NPASS Compound

Structure

CID116622 OpenBabel06191715472D 26 28 0 0 0 0 0 0 0 0999 V2000 -2.4249 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6166 1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4249 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4249 0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4249 0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 3.7333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6166 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 2.4249 4.2000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 4.2000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 -2.3333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4249 -2.3333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 3.2667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 3.2667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 -1.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 -1.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 17 2 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 25 2 0 0 0 0 16 26 1 0 0 0 0 M CHG 1 18 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.04
Volume:	324.255
LogP:	1.668
LogD:	3.21
LogS:	-3.197
# Rotatable Bonds:	4
TPSA:	165.97
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	3.105
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.217
MDCK Permeability:	4.383479790703859e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.811

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	82.42512512207031%
Volume Distribution (VD):	0.374
Pgp-substrate:	14.848577499389648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.025
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.852
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.523
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.337
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC116622

Natural Product ID:	NPC116622
*Common Name:**	5,6,9,10-Tetracarboxy-Benzo[B][1,8]Naphthyridin-10-Ium
IUPAC Name:	benzo[b][1,8]naphthyridin-10-ium-5,6,9,10-tetracarboxylic acid
Synonyms:
Standard InCHIKey:	FUODMOGKIDHLFS-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C16H8N2O8/c19-13(20)7-3-4-8(14(21)22)11-9(7)10(15(23)24)6-2-1-5-17-12(6)18(11)16(25)26/h1-5H,(H3-,19,20,21,22,23,24,25,26)/p+1
SMILES:	OC(=O)c1ccc(c2c1[n+](C(=O)O)c1c(c2C(=O)O)cccn1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494069
PubChem CID:	44568607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002552] Quinoline carboxylic acids

*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
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	seed	n.a.	PMID[10898633]
NPO12953	Aplysia fasciata	Species	Aplysiidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[1402961]
NPO12953	Aplysia fasciata	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9170292]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7647	Potamogeton natans	Species	Potamogetonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7647	Potamogeton natans	Species	Potamogetonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8250	Dicoma tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7647	Potamogeton natans	Species	Potamogetonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5592	Ligularia tussilaginea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12953	Aplysia fasciata	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9992	Geigeria burkei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Ki	5

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	102500.0	nM	PMID[509368]
NPT2	Others	Unspecified	Ki	=	102300.0	nM	PMID[509368]
NPT2	Others	Unspecified	Ki	=	97100.0	nM	PMID[509368]
NPT2	Others	Unspecified	Ki	=	94000.0	nM	PMID[509368]
NPT2	Others	Unspecified	Ki	=	104680.0	nM	PMID[509368]

☑ 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 NPC116622 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	531
0.1-0.2	3344
0.2-0.3	13520
0.3-0.4	16611
