NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.09
Volume:	244.139
LogP:	3.013
LogD:	2.531
LogS:	-3.25
# Rotatable Bonds:	3
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	3.081
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.543
MDCK Permeability:	2.0017385395476595e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	94.9533920288086%
Volume Distribution (VD):	0.523
Pgp-substrate:	3.752189874649048%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.439
CYP2C19-inhibitor:	0.919
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	5.926
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.847
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.956
Carcinogencity:	0.331
Eye Corrosion:	0.451
Eye Irritation:	0.972
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC286608

Natural Product ID:	NPC286608
*Common Name:**	Kavain
IUPAC Name:	(2R)-4-methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
Synonyms:	(+)-Kavain; Kawaih; Kawain
Standard InCHIKey:	XEAQIWGXBXCYFX-GUOLPTJISA-N
Standard InCHI:	InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
SMILES:	COC1=CC(=O)O[C@@H](/C=C/c2ccccc2)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL578607
PubChem CID:	5281565
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	4
Others	19
Potency	26

Activity Type	# Activity
Individual Protein	13
Organism	22
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	354.8	nM	PMID[571032]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	PMID[571032]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	16353.5	nM	PMID[571032]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	2238.7	nM	PMID[571031]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[571031]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	5308.0	nM	PMID[571031]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1122.0	nM	PMID[571032]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	50118.7	nM	PMID[571031]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	33491.5	nM	PMID[571031]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[571032]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	55728.4	nM	PMID[15568794]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	69567.3	nM	PMID[25856683]
NPT2	Others	Unspecified		IC50	=	32.0	ug.mL-1	PMID[571029]
NPT27	Others	Unspecified		IC50	=	166.0	ug.mL-1	PMID[571029]
NPT2	Others	Unspecified		Potency	=	15848.9	nM	PMID[571031]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	12589.3	nM	PMID[571031]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[571032]
NPT2	Others	Unspecified		Potency	n.a.	16360.1	nM	PMID[571032]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	16511.3	nM	PMID[571032]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	GI	=	0.0	%	PMID[571034]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	17.4	%	PMID[571034]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	0.0	%	PMID[571034]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	29.0	%	PMID[571034]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	0.0	%	PMID[571034]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	46.9	%	PMID[571034]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	39.7	%	PMID[571034]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	47.6	%	PMID[571034]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	46.7	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	62.6	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	59.9	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	86.1	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	75.9	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	59.2	%	PMID[571034]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	51.9	%	PMID[571034]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[571036]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[571036]
