NPASS Compound

Structure

CID59033 OpenBabel06191715392D 37 39 0 0 1 0 0 0 0 0999 V2000 2.5981 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 8.6603 4.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 5 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 5 6 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 25 2 0 0 0 0 9 13 2 0 0 0 0 9 25 1 0 0 0 0 10 27 1 0 0 0 0 11 16 2 0 0 0 0 11 35 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 6 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 4 1 6 0 0 0 15 16 1 0 0 0 0 16 22 1 0 0 0 0 17 10 1 1 0 0 0 17 18 1 0 0 0 0 17 36 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 24 1 0 0 0 0 20 30 1 6 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 22 33 2 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 23 37 1 1 0 0 0 24 36 1 0 0 0 0 24 37 1 1 0 0 0 M CHG 2 25 1 34 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	523.17
Volume:	493.379
LogP:	-1.505
LogD:	-1.095
LogS:	-1.007
# Rotatable Bonds:	10
TPSA:	210.15
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	5.353
Fsp3:	0.458
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.135
MDCK Permeability:	8.714036812307313e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.99
20% Bioavailability (F20%):	0.5
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	21.52115821838379%
Volume Distribution (VD):	0.208
Pgp-substrate:	70.40177154541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	1.562
Half-life (T1/2):	0.951

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.107
Carcinogencity:	0.912
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC59033

Natural Product ID:	NPC59033
*Common Name:**	Lonijaposide C
IUPAC Name:	5-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-hydroxyethyl)pyridin-1-ium-3-carboxylate
Synonyms:	Lonijaposide C
Standard InCHIKey:	DXFHNEGQVDLRDO-KBCYOOEFSA-N
Standard InCHI:	InChI=1S/C24H29NO12/c1-2-14-15(4-3-12-7-13(21(31)32)9-25(8-12)5-6-26)16(22(33)34)11-35-23(14)37-24-20(30)19(29)18(28)17(10-27)36-24/h2-4,7-9,11,14-15,17-20,23-24,26-30H,1,5-6,10H2,(H-,31,32,33,34)/b4-3+/t14-,15+,17-,18-,19+,20-,23+,24+/m1/s1
SMILES:	C=C[C@@H]1[C@H](/C=C/c2cc(c[n+](CCO)c2)C(=O)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515693
PubChem CID:	24879106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	69.5	%	PMID[460996]

☑ 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 NPC59033 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	282
0.1-0.2	1428
0.2-0.3	6467
0.3-0.4	12914
0.4-0.5	16341
0.5-0.6	4442
0.6-0.7	586
0.7-0.8	212
0.8-0.85	5
0.85-0.9	8
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.983	High Similarity	NPC329024
0.9775	High Similarity	NPC79223
0.9774	High Similarity	NPC317672
0.9669	High Similarity	NPC25442
0.9669	High Similarity	NPC12944
0.9663	High Similarity	NPC320748
0.9663	High Similarity	NPC324245
0.9563	High Similarity	NPC156044
0.9503	High Similarity	NPC32451
0.9396	High Similarity	NPC328559
0.9309	High Similarity	NPC111732
0.8933	High Similarity	NPC327373
0.8933	High Similarity	NPC325093
0.8833	High Similarity	NPC318020
0.8736	High Similarity	NPC328798
0.8722	High Similarity	NPC322043
0.8689	High Similarity	NPC182814
0.8595	High Similarity	NPC127647
0.8533	High Similarity	NPC325775
0.8497	Intermediate Similarity	NPC309498
0.8407	Intermediate Similarity	NPC317010
0.8377	Intermediate Similarity	NPC160127
0.8377	Intermediate Similarity	NPC50997
0.836	Intermediate Similarity	NPC20593
0.8	Intermediate Similarity	NPC472752
0.7865	Intermediate Similarity	NPC263455
0.7854	Intermediate Similarity	NPC477910
0.7794	Intermediate Similarity	NPC476467
0.7794	Intermediate Similarity	NPC472553
0.7772	Intermediate Similarity	NPC63041
0.7734	Intermediate Similarity	NPC472550
