NPASS Compound

Structure

NPC86809 OpenBabel07101718292D 46 51 0 0 1 0 0 0 0 0999 V2000 -7.5001 6.2547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3334 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3335 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8333 -1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1667 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0001 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 6.2547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6668 5.7736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 0.4811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3334 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0001 5.7736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6667 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0001 2.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8333 0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1667 3.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8333 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0001 4.8113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 2.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1667 4.3302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6668 4.8113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6667 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5001 3.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 -1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 4.3302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8333 0.4811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1667 6.2547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6667 2.8868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 3.3679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 2.8868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 4.8113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5001 4.3302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6667 -0.9623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3335 3.8491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6667 -1.9245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5001 2.4057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 3.3679 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 3 43 1 0 0 0 0 4 44 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 1 1 6 0 0 0 11 27 1 0 0 0 0 12 2 1 1 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 21 2 0 0 0 0 15 33 1 0 0 0 0 16 22 2 0 0 0 0 16 34 1 0 0 0 0 17 19 2 0 0 0 0 17 45 1 0 0 0 0 18 20 2 0 0 0 0 18 46 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 37 2 0 0 0 0 26 38 2 0 0 0 0 27 31 1 1 0 0 0 27 39 1 0 0 0 0 28 32 1 6 0 0 0 28 40 1 0 0 0 0 29 41 2 0 0 0 0 29 43 1 0 0 0 0 30 42 2 0 0 0 0 30 44 1 0 0 0 0 31 29 1 1 0 0 0 31 45 1 0 0 0 0 32 30 1 6 0 0 0 32 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.16
Volume:	602.115
LogP:	2.43
LogD:	0.963
LogS:	-3.759
# Rotatable Bonds:	5
TPSA:	220.26
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	5.406
Fsp3:	0.438
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:	-6.034
MDCK Permeability:	2.1512325474759564e-05
Pgp-inhibitor:	0.473
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.173
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.687

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	90.02738189697266%
Volume Distribution (VD):	0.612
Pgp-substrate:	3.3108041286468506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.734
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	10.215
Half-life (T1/2):	0.016

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.859
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.252
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC86809

Natural Product ID:	NPC86809
*Common Name:**	Secalonic Acid A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DRYDKQOPVBDZMQ-ZKHWAINJSA-N
Standard InCHI:	InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,33-36,39-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m1/s1
