NPASS Compound

Structure

CID152722 OpenBabel06191715522D 23 24 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 21 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 18 1 6 0 0 0 12 14 1 0 0 0 0 12 19 1 1 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.11
Volume:	304.79
LogP:	-0.628
LogD:	-0.514
LogS:	-0.528
# Rotatable Bonds:	5
TPSA:	138.07
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	3.553
Fsp3:	0.571
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:	-5.958
MDCK Permeability:	4.475496825762093e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.316
Human Intestinal Absorption (HIA):	0.47
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.655

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	28.333988189697266%
Volume Distribution (VD):	0.713
Pgp-substrate:	47.29710388183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.532
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.36
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	3.84
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.692
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.052
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC152722

Natural Product ID:	NPC152722
*Common Name:**	Leonuriside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	leonuriside
Standard InCHIKey:	NOQYJICHFNSIFZ-DIACKHNESA-N
Standard InCHI:	InChI=1S/C14H20O9/c1-20-7-3-6(16)4-8(21-2)13(7)23-14-12(19)11(18)10(17)9(5-15)22-14/h3-4,9-12,14-19H,5H2,1-2H3/t9-,10-,11+,12-,14+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(OC)cc(cc2OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464406
PubChem CID:	14237626
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	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	6
Others	6

Activity Type	# Activity
Cell Line	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534845]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534845]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534845]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534845]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534845]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[534846]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[534846]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.4	uM	PMID[534846]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	39.0	uM	PMID[534846]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[534846]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[534847]

☑ 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 NPC152722 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	357
0.1-0.2	2309
0.2-0.3	8481
0.3-0.4	11566
0.4-0.5	5120
0.5-0.6	7608
0.6-0.7	5770
0.7-0.8	1349
0.8-0.85	99
0.85-0.9	19
0.9-0.95	9
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC192810
0.9829	High Similarity	NPC221090
0.9826	High Similarity	NPC276195
0.9664	High Similarity	NPC469622
0.9664	High Similarity	NPC189589
0.9664	High Similarity	NPC298845
0.9583	High Similarity	NPC37074
0.9576	High Similarity	NPC217854
0.9496	High Similarity	NPC25817
0.9421	High Similarity	NPC469621
0.935	High Similarity	NPC208769
0.935	High Similarity	NPC60756
0.9339	High Similarity	NPC171533
0.9274	High Similarity	NPC287780
0.9187	High Similarity	NPC247146
0.9145	High Similarity	NPC9248
0.9127	High Similarity	NPC60982
0.9052	High Similarity	NPC142319
0.8908	High Similarity	NPC228907
0.8769	High Similarity	NPC104167
0.875	High Similarity	NPC299144
0.8682	High Similarity	NPC49074
0.864	High Similarity	NPC12308
0.8618	High Similarity	NPC57751
0.8615	High Similarity	NPC13745
0.8615	High Similarity	NPC251981
0.8615	High Similarity	NPC48863
0.8605	High Similarity	NPC162093
0.8605	High Similarity	NPC470270
0.8538	High Similarity	NPC215833
