NPASS Compound

Structure

CID328559 OpenBabel06191716202D 41 43 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 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 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 7.7942 -2.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 0 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 11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 6.9282 -4.0000 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 11.2583 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -1.0000 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 -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 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 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 3 2 0 0 0 0 2 38 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 2 0 0 0 0 8 28 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 28 2 0 0 0 0 11 15 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 18 2 0 0 0 0 13 39 1 0 0 0 0 15 24 1 0 0 0 0 16 3 1 1 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 18 25 1 0 0 0 0 19 12 1 6 0 0 0 19 21 1 0 0 0 0 19 40 1 0 0 0 0 20 30 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 27 1 0 0 0 0 23 34 1 1 0 0 0 24 35 2 0 0 0 0 24 36 1 0 0 0 0 25 37 2 0 0 0 0 25 38 1 0 0 0 0 26 39 1 0 0 0 0 26 41 1 6 0 0 0 27 40 1 0 0 0 0 27 41 1 6 0 0 0 M CHG 2 28 1 36 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	579.2
Volume:	551.42
LogP:	-1.643
LogD:	-1.16
LogS:	-0.932
# Rotatable Bonds:	13
TPSA:	216.22
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	5.343
Fsp3:	0.481
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:	-6.111
MDCK Permeability:	8.572930528316647e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.726
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.324
Plasma Protein Binding (PPB):	23.491525650024414%
Volume Distribution (VD):	0.227
Pgp-substrate:	68.07654571533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.519
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.087
Skin Sensitization:	0.036
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.094

Download Data

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

Natural Product: NPC328559

Natural Product ID:	NPC328559
*Common Name:**	Lonijaposide H
IUPAC Name:	1-(3-carboxypropyl)-5-[(2E)-2-[(2S,3R)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydropyran-4-ylidene]ethyl]pyridin-1-ium-3-carboxylate
Synonyms:	Lonijaposide H
Standard InCHIKey:	UVMYLENKGIUJAG-ICNBXRGLSA-N
Standard InCHI:	InChI=1S/C27H33NO13/c1-3-16-17(7-6-14-9-15(24(35)36)11-28(10-14)8-4-5-20(30)31)18(25(37)38-2)13-39-26(16)41-27-23(34)22(33)21(32)19(12-29)40-27/h3,7,9-11,13,16,19,21-23,26-27,29,32-34H,1,4-6,8,12H2,2H3,(H-,30,31,35,36)/b17-7+/t16-,19-,21-,22+,23-,26+,27+/m1/s1
SMILES:	COC(=O)C1=COC(C(C1=CCC2=CC(=C[N+](=C2)CCCC(=O)O)C(=O)[O-])C=C)OC3C(C(C(C(O3)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928046
PubChem CID:	56599868
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:0002207] O-glycosyl compounds

*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	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	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	=	68.6	%	PMID[468381]