0.7734	Intermediate Similarity	NPC48042
0.7734	Intermediate Similarity	NPC304179
0.7729	Intermediate Similarity	NPC471014
0.7729	Intermediate Similarity	NPC475408
0.7692	Intermediate Similarity	NPC144779
0.7692	Intermediate Similarity	NPC294579
0.7681	Intermediate Similarity	NPC470306
0.7656	Intermediate Similarity	NPC216428
0.7656	Intermediate Similarity	NPC472555
0.7644	Intermediate Similarity	NPC6981
0.7644	Intermediate Similarity	NPC471016
0.7633	Intermediate Similarity	NPC228331
0.7633	Intermediate Similarity	NPC319128
0.763	Intermediate Similarity	NPC477911
0.7629	Intermediate Similarity	NPC75544
0.7621	Intermediate Similarity	NPC292517
0.7611	Intermediate Similarity	NPC312860
0.7608	Intermediate Similarity	NPC62367
0.7583	Intermediate Similarity	NPC477912
0.7571	Intermediate Similarity	NPC84815
0.7571	Intermediate Similarity	NPC301368
0.757	Intermediate Similarity	NPC211920
0.757	Intermediate Similarity	NPC124029
0.756	Intermediate Similarity	NPC206343
0.756	Intermediate Similarity	NPC162812
0.756	Intermediate Similarity	NPC477908
0.7559	Intermediate Similarity	NPC233727
0.7559	Intermediate Similarity	NPC477902
0.7523	Intermediate Similarity	NPC148860
0.7512	Intermediate Similarity	NPC42678
0.7512	Intermediate Similarity	NPC477907
0.7512	Intermediate Similarity	NPC471980
0.7512	Intermediate Similarity	NPC30570
0.7512	Intermediate Similarity	NPC477909
0.75	Intermediate Similarity	NPC165837
0.7477	Intermediate Similarity	NPC328154
0.7477	Intermediate Similarity	NPC475137
0.7477	Intermediate Similarity	NPC473850
0.7477	Intermediate Similarity	NPC475498
0.7472	Intermediate Similarity	NPC167400
0.7465	Intermediate Similarity	NPC477906
0.7465	Intermediate Similarity	NPC127720
0.7465	Intermediate Similarity	NPC127026
0.7464	Intermediate Similarity	NPC264674
0.7452	Intermediate Similarity	NPC323551
0.7452	Intermediate Similarity	NPC280473
0.7449	Intermediate Similarity	NPC44354
0.7442	Intermediate Similarity	NPC473506
0.743	Intermediate Similarity	NPC250807
0.743	Intermediate Similarity	NPC76565
0.743	Intermediate Similarity	NPC57797
0.7429	Intermediate Similarity	NPC207531
0.7418	Intermediate Similarity	NPC107287
0.7416	Intermediate Similarity	NPC51008
0.7416	Intermediate Similarity	NPC41724
0.7407	Intermediate Similarity	NPC273532
0.7407	Intermediate Similarity	NPC475601
0.7407	Intermediate Similarity	NPC249614
0.7404	Intermediate Similarity	NPC470189
0.7404	Intermediate Similarity	NPC40919
0.7396	Intermediate Similarity	NPC164340
0.7389	Intermediate Similarity	NPC155792
0.7385	Intermediate Similarity	NPC150698
0.7385	Intermediate Similarity	NPC96801
0.7381	Intermediate Similarity	NPC4421
0.7374	Intermediate Similarity	NPC114974
0.7373	Intermediate Similarity	NPC475644
0.7373	Intermediate Similarity	NPC471190
0.7373	Intermediate Similarity	NPC475362
0.7373	Intermediate Similarity	NPC470486
0.7373	Intermediate Similarity	NPC471977
0.7366	Intermediate Similarity	NPC289086
0.7364	Intermediate Similarity	NPC170751
0.7358	Intermediate Similarity	NPC319556
0.7352	Intermediate Similarity	NPC469748
0.7351	Intermediate Similarity	NPC113812
0.7346	Intermediate Similarity	NPC193361
0.7346	Intermediate Similarity	NPC62844
0.7343	Intermediate Similarity	NPC470190
0.7327	Intermediate Similarity	NPC475631
0.7327	Intermediate Similarity	NPC328186
0.7327	Intermediate Similarity	NPC122968
0.7327	Intermediate Similarity	NPC228377
0.7327	Intermediate Similarity	NPC477787
0.7327	Intermediate Similarity	NPC475600
0.7327	Intermediate Similarity	NPC476110
0.7327	Intermediate Similarity	NPC87152
0.7327	Intermediate Similarity	NPC146824
0.7318	Intermediate Similarity	NPC159630
0.7318	Intermediate Similarity	NPC230085
0.7313	Intermediate Similarity	NPC109922