0.4-0.5	4934
0.5-0.6	2607
0.6-0.7	1059
0.7-0.8	89
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7664	Intermediate Similarity	NPC474916
0.7626	Intermediate Similarity	NPC243850
0.7294	Intermediate Similarity	NPC90229
0.7281	Intermediate Similarity	NPC62995
0.7243	Intermediate Similarity	NPC278434
0.7163	Intermediate Similarity	NPC254762
0.7156	Intermediate Similarity	NPC256268
0.7136	Intermediate Similarity	NPC243058
0.713	Intermediate Similarity	NPC57398
0.7109	Intermediate Similarity	NPC219848
0.707	Intermediate Similarity	NPC282103
0.7061	Intermediate Similarity	NPC309845
0.7056	Intermediate Similarity	NPC147983
0.7056	Intermediate Similarity	NPC177996
0.7054	Intermediate Similarity	NPC328318
0.7054	Intermediate Similarity	NPC328596
0.7043	Intermediate Similarity	NPC317752
0.7037	Intermediate Similarity	NPC90415
0.7024	Intermediate Similarity	NPC74619
0.7023	Intermediate Similarity	NPC203635
0.7023	Intermediate Similarity	NPC285923
0.7	Intermediate Similarity	NPC318299
0.6995	Remote Similarity	NPC164340
0.696	Remote Similarity	NPC317373
0.6933	Remote Similarity	NPC471944
0.693	Remote Similarity	NPC193238
0.6916	Remote Similarity	NPC327592
0.6909	Remote Similarity	NPC138370
0.6897	Remote Similarity	NPC282247
0.6895	Remote Similarity	NPC472289
0.6892	Remote Similarity	NPC146724
0.6872	Remote Similarity	NPC327769
0.6867	Remote Similarity	NPC237740
0.6866	Remote Similarity	NPC207851
0.6857	Remote Similarity	NPC41717
0.6854	Remote Similarity	NPC139763
0.685	Remote Similarity	NPC63109
0.6849	Remote Similarity	NPC229893
0.6844	Remote Similarity	NPC81535
0.6842	Remote Similarity	NPC314648
0.6825	Remote Similarity	NPC471536
0.6818	Remote Similarity	NPC44354
0.681	Remote Similarity	NPC72956
0.6809	Remote Similarity	NPC469727
0.6791	Remote Similarity	NPC157583
0.6791	Remote Similarity	NPC237188
0.6787	Remote Similarity	NPC83111
0.6781	Remote Similarity	NPC153980
0.6781	Remote Similarity	NPC6865
0.6781	Remote Similarity	NPC471194
0.6781	Remote Similarity	NPC471193
0.6778	Remote Similarity	NPC130570
0.6776	Remote Similarity	NPC477549
0.6753	Remote Similarity	NPC266249
0.6751	Remote Similarity	NPC48317
0.6746	Remote Similarity	NPC322644
0.6744	Remote Similarity	NPC84347
0.6737	Remote Similarity	NPC27041
0.6736	Remote Similarity	NPC216612
0.6723	Remote Similarity	NPC276657
0.6722	Remote Similarity	NPC473506
0.6711	Remote Similarity	NPC109922
0.671	Remote Similarity	NPC314297
0.671	Remote Similarity	NPC315545
0.6708	Remote Similarity	NPC76565
0.6707	Remote Similarity	NPC72905
0.6707	Remote Similarity	NPC171393
0.6707	Remote Similarity	NPC295452
0.6698	Remote Similarity	NPC303225
0.6697	Remote Similarity	NPC477891
0.6695	Remote Similarity	NPC471192
0.6695	Remote Similarity	NPC314834
0.6695	Remote Similarity	NPC470020
0.6695	Remote Similarity	NPC123839
0.6694	Remote Similarity	NPC476491
0.6694	Remote Similarity	NPC475631
0.6694	Remote Similarity	NPC87152
0.6694	Remote Similarity	NPC475600
0.6694	Remote Similarity	NPC74575
0.6694	Remote Similarity	NPC476110
0.6682	Remote Similarity	NPC114974
0.6681	Remote Similarity	NPC74360
0.6681	Remote Similarity	NPC116555
0.668	Remote Similarity	NPC475303
0.668	Remote Similarity	NPC475596
0.668	Remote Similarity	NPC475498
0.668	Remote Similarity	NPC475137
0.668	Remote Similarity	NPC477112
0.6667	Remote Similarity	NPC471977
0.6667	Remote Similarity	NPC203754
0.6667	Remote Similarity	NPC313796
0.6667	Remote Similarity	NPC150048
0.6667	Remote Similarity	NPC470486
0.6667	Remote Similarity	NPC82370
0.6667	Remote Similarity	NPC475644
0.6667	Remote Similarity	NPC220851
0.6667	Remote Similarity	NPC315638
0.6667	Remote Similarity	NPC314855
0.6667	Remote Similarity	NPC170751
0.6667	Remote Similarity	NPC183805
0.6667	Remote Similarity	NPC471190
0.6667	Remote Similarity	NPC313345
0.6654	Remote Similarity	NPC137353
0.6653	Remote Similarity	NPC208522
0.6653	Remote Similarity	NPC30456
0.6652	Remote Similarity	NPC212213