☑ 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 NPC328559 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	265
0.1-0.2	1460
0.2-0.3	5979
0.3-0.4	12559
0.4-0.5	16405
0.5-0.6	5115
0.6-0.7	655
0.7-0.8	231
0.8-0.85	11
0.85-0.9	6
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC32451
0.9721	High Similarity	NPC324245
0.9721	High Similarity	NPC320748
0.9613	High Similarity	NPC79223
0.9611	High Similarity	NPC317672
0.9556	High Similarity	NPC329024
0.9409	High Similarity	NPC156044
0.9396	High Similarity	NPC59033
0.9301	High Similarity	NPC12944
0.9301	High Similarity	NPC25442
0.8964	High Similarity	NPC111732
0.8901	High Similarity	NPC325775
0.8696	High Similarity	NPC328798
0.8681	High Similarity	NPC327373
0.8681	High Similarity	NPC322043
0.8557	High Similarity	NPC309498
0.8478	Intermediate Similarity	NPC325093
0.8457	Intermediate Similarity	NPC127647
0.8387	Intermediate Similarity	NPC318020
0.8351	Intermediate Similarity	NPC182814
0.8333	Intermediate Similarity	NPC472752
0.8135	Intermediate Similarity	NPC20593
0.8075	Intermediate Similarity	NPC317010
0.8061	Intermediate Similarity	NPC160127
0.8061	Intermediate Similarity	NPC50997
0.803	Intermediate Similarity	NPC476467
0.8	Intermediate Similarity	NPC477910
0.7961	Intermediate Similarity	NPC475408
0.7961	Intermediate Similarity	NPC471014
0.7941	Intermediate Similarity	NPC472553
0.7913	Intermediate Similarity	NPC470306
0.7882	Intermediate Similarity	NPC48042
0.7882	Intermediate Similarity	NPC304179
0.7882	Intermediate Similarity	NPC472550
0.7874	Intermediate Similarity	NPC471016
0.7867	Intermediate Similarity	NPC475498
0.7867	Intermediate Similarity	NPC475137
0.7837	Intermediate Similarity	NPC62367
0.7837	Intermediate Similarity	NPC294579
0.7837	Intermediate Similarity	NPC144779
0.7833	Intermediate Similarity	NPC63041
0.783	Intermediate Similarity	NPC473506
0.782	Intermediate Similarity	NPC76565
0.781	Intermediate Similarity	NPC477912
0.7799	Intermediate Similarity	NPC472555
0.7799	Intermediate Similarity	NPC301368
0.7799	Intermediate Similarity	NPC84815
0.7799	Intermediate Similarity	NPC216428
0.7793	Intermediate Similarity	NPC211920
0.7793	Intermediate Similarity	NPC124029
0.7788	Intermediate Similarity	NPC6981
0.7783	Intermediate Similarity	NPC477902
0.7783	Intermediate Similarity	NPC233727
0.7778	Intermediate Similarity	NPC228331
0.7778	Intermediate Similarity	NPC319128
0.7773	Intermediate Similarity	NPC477911
0.7767	Intermediate Similarity	NPC292517
0.7757	Intermediate Similarity	NPC471190
0.7757	Intermediate Similarity	NPC471977
0.7757	Intermediate Similarity	NPC470486
0.7757	Intermediate Similarity	NPC475644
0.7746	Intermediate Similarity	NPC148860
0.7742	Intermediate Similarity	NPC170751
0.774	Intermediate Similarity	NPC42678
0.774	Intermediate Similarity	NPC477907
0.774	Intermediate Similarity	NPC477909
0.7736	Intermediate Similarity	NPC471980
0.771	Intermediate Similarity	NPC476110
0.771	Intermediate Similarity	NPC475631
0.771	Intermediate Similarity	NPC475600
0.771	Intermediate Similarity	NPC87152
0.7703	Intermediate Similarity	NPC206343
0.7703	Intermediate Similarity	NPC477908
0.7703	Intermediate Similarity	NPC162812
0.77	Intermediate Similarity	NPC473850
0.77	Intermediate Similarity	NPC328154
0.7692	Intermediate Similarity	NPC264674
0.7689	Intermediate Similarity	NPC127720
0.7689	Intermediate Similarity	NPC127026
0.7685	Intermediate Similarity	NPC477906
0.7681	Intermediate Similarity	NPC323551
0.7681	Intermediate Similarity	NPC280473
0.7674	Intermediate Similarity	NPC475362
0.7656	Intermediate Similarity	NPC207531
0.7656	Intermediate Similarity	NPC30570
0.7653	Intermediate Similarity	NPC57797
0.7653	Intermediate Similarity	NPC250807
0.765	Intermediate Similarity	NPC30456
0.7644	Intermediate Similarity	NPC41724
0.7644	Intermediate Similarity	NPC165837
0.7644	Intermediate Similarity	NPC51008
0.7633	Intermediate Similarity	NPC40919
0.7633	Intermediate Similarity	NPC470189
0.7628	Intermediate Similarity	NPC475601
0.7628	Intermediate Similarity	NPC146824
0.7608	Intermediate Similarity	NPC4421
0.7604	Intermediate Similarity	NPC475303
0.7604	Intermediate Similarity	NPC96801