0.7297	Intermediate Similarity	NPC138018
0.7295	Intermediate Similarity	NPC475835
0.7277	Intermediate Similarity	NPC75600
0.7277	Intermediate Similarity	NPC187494
0.7277	Intermediate Similarity	NPC212768
0.7277	Intermediate Similarity	NPC6576
0.7277	Intermediate Similarity	NPC473115
0.7277	Intermediate Similarity	NPC473089
0.7277	Intermediate Similarity	NPC158020
0.7273	Intermediate Similarity	NPC30456
0.7256	Intermediate Similarity	NPC477903
0.7256	Intermediate Similarity	NPC253314
0.7245	Intermediate Similarity	NPC207851
0.724	Intermediate Similarity	NPC237702
0.7235	Intermediate Similarity	NPC26881
0.7227	Intermediate Similarity	NPC316841
0.7227	Intermediate Similarity	NPC473689
0.7227	Intermediate Similarity	NPC475596
0.7227	Intermediate Similarity	NPC292416
0.7227	Intermediate Similarity	NPC475303
0.7222	Intermediate Similarity	NPC235364
0.7209	Intermediate Similarity	NPC477901
0.7207	Intermediate Similarity	NPC475426
0.7207	Intermediate Similarity	NPC327769
0.7207	Intermediate Similarity	NPC35208
0.7204	Intermediate Similarity	NPC244856
0.7198	Intermediate Similarity	NPC112741
0.7195	Intermediate Similarity	NPC320324
0.7195	Intermediate Similarity	NPC244839
0.7195	Intermediate Similarity	NPC319880
0.7178	Intermediate Similarity	NPC135950
0.7169	Intermediate Similarity	NPC14116
0.7169	Intermediate Similarity	NPC285411
0.7162	Intermediate Similarity	NPC238278
0.7156	Intermediate Similarity	NPC477900
0.7156	Intermediate Similarity	NPC477899
0.7143	Intermediate Similarity	NPC477788
0.7143	Intermediate Similarity	NPC474217
0.7136	Intermediate Similarity	NPC134384
0.7136	Intermediate Similarity	NPC311196
0.713	Intermediate Similarity	NPC475406
0.7122	Intermediate Similarity	NPC103361
0.712	Intermediate Similarity	NPC319456
0.7104	Intermediate Similarity	NPC91125
0.7103	Intermediate Similarity	NPC476114
0.7098	Intermediate Similarity	NPC57453
0.7098	Intermediate Similarity	NPC327904
0.7098	Intermediate Similarity	NPC38959
0.709	Intermediate Similarity	NPC71079
0.7089	Intermediate Similarity	NPC236424
0.7089	Intermediate Similarity	NPC306644
0.708	Intermediate Similarity	NPC253482
0.7074	Intermediate Similarity	NPC475533
0.7056	Intermediate Similarity	NPC274842
0.7043	Intermediate Similarity	NPC475315
0.7043	Intermediate Similarity	NPC324619
0.7031	Intermediate Similarity	NPC180668
0.7031	Intermediate Similarity	NPC476090
0.7031	Intermediate Similarity	NPC471013
0.7031	Intermediate Similarity	NPC148896
0.7016	Intermediate Similarity	NPC85918
0.7009	Intermediate Similarity	NPC472435
0.6995	Remote Similarity	NPC471546
0.6995	Remote Similarity	NPC56170
0.6987	Remote Similarity	NPC475648
0.6986	Remote Similarity	NPC476115
0.6979	Remote Similarity	NPC278366
0.6979	Remote Similarity	NPC127730
0.6966	Remote Similarity	NPC471015
0.6964	Remote Similarity	NPC213143
0.6959	Remote Similarity	NPC82070
0.6957	Remote Similarity	NPC123395
0.6957	Remote Similarity	NPC474767
0.6955	Remote Similarity	NPC475271
0.695	Remote Similarity	NPC133591
0.6939	Remote Similarity	NPC476419
0.6936	Remote Similarity	NPC478045
0.692	Remote Similarity	NPC472436

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 NPC59033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	491
0.2-0.3	807
0.3-0.4	1825
0.4-0.5	3647
0.5-0.6	1845
0.6-0.7	338
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8071	Intermediate Similarity	NPD7396	Approved
0.7672	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD820	Phase 3
0.75	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD9074	Approved
0.7472	Intermediate Similarity	NPD9075	Approved
0.7247	Intermediate Similarity	NPD107	Approved
0.7198	Intermediate Similarity	NPD9271	Approved
0.715	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8326	Phase 3