SMILES:	COC(=O)[C@@]12Oc3ccc(c(c3C(=O)C2=C(C[C@H]([C@@H]1O)C)O)O)c1ccc2c(c1O)C(=O)C1=C(O)C[C@H]([C@@H]([C@]1(O2)C(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500027
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO20214	Ruprechtia tangarana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932125]
NPO40075	Clohesyomyces sp.	Species	Lindgomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27964996]
NPO20214	Ruprechtia tangarana	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
ED50	1
IC50	2
MIC	7
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	4
NON-MOLECULAR	5
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.5	ug ml-1	PMID[509483]
NPT1323	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A)	Inhibition	=	64.5	%	PMID[509484]
NPT1323	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A)	Inhibition	=	39.1	%	PMID[509484]
NPT1323	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A)	IC50	=	28600.0	nM	PMID[509484]
NPT1323	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A)	TIME	=	1.117	hr	PMID[509484]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.0	ug.mL-1	PMID[509483]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	32.0	ug.mL-1	PMID[509483]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	75.0	ug.mL-1	PMID[509485]
NPT2	Others	Unspecified		IC50	=	1400000.0	nM	PMID[509485]

☑ 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 NPC86809 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	372
0.1-0.2	1495
0.2-0.3	3395
0.3-0.4	8043
0.4-0.5	10382
0.5-0.6	4506
0.6-0.7	6028
0.7-0.8	6628
0.8-0.85	1626
0.85-0.9	191
0.9-0.95	18
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98667
1.0	High Similarity	NPC232412
0.9939	High Similarity	NPC469345
0.9693	High Similarity	NPC251144
0.9693	High Similarity	NPC241387
0.9639	High Similarity	NPC477682
0.9639	High Similarity	NPC477683
0.9512	High Similarity	NPC297195
0.9512	High Similarity	NPC207574
0.9512	High Similarity	NPC291795
0.9357	High Similarity	NPC197972
0.9341	High Similarity	NPC154986
0.9253	High Similarity	NPC48474
0.9157	High Similarity	NPC178173
0.8994	High Similarity	NPC241874
0.8947	High Similarity	NPC294149
0.8941	High Similarity	NPC472620
0.8935	High Similarity	NPC217378
0.8895	High Similarity	NPC324220
0.8895	High Similarity	NPC312630
0.8862	High Similarity	NPC473961
0.8851	High Similarity	NPC208069
0.8824	High Similarity	NPC472619
0.8788	High Similarity	NPC146636
0.8779	High Similarity	NPC476139
0.8779	High Similarity	NPC469393
0.8772	High Similarity	NPC193698
0.8764	High Similarity	NPC314672
0.875	High Similarity	NPC106700
0.875	High Similarity	NPC472059
0.8736	High Similarity	NPC476199
0.8736	High Similarity	NPC476210
0.8713	High Similarity	NPC54903
0.8713	High Similarity	NPC473096
0.8713	High Similarity	NPC177480
0.8713	High Similarity	NPC286074
0.8713	High Similarity	NPC326877
0.8713	High Similarity	NPC473095
0.8698	High Similarity	NPC472053
0.8698	High Similarity	NPC63438
0.8683	High Similarity	NPC125969
0.8683	High Similarity	NPC186113
0.8675	High Similarity	NPC20530
0.8675	High Similarity	NPC10754
0.8675	High Similarity	NPC215917
0.8675	High Similarity	NPC164427
0.8674	High Similarity	NPC282474
0.8674	High Similarity	NPC470198
0.8674	High Similarity	NPC316274
0.8674	High Similarity	NPC470193
0.8674	High Similarity	NPC470196
0.8674	High Similarity	NPC470200
0.8674	High Similarity	NPC470194
0.8674	High Similarity	NPC470197
0.8674	High Similarity	NPC470195
0.8671	High Similarity	NPC476152
0.8671	High Similarity	NPC476229
0.8671	High Similarity	NPC476311
0.8663	High Similarity	NPC74559
0.8659	High Similarity	NPC207346
0.8659	High Similarity	NPC46564
0.8655	High Similarity	NPC225419
0.8655	High Similarity	NPC473094
0.8655	High Similarity	NPC472622
0.8655	High Similarity	NPC292233
0.8652	High Similarity	NPC282636
0.8652	High Similarity	NPC294863
0.8647	High Similarity	NPC472057
0.8647	High Similarity	NPC472051
0.8639	High Similarity	NPC473022
0.8636	High Similarity	NPC475161
0.8636	High Similarity	NPC477860