0.7604	Intermediate Similarity	NPC150698
0.7604	Intermediate Similarity	NPC475596
0.7583	Intermediate Similarity	NPC319556
0.7582	Intermediate Similarity	NPC107287
0.758	Intermediate Similarity	NPC327769
0.758	Intermediate Similarity	NPC475426
0.758	Intermediate Similarity	NPC35208
0.7573	Intermediate Similarity	NPC470190
0.7571	Intermediate Similarity	NPC193361
0.7571	Intermediate Similarity	NPC62844
0.7569	Intermediate Similarity	NPC469748
0.7566	Intermediate Similarity	NPC249614
0.7546	Intermediate Similarity	NPC122968
0.7546	Intermediate Similarity	NPC328186
0.7546	Intermediate Similarity	NPC228377
0.7546	Intermediate Similarity	NPC477787
0.7541	Intermediate Similarity	NPC263455
0.7534	Intermediate Similarity	NPC237702
0.7524	Intermediate Similarity	NPC475835
0.7524	Intermediate Similarity	NPC274842
0.7523	Intermediate Similarity	NPC292416
0.7523	Intermediate Similarity	NPC473689
0.7513	Intermediate Similarity	NPC44354
0.7512	Intermediate Similarity	NPC244856
0.7512	Intermediate Similarity	NPC289086
0.75	Intermediate Similarity	NPC187494
0.75	Intermediate Similarity	NPC75600
0.75	Intermediate Similarity	NPC473115
0.75	Intermediate Similarity	NPC212768
0.75	Intermediate Similarity	NPC6576
0.75	Intermediate Similarity	NPC158020
0.75	Intermediate Similarity	NPC473089
0.7489	Intermediate Similarity	NPC319880
0.7489	Intermediate Similarity	NPC244839
0.7489	Intermediate Similarity	NPC320324
0.7477	Intermediate Similarity	NPC477903
0.7476	Intermediate Similarity	NPC236424
0.7476	Intermediate Similarity	NPC306644
0.7463	Intermediate Similarity	NPC109922
0.7454	Intermediate Similarity	NPC26881
0.7443	Intermediate Similarity	NPC316841
0.7442	Intermediate Similarity	NPC235364
0.743	Intermediate Similarity	NPC477901
0.7421	Intermediate Similarity	NPC475406
0.7387	Intermediate Similarity	NPC38959
0.7387	Intermediate Similarity	NPC327904
0.7385	Intermediate Similarity	NPC285411
0.7385	Intermediate Similarity	NPC14116
0.7376	Intermediate Similarity	NPC238278
0.7373	Intermediate Similarity	NPC477899
0.7373	Intermediate Similarity	NPC477900
0.7366	Intermediate Similarity	NPC253482
0.7366	Intermediate Similarity	NPC155792
0.7363	Intermediate Similarity	NPC112741
0.7361	Intermediate Similarity	NPC477788
0.7352	Intermediate Similarity	NPC134384
0.7352	Intermediate Similarity	NPC311196
0.7337	Intermediate Similarity	NPC75544
0.7318	Intermediate Similarity	NPC91125
0.7297	Intermediate Similarity	NPC312860
0.7293	Intermediate Similarity	NPC230085
0.7293	Intermediate Similarity	NPC159630
0.7281	Intermediate Similarity	NPC475533
0.7269	Intermediate Similarity	NPC475648
0.7264	Intermediate Similarity	NPC114974
0.7253	Intermediate Similarity	NPC167400
0.7249	Intermediate Similarity	NPC324619
0.7249	Intermediate Similarity	NPC475315
0.7241	Intermediate Similarity	NPC135950
0.7235	Intermediate Similarity	NPC253314
0.7228	Intermediate Similarity	NPC471546
0.721	Intermediate Similarity	NPC326930
0.721	Intermediate Similarity	NPC475301
0.7194	Intermediate Similarity	NPC164340
0.7184	Intermediate Similarity	NPC103361
0.7176	Intermediate Similarity	NPC82070
0.7175	Intermediate Similarity	NPC213143
0.7167	Intermediate Similarity	NPC471015
0.7162	Intermediate Similarity	NPC471013
0.7162	Intermediate Similarity	NPC180668
0.7162	Intermediate Similarity	NPC148896
0.7143	Intermediate Similarity	NPC113812
0.712	Intermediate Similarity	NPC474217
0.7113	Intermediate Similarity	NPC273532
0.7106	Intermediate Similarity	NPC13603
0.7101	Intermediate Similarity	NPC328928
0.7097	Intermediate Similarity	NPC314270
0.7089	Intermediate Similarity	NPC473833
0.7087	Intermediate Similarity	NPC476090
0.7068	Intermediate Similarity	NPC71079
0.7064	Intermediate Similarity	NPC85879
0.7064	Intermediate Similarity	NPC53255
0.7064	Intermediate Similarity	NPC478045
0.7064	Intermediate Similarity	NPC52254
0.7039	Intermediate Similarity	NPC10904
0.7028	Intermediate Similarity	NPC474905
0.7024	Intermediate Similarity	NPC103230
0.7014	Intermediate Similarity	NPC475271
0.7005	Intermediate Similarity	NPC476114
0.7004	Intermediate Similarity	NPC57453
0.7	Intermediate Similarity	NPC138018
0.6995	Remote Similarity	NPC85918