0.715	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8325	Phase 3
0.7149	Intermediate Similarity	NPD8468	Phase 2
0.7062	Intermediate Similarity	NPD6529	Discontinued
0.7053	Intermediate Similarity	NPD5088	Discontinued
0.701	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3794	Approved
0.7009	Intermediate Similarity	NPD3795	Approved
0.6952	Remote Similarity	NPD2831	Approved
0.6851	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8479	Phase 2
0.6818	Remote Similarity	NPD3280	Approved
0.6816	Remote Similarity	NPD5640	Discontinued
0.6816	Remote Similarity	NPD1096	Discontinued
0.6808	Remote Similarity	NPD3371	Approved
0.68	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD6298	Discontinued
0.6786	Remote Similarity	NPD4086	Phase 1
0.678	Remote Similarity	NPD2336	Approved
0.675	Remote Similarity	NPD9510	Approved
0.672	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4301	Approved
0.6696	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8370	Discontinued
0.6667	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD4376	Phase 3
0.6667	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2307	Discontinued
0.665	Remote Similarity	NPD3321	Discontinued
0.665	Remote Similarity	NPD6641	Approved
0.665	Remote Similarity	NPD8063	Discontinued
0.665	Remote Similarity	NPD6642	Approved
0.6636	Remote Similarity	NPD3947	Discontinued
0.6635	Remote Similarity	NPD4526	Approved
0.6635	Remote Similarity	NPD4528	Approved
0.6635	Remote Similarity	NPD1173	Approved
0.6635	Remote Similarity	NPD4529	Approved
0.6623	Remote Similarity	NPD8409	Suspended
0.662	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD9506	Approved
0.6606	Remote Similarity	NPD4417	Approved
0.6606	Remote Similarity	NPD4989	Phase 2
0.6605	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD2511	Approved
0.6584	Remote Similarity	NPD1643	Phase 3
0.6581	Remote Similarity	NPD1483	Discontinued
0.6577	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7878	Phase 2
0.6576	Remote Similarity	NPD2896	Discontinued
0.6567	Remote Similarity	NPD7886	Phase 2
0.6567	Remote Similarity	NPD7885	Phase 2
0.6561	Remote Similarity	NPD3394	Approved
0.6561	Remote Similarity	NPD3389	Approved
0.6561	Remote Similarity	NPD3393	Approved
0.6556	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD9364	Phase 2
0.6553	Remote Similarity	NPD9363	Approved
0.6553	Remote Similarity	NPD4948	Discontinued
0.655	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6770	Approved
0.6544	Remote Similarity	NPD2510	Approved
0.6544	Remote Similarity	NPD2509	Approved
0.6526	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4427	Phase 2
0.6522	Remote Similarity	NPD4021	Phase 2
0.6516	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5149	Phase 2
0.6509	Remote Similarity	NPD5891	Approved
0.6509	Remote Similarity	NPD7777	Approved
0.6509	Remote Similarity	NPD7778	Approved
0.6509	Remote Similarity	NPD53	Approved
0.6509	Remote Similarity	NPD3006	Discontinued
0.6507	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD9382	Approved
0.6495	Remote Similarity	NPD9383	Approved
0.6495	Remote Similarity	NPD3911	Approved
0.6493	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3813	Approved
0.6484	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4805	Approved
0.6471	Remote Similarity	NPD9362	Approved
0.6471	Remote Similarity	NPD3178	Discontinued
0.6462	Remote Similarity	NPD5255	Approved
0.646	Remote Similarity	NPD8356	Approved
0.6459	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5475	Discontinued
0.6453	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4506	Discontinued
0.6438	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1649	Discontinued
0.6413	Remote Similarity	NPD5490	Discontinued