0.8538	High Similarity	NPC69513
0.8538	High Similarity	NPC132895
0.8522	High Similarity	NPC232654
0.8496	Intermediate Similarity	NPC98777
0.8496	Intermediate Similarity	NPC212770
0.8485	Intermediate Similarity	NPC164857
0.8473	Intermediate Similarity	NPC107478
0.8421	Intermediate Similarity	NPC65530
0.8421	Intermediate Similarity	NPC59324
0.8409	Intermediate Similarity	NPC470236
0.839	Intermediate Similarity	NPC247871
0.8385	Intermediate Similarity	NPC166168
0.8382	Intermediate Similarity	NPC252169
0.8374	Intermediate Similarity	NPC214289
0.8372	Intermediate Similarity	NPC248355
0.8372	Intermediate Similarity	NPC166040
0.8361	Intermediate Similarity	NPC76915
0.8361	Intermediate Similarity	NPC151617
0.8346	Intermediate Similarity	NPC242028
0.8346	Intermediate Similarity	NPC203230
0.8309	Intermediate Similarity	NPC475084
0.8309	Intermediate Similarity	NPC189115
0.8309	Intermediate Similarity	NPC469559
0.8308	Intermediate Similarity	NPC262606
0.8295	Intermediate Similarity	NPC302378
0.8295	Intermediate Similarity	NPC40377
0.8291	Intermediate Similarity	NPC124712
0.8284	Intermediate Similarity	NPC195196
0.8281	Intermediate Similarity	NPC233559
0.8273	Intermediate Similarity	NPC227902
0.8258	Intermediate Similarity	NPC294166
0.8258	Intermediate Similarity	NPC115022
0.8254	Intermediate Similarity	NPC126216
0.8254	Intermediate Similarity	NPC105147
0.8254	Intermediate Similarity	NPC228875
0.824	Intermediate Similarity	NPC205850
0.8235	Intermediate Similarity	NPC469661
0.8231	Intermediate Similarity	NPC218003
0.8231	Intermediate Similarity	NPC307110
0.8217	Intermediate Similarity	NPC140750
0.8214	Intermediate Similarity	NPC478237
0.8214	Intermediate Similarity	NPC175976
0.8195	Intermediate Similarity	NPC87696
0.8188	Intermediate Similarity	NPC473045
0.8188	Intermediate Similarity	NPC25292
0.8182	Intermediate Similarity	NPC85799
0.8182	Intermediate Similarity	NPC303422
0.8182	Intermediate Similarity	NPC26080
0.8182	Intermediate Similarity	NPC165686
0.8175	Intermediate Similarity	NPC226712
0.8168	Intermediate Similarity	NPC80600
0.8168	Intermediate Similarity	NPC472024
0.8162	Intermediate Similarity	NPC210478
0.8154	Intermediate Similarity	NPC198487
0.8134	Intermediate Similarity	NPC185778
0.8134	Intermediate Similarity	NPC238243
0.8129	Intermediate Similarity	NPC277867
0.8129	Intermediate Similarity	NPC475096
0.8129	Intermediate Similarity	NPC161700
0.812	Intermediate Similarity	NPC307875
0.812	Intermediate Similarity	NPC25821
0.8116	Intermediate Similarity	NPC473044
0.8106	Intermediate Similarity	NPC65942
0.8106	Intermediate Similarity	NPC121376
0.8106	Intermediate Similarity	NPC248307
0.8095	Intermediate Similarity	NPC269242
0.8092	Intermediate Similarity	NPC26653
0.8092	Intermediate Similarity	NPC97326
0.8092	Intermediate Similarity	NPC270849
0.8074	Intermediate Similarity	NPC138350
0.8074	Intermediate Similarity	NPC25695
0.8074	Intermediate Similarity	NPC3293
0.8074	Intermediate Similarity	NPC40664
0.8074	Intermediate Similarity	NPC172818
0.8074	Intermediate Similarity	NPC165482
0.8074	Intermediate Similarity	NPC197723
0.8071	Intermediate Similarity	NPC190714
0.8071	Intermediate Similarity	NPC125755
0.8071	Intermediate Similarity	NPC99515
0.806	Intermediate Similarity	NPC310854
0.806	Intermediate Similarity	NPC188555
0.806	Intermediate Similarity	NPC130496
0.8045	Intermediate Similarity	NPC252833
0.8043	Intermediate Similarity	NPC5262
0.8043	Intermediate Similarity	NPC472714
0.8042	Intermediate Similarity	NPC213197
0.803	Intermediate Similarity	NPC470079
0.8028	Intermediate Similarity	NPC206264
0.8028	Intermediate Similarity	NPC212670
0.8028	Intermediate Similarity	NPC313334
0.8016	Intermediate Similarity	NPC60589
0.8016	Intermediate Similarity	NPC469708