NPT2	Others	Unspecified		Potency	n.a.	31338.4	nM	PMID[1967654]
NPT2	Others	Unspecified		Potency	n.a.	69567.3	nM	PMID[9213587]
NPT2	Others	Unspecified		Potency	n.a.	27695.2	nM	PMID[19733087]
NPT2	Others	Unspecified		Potency	n.a.	69567.3	nM	PMID[19223646]
NPT2	Others	Unspecified		Potency	n.a.	19606.7	nM	PMID[26035018]
NPT2	Others	Unspecified		Potency	n.a.	62528.3	nM	PMID[1982768]
NPT2	Others	Unspecified		Potency	n.a.	7805.6	nM	PMID[24689881]
NPT2	Others	Unspecified		Potency	n.a.	24683.4	nM	PMID[8277313]
NPT2	Others	Unspecified		Potency	n.a.	11025.7	nM	PMID[19012394]

☑ 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 NPC286608 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	180
0.1-0.2	1326
0.2-0.3	4199
0.3-0.4	12265
0.4-0.5	13626
0.5-0.6	9680
0.6-0.7	1219
0.7-0.8	169
0.8-0.85	22
0.85-0.9	5
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169050
0.9383	High Similarity	NPC99240
0.931	High Similarity	NPC23453
0.9268	High Similarity	NPC127491
0.9268	High Similarity	NPC324835
0.9268	High Similarity	NPC308619
0.9059	High Similarity	NPC96625
0.9048	High Similarity	NPC53299
0.9024	High Similarity	NPC89950
0.9024	High Similarity	NPC71795
0.878	High Similarity	NPC167577
0.878	High Similarity	NPC78517
0.8659	High Similarity	NPC176228
0.8642	High Similarity	NPC175393
0.8571	High Similarity	NPC303245
0.8537	High Similarity	NPC3672
0.8537	High Similarity	NPC287790
0.8444	Intermediate Similarity	NPC472319
0.8372	Intermediate Similarity	NPC243289
0.8372	Intermediate Similarity	NPC208183
0.8352	Intermediate Similarity	NPC77273
0.8315	Intermediate Similarity	NPC304760
0.8222	Intermediate Similarity	NPC173443
0.8211	Intermediate Similarity	NPC98911
0.8211	Intermediate Similarity	NPC472318
0.8182	Intermediate Similarity	NPC58616
0.8172	Intermediate Similarity	NPC5472
0.8144	Intermediate Similarity	NPC234305
0.8132	Intermediate Similarity	NPC240108
0.8132	Intermediate Similarity	NPC213156
0.8105	Intermediate Similarity	NPC154517
0.8105	Intermediate Similarity	NPC135951
0.8081	Intermediate Similarity	NPC477251
0.8061	Intermediate Similarity	NPC85977
0.8043	Intermediate Similarity	NPC119631
0.8021	Intermediate Similarity	NPC80115
0.8	Intermediate Similarity	NPC47536
0.8	Intermediate Similarity	NPC89377
0.7941	Intermediate Similarity	NPC474157
0.7921	Intermediate Similarity	NPC40178
0.7907	Intermediate Similarity	NPC170484
0.79	Intermediate Similarity	NPC472316
0.79	Intermediate Similarity	NPC474376
0.79	Intermediate Similarity	NPC136962
0.79	Intermediate Similarity	NPC472315
0.79	Intermediate Similarity	NPC475203
0.7879	Intermediate Similarity	NPC171831
0.7879	Intermediate Similarity	NPC242913
0.7879	Intermediate Similarity	NPC109637
0.7879	Intermediate Similarity	NPC280616
0.7826	Intermediate Similarity	NPC220893
0.7816	Intermediate Similarity	NPC121800
0.78	Intermediate Similarity	NPC127676
0.7778	Intermediate Similarity	NPC82426
0.7778	Intermediate Similarity	NPC179686
0.7778	Intermediate Similarity	NPC475710
0.7778	Intermediate Similarity	NPC91820
0.7742	Intermediate Similarity	NPC185501
0.7723	Intermediate Similarity	NPC37115
0.7714	Intermediate Similarity	NPC308744
0.7708	Intermediate Similarity	NPC30361
