NPASS Compound

Structure

CID320748 OpenBabel06191716152D 36 38 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 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -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 -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 5 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 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 0.0000 -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 4 2 0 0 0 0 2 25 1 0 0 0 0 3 33 1 0 0 0 0 5 6 2 0 0 0 0 5 12 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 26 1 0 0 0 0 11 16 2 0 0 0 0 11 34 1 0 0 0 0 13 21 1 0 0 0 0 14 4 1 6 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 6 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 35 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 24 1 0 0 0 0 20 29 1 6 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 23 36 1 1 0 0 0 24 35 1 0 0 0 0 24 36 1 1 0 0 0 M CHG 2 25 1 31 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	507.17
Volume:	484.588
LogP:	-1.561
LogD:	-0.882
LogS:	-1.041
# Rotatable Bonds:	9
TPSA:	178.92
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	5.314
Fsp3:	0.458
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.799
MDCK Permeability:	8.253232226707041e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.697
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.293
Plasma Protein Binding (PPB):	25.69161033630371%
Volume Distribution (VD):	0.317
Pgp-substrate:	69.46931457519531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	1.623
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.051
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC320748

Natural Product ID:	NPC320748
*Common Name:**	Lonijaposide G
IUPAC Name:	5-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-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-methylpyridin-1-ium-3-carboxylate
Synonyms:	Lonijaposide G
Standard InCHIKey:	YEXJLSCDDBIEPB-DFEUVTCYSA-N
Standard InCHI:	InChI=1S/C24H29NO11/c1-4-14-15(6-5-12-7-13(21(30)31)9-25(2)8-12)16(22(32)33-3)11-34-23(14)36-24-20(29)19(28)18(27)17(10-26)35-24/h4-9,11,14-15,17-20,23-24,26-29H,1,10H2,2-3H3/b6-5+/t14-,15+,17-,18-,19+,20-,23+,24+/m1/s1
SMILES:	C[N+]1=CC(=CC(=C1)C(=O)[O-])C=CC2C(C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928045
PubChem CID:	56599669
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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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	<	30.0	%	PMID[501441]

☑ 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 NPC320748 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	261
0.1-0.2	1400
0.2-0.3	5711
0.3-0.4	12390
0.4-0.5	16726
0.5-0.6	5294
0.6-0.7	652
0.7-0.8	227
0.8-0.85	15
0.85-0.9	9
0.9-0.95	3
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324245
0.9887	High Similarity	NPC79223
0.9831	High Similarity	NPC32451
0.983	High Similarity	NPC329024
0.9721	High Similarity	NPC328559
0.9663	High Similarity	NPC59033
0.9663	High Similarity	NPC317672
0.9563	High Similarity	NPC156044
0.9454	High Similarity	NPC12944
0.9454	High Similarity	NPC25442
0.9005	High Similarity	NPC111732
0.8933	High Similarity	NPC327373
0.884	High Similarity	NPC328798
0.884	High Similarity	NPC325775
0.8722	High Similarity	NPC325093
0.8722	High Similarity	NPC322043
0.8696	High Similarity	NPC127647
0.8691	High Similarity	NPC309498
0.8626	High Similarity	NPC318020
0.8587	High Similarity	NPC182814
0.8274	Intermediate Similarity	NPC472752
0.8119	Intermediate Similarity	NPC477910
0.8108	Intermediate Similarity	NPC317010
0.8093	Intermediate Similarity	NPC160127
0.8093	Intermediate Similarity	NPC50997
0.8073	Intermediate Similarity	NPC20593