0.6651	Remote Similarity	NPC208060
0.6639	Remote Similarity	NPC322482
0.6636	Remote Similarity	NPC164664
0.662	Remote Similarity	NPC114637
0.6614	Remote Similarity	NPC142385
0.6611	Remote Similarity	NPC472555
0.6609	Remote Similarity	NPC211813
0.6606	Remote Similarity	NPC476341
0.6605	Remote Similarity	NPC273532
0.6599	Remote Similarity	NPC475426
0.6599	Remote Similarity	NPC182222
0.6597	Remote Similarity	NPC477908
0.6597	Remote Similarity	NPC267811
0.6597	Remote Similarity	NPC206343
0.6593	Remote Similarity	NPC135950
0.6589	Remote Similarity	NPC70949
0.6585	Remote Similarity	NPC49547
0.6585	Remote Similarity	NPC207686
0.6584	Remote Similarity	NPC132631
0.6584	Remote Similarity	NPC103687
0.658	Remote Similarity	NPC200836
0.658	Remote Similarity	NPC53144
0.6579	Remote Similarity	NPC131887
0.6577	Remote Similarity	NPC17273
0.6577	Remote Similarity	NPC141612
0.6577	Remote Similarity	NPC135601
0.6575	Remote Similarity	NPC24864
0.6575	Remote Similarity	NPC471997
0.6574	Remote Similarity	NPC477976
0.657	Remote Similarity	NPC250807
0.657	Remote Similarity	NPC57797
0.6568	Remote Similarity	NPC471603
0.6568	Remote Similarity	NPC244856
0.6562	Remote Similarity	NPC154339
0.6557	Remote Similarity	NPC146824
0.6557	Remote Similarity	NPC328186
0.6557	Remote Similarity	NPC122968
0.6557	Remote Similarity	NPC477787
0.6557	Remote Similarity	NPC228377
0.6552	Remote Similarity	NPC289086
0.6546	Remote Similarity	NPC470022
0.6545	Remote Similarity	NPC292416
0.6545	Remote Similarity	NPC316841
0.6545	Remote Similarity	NPC477906
0.6545	Remote Similarity	NPC473689
0.6545	Remote Similarity	NPC144114
0.6544	Remote Similarity	NPC317054
0.6543	Remote Similarity	NPC473850
0.6543	Remote Similarity	NPC476818
0.6542	Remote Similarity	NPC56233
0.6542	Remote Similarity	NPC216428
0.6538	Remote Similarity	NPC171787
0.6532	Remote Similarity	NPC35208
0.6532	Remote Similarity	NPC475406
0.6531	Remote Similarity	NPC156003
0.6531	Remote Similarity	NPC475362
0.6529	Remote Similarity	NPC477911
0.6528	Remote Similarity	NPC249614
0.6527	Remote Similarity	NPC472285
0.6526	Remote Similarity	NPC265100
0.6524	Remote Similarity	NPC82053
0.6524	Remote Similarity	NPC238457
0.6518	Remote Similarity	NPC319880
0.6518	Remote Similarity	NPC244839
0.6518	Remote Similarity	NPC255909
0.6518	Remote Similarity	NPC320324
0.6517	Remote Similarity	NPC77101
0.6516	Remote Similarity	NPC470018
0.6512	Remote Similarity	NPC278874
0.651	Remote Similarity	NPC270515
0.6507	Remote Similarity	NPC102008
0.6507	Remote Similarity	NPC239954
0.6506	Remote Similarity	NPC38959
0.6506	Remote Similarity	NPC327904
0.6504	Remote Similarity	NPC216550
0.6502	Remote Similarity	NPC194040
0.6502	Remote Similarity	NPC62749
0.65	Remote Similarity	NPC62367
0.6498	Remote Similarity	NPC111732
0.6498	Remote Similarity	NPC219087
0.6496	Remote Similarity	NPC178858
0.6492	Remote Similarity	NPC237702
0.6492	Remote Similarity	NPC220852
0.6491	Remote Similarity	NPC128244
0.6489	Remote Similarity	NPC469489
0.6486	Remote Similarity	NPC471742
0.6486	Remote Similarity	NPC21429
0.6485	Remote Similarity	NPC477909
0.6485	Remote Similarity	NPC477907
0.6485	Remote Similarity	NPC42678
0.6484	Remote Similarity	NPC111275
0.6481	Remote Similarity	NPC472259
0.648	Remote Similarity	NPC285343
0.6479	Remote Similarity	NPC88970

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 NPC116622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	657
0.2-0.3	943
0.3-0.4	2116
0.4-0.5	2344
0.5-0.6	1880
0.6-0.7	843
0.7-0.8	90
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8257	Intermediate Similarity	NPD5827	Discontinued
0.8145	Intermediate Similarity	NPD3222	Phase 2
0.7867	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7767	Approved
0.7749	Intermediate Similarity	NPD6142	Phase 3
0.7702	Intermediate Similarity	NPD5821	Approved
0.7668	Intermediate Similarity	NPD5490	Discontinued
0.7667	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD4938	Phase 2
0.7589	Intermediate Similarity	NPD6733	Discontinued
