NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	2.922
LogD:	2.773
LogS:	-3.817
# Rotatable Bonds:	3
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	3.281
Fsp3:	0.267
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:	-4.669
MDCK Permeability:	2.3995553419808857e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.653

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.374
Plasma Protein Binding (PPB):	96.65190124511719%
Volume Distribution (VD):	0.349
Pgp-substrate:	3.494689702987671%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.923
CYP2D6-substrate:	0.714
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	10.898
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.79
AMES Toxicity:	0.878
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.947
Carcinogencity:	0.74
Eye Corrosion:	0.053
Eye Irritation:	0.497
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC193484

Natural Product ID:	NPC193484
*Common Name:**	Methysticin
IUPAC Name:	(2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
Synonyms:	(+)-Methysticin; Methylsticin; Methysticin
Standard InCHIKey:	GTEXBOVBADJOQH-FWEMWIAWSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1
SMILES:	COC1=CC(=O)O[C@@H](/C=C/c2ccc3c(c2)OCO3)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL579224
PubChem CID:	5281567
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001761] Kavalactones

*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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	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	2
Others	22
Potency	27

Activity Type	# Activity
Individual Protein	17
Organism	20
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[511510]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PMID[511510]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	125.9	nM	PMID[511510]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	2511.9	nM	PMID[511510]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[511510]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[511510]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	6682.4	nM	PMID[511510]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	31622.8	nM	PMID[511510]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	84.1	nM	PMID[511510]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-4.34	%	PMID[511512]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[511510]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	6622.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	0.19	ug.mL-1	PMID[511508]
NPT27	Others	Unspecified		IC50	=	392.0	ug.mL-1	PMID[511508]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	5011.9	nM	PMID[511510]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[511510]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	0.15	%	PMID[511512]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	GI	=	0.0	%	PMID[511513]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	36.2	%	PMID[511513]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	11.6	%	PMID[511513]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	33.9	%	PMID[511513]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	37.1	%	PMID[511513]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	0.0	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	83.9	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	75.4	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	56.0	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	55.0	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	60.0	%	PMID[511513]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	50.0	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	53.1	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	61.2	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	73.3	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	71.1	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	55.6	%	PMID[511513]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	48.1	%	PMID[511513]
NPT610	Others	Molecular identity unknown		Potency	n.a.	891.3	nM	PMID[511510]