0.767	Intermediate Similarity	NPC149545
0.7647	Intermediate Similarity	NPC32203
0.7647	Intermediate Similarity	NPC277788
0.7647	Intermediate Similarity	NPC206800
0.7647	Intermediate Similarity	NPC20485
0.764	Intermediate Similarity	NPC323103
0.764	Intermediate Similarity	NPC103387
0.7629	Intermediate Similarity	NPC249912
0.7629	Intermediate Similarity	NPC325499
0.7629	Intermediate Similarity	NPC276775
0.7629	Intermediate Similarity	NPC270654
0.7629	Intermediate Similarity	NPC92754
0.7624	Intermediate Similarity	NPC209632
0.7624	Intermediate Similarity	NPC128730
0.7619	Intermediate Similarity	NPC272524
0.76	Intermediate Similarity	NPC304638
0.7586	Intermediate Similarity	NPC50192
0.7573	Intermediate Similarity	NPC474364
0.7556	Intermediate Similarity	NPC270507
0.7553	Intermediate Similarity	NPC108026
0.7551	Intermediate Similarity	NPC78701
0.7551	Intermediate Similarity	NPC225060
0.7551	Intermediate Similarity	NPC35448
0.7549	Intermediate Similarity	NPC51174
0.7549	Intermediate Similarity	NPC176971
0.7549	Intermediate Similarity	NPC326447
0.7525	Intermediate Similarity	NPC114594
0.75	Intermediate Similarity	NPC273837
0.7477	Intermediate Similarity	NPC474685
0.7476	Intermediate Similarity	NPC475465
0.7476	Intermediate Similarity	NPC151530
0.7476	Intermediate Similarity	NPC472314
0.7476	Intermediate Similarity	NPC157473
0.7475	Intermediate Similarity	NPC146351
0.7475	Intermediate Similarity	NPC171843
0.7475	Intermediate Similarity	NPC118343
0.7453	Intermediate Similarity	NPC161611
0.7426	Intermediate Similarity	NPC474365
0.7426	Intermediate Similarity	NPC301943
0.7426	Intermediate Similarity	NPC60679
0.7423	Intermediate Similarity	NPC130398
0.7407	Intermediate Similarity	NPC476476
0.7404	Intermediate Similarity	NPC269023
0.7404	Intermediate Similarity	NPC281604
0.7404	Intermediate Similarity	NPC114741
0.7404	Intermediate Similarity	NPC99846
0.7404	Intermediate Similarity	NPC182549
0.74	Intermediate Similarity	NPC253746
0.74	Intermediate Similarity	NPC70624
0.74	Intermediate Similarity	NPC42211
0.7391	Intermediate Similarity	NPC294134
0.7383	Intermediate Similarity	NPC87069
0.7358	Intermediate Similarity	NPC234376
0.7353	Intermediate Similarity	NPC2518
0.7353	Intermediate Similarity	NPC283546
0.7353	Intermediate Similarity	NPC269644
0.7349	Intermediate Similarity	NPC311343
0.7333	Intermediate Similarity	NPC165212
0.7327	Intermediate Similarity	NPC94343
0.7315	Intermediate Similarity	NPC210092
0.7308	Intermediate Similarity	NPC260952
0.73	Intermediate Similarity	NPC325497
0.7294	Intermediate Similarity	NPC155429
0.7294	Intermediate Similarity	NPC326200
0.729	Intermediate Similarity	NPC265002
0.7283	Intermediate Similarity	NPC44546
0.7282	Intermediate Similarity	NPC288760
0.7282	Intermediate Similarity	NPC139891
0.7282	Intermediate Similarity	NPC227255
0.7282	Intermediate Similarity	NPC238115
0.7282	Intermediate Similarity	NPC472919
0.7282	Intermediate Similarity	NPC473855
0.7264	Intermediate Similarity	NPC323007
0.7262	Intermediate Similarity	NPC16190
0.7262	Intermediate Similarity	NPC235059
0.7262	Intermediate Similarity	NPC98880
0.7262	Intermediate Similarity	NPC169222
0.7253	Intermediate Similarity	NPC106313
0.7248	Intermediate Similarity	NPC149691
0.7245	Intermediate Similarity	NPC473347
0.7238	Intermediate Similarity	NPC206341
0.7238	Intermediate Similarity	NPC83628
0.7238	Intermediate Similarity	NPC184633
0.7238	Intermediate Similarity	NPC469636
0.7238	Intermediate Similarity	NPC265407
0.7232	Intermediate Similarity	NPC475827
