NPASS Compound

Structure

CID325775 OpenBabel06191716182D 38 40 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 8.6603 0.0000 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 8.6603 4.0000 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 8.6603 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 6.9282 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 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 9.5263 4.5000 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 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 10.3923 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 5.5000 0.0000 O 0 5 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 -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 35 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 15 1 0 0 0 0 7 20 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 12 15 2 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 2 0 0 0 0 14 36 1 0 0 0 0 16 3 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 9 1 6 0 0 0 17 18 1 0 0 0 0 18 24 1 0 0 0 0 19 13 1 1 0 0 0 19 21 1 0 0 0 0 19 37 1 0 0 0 0 20 29 2 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 6 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 25 38 1 1 0 0 0 26 37 1 0 0 0 0 26 38 1 1 0 0 0 M CHG 2 27 1 30 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	535.21
Volume:	519.18
LogP:	-1.263
LogD:	-0.854
LogS:	-0.857
# Rotatable Bonds:	12
TPSA:	178.92
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	5.256
Fsp3:	0.5
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:	-5.77
MDCK Permeability:	9.042645251611248e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.905
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	24.15538787841797%
Volume Distribution (VD):	0.276
Pgp-substrate:	64.8439712524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	1.572
Half-life (T1/2):	0.955

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.507
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.183
Carcinogencity:	0.871
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC325775

Natural Product ID:	NPC325775
*Common Name:**	Lonijaposide N
IUPAC Name:	4-[3-[(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]pyridin-1-ium-1-yl]butanoate
Synonyms:	Lonijaposide N
Standard InCHIKey:	PJIVLFIKRZQZOE-URGZVSNXSA-N
Standard InCHI:	InChI=1S/C26H33NO11/c1-3-16-17(9-8-15-6-4-10-27(12-15)11-5-7-20(29)30)18(24(34)35-2)14-36-25(16)38-26-23(33)22(32)21(31)19(13-28)37-26/h3-4,6,8-10,12,14,16-17,19,21-23,25-26,28,31-33H,1,5,7,11,13H2,2H3/b9-8+/t16-,17+,19-,21-,22+,23-,25+,26+/m1/s1
SMILES:	COC(=O)C1=COC(C(C1C=CC2=C[N+](=CC=C2)CCCC(=O)[O-])C=C)OC3C(C(C(C(O3)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928052
PubChem CID:	56600069
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	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	<	30.0	%	PMID[466139]

☑ 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 NPC325775 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	239
0.1-0.2	1230
0.2-0.3	4904
0.3-0.4	15609
0.4-0.5	15789
0.5-0.6	4032
0.6-0.7	761
0.7-0.8	110
0.8-0.85	3
0.85-0.9	11
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC328798
0.9759	High Similarity	NPC322043
0.9524	High Similarity	NPC325093
0.9524	High Similarity	NPC327373
0.9477	High Similarity	NPC127647
0.9412	High Similarity	NPC318020
0.936	High Similarity	NPC182814
0.9096	High Similarity	NPC20593
0.9006	High Similarity	NPC32451
0.8901	High Similarity	NPC328559
0.8895	High Similarity	NPC160127
0.8895	High Similarity	NPC50997
0.884	High Similarity	NPC320748
0.884	High Similarity	NPC324245
0.8743	High Similarity	NPC79223
0.8736	High Similarity	NPC317672
0.8681	High Similarity	NPC329024
0.8564	High Similarity	NPC156044
