NPASS Compound

Structure

NPC471546 OpenBabel07101719252D 41 44 0 0 1 0 0 0 0 0999 V2000 -1.6845 -11.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 -10.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -9.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -8.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -8.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -7.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -6.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -5.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 -0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2569 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 -0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3776 2.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 2.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 3.9067 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 3.9067 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 1.9067 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 3.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6527 0.4296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.5933 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 31 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 0 0 0 0 23 37 2 0 0 0 0 24 13 1 1 0 0 0 24 40 1 0 0 0 0 25 39 1 6 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 29 2 0 0 0 0 27 35 1 0 0 0 0 28 33 1 0 0 0 0 28 36 2 0 0 0 0 29 34 1 0 0 0 0 29 36 1 0 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 41 1 0 0 0 0 32 19 1 1 0 0 0 32 40 1 0 0 0 0 32 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	609.24
Volume:	600.785
LogP:	7.551
LogD:	3.781
LogS:	-6.995
# Rotatable Bonds:	15
TPSA:	74.72
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	5.031
Fsp3:	0.656
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.72
MDCK Permeability:	2.566762486821972e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.144
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	102.2226333618164%
Volume Distribution (VD):	3.013
Pgp-substrate:	0.7533825635910034%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.772
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.298
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	8.538
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.685
Human Hepatotoxicity (H-HT):	0.774
Drug-inuced Liver Injury (DILI):	0.618
AMES Toxicity:	0.416
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.975
Carcinogencity:	0.795
Eye Corrosion:	0.005
Eye Irritation:	0.049
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC471546

Natural Product ID:	NPC471546
*Common Name:**	2,6-Dichloro-5-Fluoro-Nicotinic Acid (2R,4R,6R)-11-Oxo-2-Tridecyl-1,7-Dioxa-Dispiro[5.1.5.2]Pentadeca-9,12-Dien-4-Yl Ester
IUPAC Name:	[(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl] 2,6-dichloro-5-fluoropyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	HUXCOQYEBXUXMX-NCLPYWGKSA-N
Standard InCHI:	InChI=1S/C32H42Cl2FNO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-24-20-25(39-30(38)26-21-27(35)29(34)36-28(26)33)22-32(40-24)19-18-31(41-32)16-14-23(37)15-17-31/h14-17,21,24-25H,2-13,18-20,22H2,1H3/t24-,25-,32-/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(CC2(O1)CCC3(O2)C=CC(=O)C=C3)OC(=O)C4=CC(=C(N=C4Cl)Cl)F
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256112
PubChem CID:	24853744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives [CHEMONTID:0002414] Pyridinecarboxylic 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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	22.2	uM	PMID[531456]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	17.9	uM	PMID[531456]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	14.6	uM	PMID[531456]

☑ 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 NPC471546 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	342