0.6411	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5901	Discontinued
0.6404	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2809	Approved
0.6389	Remote Similarity	NPD9284	Approved
0.6387	Remote Similarity	NPD1270	Approved
0.6376	Remote Similarity	NPD8289	Discontinued
0.6376	Remote Similarity	NPD7426	Phase 1
0.6376	Remote Similarity	NPD7001	Phase 3
0.6372	Remote Similarity	NPD5228	Phase 3
0.6364	Remote Similarity	NPD5022	Discontinued
0.6364	Remote Similarity	NPD4804	Approved
0.6356	Remote Similarity	NPD1926	Approved
0.6355	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8430	Approved
0.6345	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4923	Phase 1
0.6341	Remote Similarity	NPD1618	Phase 2
0.6332	Remote Similarity	NPD3925	Approved
0.633	Remote Similarity	NPD4034	Approved
0.633	Remote Similarity	NPD944	Approved
0.633	Remote Similarity	NPD6987	Phase 1
0.633	Remote Similarity	NPD4037	Approved
0.633	Remote Similarity	NPD31	Approved
0.633	Remote Similarity	NPD4038	Approved
0.633	Remote Similarity	NPD4033	Approved
0.633	Remote Similarity	NPD32	Approved
0.633	Remote Similarity	NPD4039	Approved
0.633	Remote Similarity	NPD4122	Approved
0.633	Remote Similarity	NPD4036	Approved
0.633	Remote Similarity	NPD4035	Approved
0.6327	Remote Similarity	NPD2581	Approved
0.6327	Remote Similarity	NPD7404	Approved
0.6327	Remote Similarity	NPD2582	Approved
0.6324	Remote Similarity	NPD272	Approved
0.6318	Remote Similarity	NPD7467	Discontinued
0.6316	Remote Similarity	NPD8021	Approved
0.6316	Remote Similarity	NPD8020	Approved
0.631	Remote Similarity	NPD1380	Discovery
0.6309	Remote Similarity	NPD7031	Phase 1
0.6301	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7010	Phase 3
0.6298	Remote Similarity	NPD3082	Discontinued
0.6298	Remote Similarity	NPD9080	Approved
0.6293	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8375	Approved
0.6289	Remote Similarity	NPD510	Phase 1
0.6286	Remote Similarity	NPD7233	Approved
0.6286	Remote Similarity	NPD7234	Approved
0.6284	Remote Similarity	NPD5513	Phase 2
0.6283	Remote Similarity	NPD1623	Approved
0.6281	Remote Similarity	NPD6635	Approved
0.6278	Remote Similarity	NPD7069	Discontinued
0.6274	Remote Similarity	NPD6569	Phase 2
0.6274	Remote Similarity	NPD981	Phase 2
0.6269	Remote Similarity	NPD5862	Discovery
0.6268	Remote Similarity	NPD4375	Approved
0.6262	Remote Similarity	NPD5898	Approved
0.6262	Remote Similarity	NPD5897	Approved
0.6262	Remote Similarity	NPD5899	Approved
0.6261	Remote Similarity	NPD7576	Discontinued
0.6256	Remote Similarity	NPD6182	Approved
0.6256	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD43	Approved
0.6256	Remote Similarity	NPD4903	Approved
0.6256	Remote Similarity	NPD4906	Approved
0.6256	Remote Similarity	NPD4905	Approved
0.625	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.625	Remote Similarity	NPD721	Approved
0.625	Remote Similarity	NPD3569	Discontinued
0.6244	Remote Similarity	NPD1032	Phase 2
0.6244	Remote Similarity	NPD6361	Phase 2
0.624	Remote Similarity	NPD6351	Discovery
0.624	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6716	Phase 1
0.6233	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.623	Remote Similarity	NPD1352	Discontinued
0.6228	Remote Similarity	NPD1996	Discontinued
0.6227	Remote Similarity	NPD4904	Approved
0.6222	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD4500	Approved
0.6221	Remote Similarity	NPD4501	Approved
0.622	Remote Similarity	NPD4889	Approved
0.622	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1382	Phase 2
0.6211	Remote Similarity	NPD1383	Phase 3
0.6209	Remote Similarity	NPD1657	Approved
0.6209	Remote Similarity	NPD6068	Discontinued
0.6207	Remote Similarity	NPD2123	Phase 3

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