0.8015	Intermediate Similarity	NPC138738
0.8015	Intermediate Similarity	NPC470413
0.8015	Intermediate Similarity	NPC124149
0.8015	Intermediate Similarity	NPC262328
0.8015	Intermediate Similarity	NPC87777
0.8014	Intermediate Similarity	NPC39657
0.8	Intermediate Similarity	NPC110677
0.7986	Intermediate Similarity	NPC37793
0.7985	Intermediate Similarity	NPC6836
0.797	Intermediate Similarity	NPC469698
0.797	Intermediate Similarity	NPC9912
0.797	Intermediate Similarity	NPC473412
0.797	Intermediate Similarity	NPC475067
0.7958	Intermediate Similarity	NPC130449
0.7958	Intermediate Similarity	NPC248132
0.7958	Intermediate Similarity	NPC96294
0.7956	Intermediate Similarity	NPC100389
0.7953	Intermediate Similarity	NPC469412
0.7953	Intermediate Similarity	NPC198734
0.7941	Intermediate Similarity	NPC186418
0.7941	Intermediate Similarity	NPC37468
0.7939	Intermediate Similarity	NPC216836
0.7931	Intermediate Similarity	NPC78809
0.7929	Intermediate Similarity	NPC473046
0.7929	Intermediate Similarity	NPC118385
0.7929	Intermediate Similarity	NPC297342
0.7929	Intermediate Similarity	NPC187774
0.7929	Intermediate Similarity	NPC469313
0.7929	Intermediate Similarity	NPC138227
0.7929	Intermediate Similarity	NPC76176
0.7929	Intermediate Similarity	NPC472712
0.7929	Intermediate Similarity	NPC168579
0.7929	Intermediate Similarity	NPC472713
0.7926	Intermediate Similarity	NPC470881
0.7926	Intermediate Similarity	NPC35731
0.7926	Intermediate Similarity	NPC170694
0.7926	Intermediate Similarity	NPC187194
0.7923	Intermediate Similarity	NPC470510
0.791	Intermediate Similarity	NPC35932
0.791	Intermediate Similarity	NPC184447
0.791	Intermediate Similarity	NPC160991
0.791	Intermediate Similarity	NPC7903
0.791	Intermediate Similarity	NPC16208
0.7902	Intermediate Similarity	NPC51328
0.7902	Intermediate Similarity	NPC106138
0.7902	Intermediate Similarity	NPC55158
0.7902	Intermediate Similarity	NPC286235
0.7895	Intermediate Similarity	NPC469612
0.7895	Intermediate Similarity	NPC474491
0.7895	Intermediate Similarity	NPC469614
0.7887	Intermediate Similarity	NPC41844
0.7887	Intermediate Similarity	NPC473480
0.7887	Intermediate Similarity	NPC15538
0.7883	Intermediate Similarity	NPC134260
0.7872	Intermediate Similarity	NPC307466
0.7868	Intermediate Similarity	NPC472337
0.7868	Intermediate Similarity	NPC55040
0.7863	Intermediate Similarity	NPC473960
0.7847	Intermediate Similarity	NPC472710
0.7847	Intermediate Similarity	NPC472709
0.7847	Intermediate Similarity	NPC114740
0.7846	Intermediate Similarity	NPC287429
0.7842	Intermediate Similarity	NPC89686
0.7842	Intermediate Similarity	NPC210192
0.7842	Intermediate Similarity	NPC273932
0.7842	Intermediate Similarity	NPC257095
0.7836	Intermediate Similarity	NPC472597
0.7836	Intermediate Similarity	NPC30043
0.7836	Intermediate Similarity	NPC469625
0.7836	Intermediate Similarity	NPC469613
0.782	Intermediate Similarity	NPC285339
0.782	Intermediate Similarity	NPC470258
0.782	Intermediate Similarity	NPC218856
0.782	Intermediate Similarity	NPC45824
0.782	Intermediate Similarity	NPC226788
0.782	Intermediate Similarity	NPC190629
0.782	Intermediate Similarity	NPC202582
0.782	Intermediate Similarity	NPC3439

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 NPC152722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1086
0.2-0.3	2927
0.3-0.4	2589
0.4-0.5	1299
0.5-0.6	780
0.6-0.7	174
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8175	Intermediate Similarity	NPD1091	Approved
0.8028	Intermediate Similarity	NPD1653	Approved
0.8017	Intermediate Similarity	NPD291	Approved
0.7851	Intermediate Similarity	NPD556	Approved
0.7556	Intermediate Similarity	NPD3027	Phase 3
0.7518	Intermediate Similarity	NPD1613	Approved
0.7518	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3454	Phase 3
