NPASS Compound

Structure

NPC166168 OpenBabel07101718242D 21 22 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 1.7321 -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 -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 0.8660 -1.5000 0.0000 O 0 0 0 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 2.5981 2.5000 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 -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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 6 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 5 1 6 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 1 0 0 0 10 11 1 0 0 0 0 10 18 1 6 0 0 0 11 13 1 0 0 0 0 11 19 1 1 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.1
Volume:	278.704
LogP:	-1.01
LogD:	-0.737
LogS:	-0.712
# Rotatable Bonds:	4
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	3.661
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.039
MDCK Permeability:	3.757526428671554e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.674
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	15.770852088928223%
Volume Distribution (VD):	0.458
Pgp-substrate:	67.68624114990234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	1.717
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.364
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.745
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.201
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC166168

Natural Product ID:	NPC166168
*Common Name:**	Idesin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2-hydroxy-6-(hydroxymethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QHQPAWAPIKTLIR-HMUNZLOLSA-N
Standard InCHI:	InChI=1S/C13H18O8/c14-4-6-2-1-3-7(16)12(6)21-13-11(19)10(18)9(17)8(5-15)20-13/h1-3,8-11,13-19H,4-5H2/t8-,9-,10+,11-,13+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(O)cccc2CO)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385171
PubChem CID:	21591972
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
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23628332]
NPO27632	Idesia polycarpa	Species	Salicaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	127200.0	nM	PMID[471310]

☑ 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 NPC166168 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	433
0.1-0.2	1748
0.2-0.3	5293
0.3-0.4	11338
0.4-0.5	6399
0.5-0.6	5489
0.6-0.7	7640
0.7-0.8	3567
0.8-0.85	616
0.85-0.9	138
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC87696
0.9444	High Similarity	NPC40377
0.937	High Similarity	NPC166040
0.9313	High Similarity	NPC104167
0.9254	High Similarity	NPC475084
0.9225	High Similarity	NPC248307
0.9225	High Similarity	NPC65942
0.9219	High Similarity	NPC248355
0.9219	High Similarity	NPC307110
0.9194	High Similarity	NPC226712
0.9185	High Similarity	NPC252169
0.9154	High Similarity	NPC299144
0.9154	High Similarity	NPC470270
0.9147	High Similarity	NPC472024
0.9147	High Similarity	NPC80600
0.9141	High Similarity	NPC302378
0.9098	High Similarity	NPC138738
0.9098	High Similarity	NPC59324
0.9098	High Similarity	NPC65530
0.9098	High Similarity	NPC470413
0.9084	High Similarity	NPC6836
0.9084	High Similarity	NPC132895
0.9084	High Similarity	NPC49074
0.9084	High Similarity	NPC25821
0.9077	High Similarity	NPC9912
0.907	High Similarity	NPC270849
0.907	High Similarity	NPC97326
0.907	High Similarity	NPC26653
0.9051	High Similarity	NPC475096
0.9037	High Similarity	NPC469661
0.903	High Similarity	NPC212770
0.903	High Similarity	NPC98777
0.9023	High Similarity	NPC203230
0.9023	High Similarity	NPC186418
0.9023	High Similarity	NPC242028
0.9015	High Similarity	NPC35731
0.9015	High Similarity	NPC48863
0.9015	High Similarity	NPC470881
0.9015	High Similarity	NPC13745
0.9015	High Similarity	NPC251981
0.9015	High Similarity	NPC107478
0.9008	High Similarity	NPC162093
0.9008	High Similarity	NPC252833
0.8986	High Similarity	NPC125755
0.8986	High Similarity	NPC199928
0.8986	High Similarity	NPC99515
0.8986	High Similarity	NPC190714
0.8978	High Similarity	NPC292443
0.8978	High Similarity	NPC469313
0.8978	High Similarity	NPC138227
0.8978	High Similarity	NPC76176
0.8978	High Similarity	NPC232228
0.8978	High Similarity	NPC168579
0.8971	High Similarity	NPC189115