0.7232	Intermediate Similarity	NPC474223
0.7228	Intermediate Similarity	NPC107101
0.7228	Intermediate Similarity	NPC13755
0.7212	Intermediate Similarity	NPC30594
0.7212	Intermediate Similarity	NPC37622
0.72	Intermediate Similarity	NPC175298
0.72	Intermediate Similarity	NPC179411
0.7196	Intermediate Similarity	NPC139946
0.7196	Intermediate Similarity	NPC477250
0.7196	Intermediate Similarity	NPC474314
0.7196	Intermediate Similarity	NPC470825
0.7182	Intermediate Similarity	NPC190298
0.7182	Intermediate Similarity	NPC128633
0.7176	Intermediate Similarity	NPC95289
0.7174	Intermediate Similarity	NPC288903
0.7157	Intermediate Similarity	NPC84325
0.7157	Intermediate Similarity	NPC307425
0.7157	Intermediate Similarity	NPC188895
0.7156	Intermediate Similarity	NPC87563
0.7143	Intermediate Similarity	NPC281356
0.7143	Intermediate Similarity	NPC470391
0.7143	Intermediate Similarity	NPC156648
0.713	Intermediate Similarity	NPC128368
0.713	Intermediate Similarity	NPC474176
0.7129	Intermediate Similarity	NPC203925
0.7117	Intermediate Similarity	NPC45104
0.7115	Intermediate Similarity	NPC269457
0.7113	Intermediate Similarity	NPC476484
0.7111	Intermediate Similarity	NPC469894
0.7105	Intermediate Similarity	NPC193484
0.7103	Intermediate Similarity	NPC231251
0.7103	Intermediate Similarity	NPC477247
0.7103	Intermediate Similarity	NPC210089
0.7103	Intermediate Similarity	NPC43584
0.7103	Intermediate Similarity	NPC476003
0.7103	Intermediate Similarity	NPC141068
0.7103	Intermediate Similarity	NPC25067
0.7103	Intermediate Similarity	NPC88868
0.7103	Intermediate Similarity	NPC183700
0.7091	Intermediate Similarity	NPC471616
0.7091	Intermediate Similarity	NPC473507
0.7091	Intermediate Similarity	NPC216387
0.7083	Intermediate Similarity	NPC9822
0.708	Intermediate Similarity	NPC193193
0.708	Intermediate Similarity	NPC31314
0.7075	Intermediate Similarity	NPC291837
0.7054	Intermediate Similarity	NPC265547
0.7054	Intermediate Similarity	NPC96705
0.7048	Intermediate Similarity	NPC119271
0.7043	Intermediate Similarity	NPC474254
0.7043	Intermediate Similarity	NPC474159
0.7037	Intermediate Similarity	NPC185840
0.7037	Intermediate Similarity	NPC158282

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 NPC286608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	913
0.2-0.3	1338
0.3-0.4	3381
0.4-0.5	2182
0.5-0.6	1045
0.6-0.7	119
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1282	Approved
0.7826	Intermediate Similarity	NPD689	Discontinued
0.7647	Intermediate Similarity	NPD9716	Approved
0.7551	Intermediate Similarity	NPD5926	Approved
0.7549	Intermediate Similarity	NPD3134	Approved
0.7525	Intermediate Similarity	NPD5909	Discontinued
0.75	Intermediate Similarity	NPD2067	Discontinued
0.7476	Intermediate Similarity	NPD1358	Approved
0.7475	Intermediate Similarity	NPD1238	Approved
0.7363	Intermediate Similarity	NPD3971	Phase 1
0.7282	Intermediate Similarity	NPD9697	Approved
0.7196	Intermediate Similarity	NPD969	Suspended
0.7182	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6647	Phase 2
0.7021	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2182	Approved
0.6857	Remote Similarity	NPD164	Approved
0.6837	Remote Similarity	NPD3673	Approved
0.6837	Remote Similarity	NPD3672	Approved
0.6832	Remote Similarity	NPD1989	Approved
0.6813	Remote Similarity	NPD227	Approved
0.6813	Remote Similarity	NPD225	Approved
0.68	Remote Similarity	NPD1202	Approved
0.6796	Remote Similarity	NPD7798	Approved
0.6792	Remote Similarity	NPD5048	Discontinued
0.6771	Remote Similarity	NPD9259	Approved