0.735	Intermediate Similarity	NPD9296	Approved
0.7279	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9365	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7534	Approved
0.7176	Intermediate Similarity	NPD7533	Approved
0.7121	Intermediate Similarity	NPD1357	Approved
0.7101	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9295	Approved
0.7063	Intermediate Similarity	NPD7054	Approved
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7019	Intermediate Similarity	NPD7472	Approved
0.6994	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6674	Discontinued
0.6984	Remote Similarity	NPD290	Approved
0.6966	Remote Similarity	NPD7266	Discontinued
0.6963	Remote Similarity	NPD3705	Approved
0.6923	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1548	Phase 1
0.6905	Remote Similarity	NPD968	Approved
0.6894	Remote Similarity	NPD3818	Discontinued
0.6894	Remote Similarity	NPD7228	Approved
0.689	Remote Similarity	NPD7808	Phase 3
0.6883	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD6234	Discontinued
0.6871	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD6797	Phase 2
0.6861	Remote Similarity	NPD2983	Phase 2
0.6861	Remote Similarity	NPD2982	Phase 2
0.6859	Remote Similarity	NPD4966	Approved
0.6859	Remote Similarity	NPD4967	Phase 2
0.6859	Remote Similarity	NPD4965	Approved
0.6857	Remote Similarity	NPD4908	Phase 1
0.685	Remote Similarity	NPD9552	Approved
0.6849	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9094	Approved
0.6838	Remote Similarity	NPD1610	Phase 2
0.6829	Remote Similarity	NPD7251	Discontinued
0.6818	Remote Similarity	NPD191	Approved
0.6788	Remote Similarity	NPD2981	Phase 2
0.6761	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1798	Approved
0.6741	Remote Similarity	NPD1797	Approved
0.6739	Remote Similarity	NPD4749	Approved
0.6718	Remote Similarity	NPD7843	Approved
0.6715	Remote Similarity	NPD422	Phase 1
0.6687	Remote Similarity	NPD7199	Phase 2
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD2684	Approved
0.6646	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD228	Approved
0.6624	Remote Similarity	NPD2801	Approved
0.6623	Remote Similarity	NPD5058	Phase 3
0.6614	Remote Similarity	NPD9501	Approved
0.6593	Remote Similarity	NPD1103	Approved
0.6593	Remote Similarity	NPD1102	Approved
0.6567	Remote Similarity	NPD6671	Approved
0.6567	Remote Similarity	NPD7157	Approved
0.6564	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6166	Phase 2
0.6564	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3384	Approved
0.6561	Remote Similarity	NPD3383	Approved
0.6561	Remote Similarity	NPD3382	Approved
0.6549	Remote Similarity	NPD2861	Phase 2
0.6528	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6559	Discontinued
0.6527	Remote Similarity	NPD7240	Approved
0.6525	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9093	Approved
0.6519	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.6503	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD9299	Approved
0.6491	Remote Similarity	NPD6843	Phase 3
0.6491	Remote Similarity	NPD6842	Approved
0.6491	Remote Similarity	NPD6841	Approved
0.6483	Remote Similarity	NPD6233	Phase 2
0.6466	Remote Similarity	NPD9089	Approved
0.6463	Remote Similarity	NPD2223	Approved
0.6463	Remote Similarity	NPD2224	Approved
0.6458	Remote Similarity	NPD4625	Phase 3
0.6446	Remote Similarity	NPD5844	Phase 1
0.6439	Remote Similarity	NPD2673	Approved
0.6439	Remote Similarity	NPD2671	Approved
0.6434	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD2250	Discontinued
0.6433	Remote Similarity	NPD4678	Approved
0.6433	Remote Similarity	NPD4675	Approved
0.6419	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4538	Approved
0.6419	Remote Similarity	NPD4536	Approved