0.8533	High Similarity	NPC59033
0.8457	Intermediate Similarity	NPC25442
0.8457	Intermediate Similarity	NPC12944
0.8061	Intermediate Similarity	NPC111732
0.7938	Intermediate Similarity	NPC309498
0.7789	Intermediate Similarity	NPC292517
0.7723	Intermediate Similarity	NPC162812
0.7716	Intermediate Similarity	NPC474905
0.7673	Intermediate Similarity	NPC30570
0.7638	Intermediate Similarity	NPC472752
0.7598	Intermediate Similarity	NPC474217
0.7598	Intermediate Similarity	NPC82070
0.7542	Intermediate Similarity	NPC71079
0.7538	Intermediate Similarity	NPC475835
0.75	Intermediate Similarity	NPC477910
0.7476	Intermediate Similarity	NPC52254
0.7475	Intermediate Similarity	NPC476115
0.7459	Intermediate Similarity	NPC85918
0.7438	Intermediate Similarity	NPC476467
0.7438	Intermediate Similarity	NPC472553
0.7433	Intermediate Similarity	NPC317010
0.7418	Intermediate Similarity	NPC278366
0.7418	Intermediate Similarity	NPC127730
0.7416	Intermediate Similarity	NPC475271
0.7415	Intermediate Similarity	NPC476114
0.7379	Intermediate Similarity	NPC475408
0.7379	Intermediate Similarity	NPC471014
0.7376	Intermediate Similarity	NPC472550
0.7376	Intermediate Similarity	NPC48042
0.7376	Intermediate Similarity	NPC304179
0.7343	Intermediate Similarity	NPC294579
0.7343	Intermediate Similarity	NPC144779
0.733	Intermediate Similarity	NPC470306
0.7327	Intermediate Similarity	NPC63041
0.7308	Intermediate Similarity	NPC472555
0.7299	Intermediate Similarity	NPC475137
0.7299	Intermediate Similarity	NPC475498
0.7295	Intermediate Similarity	NPC6981
0.7295	Intermediate Similarity	NPC471016
0.7286	Intermediate Similarity	NPC477911
0.7282	Intermediate Similarity	NPC319128
0.7282	Intermediate Similarity	NPC228331
0.7264	Intermediate Similarity	NPC473506
0.726	Intermediate Similarity	NPC62367
0.7251	Intermediate Similarity	NPC76565
0.7238	Intermediate Similarity	NPC477912
0.723	Intermediate Similarity	NPC124029
0.723	Intermediate Similarity	NPC211920
0.7225	Intermediate Similarity	NPC301368
0.7225	Intermediate Similarity	NPC216428
0.7225	Intermediate Similarity	NPC84815
0.7219	Intermediate Similarity	NPC322488
0.7217	Intermediate Similarity	NPC233727
0.7217	Intermediate Similarity	NPC477902
0.7212	Intermediate Similarity	NPC472435
0.7212	Intermediate Similarity	NPC477908
0.7212	Intermediate Similarity	NPC206343
0.7196	Intermediate Similarity	NPC471190
0.7196	Intermediate Similarity	NPC470486
0.7196	Intermediate Similarity	NPC471977
0.7196	Intermediate Similarity	NPC475644
0.7193	Intermediate Similarity	NPC472436
0.7189	Intermediate Similarity	NPC170751
0.7183	Intermediate Similarity	NPC148860
0.7174	Intermediate Similarity	NPC477975
0.717	Intermediate Similarity	NPC471980
0.7163	Intermediate Similarity	NPC477909
0.7163	Intermediate Similarity	NPC477907
0.7163	Intermediate Similarity	NPC42678
0.7158	Intermediate Similarity	NPC471997
0.715	Intermediate Similarity	NPC165837
0.715	Intermediate Similarity	NPC476110
0.715	Intermediate Similarity	NPC87152
0.715	Intermediate Similarity	NPC475600
0.715	Intermediate Similarity	NPC475631
0.7143	Intermediate Similarity	NPC238457
0.7136	Intermediate Similarity	NPC473850
0.7136	Intermediate Similarity	NPC328154
0.713	Intermediate Similarity	NPC477906
0.7123	Intermediate Similarity	NPC127720
0.7123	Intermediate Similarity	NPC127026
0.7122	Intermediate Similarity	NPC477548
0.7121	Intermediate Similarity	NPC109922
0.7116	Intermediate Similarity	NPC475362
0.7115	Intermediate Similarity	NPC274842
0.7115	Intermediate Similarity	NPC264674
0.7101	Intermediate Similarity	NPC244856
0.7101	Intermediate Similarity	NPC280473
0.7101	Intermediate Similarity	NPC323551
0.7097	Intermediate Similarity	NPC30456
0.7095	Intermediate Similarity	NPC314270
0.7095	Intermediate Similarity	NPC174788
