0.5-0.6	850
0.6-0.7	408
0.7-0.8	57
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9009	High Similarity	NPD228	Approved
0.8852	High Similarity	NPD3027	Phase 3
0.8537	High Similarity	NPD1530	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD2982	Phase 2
0.8361	Intermediate Similarity	NPD2983	Phase 2
0.8346	Intermediate Similarity	NPD1613	Approved
0.8346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD2981	Phase 2
0.8095	Intermediate Similarity	NPD3018	Phase 2
0.8065	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD9296	Approved
0.7951	Intermediate Similarity	NPD1357	Approved
0.7946	Intermediate Similarity	NPD1242	Phase 1
0.7869	Intermediate Similarity	NPD1548	Phase 1
0.7812	Intermediate Similarity	NPD9494	Approved
0.7786	Intermediate Similarity	NPD1558	Phase 1
0.776	Intermediate Similarity	NPD1610	Phase 2
0.775	Intermediate Similarity	NPD5283	Phase 1
0.7727	Intermediate Similarity	NPD230	Phase 1
0.7638	Intermediate Similarity	NPD4749	Approved
0.7634	Intermediate Similarity	NPD3145	Approved
0.7634	Intermediate Similarity	NPD3144	Approved
0.7619	Intermediate Similarity	NPD422	Phase 1
0.7619	Intermediate Similarity	NPD3705	Approved
0.7609	Intermediate Similarity	NPD2219	Phase 1
0.7576	Intermediate Similarity	NPD2674	Phase 3
0.7565	Intermediate Similarity	NPD940	Approved
0.7565	Intermediate Similarity	NPD846	Approved
0.7542	Intermediate Similarity	NPD290	Approved
0.7535	Intermediate Similarity	NPD1653	Approved
0.7519	Intermediate Similarity	NPD3620	Phase 2
0.7519	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD4357	Discontinued
0.7481	Intermediate Similarity	NPD6111	Discontinued
0.7481	Intermediate Similarity	NPD4908	Phase 1
0.7479	Intermediate Similarity	NPD2684	Approved
0.7462	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1934	Approved
0.7445	Intermediate Similarity	NPD3540	Phase 1
0.7431	Intermediate Similarity	NPD9094	Approved
0.7417	Intermediate Similarity	NPD3022	Approved
0.7417	Intermediate Similarity	NPD3021	Approved
0.7414	Intermediate Similarity	NPD291	Approved
0.7397	Intermediate Similarity	NPD2801	Approved
0.7376	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD3539	Phase 1
0.7368	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3882	Suspended
0.7293	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD4750	Phase 3
0.7236	Intermediate Similarity	NPD7843	Approved
0.7213	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1091	Approved
0.72	Intermediate Similarity	NPD7157	Approved
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7192	Intermediate Similarity	NPD4678	Approved
0.7192	Intermediate Similarity	NPD4675	Approved
0.7167	Intermediate Similarity	NPD968	Approved
0.7162	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1240	Approved
0.7123	Intermediate Similarity	NPD4005	Discontinued
0.7113	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1358	Approved
0.7097	Intermediate Similarity	NPD9377	Approved
0.7097	Intermediate Similarity	NPD9379	Approved
0.7095	Intermediate Similarity	NPD37	Approved
0.7092	Intermediate Similarity	NPD3060	Approved
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6671	Approved
0.7063	Intermediate Similarity	NPD7124	Phase 2
0.7054	Intermediate Similarity	NPD9384	Approved
0.7054	Intermediate Similarity	NPD9381	Approved
0.7054	Intermediate Similarity	NPD9295	Approved
0.7029	Intermediate Similarity	NPD1607	Approved
0.7015	Intermediate Similarity	NPD2861	Phase 2
0.7014	Intermediate Similarity	NPD5297	Approved
0.6985	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4237	Approved
0.6972	Remote Similarity	NPD4236	Phase 3
0.697	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9622	Approved
0.6968	Remote Similarity	NPD6166	Phase 2
0.6968	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1424	Approved
0.696	Remote Similarity	NPD821	Approved