0.1-0.2	1533
0.2-0.3	5866
0.3-0.4	14547
0.4-0.5	16614
0.5-0.6	3382
0.6-0.7	344
0.7-0.8	68
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7488	Intermediate Similarity	NPC472752
0.7427	Intermediate Similarity	NPC165837
0.738	Intermediate Similarity	NPC191310
0.7379	Intermediate Similarity	NPC280473
0.7379	Intermediate Similarity	NPC323551
0.7343	Intermediate Similarity	NPC51008
0.7343	Intermediate Similarity	NPC41724
0.7308	Intermediate Similarity	NPC264674
0.7295	Intermediate Similarity	NPC472553
0.7273	Intermediate Similarity	NPC193361
0.7273	Intermediate Similarity	NPC62844
0.7268	Intermediate Similarity	NPC470190
0.7255	Intermediate Similarity	NPC309498
0.725	Intermediate Similarity	NPC324245
0.725	Intermediate Similarity	NPC320748
0.7233	Intermediate Similarity	NPC48042
0.7233	Intermediate Similarity	NPC304179
0.7233	Intermediate Similarity	NPC472550
0.7228	Intermediate Similarity	NPC328559
0.7228	Intermediate Similarity	NPC32451
0.7225	Intermediate Similarity	NPC4421
0.7217	Intermediate Similarity	NPC477901
0.719	Intermediate Similarity	NPC207531
0.719	Intermediate Similarity	NPC470306
0.7183	Intermediate Similarity	NPC477903
0.7178	Intermediate Similarity	NPC79223
0.717	Intermediate Similarity	NPC472555
0.7163	Intermediate Similarity	NPC40919
0.7163	Intermediate Similarity	NPC470189
0.7156	Intermediate Similarity	NPC477908
0.7156	Intermediate Similarity	NPC206343
0.7156	Intermediate Similarity	NPC471014
0.7156	Intermediate Similarity	NPC471016
0.7156	Intermediate Similarity	NPC475408
0.7156	Intermediate Similarity	NPC6981
0.715	Intermediate Similarity	NPC235364
0.7143	Intermediate Similarity	NPC319128
0.7143	Intermediate Similarity	NPC228331
0.7129	Intermediate Similarity	NPC476467
0.7123	Intermediate Similarity	NPC294579
0.7123	Intermediate Similarity	NPC6576
0.7123	Intermediate Similarity	NPC212768
0.7123	Intermediate Similarity	NPC319556
0.7123	Intermediate Similarity	NPC144779
0.7123	Intermediate Similarity	NPC473115
0.7123	Intermediate Similarity	NPC62367
0.7123	Intermediate Similarity	NPC75600
0.7123	Intermediate Similarity	NPC158020
0.7123	Intermediate Similarity	NPC473089
0.7122	Intermediate Similarity	NPC289086
0.7114	Intermediate Similarity	NPC329024
0.7109	Intermediate Similarity	NPC42678
0.7109	Intermediate Similarity	NPC477909
0.7109	Intermediate Similarity	NPC477907
0.7109	Intermediate Similarity	NPC477910
0.7101	Intermediate Similarity	NPC63041
0.7089	Intermediate Similarity	NPC301368
0.7089	Intermediate Similarity	NPC84815
0.7089	Intermediate Similarity	NPC216428
0.7083	Intermediate Similarity	NPC477899
0.7083	Intermediate Similarity	NPC26881
0.7083	Intermediate Similarity	NPC477902
0.7083	Intermediate Similarity	NPC233727
0.7083	Intermediate Similarity	NPC477900
0.707	Intermediate Similarity	NPC477911
0.7053	Intermediate Similarity	NPC156044
0.7042	Intermediate Similarity	NPC187494
0.7023	Intermediate Similarity	NPC477912
0.7018	Intermediate Similarity	NPC124029
0.6995	Remote Similarity	NPC317672
0.6995	Remote Similarity	NPC59033
0.6991	Remote Similarity	NPC127026
0.6991	Remote Similarity	NPC127720
0.6991	Remote Similarity	NPC477788
0.6959	Remote Similarity	NPC471980
0.6959	Remote Similarity	NPC76565
0.6959	Remote Similarity	NPC57797
0.6959	Remote Similarity	NPC250807
0.6957	Remote Similarity	NPC107287
0.6957	Remote Similarity	NPC25442
0.6957	Remote Similarity	NPC12944
0.6955	Remote Similarity	NPC91125
0.6947	Remote Similarity	NPC470894
0.6941	Remote Similarity	NPC475601
0.6941	Remote Similarity	NPC211920
0.6927	Remote Similarity	NPC475137
0.6927	Remote Similarity	NPC473850
0.6927	Remote Similarity	NPC328154
0.6927	Remote Similarity	NPC475498
0.6923	Remote Similarity	NPC477906
0.6895	Remote Similarity	NPC473506
0.6895	Remote Similarity	NPC148860
0.6887	Remote Similarity	NPC111732
0.6864	Remote Similarity	NPC146824
0.6864	Remote Similarity	NPC228377