0.7089	Intermediate Similarity	NPC57797
0.7089	Intermediate Similarity	NPC250807
0.7088	Intermediate Similarity	NPC138018
0.7085	Intermediate Similarity	NPC476090
0.7081	Intermediate Similarity	NPC207531
0.707	Intermediate Similarity	NPC146824
0.707	Intermediate Similarity	NPC475601
0.7067	Intermediate Similarity	NPC41724
0.7067	Intermediate Similarity	NPC51008
0.7067	Intermediate Similarity	NPC306644
0.7067	Intermediate Similarity	NPC236424
0.7053	Intermediate Similarity	NPC40919
0.7053	Intermediate Similarity	NPC470189
0.7051	Intermediate Similarity	NPC475303
0.7051	Intermediate Similarity	NPC475596
0.7051	Intermediate Similarity	NPC150698
0.7051	Intermediate Similarity	NPC96801
0.705	Intermediate Similarity	NPC149708
0.7033	Intermediate Similarity	NPC4421
0.7033	Intermediate Similarity	NPC313640
0.7032	Intermediate Similarity	NPC327769
0.7032	Intermediate Similarity	NPC475426
0.7032	Intermediate Similarity	NPC35208
0.702	Intermediate Similarity	NPC103230
0.7018	Intermediate Similarity	NPC469748
0.7014	Intermediate Similarity	NPC319556
0.701	Intermediate Similarity	NPC62510
0.701	Intermediate Similarity	NPC289086
0.7006	Intermediate Similarity	NPC471323
0.7	Intermediate Similarity	NPC62844
0.7	Intermediate Similarity	NPC193361
0.6991	Remote Similarity	NPC477787
0.6991	Remote Similarity	NPC328186
0.6991	Remote Similarity	NPC122968
0.6991	Remote Similarity	NPC228377
0.699	Remote Similarity	NPC470190
0.6986	Remote Similarity	NPC237702
0.6984	Remote Similarity	NPC477976
0.698	Remote Similarity	NPC470279
0.6972	Remote Similarity	NPC292416
0.6972	Remote Similarity	NPC473689
0.6941	Remote Similarity	NPC244839
0.6941	Remote Similarity	NPC320324
0.6941	Remote Similarity	NPC319880
0.6934	Remote Similarity	NPC473089
0.6934	Remote Similarity	NPC212768
0.6934	Remote Similarity	NPC473115
0.6934	Remote Similarity	NPC6576
0.6934	Remote Similarity	NPC75600
0.6934	Remote Similarity	NPC158020
0.6934	Remote Similarity	NPC187494
0.6933	Remote Similarity	NPC472434
0.6931	Remote Similarity	NPC249614
0.6923	Remote Similarity	NPC107287
0.6919	Remote Similarity	NPC114974
0.6916	Remote Similarity	NPC477903
0.6915	Remote Similarity	NPC319456
0.6905	Remote Similarity	NPC234078
0.6905	Remote Similarity	NPC221100
0.6898	Remote Similarity	NPC26881
0.6895	Remote Similarity	NPC316841
0.6888	Remote Similarity	NPC291759
0.6885	Remote Similarity	NPC263455
0.6884	Remote Similarity	NPC235364
0.6878	Remote Similarity	NPC475406
0.6875	Remote Similarity	NPC99891
0.6869	Remote Similarity	NPC477901
0.6857	Remote Similarity	NPC114310
0.6847	Remote Similarity	NPC474767
0.6847	Remote Similarity	NPC38959
0.6847	Remote Similarity	NPC327904
0.6837	Remote Similarity	NPC133591
0.6835	Remote Similarity	NPC14116
0.6835	Remote Similarity	NPC285411
0.6833	Remote Similarity	NPC238278
0.683	Remote Similarity	NPC253482
0.682	Remote Similarity	NPC477900
0.682	Remote Similarity	NPC477899
0.6816	Remote Similarity	NPC135950
0.6812	Remote Similarity	NPC476516
0.6806	Remote Similarity	NPC477788
0.6804	Remote Similarity	NPC311196
0.6804	Remote Similarity	NPC134384
0.6779	Remote Similarity	NPC193238
0.6773	Remote Similarity	NPC91125
0.6771	Remote Similarity	NPC57453
0.6766	Remote Similarity	NPC289786
0.6754	Remote Similarity	NPC475533
0.674	Remote Similarity	NPC475648
0.6738	Remote Similarity	NPC320064

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 NPC325775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	435
0.2-0.3	751
0.3-0.4	1751
0.4-0.5	3710
0.5-0.6	2000
0.6-0.7	327
0.7-0.8	11
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
0.7635	Intermediate Similarity	NPD8326	Phase 3
0.7635	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD8325	Phase 3
0.7525	Intermediate Similarity	NPD7396	Approved