0.6957	Remote Similarity	NPD447	Suspended
0.6954	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD4966	Approved
0.6954	Remote Similarity	NPD4965	Approved
0.6953	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7266	Discontinued
0.695	Remote Similarity	NPD1375	Discontinued
0.6944	Remote Similarity	NPD9093	Approved
0.6934	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1465	Phase 2
0.693	Remote Similarity	NPD9365	Approved
0.6929	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD1778	Approved
0.6918	Remote Similarity	NPD1351	Approved
0.6918	Remote Similarity	NPD1350	Approved
0.6918	Remote Similarity	NPD1349	Approved
0.6913	Remote Similarity	NPD5090	Approved
0.6913	Remote Similarity	NPD5089	Approved
0.6899	Remote Similarity	NPD7534	Approved
0.6899	Remote Similarity	NPD7533	Approved
0.6897	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2934	Approved
0.6897	Remote Similarity	NPD2933	Approved
0.6897	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3817	Phase 2
0.6885	Remote Similarity	NPD3134	Approved
0.6884	Remote Similarity	NPD943	Approved
0.6884	Remote Similarity	NPD4060	Phase 1
0.6881	Remote Similarity	NPD9089	Approved
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD7228	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6871	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD556	Approved
0.6853	Remote Similarity	NPD1652	Phase 2
0.685	Remote Similarity	NPD9299	Approved
0.6849	Remote Similarity	NPD4123	Phase 3
0.6846	Remote Similarity	NPD9268	Approved
0.6839	Remote Similarity	NPD6232	Discontinued
0.6838	Remote Similarity	NPD2859	Approved
0.6838	Remote Similarity	NPD2860	Approved
0.6838	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD844	Approved
0.6835	Remote Similarity	NPD7054	Approved
0.6815	Remote Similarity	NPD9619	Approved
0.6815	Remote Similarity	NPD6584	Phase 3
0.6815	Remote Similarity	NPD9620	Approved
0.6815	Remote Similarity	NPD9621	Approved
0.6807	Remote Similarity	NPD3020	Approved
0.6803	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7472	Approved
0.6792	Remote Similarity	NPD7074	Phase 3
0.6791	Remote Similarity	NPD6696	Suspended
0.6791	Remote Similarity	NPD2922	Phase 1
0.6791	Remote Similarity	NPD8651	Approved
0.6788	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.678	Remote Similarity	NPD288	Approved
0.6779	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7199	Phase 2
0.6772	Remote Similarity	NPD3818	Discontinued
0.6769	Remote Similarity	NPD9545	Approved
0.6767	Remote Similarity	NPD1608	Approved
0.6763	Remote Similarity	NPD2238	Phase 2
0.6761	Remote Similarity	NPD2161	Phase 2
0.6759	Remote Similarity	NPD6190	Approved
0.675	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5109	Approved
0.6739	Remote Similarity	NPD5111	Phase 2
0.6739	Remote Similarity	NPD5718	Phase 2
0.6739	Remote Similarity	NPD5110	Phase 2
0.6736	Remote Similarity	NPD5177	Phase 3
0.6736	Remote Similarity	NPD6674	Discontinued
0.672	Remote Similarity	NPD5451	Approved
0.6713	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2978	Approved
0.6711	Remote Similarity	NPD2977	Approved
0.6711	Remote Similarity	NPD3686	Approved
0.6711	Remote Similarity	NPD3687	Approved
0.6709	Remote Similarity	NPD7473	Discontinued
0.6692	Remote Similarity	NPD776	Approved
0.6691	Remote Similarity	NPD554	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.669	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4055	Discovery
0.6688	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3179	Approved
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD709	Approved
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD3180	Approved
0.6667	Remote Similarity	NPD7153	Discontinued
0.6646	Remote Similarity	NPD6797	Phase 2
0.6644	Remote Similarity	NPD2122	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