0.806	Intermediate Similarity	NPC472553
0.806	Intermediate Similarity	NPC476467
0.804	Intermediate Similarity	NPC63041
0.8	Intermediate Similarity	NPC48042
0.8	Intermediate Similarity	NPC472550
0.8	Intermediate Similarity	NPC304179
0.799	Intermediate Similarity	NPC475408
0.799	Intermediate Similarity	NPC471014
0.7951	Intermediate Similarity	NPC144779
0.7951	Intermediate Similarity	NPC294579
0.7941	Intermediate Similarity	NPC470306
0.7913	Intermediate Similarity	NPC472555
0.7902	Intermediate Similarity	NPC471016
0.7902	Intermediate Similarity	NPC6981
0.7892	Intermediate Similarity	NPC228331
0.7892	Intermediate Similarity	NPC319128
0.7885	Intermediate Similarity	NPC477911
0.7864	Intermediate Similarity	NPC62367
0.7837	Intermediate Similarity	NPC477912
0.7826	Intermediate Similarity	NPC84815
0.7826	Intermediate Similarity	NPC216428
0.7826	Intermediate Similarity	NPC301368
0.782	Intermediate Similarity	NPC124029
0.782	Intermediate Similarity	NPC211920
0.7816	Intermediate Similarity	NPC206343
0.7816	Intermediate Similarity	NPC477908
0.781	Intermediate Similarity	NPC477902
0.781	Intermediate Similarity	NPC233727
0.7794	Intermediate Similarity	NPC292517
0.7773	Intermediate Similarity	NPC148860
0.7767	Intermediate Similarity	NPC477907
0.7767	Intermediate Similarity	NPC42678
0.7767	Intermediate Similarity	NPC477909
0.7762	Intermediate Similarity	NPC471980
0.7756	Intermediate Similarity	NPC165837
0.7729	Intermediate Similarity	NPC162812
0.7725	Intermediate Similarity	NPC475137
0.7725	Intermediate Similarity	NPC328154
0.7725	Intermediate Similarity	NPC475498
0.7725	Intermediate Similarity	NPC473850
0.7718	Intermediate Similarity	NPC264674
0.7714	Intermediate Similarity	NPC127026
0.7714	Intermediate Similarity	NPC127720
0.771	Intermediate Similarity	NPC477906
0.7709	Intermediate Similarity	NPC107287
0.7707	Intermediate Similarity	NPC280473
0.7707	Intermediate Similarity	NPC323551
0.7689	Intermediate Similarity	NPC473506
0.7688	Intermediate Similarity	NPC249614
0.7681	Intermediate Similarity	NPC207531
0.7681	Intermediate Similarity	NPC30570
0.7678	Intermediate Similarity	NPC250807
0.7678	Intermediate Similarity	NPC76565
0.7678	Intermediate Similarity	NPC57797
0.767	Intermediate Similarity	NPC51008
0.767	Intermediate Similarity	NPC41724
0.7667	Intermediate Similarity	NPC263455
0.7659	Intermediate Similarity	NPC40919
0.7659	Intermediate Similarity	NPC470189
0.7653	Intermediate Similarity	NPC475601
0.7633	Intermediate Similarity	NPC4421
0.7629	Intermediate Similarity	NPC44354
0.7628	Intermediate Similarity	NPC150698
0.7628	Intermediate Similarity	NPC96801
0.7624	Intermediate Similarity	NPC289086
0.7617	Intermediate Similarity	NPC475644
0.7617	Intermediate Similarity	NPC475362
0.7617	Intermediate Similarity	NPC471190
0.7617	Intermediate Similarity	NPC470486
0.7617	Intermediate Similarity	NPC471977
0.7608	Intermediate Similarity	NPC319556
0.7604	Intermediate Similarity	NPC170751
0.7598	Intermediate Similarity	NPC470190
0.7596	Intermediate Similarity	NPC193361
0.7596	Intermediate Similarity	NPC62844
0.7593	Intermediate Similarity	NPC469748
0.757	Intermediate Similarity	NPC477787
0.757	Intermediate Similarity	NPC475600
0.757	Intermediate Similarity	NPC228377
0.757	Intermediate Similarity	NPC476110
0.757	Intermediate Similarity	NPC146824
0.757	Intermediate Similarity	NPC87152
0.757	Intermediate Similarity	NPC328186
0.757	Intermediate Similarity	NPC122968
0.757	Intermediate Similarity	NPC475631
0.7549	Intermediate Similarity	NPC475835
0.7524	Intermediate Similarity	NPC158020
0.7524	Intermediate Similarity	NPC75600
0.7524	Intermediate Similarity	NPC473115
0.7524	Intermediate Similarity	NPC212768
0.7524	Intermediate Similarity	NPC187494