0.75	Intermediate Similarity	NPD5088	Discontinued
0.7287	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2896	Discontinued
0.7207	Intermediate Similarity	NPD8468	Phase 2
0.7088	Intermediate Similarity	NPD820	Phase 3
0.7086	Intermediate Similarity	NPD4805	Approved
0.7051	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8409	Suspended
0.7041	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6635	Approved
0.7016	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2511	Approved
0.699	Remote Similarity	NPD7234	Approved
0.699	Remote Similarity	NPD7233	Approved
0.6978	Remote Similarity	NPD2809	Approved
0.6971	Remote Similarity	NPD4804	Approved
0.6957	Remote Similarity	NPD6529	Discontinued
0.6954	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8479	Phase 2
0.6935	Remote Similarity	NPD4529	Approved
0.6935	Remote Similarity	NPD4526	Approved
0.6935	Remote Similarity	NPD4528	Approved
0.6931	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6298	Discontinued
0.6914	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.691	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5149	Phase 2
0.6866	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4427	Phase 2
0.6813	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8063	Discontinued
0.6779	Remote Similarity	NPD7562	Approved
0.6776	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6026	Approved
0.675	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD3795	Approved
0.6745	Remote Similarity	NPD3794	Approved
0.6724	Remote Similarity	NPD8370	Discontinued
0.6718	Remote Similarity	NPD5899	Approved
0.6718	Remote Similarity	NPD5898	Approved
0.6718	Remote Similarity	NPD5897	Approved
0.6712	Remote Similarity	NPD5640	Discontinued
0.6703	Remote Similarity	NPD9271	Approved
0.6701	Remote Similarity	NPD6641	Approved
0.6701	Remote Similarity	NPD6642	Approved
0.6699	Remote Similarity	NPD3911	Approved
0.6698	Remote Similarity	NPD7069	Discontinued
0.6683	Remote Similarity	NPD6361	Phase 2
0.6682	Remote Similarity	NPD4086	Phase 1
0.6667	Remote Similarity	NPD4889	Approved
0.665	Remote Similarity	NPD4500	Approved
0.665	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4501	Approved
0.6634	Remote Similarity	NPD7777	Approved
0.6634	Remote Similarity	NPD53	Approved
0.6634	Remote Similarity	NPD7778	Approved
0.6633	Remote Similarity	NPD4375	Approved
0.6632	Remote Similarity	NPD43	Approved
0.6632	Remote Similarity	NPD6182	Approved
0.6632	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD2581	Approved
0.6631	Remote Similarity	NPD2582	Approved
0.6629	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1380	Discovery
0.6615	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD9206	Approved
0.6609	Remote Similarity	NPD9207	Approved
0.6609	Remote Similarity	NPD8375	Approved
0.6603	Remote Similarity	NPD32	Approved
0.6603	Remote Similarity	NPD4038	Approved
0.6603	Remote Similarity	NPD31	Approved
0.6603	Remote Similarity	NPD4034	Approved
0.6603	Remote Similarity	NPD4033	Approved
0.6603	Remote Similarity	NPD4037	Approved
0.6603	Remote Similarity	NPD4039	Approved
0.6603	Remote Similarity	NPD4122	Approved
0.6603	Remote Similarity	NPD4036	Approved
0.6603	Remote Similarity	NPD4035	Approved
0.6599	Remote Similarity	NPD8408	Discontinued
0.6596	Remote Similarity	NPD5255	Approved
0.6595	Remote Similarity	NPD510	Phase 1
0.6593	Remote Similarity	NPD9075	Approved
0.6593	Remote Similarity	NPD9074	Approved
0.6587	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6206	Phase 1
0.6574	Remote Similarity	NPD4989	Phase 2
0.6571	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6479	Discontinued
0.6567	Remote Similarity	NPD4334	Discontinued
0.6567	Remote Similarity	NPD4021	Phase 2
0.6562	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3280	Approved