0.8971	High Similarity	NPC469559
0.8963	High Similarity	NPC106944
0.8939	High Similarity	NPC215833
0.8939	High Similarity	NPC69513
0.8921	High Similarity	NPC41844
0.8921	High Similarity	NPC227902
0.8913	High Similarity	NPC161700
0.8913	High Similarity	NPC277867
0.8906	High Similarity	NPC12308
0.8906	High Similarity	NPC470510
0.8905	High Similarity	NPC37793
0.8889	High Similarity	NPC100389
0.8881	High Similarity	NPC52277
0.8881	High Similarity	NPC177035
0.8881	High Similarity	NPC199459
0.8881	High Similarity	NPC164857
0.8872	High Similarity	NPC476411
0.8872	High Similarity	NPC187194
0.8857	High Similarity	NPC175976
0.8841	High Similarity	NPC473045
0.8841	High Similarity	NPC25292
0.8824	High Similarity	NPC202700
0.8815	High Similarity	NPC304152
0.8815	High Similarity	NPC195196
0.881	High Similarity	NPC269242
0.8806	High Similarity	NPC470236
0.8794	High Similarity	NPC206264
0.8794	High Similarity	NPC212670
0.8794	High Similarity	NPC313334
0.879	High Similarity	NPC9248
0.8786	High Similarity	NPC31325
0.8786	High Similarity	NPC15538
0.8786	High Similarity	NPC114505
0.8786	High Similarity	NPC224674
0.8786	High Similarity	NPC275284
0.8786	High Similarity	NPC193473
0.8786	High Similarity	NPC213074
0.8786	High Similarity	NPC15956
0.8786	High Similarity	NPC473480
0.8779	High Similarity	NPC218003
0.8768	High Similarity	NPC473044
0.8768	High Similarity	NPC185307
0.8768	High Similarity	NPC478239
0.8768	High Similarity	NPC46092
0.8768	High Similarity	NPC470950
0.8759	High Similarity	NPC186406
0.8741	High Similarity	NPC157554
0.8741	High Similarity	NPC37468
0.874	High Similarity	NPC266045
0.8732	High Similarity	NPC471214
0.8723	High Similarity	NPC280945
0.8722	High Similarity	NPC165686
0.8722	High Similarity	NPC85799
0.8722	High Similarity	NPC26080
0.8722	High Similarity	NPC303422
0.8712	High Similarity	NPC262606
0.8705	High Similarity	NPC283995
0.8705	High Similarity	NPC470235
0.8705	High Similarity	NPC129417
0.8702	High Similarity	NPC146540
0.8702	High Similarity	NPC72529
0.8696	High Similarity	NPC253878
0.8696	High Similarity	NPC157816
0.8696	High Similarity	NPC476356
0.8676	High Similarity	NPC477797
0.8676	High Similarity	NPC477798
0.8676	High Similarity	NPC134260
0.8671	High Similarity	NPC213197
0.8667	High Similarity	NPC55040
0.8661	High Similarity	NPC469412
0.8661	High Similarity	NPC198734
0.8657	High Similarity	NPC294166
0.8657	High Similarity	NPC115022
0.8652	High Similarity	NPC39657
0.8647	High Similarity	NPC121376
0.8643	High Similarity	NPC22150
0.8643	High Similarity	NPC476301
0.8643	High Similarity	NPC18979
0.8643	High Similarity	NPC43508
0.8643	High Similarity	NPC38041
0.8643	High Similarity	NPC279298
0.8643	High Similarity	NPC469586
0.8636	High Similarity	NPC86030
0.8636	High Similarity	NPC5851
0.8633	High Similarity	NPC81638
0.8626	High Similarity	NPC111247
0.8626	High Similarity	NPC41706
0.8626	High Similarity	NPC183181
0.8626	High Similarity	NPC163332
0.8626	High Similarity	NPC292056
0.8626	High Similarity	NPC118787
0.8626	High Similarity	NPC147821
0.8626	High Similarity	NPC319625
0.8623	High Similarity	NPC471414
0.8623	High Similarity	NPC472711
0.8623	High Similarity	NPC210192
0.8613	High Similarity	NPC292487
0.8613	High Similarity	NPC226005
0.8611	High Similarity	NPC21902
0.8603	High Similarity	NPC25695
0.8603	High Similarity	NPC302701
0.8603	High Similarity	NPC172818
0.8603	High Similarity	NPC475628
0.8603	High Similarity	NPC16435
0.8603	High Similarity	NPC269091
0.8603	High Similarity	NPC306441
0.8601	High Similarity	NPC472709
0.8601	High Similarity	NPC98624
0.8601	High Similarity	NPC472710
0.8594	High Similarity	NPC470804
0.8593	High Similarity	NPC188555
0.8593	High Similarity	NPC478085
0.8593	High Similarity	NPC170694
0.8593	High Similarity	NPC130496
0.8583	High Similarity	NPC60589
0.8583	High Similarity	NPC469708
0.8582	High Similarity	NPC15658
0.8582	High Similarity	NPC7903
0.8582	High Similarity	NPC219876
0.8582	High Similarity	NPC261619
0.8582	High Similarity	NPC16208
0.8582	High Similarity	NPC78770
0.8582	High Similarity	NPC185604
0.8582	High Similarity	NPC184447
0.8582	High Similarity	NPC112861
0.8582	High Similarity	NPC35932
0.8582	High Similarity	NPC126029
0.8582	High Similarity	NPC160991
0.8582	High Similarity	NPC61477
0.8571	High Similarity	NPC79429