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 NPC328559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	504
0.2-0.3	814
0.3-0.4	1770
0.4-0.5	3574
0.5-0.6	1949
0.6-0.7	342
0.7-0.8	14
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
0.8131	Intermediate Similarity	NPD7396	Approved
0.8021	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD820	Phase 3
0.766	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD9271	Approved
0.7357	Intermediate Similarity	NPD8468	Phase 2
0.729	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8325	Phase 3
0.729	Intermediate Similarity	NPD8326	Phase 3
0.7253	Intermediate Similarity	NPD9075	Approved
0.7253	Intermediate Similarity	NPD9074	Approved
0.715	Intermediate Similarity	NPD3794	Approved
0.715	Intermediate Similarity	NPD3795	Approved
0.7127	Intermediate Similarity	NPD107	Approved
0.711	Intermediate Similarity	NPD8479	Phase 2
0.7095	Intermediate Similarity	NPD2831	Approved
0.7042	Intermediate Similarity	NPD6529	Discontinued
0.7031	Intermediate Similarity	NPD5088	Discontinued
0.6961	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD3280	Approved
0.6934	Remote Similarity	NPD3947	Discontinued
0.6908	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5149	Phase 2
0.6881	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5640	Discontinued
0.6866	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6298	Discontinued
0.6837	Remote Similarity	NPD2509	Approved
0.6837	Remote Similarity	NPD2510	Approved
0.6831	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4376	Phase 3
0.68	Remote Similarity	NPD6642	Approved
0.68	Remote Similarity	NPD6641	Approved
0.6773	Remote Similarity	NPD3393	Approved
0.6773	Remote Similarity	NPD3394	Approved
0.6773	Remote Similarity	NPD3389	Approved
0.6771	Remote Similarity	NPD4301	Approved
0.6753	Remote Similarity	NPD8409	Suspended
0.6743	Remote Similarity	NPD4417	Approved
0.6729	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1096	Discontinued
0.6715	Remote Similarity	NPD8063	Discontinued
0.6714	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3371	Approved
0.6699	Remote Similarity	NPD4528	Approved
0.6699	Remote Similarity	NPD4526	Approved
0.6699	Remote Similarity	NPD4529	Approved
0.6696	Remote Similarity	NPD4086	Phase 1
0.6695	Remote Similarity	NPD7886	Phase 2
0.6695	Remote Similarity	NPD7885	Phase 2
0.6683	Remote Similarity	NPD2336	Approved
0.6682	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4989	Phase 2
0.6667	Remote Similarity	NPD8370	Discontinued
0.6667	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1643	Phase 3
0.6638	Remote Similarity	NPD1483	Discontinued
0.6638	Remote Similarity	NPD3006	Discontinued
0.6637	Remote Similarity	NPD7878	Phase 2
0.6636	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2511	Approved
0.6579	Remote Similarity	NPD8289	Discontinued
0.6575	Remote Similarity	NPD4506	Discontinued
0.6573	Remote Similarity	NPD7777	Approved
0.6573	Remote Similarity	NPD53	Approved
0.6573	Remote Similarity	NPD7778	Approved
0.6571	Remote Similarity	NPD6665	Discontinued
0.6569	Remote Similarity	NPD9510	Approved
0.6559	Remote Similarity	NPD2896	Discontinued
0.6557	Remote Similarity	NPD2307	Discontinued
0.6545	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6770	Approved
0.6512	Remote Similarity	NPD5228	Phase 3
0.6507	Remote Similarity	NPD4021	Phase 2
0.6496	Remote Similarity	NPD5891	Approved
0.6494	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5022	Discontinued
0.6489	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7069	Discontinued
0.6471	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6987	Phase 1
0.6462	Remote Similarity	NPD1173	Approved
0.646	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1270	Approved
0.6455	Remote Similarity	NPD4805	Approved
0.6455	Remote Similarity	NPD7467	Discontinued
0.6447	Remote Similarity	NPD8356	Approved