0.6559	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8122	Approved
0.6531	Remote Similarity	NPD8123	Approved
0.6526	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2831	Approved
0.6522	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4703	Approved
0.6522	Remote Similarity	NPD4702	Approved
0.6519	Remote Similarity	NPD1382	Phase 2
0.6519	Remote Similarity	NPD1383	Phase 3
0.6517	Remote Similarity	NPD8020	Approved
0.6517	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8021	Approved
0.6515	Remote Similarity	NPD3386	Phase 2
0.6515	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2510	Approved
0.6509	Remote Similarity	NPD2509	Approved
0.6502	Remote Similarity	NPD2336	Approved
0.6502	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6068	Discontinued
0.6484	Remote Similarity	NPD3717	Discontinued
0.6484	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5862	Discovery
0.6471	Remote Similarity	NPD6665	Discontinued
0.6471	Remote Similarity	NPD4376	Phase 3
0.6467	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD107	Approved
0.6463	Remote Similarity	NPD7886	Phase 2
0.6463	Remote Similarity	NPD7885	Phase 2
0.6456	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6281	Approved
0.6453	Remote Similarity	NPD3321	Discontinued
0.6452	Remote Similarity	NPD3393	Approved
0.6452	Remote Similarity	NPD3394	Approved
0.6452	Remote Similarity	NPD3389	Approved
0.645	Remote Similarity	NPD1096	Discontinued
0.6432	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1270	Approved
0.6429	Remote Similarity	NPD7561	Approved
0.6425	Remote Similarity	NPD5611	Phase 2
0.6425	Remote Similarity	NPD8356	Approved
0.6415	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8289	Discontinued
0.6411	Remote Similarity	NPD5228	Phase 3
0.6408	Remote Similarity	NPD7944	Discontinued
0.64	Remote Similarity	NPD8374	Phase 3
0.64	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5487	Phase 1
0.6394	Remote Similarity	NPD6261	Phase 3
0.6393	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4315	Phase 2
0.639	Remote Similarity	NPD6569	Phase 2
0.6389	Remote Similarity	NPD9506	Approved
0.638	Remote Similarity	NPD5147	Discontinued
0.6377	Remote Similarity	NPD2307	Discontinued
0.6374	Remote Similarity	NPD1649	Discontinued
0.6372	Remote Similarity	NPD5072	Discontinued
0.6368	Remote Similarity	NPD6178	Phase 3
0.6368	Remote Similarity	NPD3947	Discontinued
0.6368	Remote Similarity	NPD3569	Discontinued
0.6364	Remote Similarity	NPD6248	Phase 2
0.6364	Remote Similarity	NPD1032	Phase 2
0.6364	Remote Similarity	NPD6249	Phase 2
0.636	Remote Similarity	NPD8329	Phase 3
0.6359	Remote Similarity	NPD3813	Approved
0.6355	Remote Similarity	NPD7467	Discontinued
0.6349	Remote Similarity	NPD2061	Approved
0.6343	Remote Similarity	NPD9284	Approved
0.6338	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7957	Phase 1
0.6338	Remote Similarity	NPD7010	Phase 3
0.6329	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3815	Phase 1
0.6313	Remote Similarity	NPD3816	Phase 1
0.6311	Remote Similarity	NPD8430	Approved
0.6308	Remote Similarity	NPD4638	Approved
0.6308	Remote Similarity	NPD4639	Approved
0.6308	Remote Similarity	NPD4640	Approved
0.6305	Remote Similarity	NPD5444	Phase 1
0.6298	Remote Similarity	NPD201	Phase 2
0.6298	Remote Similarity	NPD200	Phase 2
0.6294	Remote Similarity	NPD2077	Approved
0.6294	Remote Similarity	NPD2076	Approved
0.629	Remote Similarity	NPD7469	Discontinued
0.6288	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7483	Phase 2
0.6287	Remote Similarity	NPD2091	Phase 2
0.6287	Remote Similarity	NPD2096	Phase 2
0.6287	Remote Similarity	NPD7482	Phase 2
0.6286	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7000	Clinical (unspecified phase)

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