NPT2	Others	Unspecified		Potency	n.a.	9354.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	46882.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	65.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10408.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	58.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	414.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14825.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10495.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	52603.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	41784.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	8267.4	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 NPC193484 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	303
0.1-0.2	1534
0.2-0.3	5056
0.3-0.4	11661
0.4-0.5	6352
0.5-0.6	7263
0.6-0.7	8239
0.7-0.8	2103
0.8-0.85	155
0.85-0.9	23
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC85830
0.9391	High Similarity	NPC212643
0.9391	High Similarity	NPC199209
0.9322	High Similarity	NPC114845
0.9231	High Similarity	NPC69670
0.9068	High Similarity	NPC57501
0.8974	High Similarity	NPC111225
0.886	High Similarity	NPC127326
0.8824	High Similarity	NPC277460
0.877	High Similarity	NPC256167
0.8678	High Similarity	NPC2058
0.8644	High Similarity	NPC294941
0.8626	High Similarity	NPC20796
0.8621	High Similarity	NPC31279
0.8595	High Similarity	NPC37858
0.8583	High Similarity	NPC476748
0.8561	High Similarity	NPC226005
0.8547	High Similarity	NPC245552
0.8525	High Similarity	NPC202474
0.8512	High Similarity	NPC124916
0.8473	Intermediate Similarity	NPC240915
0.8473	Intermediate Similarity	NPC73071
0.8468	Intermediate Similarity	NPC288238
0.8462	Intermediate Similarity	NPC179309
0.8455	Intermediate Similarity	NPC204466
0.843	Intermediate Similarity	NPC33271
0.8425	Intermediate Similarity	NPC64948
0.8421	Intermediate Similarity	NPC109637
0.8409	Intermediate Similarity	NPC157554
0.8409	Intermediate Similarity	NPC37468
0.8403	Intermediate Similarity	NPC303522
0.84	Intermediate Similarity	NPC21238
0.8397	Intermediate Similarity	NPC7163
0.8387	Intermediate Similarity	NPC70752
0.8374	Intermediate Similarity	NPC222175
0.8374	Intermediate Similarity	NPC344161
0.8361	Intermediate Similarity	NPC159916
0.8361	Intermediate Similarity	NPC164706
0.8361	Intermediate Similarity	NPC137537
0.8361	Intermediate Similarity	NPC272471
0.8361	Intermediate Similarity	NPC107588
0.8361	Intermediate Similarity	NPC70744
0.8346	Intermediate Similarity	NPC166184
0.8333	Intermediate Similarity	NPC246704
0.8321	Intermediate Similarity	NPC205915
0.8306	Intermediate Similarity	NPC471877
0.8306	Intermediate Similarity	NPC267064
0.8293	Intermediate Similarity	NPC119949
0.8284	Intermediate Similarity	NPC100389
0.8271	Intermediate Similarity	NPC143895
0.8271	Intermediate Similarity	NPC102260
0.8271	Intermediate Similarity	NPC186418
0.8271	Intermediate Similarity	NPC230968
0.8268	Intermediate Similarity	NPC289459
0.8268	Intermediate Similarity	NPC27352
0.8254	Intermediate Similarity	NPC279379
0.8248	Intermediate Similarity	NPC110063
0.8248	Intermediate Similarity	NPC297342
0.8246	Intermediate Similarity	NPC310905
0.8246	Intermediate Similarity	NPC12714
0.824	Intermediate Similarity	NPC80241
0.824	Intermediate Similarity	NPC301641
0.824	Intermediate Similarity	NPC310373
0.8231	Intermediate Similarity	NPC19242
0.8222	Intermediate Similarity	NPC278076
0.8217	Intermediate Similarity	NPC226862
0.8217	Intermediate Similarity	NPC165128
0.8217	Intermediate Similarity	NPC57119
0.8217	Intermediate Similarity	NPC158471
0.8205	Intermediate Similarity	NPC258171
0.8203	Intermediate Similarity	NPC127604
0.8203	Intermediate Similarity	NPC120225
0.8203	Intermediate Similarity	NPC213552
0.8197	Intermediate Similarity	NPC268317
0.8195	Intermediate Similarity	NPC55040
0.8195	Intermediate Similarity	NPC477301
0.8189	Intermediate Similarity	NPC146886
0.8189	Intermediate Similarity	NPC20443
0.8189	Intermediate Similarity	NPC60517
0.8188	Intermediate Similarity	NPC83743
0.8188	Intermediate Similarity	NPC262182
0.8188	Intermediate Similarity	NPC287615
0.8188	Intermediate Similarity	NPC216819
0.8188	Intermediate Similarity	NPC476450