0.6864	Remote Similarity	NPC87152
0.6864	Remote Similarity	NPC475631
0.6864	Remote Similarity	NPC328186
0.6864	Remote Similarity	NPC14116
0.6864	Remote Similarity	NPC476110
0.6864	Remote Similarity	NPC477787
0.6864	Remote Similarity	NPC285411
0.6864	Remote Similarity	NPC122968
0.6864	Remote Similarity	NPC475600
0.6847	Remote Similarity	NPC150698
0.6847	Remote Similarity	NPC96801
0.6833	Remote Similarity	NPC134384
0.6833	Remote Similarity	NPC475362
0.6833	Remote Similarity	NPC311196
0.6833	Remote Similarity	NPC471977
0.6833	Remote Similarity	NPC470486
0.6833	Remote Similarity	NPC475644
0.6833	Remote Similarity	NPC471190
0.6822	Remote Similarity	NPC274842
0.6816	Remote Similarity	NPC469748
0.6816	Remote Similarity	NPC213143
0.681	Remote Similarity	NPC475835
0.6808	Remote Similarity	NPC244856
0.6792	Remote Similarity	NPC314834
0.6776	Remote Similarity	NPC236424
0.6776	Remote Similarity	NPC306644
0.6771	Remote Similarity	NPC475303
0.6771	Remote Similarity	NPC473689
0.6771	Remote Similarity	NPC292416
0.6771	Remote Similarity	NPC316841
0.6771	Remote Similarity	NPC475596
0.6769	Remote Similarity	NPC84347
0.6756	Remote Similarity	NPC327769
0.6756	Remote Similarity	NPC475426
0.6756	Remote Similarity	NPC35208
0.6741	Remote Similarity	NPC320324
0.6741	Remote Similarity	NPC30456
0.6741	Remote Similarity	NPC244839
0.6741	Remote Similarity	NPC319880
0.6739	Remote Similarity	NPC112741
0.6711	Remote Similarity	NPC238278
0.6711	Remote Similarity	NPC237702
0.6701	Remote Similarity	NPC249614
0.6683	Remote Similarity	NPC135950
0.6683	Remote Similarity	NPC44354
0.6682	Remote Similarity	NPC162812
0.6682	Remote Similarity	NPC314855
0.6682	Remote Similarity	NPC313345
0.6682	Remote Similarity	NPC315638
0.6682	Remote Similarity	NPC313796
0.6681	Remote Similarity	NPC170751
0.6681	Remote Similarity	NPC475406
0.6667	Remote Similarity	NPC317010
0.6667	Remote Similarity	NPC317572
0.6652	Remote Similarity	NPC38959
0.6652	Remote Similarity	NPC327904
0.6651	Remote Similarity	NPC292517
0.6651	Remote Similarity	NPC315545
0.6651	Remote Similarity	NPC314297
0.6638	Remote Similarity	NPC253482
0.6635	Remote Similarity	NPC123395
0.6635	Remote Similarity	NPC103361
0.6634	Remote Similarity	NPC103230
0.6603	Remote Similarity	NPC470279
0.657	Remote Similarity	NPC109922
0.656	Remote Similarity	NPC30570
0.6552	Remote Similarity	NPC475648
0.6496	Remote Similarity	NPC475533
0.6493	Remote Similarity	NPC155792
0.6479	Remote Similarity	NPC314648
0.6473	Remote Similarity	NPC192306
0.6468	Remote Similarity	NPC324619
0.6468	Remote Similarity	NPC475315
0.6453	Remote Similarity	NPC471013
0.6453	Remote Similarity	NPC180668
0.6453	Remote Similarity	NPC148896
0.6398	Remote Similarity	NPC159630
0.6398	Remote Similarity	NPC230085
0.639	Remote Similarity	NPC325775
0.639	Remote Similarity	NPC328798
0.6389	Remote Similarity	NPC470280
0.6387	Remote Similarity	NPC263455
0.6364	Remote Similarity	NPC57453
0.6355	Remote Similarity	NPC327373
0.6351	Remote Similarity	NPC102008
0.6345	Remote Similarity	NPC10904
0.6341	Remote Similarity	NPC194040
0.6326	Remote Similarity	NPC132539
0.6324	Remote Similarity	NPC320394
0.631	Remote Similarity	NPC471323
0.6307	Remote Similarity	NPC326930
0.6307	Remote Similarity	NPC53255
0.6307	Remote Similarity	NPC85879
0.6307	Remote Similarity	NPC475301
0.6293	Remote Similarity	NPC282103
0.6287	Remote Similarity	NPC164340
0.6281	Remote Similarity	NPC13603
0.6278	Remote Similarity	NPC82070
0.6277	Remote Similarity	NPC167400
0.6273	Remote Similarity	NPC318299
0.6266	Remote Similarity	NPC471015
0.6262	Remote Similarity	NPC90415
0.6262	Remote Similarity	NPC160381
0.6255	Remote Similarity	NPC476514
0.625	Remote Similarity	NPC52254

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 NPC471546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	585
0.2-0.3	781
0.3-0.4	2035
0.4-0.5	4057
0.5-0.6	1356
0.6-0.7	108
0.7-0.8	2
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