0.8631	High Similarity	NPC471976
0.8621	High Similarity	NPC162248
0.8614	High Similarity	NPC111341
0.8614	High Similarity	NPC48579
0.8614	High Similarity	NPC304207
0.8614	High Similarity	NPC476169
0.8614	High Similarity	NPC207809
0.8614	High Similarity	NPC259710
0.8614	High Similarity	NPC217706
0.8614	High Similarity	NPC237560
0.8614	High Similarity	NPC304745
0.8613	High Similarity	NPC473113
0.8613	High Similarity	NPC477529
0.8613	High Similarity	NPC476159
0.8606	High Similarity	NPC210597
0.8606	High Similarity	NPC217149
0.8606	High Similarity	NPC216035
0.8606	High Similarity	NPC475790
0.8605	High Similarity	NPC102810
0.8605	High Similarity	NPC5319
0.8605	High Similarity	NPC476216
0.8596	High Similarity	NPC120857
0.8596	High Similarity	NPC17274
0.8596	High Similarity	NPC85047
0.8596	High Similarity	NPC469394
0.8596	High Similarity	NPC472621
0.8589	High Similarity	NPC191634
0.8588	High Similarity	NPC475148
0.8588	High Similarity	NPC475656
0.858	High Similarity	NPC476929
0.858	High Similarity	NPC473607
0.858	High Similarity	NPC3629
0.858	High Similarity	NPC84494
0.858	High Similarity	NPC245059
0.858	High Similarity	NPC97812
0.858	High Similarity	NPC244903
0.8571	High Similarity	NPC475246
0.8564	High Similarity	NPC470199
0.8564	High Similarity	NPC314459
0.8563	High Similarity	NPC470336
0.8563	High Similarity	NPC470335
0.8555	High Similarity	NPC313304
0.8555	High Similarity	NPC103307
0.8554	High Similarity	NPC311579
0.8554	High Similarity	NPC268193
0.8554	High Similarity	NPC326592
0.8554	High Similarity	NPC248793
0.8554	High Similarity	NPC109594
0.8554	High Similarity	NPC112701
0.8554	High Similarity	NPC180301
0.8554	High Similarity	NPC203080
0.8554	High Similarity	NPC236756
0.8554	High Similarity	NPC209760
0.8554	High Similarity	NPC100134
0.8547	High Similarity	NPC470341
0.8547	High Similarity	NPC324522
0.8547	High Similarity	NPC472058
0.8547	High Similarity	NPC105414
0.8547	High Similarity	NPC8965
0.8547	High Similarity	NPC234497
0.8545	High Similarity	NPC295650
0.8545	High Similarity	NPC254412
0.8545	High Similarity	NPC474023
0.8545	High Similarity	NPC262039
0.8545	High Similarity	NPC278476
0.8545	High Similarity	NPC319910
0.8545	High Similarity	NPC474021
0.8545	High Similarity	NPC262038
0.8539	High Similarity	NPC75574
0.8538	High Similarity	NPC62261
0.8533	High Similarity	NPC131405
0.8531	High Similarity	NPC470452
0.8531	High Similarity	NPC164047
0.8531	High Similarity	NPC470453
0.8531	High Similarity	NPC470448
0.8529	High Similarity	NPC259834
0.8529	High Similarity	NPC472402
0.8523	High Similarity	NPC233978
0.8523	High Similarity	NPC470334
0.8521	High Similarity	NPC472055
0.8514	High Similarity	NPC68381
0.8514	High Similarity	NPC63105
0.8514	High Similarity	NPC199533
0.8514	High Similarity	NPC3718
0.8514	High Similarity	NPC470454
0.8512	High Similarity	NPC246466
0.8506	High Similarity	NPC271848
0.8506	High Similarity	NPC212038
0.8506	High Similarity	NPC262580
0.8506	High Similarity	NPC289396
0.8506	High Similarity	NPC118128
0.8506	High Similarity	NPC257667
0.8506	High Similarity	NPC472454
0.8506	High Similarity	NPC315619
0.8506	High Similarity	NPC121333
0.8506	High Similarity	NPC186847
0.8506	High Similarity	NPC91650
0.8506	High Similarity	NPC81332
0.8503	High Similarity	NPC326910
0.8503	High Similarity	NPC477958
0.8503	High Similarity	NPC471116
0.8497	Intermediate Similarity	NPC20734
0.8497	Intermediate Similarity	NPC246274
0.8497	Intermediate Similarity	NPC41598
0.8497	Intermediate Similarity	NPC476146
0.8497	Intermediate Similarity	NPC75141
0.8497	Intermediate Similarity	NPC55422
0.8497	Intermediate Similarity	NPC40089
0.8497	Intermediate Similarity	NPC158329
0.8497	Intermediate Similarity	NPC47634
0.8497	Intermediate Similarity	NPC242395
0.8494	Intermediate Similarity	NPC56232
0.8494	Intermediate Similarity	NPC244583
0.8494	Intermediate Similarity	NPC321363
0.8494	Intermediate Similarity	NPC253904
0.8494	Intermediate Similarity	NPC150123
0.8494	Intermediate Similarity	NPC275878
0.8494	Intermediate Similarity	NPC10807