0.7524	Intermediate Similarity	NPC6576
0.7524	Intermediate Similarity	NPC473089
0.7512	Intermediate Similarity	NPC30456
0.75	Intermediate Similarity	NPC477903
0.7486	Intermediate Similarity	NPC112741
0.7477	Intermediate Similarity	NPC26881
0.7477	Intermediate Similarity	NPC237702
0.7465	Intermediate Similarity	NPC316841
0.7465	Intermediate Similarity	NPC475596
0.7465	Intermediate Similarity	NPC473689
0.7465	Intermediate Similarity	NPC475303
0.7465	Intermediate Similarity	NPC235364
0.7465	Intermediate Similarity	NPC292416
0.7453	Intermediate Similarity	NPC477901
0.7443	Intermediate Similarity	NPC475426
0.7443	Intermediate Similarity	NPC35208
0.7443	Intermediate Similarity	NPC327769
0.7431	Intermediate Similarity	NPC319880
0.7431	Intermediate Similarity	NPC244839
0.7431	Intermediate Similarity	NPC320324
0.7418	Intermediate Similarity	NPC312860
0.7416	Intermediate Similarity	NPC230085
0.7416	Intermediate Similarity	NPC159630
0.7407	Intermediate Similarity	NPC14116
0.7407	Intermediate Similarity	NPC285411
0.74	Intermediate Similarity	NPC109922
0.7397	Intermediate Similarity	NPC238278
0.7395	Intermediate Similarity	NPC477899
0.7395	Intermediate Similarity	NPC477900
0.7389	Intermediate Similarity	NPC155792
0.7383	Intermediate Similarity	NPC477788
0.7374	Intermediate Similarity	NPC167400
0.7373	Intermediate Similarity	NPC311196
0.7373	Intermediate Similarity	NPC134384
0.7368	Intermediate Similarity	NPC244856
0.7364	Intermediate Similarity	NPC475406
0.736	Intermediate Similarity	NPC75544
0.7339	Intermediate Similarity	NPC91125
0.7333	Intermediate Similarity	NPC236424
0.7333	Intermediate Similarity	NPC306644
0.733	Intermediate Similarity	NPC38959
0.733	Intermediate Similarity	NPC327904
0.7309	Intermediate Similarity	NPC253482
0.7306	Intermediate Similarity	NPC164340
0.7301	Intermediate Similarity	NPC475533
0.7299	Intermediate Similarity	NPC274842
0.7269	Intermediate Similarity	NPC324619
0.7269	Intermediate Similarity	NPC475315
0.7264	Intermediate Similarity	NPC135950
0.7258	Intermediate Similarity	NPC113812
0.7257	Intermediate Similarity	NPC180668
0.7257	Intermediate Similarity	NPC471013
0.7257	Intermediate Similarity	NPC148896
0.7256	Intermediate Similarity	NPC253314
0.725	Intermediate Similarity	NPC471546
0.7212	Intermediate Similarity	NPC475648
0.7206	Intermediate Similarity	NPC103361
0.72	Intermediate Similarity	NPC114974
0.7196	Intermediate Similarity	NPC82070
0.7195	Intermediate Similarity	NPC213143
0.7186	Intermediate Similarity	NPC471015
0.7135	Intermediate Similarity	NPC273532
0.713	Intermediate Similarity	NPC10904
0.7105	Intermediate Similarity	NPC476090
0.7098	Intermediate Similarity	NPC57453
0.7098	Intermediate Similarity	NPC191310
0.7083	Intermediate Similarity	NPC52254
0.7082	Intermediate Similarity	NPC53255
0.7082	Intermediate Similarity	NPC472435
0.7082	Intermediate Similarity	NPC475301
0.7082	Intermediate Similarity	NPC85879
0.7082	Intermediate Similarity	NPC478045
0.7082	Intermediate Similarity	NPC326930
0.7053	Intermediate Similarity	NPC474217
0.7051	Intermediate Similarity	NPC13603
0.7048	Intermediate Similarity	NPC474905
0.7044	Intermediate Similarity	NPC103230
0.7039	Intermediate Similarity	NPC123395
0.7032	Intermediate Similarity	NPC475271
0.7023	Intermediate Similarity	NPC476114
0.7021	Intermediate Similarity	NPC138018
0.7	Intermediate Similarity	NPC71079
0.6995	Remote Similarity	NPC56170

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 NPC320748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	499
0.2-0.3	782
0.3-0.4	1718
0.4-0.5	3658
0.5-0.6	1949
0.6-0.7	348
0.7-0.8	15
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
0.8256	Intermediate Similarity	NPD7396	Approved
0.7957	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD820	Phase 3