0.75	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7396	Approved
0.6995	Remote Similarity	NPD6641	Approved
0.6995	Remote Similarity	NPD6642	Approved
0.6957	Remote Similarity	NPD2831	Approved
0.6935	Remote Similarity	NPD820	Phase 3
0.6825	Remote Similarity	NPD4506	Discontinued
0.6739	Remote Similarity	NPD9271	Approved
0.6714	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6770	Approved
0.6591	Remote Similarity	NPD3280	Approved
0.6587	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8468	Phase 2
0.6553	Remote Similarity	NPD4528	Approved
0.6553	Remote Similarity	NPD4526	Approved
0.6553	Remote Similarity	NPD4529	Approved
0.6548	Remote Similarity	NPD1586	Approved
0.6498	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4301	Approved
0.6479	Remote Similarity	NPD3947	Discontinued
0.645	Remote Similarity	NPD1587	Approved
0.6447	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7878	Phase 2
0.6416	Remote Similarity	NPD3259	Approved
0.6413	Remote Similarity	NPD107	Approved
0.6393	Remote Similarity	NPD3795	Approved
0.6393	Remote Similarity	NPD3794	Approved
0.6389	Remote Similarity	NPD2510	Approved
0.6389	Remote Similarity	NPD2509	Approved
0.6364	Remote Similarity	NPD3257	Approved
0.6364	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1926	Approved
0.6351	Remote Similarity	NPD7777	Approved
0.6351	Remote Similarity	NPD53	Approved
0.6351	Remote Similarity	NPD7778	Approved
0.6335	Remote Similarity	NPD3389	Approved
0.6335	Remote Similarity	NPD3394	Approved
0.6335	Remote Similarity	NPD3393	Approved
0.6323	Remote Similarity	NPD3258	Approved
0.6301	Remote Similarity	NPD4417	Approved
0.6301	Remote Similarity	NPD5475	Discontinued
0.629	Remote Similarity	NPD1638	Discovery
0.6279	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD9074	Approved
0.6277	Remote Similarity	NPD9075	Approved
0.6276	Remote Similarity	NPD5088	Discontinued
0.6272	Remote Similarity	NPD4328	Approved
0.6267	Remote Similarity	NPD3371	Approved
0.625	Remote Similarity	NPD2564	Approved
0.625	Remote Similarity	NPD2076	Approved
0.625	Remote Similarity	NPD2077	Approved
0.625	Remote Similarity	NPD2565	Phase 2
0.625	Remote Similarity	NPD4524	Discontinued
0.6234	Remote Similarity	NPD8102	Discontinued
0.6216	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD1630	Approved
0.6204	Remote Similarity	NPD6176	Phase 1
0.619	Remote Similarity	NPD4315	Phase 2
0.619	Remote Similarity	NPD6962	Phase 2
0.6188	Remote Similarity	NPD8160	Phase 2
0.6184	Remote Similarity	NPD3925	Approved
0.6183	Remote Similarity	NPD7611	Approved
0.6178	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8326	Phase 3
0.6161	Remote Similarity	NPD8325	Phase 3
0.6161	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4948	Discontinued
0.6154	Remote Similarity	NPD5891	Approved
0.615	Remote Similarity	NPD5003	Discontinued
0.6147	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4500	Approved
0.614	Remote Similarity	NPD4501	Approved
0.6132	Remote Similarity	NPD8463	Approved
0.6127	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4334	Discontinued
0.6119	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1631	Approved
0.6109	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD3315	Phase 3
0.6103	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD8063	Discontinued
0.6094	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6182	Approved
0.6089	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD43	Approved
0.6081	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6079	Remote Similarity	NPD8479	Phase 2
0.6076	Remote Similarity	NPD7885	Phase 2
0.6076	Remote Similarity	NPD7886	Phase 2
0.6075	Remote Similarity	NPD1229	Phase 2
0.6073	Remote Similarity	NPD7010	Phase 3
0.6071	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6529	Discontinued
0.6061	Remote Similarity	NPD7994	Phase 2
0.6059	Remote Similarity	NPD5805	Approved