0.8494	Intermediate Similarity	NPC138288
0.8494	Intermediate Similarity	NPC171651
0.8494	Intermediate Similarity	NPC243171
0.8494	Intermediate Similarity	NPC35567
0.8494	Intermediate Similarity	NPC161881
0.8492	Intermediate Similarity	NPC87583
0.8488	Intermediate Similarity	NPC476255
0.8488	Intermediate Similarity	NPC120593
0.8488	Intermediate Similarity	NPC471213
0.8488	Intermediate Similarity	NPC207575

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 NPC86809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	933
0.2-0.3	1852
0.3-0.4	2557
0.4-0.5	1932
0.5-0.6	994
0.6-0.7	384
0.7-0.8	154
0.8-0.85	19
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD7075	Discontinued
0.8605	High Similarity	NPD7804	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6801	Discontinued
0.8444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD5402	Approved
0.8363	Intermediate Similarity	NPD6959	Discontinued
0.8324	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6166	Phase 2
0.8324	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD4380	Phase 2
0.8225	Intermediate Similarity	NPD7819	Suspended
0.8202	Intermediate Similarity	NPD7808	Phase 3
0.8202	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5403	Approved
0.8192	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8156	Intermediate Similarity	NPD8313	Approved
0.8156	Intermediate Similarity	NPD8312	Approved
0.8146	Intermediate Similarity	NPD7251	Discontinued
0.8146	Intermediate Similarity	NPD6559	Discontinued
0.8122	Intermediate Similarity	NPD8150	Discontinued
0.8118	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6232	Discontinued
0.809	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5844	Phase 1
0.8072	Intermediate Similarity	NPD5401	Approved
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3817	Phase 2
0.8047	Intermediate Similarity	NPD6599	Discontinued
0.8034	Intermediate Similarity	NPD7074	Phase 3
0.8023	Intermediate Similarity	NPD7768	Phase 2
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.8022	Intermediate Similarity	NPD8434	Phase 2
0.8012	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.7989	Intermediate Similarity	NPD5494	Approved
0.7978	Intermediate Similarity	NPD7054	Approved
0.7953	Intermediate Similarity	NPD1934	Approved
0.7935	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7472	Approved
0.7919	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD7435	Discontinued
0.7831	Intermediate Similarity	NPD3750	Approved
0.7816	Intermediate Similarity	NPD3882	Suspended
0.7803	Intermediate Similarity	NPD1465	Phase 2
0.7803	Intermediate Similarity	NPD2801	Approved
0.7797	Intermediate Similarity	NPD3787	Discontinued
0.7771	Intermediate Similarity	NPD3749	Approved
0.7758	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7874	Approved
0.7751	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD6777	Approved
0.7749	Intermediate Similarity	NPD6780	Approved
0.7749	Intermediate Similarity	NPD6782	Approved
0.7749	Intermediate Similarity	NPD6776	Approved
0.7749	Intermediate Similarity	NPD6778	Approved
0.7749	Intermediate Similarity	NPD6781	Approved
0.7749	Intermediate Similarity	NPD6779	Approved
0.7722	Intermediate Similarity	NPD3818	Discontinued
0.772	Intermediate Similarity	NPD7698	Approved
0.772	Intermediate Similarity	NPD7697	Approved
0.772	Intermediate Similarity	NPD7696	Phase 3
0.7716	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7783	Phase 2
0.7711	Intermediate Similarity	NPD1549	Phase 2
0.7704	Intermediate Similarity	NPD8151	Discontinued
0.7701	Intermediate Similarity	NPD8455	Phase 2
0.768	Intermediate Similarity	NPD8320	Phase 1
0.768	Intermediate Similarity	NPD8319	Approved
0.7676	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3226	Approved
0.7653	Intermediate Similarity	NPD7701	Phase 2
0.7647	Intermediate Similarity	NPD2534	Approved
0.7647	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD2532	Approved
0.7624	Intermediate Similarity	NPD7228	Approved
0.7602	Intermediate Similarity	NPD1512	Approved