0.7784	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD9271	Approved
0.7374	Intermediate Similarity	NPD9075	Approved
0.7374	Intermediate Similarity	NPD9074	Approved
0.7247	Intermediate Similarity	NPD107	Approved
0.723	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD8325	Phase 3
0.723	Intermediate Similarity	NPD8326	Phase 3
0.7225	Intermediate Similarity	NPD8468	Phase 2
0.7198	Intermediate Similarity	NPD2831	Approved
0.717	Intermediate Similarity	NPD3794	Approved
0.717	Intermediate Similarity	NPD3795	Approved
0.7143	Intermediate Similarity	NPD6529	Discontinued
0.7053	Intermediate Similarity	NPD5088	Discontinued
0.7051	Intermediate Similarity	NPD8479	Phase 2
0.701	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3280	Approved
0.6941	Remote Similarity	NPD6298	Discontinued
0.6872	Remote Similarity	NPD3947	Discontinued
0.6864	Remote Similarity	NPD4301	Approved
0.6837	Remote Similarity	NPD4417	Approved
0.6829	Remote Similarity	NPD4376	Phase 3
0.6818	Remote Similarity	NPD6642	Approved
0.6818	Remote Similarity	NPD6641	Approved
0.6816	Remote Similarity	NPD5640	Discontinued
0.6808	Remote Similarity	NPD3371	Approved
0.68	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2336	Approved
0.6776	Remote Similarity	NPD2510	Approved
0.6776	Remote Similarity	NPD2509	Approved
0.6758	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5149	Phase 2
0.6732	Remote Similarity	NPD8063	Discontinued
0.6724	Remote Similarity	NPD1483	Discontinued
0.6712	Remote Similarity	NPD3394	Approved
0.6712	Remote Similarity	NPD3389	Approved
0.6712	Remote Similarity	NPD3393	Approved
0.6698	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8409	Suspended
0.6684	Remote Similarity	NPD2511	Approved
0.6682	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4989	Phase 2
0.6682	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4506	Discontinued
0.6651	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2307	Discontinued
0.6651	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1096	Discontinued
0.665	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7886	Phase 2
0.6638	Remote Similarity	NPD7885	Phase 2
0.6637	Remote Similarity	NPD4086	Phase 1
0.6635	Remote Similarity	NPD4526	Approved
0.6635	Remote Similarity	NPD4528	Approved
0.6635	Remote Similarity	NPD4529	Approved
0.6632	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6770	Approved
0.6602	Remote Similarity	NPD4021	Phase 2
0.6588	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1643	Phase 3
0.6584	Remote Similarity	NPD9510	Approved
0.658	Remote Similarity	NPD5891	Approved
0.658	Remote Similarity	NPD3006	Discontinued
0.6578	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7878	Phase 2
0.6576	Remote Similarity	NPD2896	Discontinued
0.6567	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1173	Approved
0.655	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8370	Discontinued
0.6538	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7010	Phase 3
0.6526	Remote Similarity	NPD5228	Phase 3
0.6524	Remote Similarity	NPD4427	Phase 2
0.6509	Remote Similarity	NPD53	Approved
0.6509	Remote Similarity	NPD7777	Approved
0.6509	Remote Similarity	NPD7778	Approved
0.6502	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD1926	Approved
0.65	Remote Similarity	NPD7069	Discontinued
0.6495	Remote Similarity	NPD3911	Approved
0.649	Remote Similarity	NPD3321	Discontinued
0.6488	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3925	Approved
0.6474	Remote Similarity	NPD1270	Approved
0.6473	Remote Similarity	NPD4948	Discontinued
0.6473	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4889	Approved
0.6455	Remote Similarity	NPD5475	Discontinued