0.6415	Remote Similarity	NPD8455	Phase 2
0.64	Remote Similarity	NPD1375	Discontinued
0.6398	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD230	Phase 1
0.6383	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5402	Approved
0.6375	Remote Similarity	NPD3817	Phase 2
0.6375	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1774	Approved
0.6364	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5647	Approved
0.6346	Remote Similarity	NPD5403	Approved
0.6341	Remote Similarity	NPD3787	Discontinued
0.6335	Remote Similarity	NPD3882	Suspended
0.6331	Remote Similarity	NPD7685	Pre-registration
0.6329	Remote Similarity	NPD4380	Phase 2
0.6327	Remote Similarity	NPD1558	Phase 1
0.6312	Remote Similarity	NPD2977	Approved
0.6312	Remote Similarity	NPD2978	Approved
0.6309	Remote Similarity	NPD7097	Phase 1
0.6296	Remote Similarity	NPD7075	Discontinued
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3496	Discontinued
0.6286	Remote Similarity	NPD915	Approved
0.6284	Remote Similarity	NPD1933	Approved
0.6275	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD3685	Discontinued
0.6267	Remote Similarity	NPD5588	Approved
0.6267	Remote Similarity	NPD5960	Phase 3
0.6266	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7213	Phase 3
0.6258	Remote Similarity	NPD1511	Approved
0.6258	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7212	Phase 2
0.625	Remote Similarity	NPD1549	Phase 2
0.6242	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6653	Approved
0.6234	Remote Similarity	NPD2219	Phase 1
0.6234	Remote Similarity	NPD6190	Approved
0.6233	Remote Similarity	NPD3180	Approved
0.6233	Remote Similarity	NPD3179	Approved
0.6225	Remote Similarity	NPD1551	Phase 2
0.6224	Remote Similarity	NPD8651	Approved
0.6218	Remote Similarity	NPD5401	Approved
0.6216	Remote Similarity	NPD3620	Phase 2
0.6216	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5125	Phase 3
0.6214	Remote Similarity	NPD5126	Approved
0.6212	Remote Similarity	NPD1358	Approved
0.6211	Remote Similarity	NPD1465	Phase 2
0.6209	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3687	Approved
0.6203	Remote Similarity	NPD3686	Approved
0.62	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3751	Discontinued
0.619	Remote Similarity	NPD1048	Approved
0.6184	Remote Similarity	NPD3540	Phase 1
0.6181	Remote Similarity	NPD6362	Approved
0.6178	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD1512	Approved
0.6176	Remote Similarity	NPD5283	Phase 1
0.6174	Remote Similarity	NPD447	Suspended
0.617	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4628	Phase 3
0.6169	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD7033	Discontinued
0.6154	Remote Similarity	NPD6799	Approved
0.6154	Remote Similarity	NPD4357	Discontinued
0.6149	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD6801	Discontinued
0.6144	Remote Similarity	NPD2424	Discontinued
0.6138	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2677	Approved
0.6129	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD776	Approved
0.6127	Remote Similarity	NPD1535	Discovery
0.6121	Remote Similarity	NPD9088	Approved
0.6121	Remote Similarity	NPD5494	Approved
0.6118	Remote Similarity	NPD6099	Approved
0.6118	Remote Similarity	NPD3539	Phase 1
0.6118	Remote Similarity	NPD6100	Approved
0.6115	Remote Similarity	NPD4123	Phase 3
0.6115	Remote Similarity	NPD7447	Phase 1
0.6111	Remote Similarity	NPD6696	Suspended
0.6111	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5772	Approved
0.6111	Remote Similarity	NPD5773	Approved
0.6107	Remote Similarity	NPD4060	Phase 1
0.6105	Remote Similarity	NPD7549	Discontinued
0.6104	Remote Similarity	NPD4236	Phase 3
0.6104	Remote Similarity	NPD4237	Approved
0.6104	Remote Similarity	NPD3060	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