0.6771	Remote Similarity	NPD9257	Approved
0.6757	Remote Similarity	NPD1241	Discontinued
0.6757	Remote Similarity	NPD6010	Discontinued
0.6739	Remote Similarity	NPD9490	Approved
0.6727	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9495	Approved
0.6696	Remote Similarity	NPD5691	Approved
0.6696	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD5535	Approved
0.6634	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD9491	Approved
0.6609	Remote Similarity	NPD9545	Approved
0.6604	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD226	Approved
0.6581	Remote Similarity	NPD3496	Discontinued
0.6579	Remote Similarity	NPD9493	Approved
0.6574	Remote Similarity	NPD5704	Approved
0.6574	Remote Similarity	NPD5705	Approved
0.6574	Remote Similarity	NPD5706	Approved
0.6571	Remote Similarity	NPD2550	Approved
0.6571	Remote Similarity	NPD2558	Approved
0.6571	Remote Similarity	NPD2549	Approved
0.6571	Remote Similarity	NPD2552	Approved
0.6571	Remote Similarity	NPD2553	Approved
0.6571	Remote Similarity	NPD2555	Approved
0.6569	Remote Similarity	NPD6049	Phase 2
0.6569	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5585	Approved
0.6545	Remote Similarity	NPD5239	Approved
0.6545	Remote Similarity	NPD5235	Approved
0.6545	Remote Similarity	NPD5236	Approved
0.6545	Remote Similarity	NPD5237	Approved
0.6545	Remote Similarity	NPD5240	Approved
0.6531	Remote Similarity	NPD1087	Approved
0.6522	Remote Similarity	NPD2347	Approved
0.6522	Remote Similarity	NPD9294	Approved
0.6509	Remote Similarity	NPD4188	Approved
0.6509	Remote Similarity	NPD4189	Approved
0.65	Remote Similarity	NPD9256	Approved
0.65	Remote Similarity	NPD9258	Approved
0.6491	Remote Similarity	NPD4198	Discontinued
0.6489	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2201	Approved
0.6476	Remote Similarity	NPD2066	Phase 3
0.6466	Remote Similarity	NPD1894	Discontinued
0.6446	Remote Similarity	NPD3266	Approved
0.6446	Remote Similarity	NPD2797	Approved
0.6446	Remote Similarity	NPD3267	Approved
0.6423	Remote Similarity	NPD6832	Phase 2
0.6422	Remote Similarity	NPD6685	Approved
0.6422	Remote Similarity	NPD968	Approved
0.6421	Remote Similarity	NPD942	Approved
0.6404	Remote Similarity	NPD2629	Approved
0.64	Remote Similarity	NPD800	Approved
0.6393	Remote Similarity	NPD1019	Discontinued
0.6389	Remote Similarity	NPD3046	Approved
0.6389	Remote Similarity	NPD3047	Approved
0.6389	Remote Similarity	NPD3048	Approved
0.6389	Remote Similarity	NPD1237	Approved
0.6372	Remote Similarity	NPD7094	Approved
0.6372	Remote Similarity	NPD6858	Approved
0.6364	Remote Similarity	NPD3225	Approved
0.6364	Remote Similarity	NPD2199	Approved
0.6364	Remote Similarity	NPD2198	Approved
0.6364	Remote Similarity	NPD650	Approved
0.6356	Remote Similarity	NPD4626	Approved
0.6356	Remote Similarity	NPD1778	Approved
0.6337	Remote Similarity	NPD1090	Approved
0.6337	Remote Similarity	NPD1086	Approved
0.6337	Remote Similarity	NPD1089	Approved
0.6333	Remote Similarity	NPD9717	Approved
0.6333	Remote Similarity	NPD6637	Approved
0.6311	Remote Similarity	NPD1563	Approved
0.6311	Remote Similarity	NPD1066	Discontinued
0.6306	Remote Similarity	NPD2684	Approved
0.63	Remote Similarity	NPD531	Approved
0.6296	Remote Similarity	NPD9261	Approved
0.6296	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1929	Approved
0.6296	Remote Similarity	NPD1930	Approved
0.629	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4359	Approved
0.6275	Remote Similarity	NPD1239	Approved
0.6273	Remote Similarity	NPD2551	Approved