0.6452	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4500	Approved
0.6449	Remote Similarity	NPD4501	Approved
0.6447	Remote Similarity	NPD8289	Discontinued
0.6435	Remote Similarity	NPD5022	Discontinued
0.6435	Remote Similarity	NPD5513	Phase 2
0.6435	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD9506	Approved
0.6429	Remote Similarity	NPD6665	Discontinued
0.6425	Remote Similarity	NPD4375	Approved
0.6417	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1649	Discontinued
0.6416	Remote Similarity	NPD4923	Phase 1
0.6413	Remote Similarity	NPD272	Approved
0.6413	Remote Similarity	NPD5490	Discontinued
0.641	Remote Similarity	NPD2581	Approved
0.641	Remote Similarity	NPD2582	Approved
0.6408	Remote Similarity	NPD3569	Discontinued
0.6406	Remote Similarity	NPD6987	Phase 1
0.6402	Remote Similarity	NPD3813	Approved
0.6398	Remote Similarity	NPD6361	Phase 2
0.6394	Remote Similarity	NPD9363	Approved
0.6394	Remote Similarity	NPD9364	Phase 2
0.6393	Remote Similarity	NPD7467	Discontinued
0.6392	Remote Similarity	NPD2809	Approved
0.639	Remote Similarity	NPD9362	Approved
0.6389	Remote Similarity	NPD9284	Approved
0.6389	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4805	Approved
0.6376	Remote Similarity	NPD7426	Phase 1
0.6373	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6635	Approved
0.6364	Remote Similarity	NPD7234	Approved
0.6364	Remote Similarity	NPD7233	Approved
0.6356	Remote Similarity	NPD1623	Approved
0.6352	Remote Similarity	NPD4373	Phase 2
0.6351	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5866	Approved
0.6347	Remote Similarity	NPD7562	Approved
0.6336	Remote Similarity	NPD6962	Phase 2
0.6333	Remote Similarity	NPD6276	Discontinued
0.633	Remote Similarity	NPD4034	Approved
0.633	Remote Similarity	NPD944	Approved
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	NPD5901	Discontinued
0.633	Remote Similarity	NPD4122	Approved
0.633	Remote Similarity	NPD4036	Approved
0.633	Remote Similarity	NPD4035	Approved
0.6327	Remote Similarity	NPD7404	Approved
0.6327	Remote Similarity	NPD9382	Approved
0.6327	Remote Similarity	NPD9383	Approved
0.6326	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4551	Phase 2
0.6316	Remote Similarity	NPD8356	Approved
0.6316	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3178	Discontinued
0.6311	Remote Similarity	NPD3386	Phase 2
0.6309	Remote Similarity	NPD7031	Phase 1
0.6308	Remote Similarity	NPD6206	Phase 1
0.63	Remote Similarity	NPD1996	Discontinued
0.6295	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5255	Approved
0.6293	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4334	Discontinued
0.6278	Remote Similarity	NPD3815	Phase 1
0.6278	Remote Similarity	NPD3816	Phase 1
0.6277	Remote Similarity	NPD4804	Approved
0.6274	Remote Similarity	NPD6569	Phase 2
0.6274	Remote Similarity	NPD981	Phase 2
0.6271	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5898	Approved
0.6262	Remote Similarity	NPD5897	Approved
0.6262	Remote Similarity	NPD5899	Approved
0.6261	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6281	Approved
0.625	Remote Similarity	NPD721	Approved
0.6244	Remote Similarity	NPD1032	Phase 2
0.6238	Remote Similarity	NPD8021	Approved
0.6238	Remote Similarity	NPD8020	Approved
0.6234	Remote Similarity	NPD6716	Phase 1
0.6233	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.623	Remote Similarity	NPD1352	Discontinued
0.6227	Remote Similarity	NPD7001	Phase 3
0.6226	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD8375	Approved
0.6223	Remote Similarity	NPD4952	Phase 3
0.6216	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4437	Phase 3
0.621	Remote Similarity	NPD6669	Phase 2
0.6209	Remote Similarity	NPD1657	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