0.8174	Intermediate Similarity	NPC179686
0.8168	Intermediate Similarity	NPC227160
0.8168	Intermediate Similarity	NPC82111
0.8148	Intermediate Similarity	NPC178290
0.814	Intermediate Similarity	NPC158737
0.814	Intermediate Similarity	NPC223807
0.814	Intermediate Similarity	NPC286683
0.814	Intermediate Similarity	NPC194841
0.8134	Intermediate Similarity	NPC11453
0.813	Intermediate Similarity	NPC65791
0.813	Intermediate Similarity	NPC185738
0.813	Intermediate Similarity	NPC280001
0.8125	Intermediate Similarity	NPC120066
0.812	Intermediate Similarity	NPC309953
0.812	Intermediate Similarity	NPC110958
0.812	Intermediate Similarity	NPC19890
0.8106	Intermediate Similarity	NPC137669
0.8106	Intermediate Similarity	NPC252833
0.8106	Intermediate Similarity	NPC7744
0.8103	Intermediate Similarity	NPC292792
0.8102	Intermediate Similarity	NPC473873
0.8102	Intermediate Similarity	NPC157816
0.8102	Intermediate Similarity	NPC104956
0.8102	Intermediate Similarity	NPC140502
0.8102	Intermediate Similarity	NPC473792
0.8092	Intermediate Similarity	NPC233224
0.8092	Intermediate Similarity	NPC477705
0.8092	Intermediate Similarity	NPC271208
0.8092	Intermediate Similarity	NPC233961
0.8092	Intermediate Similarity	NPC244799
0.8092	Intermediate Similarity	NPC339621
0.8092	Intermediate Similarity	NPC477694
0.8092	Intermediate Similarity	NPC280399
0.8092	Intermediate Similarity	NPC240722
0.8088	Intermediate Similarity	NPC202700
0.8077	Intermediate Similarity	NPC110313
0.8077	Intermediate Similarity	NPC302378
0.8077	Intermediate Similarity	NPC109275
0.8077	Intermediate Similarity	NPC210674
0.8074	Intermediate Similarity	NPC14022
0.8065	Intermediate Similarity	NPC205502
0.8062	Intermediate Similarity	NPC473960
0.806	Intermediate Similarity	NPC469808
0.8051	Intermediate Similarity	NPC227894
0.8047	Intermediate Similarity	NPC283170
0.8047	Intermediate Similarity	NPC92869
0.8047	Intermediate Similarity	NPC191768
0.8045	Intermediate Similarity	NPC241341
0.8045	Intermediate Similarity	NPC284855
0.8045	Intermediate Similarity	NPC136750
0.8045	Intermediate Similarity	NPC266848
0.8045	Intermediate Similarity	NPC6836
0.8045	Intermediate Similarity	NPC254398
0.8045	Intermediate Similarity	NPC233018
0.8045	Intermediate Similarity	NPC25821
0.8045	Intermediate Similarity	NPC36437
0.8045	Intermediate Similarity	NPC282477
0.8043	Intermediate Similarity	NPC478239
0.8034	Intermediate Similarity	NPC128730
0.8031	Intermediate Similarity	NPC211231
0.803	Intermediate Similarity	NPC219677
0.803	Intermediate Similarity	NPC477706
0.803	Intermediate Similarity	NPC192255
0.8029	Intermediate Similarity	NPC51681
0.8017	Intermediate Similarity	NPC131530
0.8015	Intermediate Similarity	NPC166040
0.8015	Intermediate Similarity	NPC295970
0.8015	Intermediate Similarity	NPC27239
0.8015	Intermediate Similarity	NPC123127
0.8015	Intermediate Similarity	NPC48315
0.8015	Intermediate Similarity	NPC248355
0.8015	Intermediate Similarity	NPC26653
0.8015	Intermediate Similarity	NPC270849
0.8015	Intermediate Similarity	NPC307110
0.8015	Intermediate Similarity	NPC83062
0.8014	Intermediate Similarity	NPC192763
0.8014	Intermediate Similarity	NPC308178
0.8014	Intermediate Similarity	NPC300262
0.8014	Intermediate Similarity	NPC261122
0.8014	Intermediate Similarity	NPC28651
0.8014	Intermediate Similarity	NPC199311
0.8014	Intermediate Similarity	NPC210611
0.8014	Intermediate Similarity	NPC80732
0.8014	Intermediate Similarity	NPC3460
0.8014	Intermediate Similarity	NPC215095
0.8014	Intermediate Similarity	NPC201148
0.8	Intermediate Similarity	NPC241634
0.7986	Intermediate Similarity	NPC15743
0.7986	Intermediate Similarity	NPC50696
0.7985	Intermediate Similarity	NPC135127
0.7985	Intermediate Similarity	NPC67247
0.7985	Intermediate Similarity	NPC471883
0.7985	Intermediate Similarity	NPC470881
0.7984	Intermediate Similarity	NPC300326
0.7984	Intermediate Similarity	NPC39793
0.7984	Intermediate Similarity	NPC58279
0.7984	Intermediate Similarity	NPC17348
0.7971	Intermediate Similarity	NPC176586
0.7971	Intermediate Similarity	NPC287124
0.7971	Intermediate Similarity	NPC210354
0.797	Intermediate Similarity	NPC319969
0.797	Intermediate Similarity	NPC171928