0.758	Intermediate Similarity	NPD2317	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6970	Phase 2
0.7477	Intermediate Similarity	NPD1173	Approved
0.7442	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7856	Phase 2
0.7333	Intermediate Similarity	NPD7857	Phase 3
0.7325	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2813	Phase 3
0.7309	Intermediate Similarity	NPD3905	Phase 3
0.7304	Intermediate Similarity	NPD6210	Phase 3
0.7301	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3918	Approved
0.7301	Intermediate Similarity	NPD3917	Approved
0.7289	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4301	Approved
0.7269	Intermediate Similarity	NPD7923	Phase 2
0.7265	Intermediate Similarity	NPD6165	Phase 2
0.7265	Intermediate Similarity	NPD6164	Phase 2
0.7257	Intermediate Similarity	NPD3915	Approved
0.7243	Intermediate Similarity	NPD4948	Discontinued
0.7222	Intermediate Similarity	NPD2336	Approved
0.7193	Intermediate Similarity	NPD2847	Phase 2
0.719	Intermediate Similarity	NPD5883	Phase 2
0.7189	Intermediate Similarity	NPD3431	Approved
0.7189	Intermediate Similarity	NPD3430	Approved
0.7184	Intermediate Similarity	NPD7398	Approved
0.7184	Intermediate Similarity	NPD7397	Approved
0.7176	Intermediate Similarity	NPD3439	Approved
0.717	Intermediate Similarity	NPD1233	Suspended
0.7161	Intermediate Similarity	NPD7887	Approved
0.7161	Intermediate Similarity	NPD7888	Approved
0.7161	Intermediate Similarity	NPD1571	Phase 2
0.7156	Intermediate Similarity	NPD3371	Approved
0.7149	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD944	Approved
0.7143	Intermediate Similarity	NPD6987	Phase 1
0.7143	Intermediate Similarity	NPD6022	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3284	Phase 3
0.713	Intermediate Similarity	NPD2881	Approved
0.713	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2879	Approved
0.7124	Intermediate Similarity	NPD4612	Discontinued
0.712	Intermediate Similarity	NPD7776	Approved
0.7119	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7694	Discontinued
0.7116	Intermediate Similarity	NPD3315	Phase 3
0.7113	Intermediate Similarity	NPD7415	Suspended
0.7111	Intermediate Similarity	NPD7010	Phase 3
0.711	Intermediate Similarity	NPD6887	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3805	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7423	Phase 2
0.7091	Intermediate Similarity	NPD2307	Discontinued
0.7087	Intermediate Similarity	NPD7188	Phase 3
0.7082	Intermediate Similarity	NPD1834	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6135	Phase 1
0.708	Intermediate Similarity	NPD6458	Discontinued
0.7075	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1572	Phase 2
0.7069	Intermediate Similarity	NPD6470	Phase 3
0.7067	Intermediate Similarity	NPD5901	Discontinued
0.7064	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD3959	Phase 2
0.7061	Intermediate Similarity	NPD5072	Discontinued
0.7061	Intermediate Similarity	NPD3962	Phase 2
0.7056	Intermediate Similarity	NPD3353	Approved
0.7054	Intermediate Similarity	NPD7052	Phase 1
0.7051	Intermediate Similarity	NPD1464	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8094	Discontinued
0.7043	Intermediate Similarity	NPD3795	Approved
0.7043	Intermediate Similarity	NPD3794	Approved
0.7035	Intermediate Similarity	NPD7568	Phase 1
0.7031	Intermediate Similarity	NPD5475	Discontinued
0.7026	Intermediate Similarity	NPD5523	Approved
0.7026	Intermediate Similarity	NPD5524	Approved
0.7023	Intermediate Similarity	NPD721	Approved
0.7022	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1641	Discontinued
0.7004	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5428	Discontinued
0.6996	Remote Similarity	NPD5116	Phase 1
0.6996	Remote Similarity	NPD1623	Approved
0.6992	Remote Similarity	NPD6752	Phase 1
0.6992	Remote Similarity	NPD6753	Phase 1
0.6991	Remote Similarity	NPD7207	Approved
0.6991	Remote Similarity	NPD7208	Approved
0.6991	Remote Similarity	NPD4299	Phase 1