0.8571	High Similarity	NPC471667
0.8571	High Similarity	NPC217635
0.8561	High Similarity	NPC5262
0.8561	High Similarity	NPC477799
0.8561	High Similarity	NPC477794
0.8561	High Similarity	NPC48309
0.8561	High Similarity	NPC145319
0.8561	High Similarity	NPC140502
0.8561	High Similarity	NPC472714
0.8561	High Similarity	NPC477800
0.8561	High Similarity	NPC60249
0.8552	High Similarity	NPC150442
0.8552	High Similarity	NPC78809
0.8551	High Similarity	NPC210478
0.855	High Similarity	NPC58607
0.855	High Similarity	NPC178284

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 NPC166168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	859
0.2-0.3	2141
0.3-0.4	2748
0.4-0.5	1549
0.5-0.6	923
0.6-0.7	504
0.7-0.8	68
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD1091	Approved
0.8794	High Similarity	NPD1653	Approved
0.8582	High Similarity	NPD1612	Clinical (unspecified phase)
0.8582	High Similarity	NPD1613	Approved
0.8284	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD3027	Phase 3
0.8209	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6674	Discontinued
0.7958	Intermediate Similarity	NPD7266	Discontinued
0.7939	Intermediate Similarity	NPD1357	Approved
0.7848	Intermediate Similarity	NPD7054	Approved
0.784	Intermediate Similarity	NPD290	Approved
0.7799	Intermediate Similarity	NPD7074	Phase 3
0.7799	Intermediate Similarity	NPD7472	Approved
0.7785	Intermediate Similarity	NPD3818	Discontinued
0.7761	Intermediate Similarity	NPD3705	Approved
0.7734	Intermediate Similarity	NPD228	Approved
0.7654	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6797	Phase 2
0.7593	Intermediate Similarity	NPD7251	Discontinued
0.7554	Intermediate Similarity	NPD2861	Phase 2
0.7546	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6671	Approved
0.7468	Intermediate Similarity	NPD1934	Approved
0.7463	Intermediate Similarity	NPD1548	Phase 1
0.7453	Intermediate Similarity	NPD7228	Approved
0.7452	Intermediate Similarity	NPD6234	Discontinued
0.744	Intermediate Similarity	NPD291	Approved
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3018	Phase 2
0.74	Intermediate Similarity	NPD1774	Approved
0.7394	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4749	Approved
0.7376	Intermediate Similarity	NPD4908	Phase 1
0.7358	Intermediate Similarity	NPD7199	Phase 2
0.7355	Intermediate Similarity	NPD37	Approved
0.7344	Intermediate Similarity	NPD968	Approved
0.7329	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4965	Approved
0.7325	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD556	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1558	Phase 1
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7843	Approved
0.7266	Intermediate Similarity	NPD2983	Phase 2
0.7266	Intermediate Similarity	NPD2982	Phase 2
0.7266	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD447	Suspended
0.7239	Intermediate Similarity	NPD7157	Approved
0.7231	Intermediate Similarity	NPD2684	Approved
0.723	Intermediate Similarity	NPD1375	Discontinued
0.7226	Intermediate Similarity	NPD1778	Approved
0.7219	Intermediate Similarity	NPD5058	Phase 3
0.7203	Intermediate Similarity	NPD4625	Phase 3
0.7197	Intermediate Similarity	NPD2978	Approved
0.7197	Intermediate Similarity	NPD2977	Approved
0.7197	Intermediate Similarity	NPD2801	Approved
0.7194	Intermediate Similarity	NPD2981	Phase 2
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7172	Intermediate Similarity	NPD4060	Phase 1
0.7171	Intermediate Similarity	NPD1511	Approved
0.7169	Intermediate Similarity	NPD7685	Pre-registration
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2677	Approved
0.7133	Intermediate Similarity	NPD5177	Phase 3
0.7122	Intermediate Similarity	NPD422	Phase 1
0.7114	Intermediate Similarity	NPD5762	Approved
0.7114	Intermediate Similarity	NPD5763	Approved
0.7107	Intermediate Similarity	NPD3882	Suspended
0.7099	Intermediate Similarity	NPD3787	Discontinued
0.7092	Intermediate Similarity	NPD8651	Approved
0.7091	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5283	Phase 1
0.7078	Intermediate Similarity	NPD1512	Approved
0.7075	Intermediate Similarity	NPD6653	Approved
0.7071	Intermediate Similarity	NPD2231	Phase 2
0.7071	Intermediate Similarity	NPD2235	Phase 2