0.797	Intermediate Similarity	NPC65183
0.797	Intermediate Similarity	NPC100223
0.797	Intermediate Similarity	NPC158526
0.797	Intermediate Similarity	NPC72046
0.797	Intermediate Similarity	NPC261812
0.797	Intermediate Similarity	NPC5423
0.797	Intermediate Similarity	NPC16830
0.797	Intermediate Similarity	NPC473924
0.797	Intermediate Similarity	NPC33611
0.797	Intermediate Similarity	NPC129687
0.7969	Intermediate Similarity	NPC108545
0.7969	Intermediate Similarity	NPC470887
0.7969	Intermediate Similarity	NPC249788
0.7967	Intermediate Similarity	NPC233669

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 NPC193484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	911
0.2-0.3	1834
0.3-0.4	2814
0.4-0.5	1719
0.5-0.6	1064
0.6-0.7	498
0.7-0.8	53
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8443	Intermediate Similarity	NPD1357	Approved
0.8362	Intermediate Similarity	NPD1358	Approved
0.824	Intermediate Similarity	NPD3705	Approved
0.813	Intermediate Similarity	NPD5536	Phase 2
0.7966	Intermediate Similarity	NPD3134	Approved
0.7805	Intermediate Similarity	NPD5283	Phase 1
0.7801	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD2492	Phase 1
0.7708	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD228	Approved
0.7639	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5691	Approved
0.7518	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.7438	Intermediate Similarity	NPD9697	Approved
0.7372	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD969	Suspended
0.7348	Intermediate Similarity	NPD2981	Phase 2
0.7343	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4110	Phase 3
0.7333	Intermediate Similarity	NPD9494	Approved
0.7328	Intermediate Similarity	NPD3496	Discontinued
0.7302	Intermediate Similarity	NPD5535	Approved
0.7293	Intermediate Similarity	NPD2983	Phase 2
0.7293	Intermediate Similarity	NPD2982	Phase 2
0.7267	Intermediate Similarity	NPD37	Approved
0.7266	Intermediate Similarity	NPD447	Suspended
0.7252	Intermediate Similarity	NPD4626	Approved
0.7246	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1241	Discontinued
0.7237	Intermediate Similarity	NPD4967	Phase 2
0.7237	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD4966	Approved
0.7226	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD556	Approved
0.719	Intermediate Similarity	NPD291	Approved
0.7177	Intermediate Similarity	NPD290	Approved
0.7176	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD1091	Approved
0.7133	Intermediate Similarity	NPD7028	Phase 2
0.7123	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2684	Approved
0.7105	Intermediate Similarity	NPD1282	Approved
0.7092	Intermediate Similarity	NPD2653	Approved
0.708	Intermediate Similarity	NPD3018	Phase 2
0.7071	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7051	Intermediate Similarity	NPD7199	Phase 2
0.7032	Intermediate Similarity	NPD919	Approved
0.7031	Intermediate Similarity	NPD7843	Approved
0.7029	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6355	Discontinued
0.7015	Intermediate Similarity	NPD1281	Approved
0.7015	Intermediate Similarity	NPD776	Approved
0.7014	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6992	Remote Similarity	NPD1778	Approved
0.6978	Remote Similarity	NPD7095	Approved
0.6975	Remote Similarity	NPD7685	Pre-registration
0.6972	Remote Similarity	NPD6653	Approved
0.697	Remote Similarity	NPD1182	Approved
0.6962	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5297	Approved
0.695	Remote Similarity	NPD4140	Approved
0.695	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1613	Approved
0.6948	Remote Similarity	NPD3817	Phase 2
0.6937	Remote Similarity	NPD3818	Discontinued
0.6929	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD7097	Phase 1
0.6918	Remote Similarity	NPD4237	Approved
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD4236	Phase 3
0.6918	Remote Similarity	NPD1652	Phase 2
0.6912	Remote Similarity	NPD4359	Approved
0.6906	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD230	Phase 1
0.6901	Remote Similarity	NPD4340	Discontinued
0.6901	Remote Similarity	NPD3657	Discovery
0.6901	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1611	Approved