0.6991	Remote Similarity	NPD7209	Approved
0.6983	Remote Similarity	NPD3393	Approved
0.6983	Remote Similarity	NPD6958	Approved
0.6983	Remote Similarity	NPD3394	Approved
0.6983	Remote Similarity	NPD6957	Approved
0.6983	Remote Similarity	NPD7112	Discontinued
0.6983	Remote Similarity	NPD3389	Approved
0.6982	Remote Similarity	NPD5446	Phase 2
0.6978	Remote Similarity	NPD6132	Phase 1
0.6971	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7404	Approved
0.6964	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6282	Discontinued
0.6955	Remote Similarity	NPD3406	Suspended
0.6955	Remote Similarity	NPD4615	Phase 2
0.6953	Remote Similarity	NPD6218	Discontinued
0.6951	Remote Similarity	NPD1982	Phase 1
0.6951	Remote Similarity	NPD5467	Phase 2
0.6942	Remote Similarity	NPD6130	Phase 1
0.694	Remote Similarity	NPD5413	Phase 2
0.6937	Remote Similarity	NPD7935	Phase 2
0.693	Remote Similarity	NPD1506	Discontinued
0.6929	Remote Similarity	NPD7173	Approved
0.6929	Remote Similarity	NPD7172	Approved
0.6929	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5533	Discontinued
0.692	Remote Similarity	NPD6829	Phase 2
0.692	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6999	Discontinued
0.6916	Remote Similarity	NPD5000	Phase 2
0.6916	Remote Similarity	NPD7103	Approved
0.6914	Remote Similarity	NPD5891	Approved
0.6911	Remote Similarity	NPD6490	Phase 2
0.691	Remote Similarity	NPD6711	Approved
0.6908	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.69	Remote Similarity	NPD2510	Approved
0.69	Remote Similarity	NPD2509	Approved
0.69	Remote Similarity	NPD6520	Phase 3
0.69	Remote Similarity	NPD6521	Phase 3
0.6894	Remote Similarity	NPD7168	Phase 3
0.6886	Remote Similarity	NPD5491	Phase 3
0.6886	Remote Similarity	NPD5489	Phase 1
0.6883	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5505	Discontinued
0.6875	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5510	Approved
0.687	Remote Similarity	NPD6715	Discontinued
0.687	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7996	Phase 2
0.6861	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1197	Approved
0.6844	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8321	Discontinued
0.6838	Remote Similarity	NPD4438	Approved
0.6835	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2443	Approved
0.6826	Remote Similarity	NPD7665	Phase 2
0.6826	Remote Similarity	NPD2442	Approved
0.6826	Remote Similarity	NPD7666	Phase 3
0.682	Remote Similarity	NPD7689	Approved
0.6816	Remote Similarity	NPD5853	Phase 3
0.6816	Remote Similarity	NPD5855	Phase 3
0.6813	Remote Similarity	NPD7851	Phase 1
0.6813	Remote Similarity	NPD7850	Discontinued
0.6812	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2008	Discontinued
0.6812	Remote Similarity	NPD7323	Phase 2
0.6811	Remote Similarity	NPD8049	Phase 2
0.6808	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5907	Phase 3
0.6802	Remote Similarity	NPD2127	Suspended
0.6795	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6226	Phase 3
0.6786	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2411	Approved
0.6781	Remote Similarity	NPD8093	Discontinued
0.678	Remote Similarity	NPD3262	Approved
0.6778	Remote Similarity	NPD5424	Discontinued
0.6778	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6986	Phase 1
0.6776	Remote Similarity	NPD5469	Phase 3
0.6767	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3013	Phase 3
0.6767	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7434	Approved
0.6756	Remote Similarity	NPD1842	Approved
0.6754	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2807	Discontinued
0.6752	Remote Similarity	NPD7616	Discontinued
0.6751	Remote Similarity	NPD4312	Approved
0.6751	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8004	Discontinued
0.6748	Remote Similarity	NPD8409	Suspended
0.6744	Remote Similarity	NPD5100	Phase 3
0.6741	Remote Similarity	NPD4998	Phase 3
0.6741	Remote Similarity	NPD7024	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