0.6273	Remote Similarity	NPD2559	Approved
0.6273	Remote Similarity	NPD812	Approved
0.6273	Remote Similarity	NPD3526	Approved
0.6273	Remote Similarity	NPD3524	Approved
0.6273	Remote Similarity	NPD811	Approved
0.6273	Remote Similarity	NPD810	Approved
0.626	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1693	Approved
0.625	Remote Similarity	NPD9260	Approved
0.625	Remote Similarity	NPD6287	Discontinued
0.625	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9250	Approved
0.6239	Remote Similarity	NPD5536	Phase 2
0.6238	Remote Similarity	NPD5346	Phase 2
0.6238	Remote Similarity	NPD5347	Phase 2
0.6218	Remote Similarity	NPD17	Approved
0.6218	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1088	Approved
0.62	Remote Similarity	NPD4793	Discontinued
0.6198	Remote Similarity	NPD1877	Discontinued
0.619	Remote Similarity	NPD3268	Approved
0.6179	Remote Similarity	NPD1203	Approved
0.6172	Remote Similarity	NPD5124	Phase 1
0.6172	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3847	Discontinued
0.6162	Remote Similarity	NPD111	Approved
0.6161	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5292	Approved
0.6154	Remote Similarity	NPD5291	Approved
0.6147	Remote Similarity	NPD5765	Approved
0.6142	Remote Similarity	NPD6233	Phase 2
0.6132	Remote Similarity	NPD1565	Approved
0.6132	Remote Similarity	NPD1566	Phase 3
0.6132	Remote Similarity	NPD1564	Approved
0.6117	Remote Similarity	NPD7609	Phase 3
0.6116	Remote Similarity	NPD1611	Approved
0.6116	Remote Similarity	NPD1281	Approved
0.6111	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD1756	Approved
0.6106	Remote Similarity	NPD5451	Approved
0.6106	Remote Similarity	NPD551	Approved
0.6106	Remote Similarity	NPD550	Approved
0.6106	Remote Similarity	NPD1752	Approved
0.6098	Remote Similarity	NPD5667	Approved
0.6095	Remote Similarity	NPD2934	Approved
0.6095	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD2933	Approved
0.6094	Remote Similarity	NPD4307	Phase 2
0.6092	Remote Similarity	NPD675	Discontinued
0.609	Remote Similarity	NPD1652	Phase 2
0.6087	Remote Similarity	NPD7843	Approved
0.6087	Remote Similarity	NPD821	Approved
0.6071	Remote Similarity	NPD9263	Approved
0.6071	Remote Similarity	NPD9264	Approved
0.6071	Remote Similarity	NPD9267	Approved
0.6066	Remote Similarity	NPD1608	Approved
0.6063	Remote Similarity	NPD1296	Phase 2
0.6063	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6798	Discontinued
0.6063	Remote Similarity	NPD1048	Approved
0.6058	Remote Similarity	NPD7631	Approved
0.6055	Remote Similarity	NPD1932	Approved
0.605	Remote Similarity	NPD1548	Phase 1
0.6048	Remote Similarity	NPD6362	Approved
0.6047	Remote Similarity	NPD1933	Approved
0.6047	Remote Similarity	NPD4340	Discontinued
0.604	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2860	Approved
0.6038	Remote Similarity	NPD2859	Approved
0.6034	Remote Similarity	NPD2650	Approved
0.6034	Remote Similarity	NPD2652	Approved
0.6032	Remote Similarity	NPD2985	Phase 3
0.6031	Remote Similarity	NPD7033	Discontinued
0.6019	Remote Similarity	NPD9712	Approved
0.6018	Remote Similarity	NPD9266	Approved
0.6018	Remote Similarity	NPD74	Approved
0.6017	Remote Similarity	NPD4574	Approved
0.6017	Remote Similarity	NPD4576	Approved
0.6016	Remote Similarity	NPD4870	Approved
0.6016	Remote Similarity	NPD4062	Phase 3
0.6	Remote Similarity	NPD1137	Approved
0.6	Remote Similarity	NPD1139	Approved
0.6	Remote Similarity	NPD719	Approved
0.6	Remote Similarity	NPD4573	Approved
0.6	Remote Similarity	NPD4571	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