0.6048	Remote Similarity	NPD7234	Approved
0.6048	Remote Similarity	NPD7233	Approved
0.6048	Remote Similarity	NPD1657	Approved
0.604	Remote Similarity	NPD5450	Discontinued
0.6038	Remote Similarity	NPD4376	Phase 3
0.6035	Remote Similarity	NPD7404	Approved
0.6035	Remote Similarity	NPD6974	Phase 3
0.6033	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5471	Phase 3
0.6028	Remote Similarity	NPD6550	Discontinued
0.6028	Remote Similarity	NPD2307	Discontinued
0.6027	Remote Similarity	NPD944	Approved
0.6019	Remote Similarity	NPD1643	Phase 3
0.6017	Remote Similarity	NPD3006	Discontinued
0.6009	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD5416	Discontinued
0.6	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD2911	Approved
0.5991	Remote Similarity	NPD2912	Approved
0.5991	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD1867	Approved
0.5983	Remote Similarity	NPD7576	Discontinued
0.5982	Remote Similarity	NPD5866	Approved
0.597	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD4369	Phase 2
0.5965	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD5420	Discontinued
0.5963	Remote Similarity	NPD7933	Approved
0.5963	Remote Similarity	NPD7931	Approved
0.5963	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7934	Discovery
0.5957	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD5411	Discontinued
0.5952	Remote Similarity	NPD5444	Phase 1
0.595	Remote Similarity	NPD6635	Approved
0.5946	Remote Similarity	NPD7232	Discontinued
0.5942	Remote Similarity	NPD5898	Approved
0.5942	Remote Similarity	NPD5899	Approved
0.5942	Remote Similarity	NPD5897	Approved
0.594	Remote Similarity	NPD4952	Phase 3
0.5939	Remote Similarity	NPD1996	Discontinued
0.5939	Remote Similarity	NPD7180	Phase 3
0.5936	Remote Similarity	NPD2567	Approved
0.5936	Remote Similarity	NPD2569	Approved
0.5935	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5293	Phase 2
0.5924	Remote Similarity	NPD4368	Phase 2
0.5915	Remote Similarity	NPD7688	Phase 1
0.5915	Remote Similarity	NPD2336	Approved
0.5913	Remote Similarity	NPD6298	Discontinued
0.5911	Remote Similarity	NPD1573	Approved
0.5911	Remote Similarity	NPD1575	Approved
0.5909	Remote Similarity	NPD2920	Discontinued
0.5909	Remote Similarity	NPD5513	Phase 2
0.5909	Remote Similarity	NPD2582	Approved
0.5909	Remote Similarity	NPD2581	Approved
0.5907	Remote Similarity	NPD4427	Phase 2
0.5907	Remote Similarity	NPD1340	Discontinued
0.5903	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6727	Phase 2
0.5899	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD6716	Phase 1
0.5891	Remote Similarity	NPD3217	Phase 2
0.589	Remote Similarity	NPD7031	Phase 1
0.5885	Remote Similarity	NPD3243	Approved
0.5882	Remote Similarity	NPD7853	Phase 2
0.5882	Remote Similarity	NPD3379	Phase 2
0.5882	Remote Similarity	NPD3380	Phase 3
0.5882	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.588	Remote Similarity	NPD7708	Approved
0.588	Remote Similarity	NPD5512	Phase 3
0.588	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1270	Approved
0.5874	Remote Similarity	NPD6486	Approved
0.5874	Remote Similarity	NPD6487	Approved
0.5872	Remote Similarity	NPD2778	Approved
0.5872	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3425	Discontinued
0.5867	Remote Similarity	NPD4911	Discontinued
0.5865	Remote Similarity	NPD4373	Phase 2
0.5865	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD2034	Discontinued
0.5862	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD2836	Approved
0.5859	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD721	Approved
0.5857	Remote Similarity	NPD4484	Phase 1
0.5856	Remote Similarity	NPD2317	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5632	Approved
0.5851	Remote Similarity	NPD6790	Phase 1
0.5851	Remote Similarity	NPD2670	Approved
0.585	Remote Similarity	NPD7803	Approved
0.5845	Remote Similarity	NPD5751	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