0.7063	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7044	Intermediate Similarity	NPD3817	Phase 2
0.7039	Intermediate Similarity	NPD6190	Approved
0.7027	Intermediate Similarity	NPD4536	Approved
0.7027	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4538	Approved
0.7027	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6843	Phase 3
0.7018	Intermediate Similarity	NPD6841	Approved
0.7018	Intermediate Similarity	NPD6842	Approved
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1933	Approved
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3686	Approved
0.6987	Remote Similarity	NPD3687	Approved
0.6986	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8312	Approved
0.6982	Remote Similarity	NPD8313	Approved
0.6981	Remote Similarity	NPD1465	Phase 2
0.698	Remote Similarity	NPD5588	Approved
0.698	Remote Similarity	NPD5960	Phase 3
0.6964	Remote Similarity	NPD7240	Approved
0.696	Remote Similarity	NPD9296	Approved
0.6954	Remote Similarity	NPD2424	Discontinued
0.6937	Remote Similarity	NPD5402	Approved
0.6928	Remote Similarity	NPD3751	Discontinued
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1048	Approved
0.6913	Remote Similarity	NPD7097	Phase 1
0.6908	Remote Similarity	NPD4236	Phase 3
0.6908	Remote Similarity	NPD4237	Approved
0.6908	Remote Similarity	NPD3060	Approved
0.6903	Remote Similarity	NPD4123	Phase 3
0.6899	Remote Similarity	NPD4678	Approved
0.6899	Remote Similarity	NPD4380	Phase 2
0.6899	Remote Similarity	NPD4675	Approved
0.6892	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD230	Phase 1
0.6892	Remote Similarity	NPD5124	Phase 1
0.6887	Remote Similarity	NPD3540	Phase 1
0.6886	Remote Similarity	NPD5844	Phase 1
0.6875	Remote Similarity	NPD558	Phase 2
0.6875	Remote Similarity	NPD5772	Approved
0.6875	Remote Similarity	NPD5773	Approved
0.6867	Remote Similarity	NPD7033	Discontinued
0.6857	Remote Similarity	NPD5125	Phase 3
0.6857	Remote Similarity	NPD5126	Approved
0.6855	Remote Similarity	NPD9365	Approved
0.6853	Remote Similarity	NPD3225	Approved
0.6853	Remote Similarity	NPD6696	Suspended
0.6835	Remote Similarity	NPD3111	Phase 1
0.6832	Remote Similarity	NPD2563	Approved
0.6832	Remote Similarity	NPD2560	Approved
0.6828	Remote Similarity	NPD9494	Approved
0.6821	Remote Similarity	NPD3539	Phase 1
0.6821	Remote Similarity	NPD6032	Approved
0.6821	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD5403	Approved
0.6815	Remote Similarity	NPD2122	Discontinued
0.6803	Remote Similarity	NPD6798	Discontinued
0.6802	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4162	Approved
0.6791	Remote Similarity	NPD3021	Approved
0.6791	Remote Similarity	NPD3022	Approved
0.6783	Remote Similarity	NPD3685	Discontinued
0.6781	Remote Similarity	NPD600	Approved
0.6781	Remote Similarity	NPD596	Approved
0.6779	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD6005	Phase 3
0.6776	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6004	Phase 3
0.6776	Remote Similarity	NPD6002	Phase 3
0.6776	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5536	Phase 2
0.6761	Remote Similarity	NPD776	Approved
0.6757	Remote Similarity	NPD840	Approved
0.6757	Remote Similarity	NPD839	Approved
0.6757	Remote Similarity	NPD2674	Phase 3
0.6757	Remote Similarity	NPD6233	Phase 2
0.6753	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4628	Phase 3
0.6753	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3892	Phase 2
0.6753	Remote Similarity	NPD4110	Phase 3
0.6748	Remote Similarity	NPD7075	Discontinued
0.6739	Remote Similarity	NPD709	Approved
0.6738	Remote Similarity	NPD9381	Approved
0.6738	Remote Similarity	NPD5846	Approved
0.6738	Remote Similarity	NPD6516	Phase 2
0.6738	Remote Similarity	NPD9384	Approved
0.6736	Remote Similarity	NPD2922	Phase 1
0.6735	Remote Similarity	NPD3180	Approved
0.6735	Remote Similarity	NPD3179	Approved
0.6732	Remote Similarity	NPD1549	Phase 2
0.6728	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1398	Phase 1
0.6713	Remote Similarity	NPD1608	Approved
0.6711	Remote Similarity	NPD2238	Phase 2
0.6711	Remote Similarity	NPD6099	Approved
0.6711	Remote Similarity	NPD6100	Approved
0.6709	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2489	Approved
0.6707	Remote Similarity	NPD27	Approved
0.6691	Remote Similarity	NPD969	Suspended

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