0.6879	Remote Similarity	NPD4062	Phase 3
0.6867	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD17	Approved
0.6863	Remote Similarity	NPD6386	Approved
0.6863	Remote Similarity	NPD6385	Approved
0.6861	Remote Similarity	NPD2922	Phase 1
0.6861	Remote Similarity	NPD1283	Approved
0.6846	Remote Similarity	NPD4357	Discontinued
0.6842	Remote Similarity	NPD1894	Discontinued
0.6839	Remote Similarity	NPD5353	Approved
0.6832	Remote Similarity	NPD7228	Approved
0.6831	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2979	Phase 3
0.6831	Remote Similarity	NPD3620	Phase 2
0.6824	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3847	Discontinued
0.6812	Remote Similarity	NPD3266	Approved
0.6812	Remote Similarity	NPD3267	Approved
0.6809	Remote Similarity	NPD5109	Approved
0.6809	Remote Similarity	NPD5110	Phase 2
0.6809	Remote Similarity	NPD5111	Phase 2
0.68	Remote Similarity	NPD4739	Approved
0.68	Remote Similarity	NPD3146	Approved
0.68	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1651	Approved
0.679	Remote Similarity	NPD7054	Approved
0.6788	Remote Similarity	NPD5327	Phase 3
0.6786	Remote Similarity	NPD6832	Phase 2
0.6786	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5762	Approved
0.6781	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD3686	Approved
0.6776	Remote Similarity	NPD4210	Discontinued
0.6776	Remote Similarity	NPD3687	Approved
0.6774	Remote Similarity	NPD2978	Approved
0.6774	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2977	Approved
0.6763	Remote Similarity	NPD1019	Discontinued
0.6759	Remote Similarity	NPD4108	Discontinued
0.6757	Remote Similarity	NPD6331	Phase 2
0.6757	Remote Similarity	NPD4628	Phase 3
0.6757	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7472	Approved
0.6742	Remote Similarity	NPD709	Approved
0.6739	Remote Similarity	NPD3225	Approved
0.6735	Remote Similarity	NPD2424	Discontinued
0.6735	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8127	Discontinued
0.6727	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9545	Approved
0.6715	Remote Similarity	NPD9717	Approved
0.6715	Remote Similarity	NPD1608	Approved
0.6715	Remote Similarity	NPD1840	Phase 2
0.6714	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2935	Discontinued
0.6712	Remote Similarity	NPD2161	Phase 2
0.6712	Remote Similarity	NPD6032	Approved
0.6711	Remote Similarity	NPD6190	Approved
0.671	Remote Similarity	NPD1934	Approved
0.6707	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9296	Approved
0.6693	Remote Similarity	NPD968	Approved
0.6692	Remote Similarity	NPD1139	Approved
0.6692	Remote Similarity	NPD1137	Approved
0.6691	Remote Similarity	NPD987	Approved
0.6691	Remote Similarity	NPD2797	Approved
0.669	Remote Similarity	NPD5718	Phase 2
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1296	Phase 2
0.669	Remote Similarity	NPD1048	Approved
0.6689	Remote Similarity	NPD4162	Approved
0.6688	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD5124	Phase 1
0.6646	Remote Similarity	NPD7074	Phase 3
0.6645	Remote Similarity	NPD6873	Phase 2
0.6645	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4870	Approved
0.6643	Remote Similarity	NPD8032	Phase 2
0.6643	Remote Similarity	NPD5647	Approved
0.6642	Remote Similarity	NPD1535	Discovery
0.6641	Remote Similarity	NPD821	Approved
0.6641	Remote Similarity	NPD1138	Approved
0.6627	Remote Similarity	NPD7808	Phase 3
0.6625	Remote Similarity	NPD1247	Approved
0.6623	Remote Similarity	NPD7458	Discontinued
0.662	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1876	Approved
0.6606	Remote Similarity	NPD6797	Phase 2
0.66	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3887	Approved
0.6599	Remote Similarity	NPD3539	Phase 1
0.6599	Remote Similarity	NPD2531	Phase 2
0.6597	Remote Similarity	NPD4307	Phase 2
0.6597	Remote Similarity	NPD1558	Phase 1
0.6594	Remote Similarity	NPD1481	Phase 2
0.6593	Remote Similarity	NPD1548	Phase 1
0.6583	Remote Similarity	NPD9365	Approved
0.6582	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3060	Approved
0.6575	Remote Similarity	NPD6896	Approved
0.6575	Remote Similarity	NPD6895	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