0.6445	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5475	Discontinued
0.6438	Remote Similarity	NPD7010	Phase 3
0.6438	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4427	Phase 2
0.6422	Remote Similarity	NPD5513	Phase 2
0.6416	Remote Similarity	NPD1926	Approved
0.641	Remote Similarity	NPD4373	Phase 2
0.6406	Remote Similarity	NPD3911	Approved
0.6398	Remote Similarity	NPD3321	Discontinued
0.6394	Remote Similarity	NPD3569	Discontinued
0.6391	Remote Similarity	NPD3925	Approved
0.6387	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4948	Discontinued
0.6381	Remote Similarity	NPD9363	Approved
0.6381	Remote Similarity	NPD9364	Phase 2
0.6377	Remote Similarity	NPD9362	Approved
0.6368	Remote Similarity	NPD7031	Phase 1
0.6368	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4500	Approved
0.6359	Remote Similarity	NPD4501	Approved
0.6355	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7233	Approved
0.6351	Remote Similarity	NPD7234	Approved
0.6349	Remote Similarity	NPD4804	Approved
0.6339	Remote Similarity	NPD5866	Approved
0.6337	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD8430	Approved
0.6335	Remote Similarity	NPD7562	Approved
0.6333	Remote Similarity	NPD4375	Approved
0.6332	Remote Similarity	NPD4923	Phase 1
0.633	Remote Similarity	NPD9506	Approved
0.6329	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6962	Phase 2
0.6322	Remote Similarity	NPD6276	Discontinued
0.6316	Remote Similarity	NPD7404	Approved
0.6316	Remote Similarity	NPD1649	Discontinued
0.6313	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.631	Remote Similarity	NPD272	Approved
0.6308	Remote Similarity	NPD6361	Phase 2
0.6305	Remote Similarity	NPD1575	Approved
0.6305	Remote Similarity	NPD1573	Approved
0.6302	Remote Similarity	NPD3813	Approved
0.63	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3178	Discontinued
0.6294	Remote Similarity	NPD2809	Approved
0.6293	Remote Similarity	NPD7426	Phase 1
0.6292	Remote Similarity	NPD6716	Phase 1
0.629	Remote Similarity	NPD7001	Phase 3
0.6286	Remote Similarity	NPD4889	Approved
0.6284	Remote Similarity	NPD9284	Approved
0.6283	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4952	Phase 3
0.6281	Remote Similarity	NPD8375	Approved
0.6276	Remote Similarity	NPD510	Phase 1
0.6272	Remote Similarity	NPD1623	Approved
0.6269	Remote Similarity	NPD6635	Approved
0.6262	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5490	Discontinued
0.6256	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4036	Approved
0.6244	Remote Similarity	NPD4033	Approved
0.6244	Remote Similarity	NPD4037	Approved
0.6244	Remote Similarity	NPD4038	Approved
0.6244	Remote Similarity	NPD32	Approved
0.6244	Remote Similarity	NPD4035	Approved
0.6244	Remote Similarity	NPD4122	Approved
0.6244	Remote Similarity	NPD5901	Discontinued
0.6244	Remote Similarity	NPD31	Approved
0.6244	Remote Similarity	NPD944	Approved
0.6244	Remote Similarity	NPD4039	Approved
0.6244	Remote Similarity	NPD4034	Approved
0.6239	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6999	Discontinued
0.6239	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD721	Approved
0.6234	Remote Similarity	NPD6825	Phase 1
0.6231	Remote Similarity	NPD9382	Approved
0.6231	Remote Similarity	NPD9383	Approved
0.6231	Remote Similarity	NPD2581	Approved
0.6231	Remote Similarity	NPD2582	Approved
0.623	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3386	Phase 2
0.6217	Remote Similarity	NPD1996	Discontinued
0.6211	Remote Similarity	NPD5293	Phase 2
0.621	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD4429	Discontinued
0.62	Remote Similarity	NPD5255	Approved
0.6199	Remote Similarity	NPD6669	Phase 2
0.6197	Remote Similarity	NPD4334	Discontinued
0.6197	Remote Similarity	NPD6068	Discontinued
0.6197	Remote Similarity	NPD1657	Approved
0.6195	Remote Similarity	NPD3816	Phase 1
0.6195	Remote Similarity	NPD3815	Phase 1

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