0.7592	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7871	Phase 2
0.759	Intermediate Similarity	NPD7870	Phase 2
0.759	Intermediate Similarity	NPD2935	Discontinued
0.7572	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7699	Phase 2
0.7552	Intermediate Similarity	NPD7700	Phase 2
0.7545	Intermediate Similarity	NPD2346	Discontinued
0.7538	Intermediate Similarity	NPD7801	Approved
0.753	Intermediate Similarity	NPD2799	Discontinued
0.753	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7485	Intermediate Similarity	NPD2796	Approved
0.7485	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7457	Intermediate Similarity	NPD920	Approved
0.7456	Intermediate Similarity	NPD2800	Approved
0.7443	Intermediate Similarity	NPD37	Approved
0.743	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD919	Approved
0.743	Intermediate Similarity	NPD6234	Discontinued
0.7425	Intermediate Similarity	NPD1510	Phase 2
0.7416	Intermediate Similarity	NPD4967	Phase 2
0.7416	Intermediate Similarity	NPD4966	Approved
0.7416	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5953	Discontinued
0.7398	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7379	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5124	Phase 1
0.7348	Intermediate Similarity	NPD1247	Approved
0.7341	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1607	Approved
0.7297	Intermediate Similarity	NPD7286	Phase 2
0.7289	Intermediate Similarity	NPD1240	Approved
0.7288	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD7240	Approved
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7268	Intermediate Similarity	NPD3926	Phase 2
0.7268	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6233	Phase 2
0.7228	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5711	Approved
0.7213	Intermediate Similarity	NPD5710	Approved
0.7209	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD6651	Approved
0.7176	Intermediate Similarity	NPD6100	Approved
0.7176	Intermediate Similarity	NPD6099	Approved
0.7175	Intermediate Similarity	NPD7458	Discontinued
0.7169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7158	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7151	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4360	Phase 2
0.7128	Intermediate Similarity	NPD4363	Phase 3
0.7126	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4625	Phase 3
0.7102	Intermediate Similarity	NPD6273	Approved
0.709	Intermediate Similarity	NPD7685	Pre-registration
0.7083	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1613	Approved
0.7079	Intermediate Similarity	NPD7584	Approved
0.7076	Intermediate Similarity	NPD5408	Approved
0.7076	Intermediate Similarity	NPD5405	Approved
0.7076	Intermediate Similarity	NPD5406	Approved
0.7076	Intermediate Similarity	NPD5404	Approved
0.7071	Intermediate Similarity	NPD8285	Discontinued
0.7065	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7045	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2403	Approved
0.7035	Intermediate Similarity	NPD5762	Approved
0.7035	Intermediate Similarity	NPD2344	Approved
0.7035	Intermediate Similarity	NPD5763	Approved
0.7022	Intermediate Similarity	NPD1653	Approved
0.7019	Intermediate Similarity	NPD8404	Phase 2
0.7018	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD2424	Discontinued
0.699	Remote Similarity	NPD6213	Phase 3
0.699	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6212	Phase 3
0.6981	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4288	Approved
0.6977	Remote Similarity	NPD2438	Suspended
0.697	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD2797	Approved
0.6968	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7907	Approved
0.6967	Remote Similarity	NPD8366	Approved
0.6964	Remote Similarity	NPD3268	Approved
0.6964	Remote Similarity	NPD7985	Registered
0.6964	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1652	Phase 2
0.695	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8067	Phase 3
0.6941	Remote Similarity	NPD447	Suspended
0.6933	Remote Similarity	NPD1610	Phase 2

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