NPASS Compound

Structure

NPC469345 OpenBabel07101718302D 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 1 0 0 0 0 0 0 0 0 0 2.5000 0.4811 0.0000 C 0 0 1 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 3 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 2 0 0 0 0 0 0 0 0 0 1.6667 0.0000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 0.8333 0.4811 0.0000 C 0 0 1 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 1 0 0 0 11 27 1 0 0 0 0 12 2 1 6 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 1 0 0 0 0 26 38 2 0 0 0 0 27 31 1 6 0 0 0 27 39 1 0 0 0 0 28 32 1 1 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 6 0 0 0 31 45 1 0 0 0 0 32 30 1 1 0 0 0 32 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	884.48
Volume:	856.665
LogP:	2.673
LogD:	1.396
LogS:	-3.684
# Rotatable Bonds:	7
TPSA:	255.91
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	6.836
Fsp3:	0.956
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.94
MDCK Permeability:	0.00020781232160516083
Pgp-inhibitor:	0.52
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.87

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	72.69743347167969%
Volume Distribution (VD):	0.124
Pgp-substrate:	6.595242977142334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	0.621
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.747
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.944
Carcinogencity:	0.327
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC469345

Natural Product ID:	NPC469345
*Common Name:**	Secalonic Acid D
IUPAC Name:	n.a.
Synonyms:	Secalonic Acid D
Standard InCHIKey:	IODWZVMVQOCZTC-NHBPCGONSA-N
Standard InCHI:	InChI=1S/C32H32O14/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/h5-8,11-12,25,27-28,33-37,39-40H,9-10H2,1-4H3/t11-,12-,25?,27+,28+,31+,32+/m0/s1
SMILES:	COC(=O)[C@]12Oc3ccc(c(c3C(C2=C(C[C@@H]([C@H]1O)C)O)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:	CHEMBL1075971
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
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919064]
NPO13590	Diploicia canescens	Species	Caliciaceae	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	2
MIC	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	280.0	nM	PMID[464265]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	3700.0	nM	PMID[464265]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	>	100.0	ug.mL-1	PMID[464266]

☑ 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 NPC469345 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
0.9939	High Similarity	NPC232412
0.9939	High Similarity	NPC98667
0.9939	High Similarity	NPC86809
0.9755	High Similarity	NPC251144
0.9755	High Similarity	NPC241387
0.9581	High Similarity	NPC477682
0.9581	High Similarity	NPC477683
0.9573	High Similarity	NPC297195
0.9573	High Similarity	NPC291795
0.9573	High Similarity	NPC207574
0.931	High Similarity	NPC48474
0.9302	High Similarity	NPC197972
0.9286	High Similarity	NPC154986
0.9102	High Similarity	NPC178173
0.9006	High Similarity	NPC294149
0.8941	High Similarity	NPC241874
0.8908	High Similarity	NPC208069
0.8889	High Similarity	NPC472620
0.8882	High Similarity	NPC217378
0.8844	High Similarity	NPC312630
0.8844	High Similarity	NPC324220
0.8837	High Similarity	NPC469393
0.8837	High Similarity	NPC476139
0.883	High Similarity	NPC193698
0.882	High Similarity	NPC314672
0.881	High Similarity	NPC473961
0.8807	High Similarity	NPC106700
0.8793	High Similarity	NPC476199
0.8793	High Similarity	NPC476210
0.8772	High Similarity	NPC54903
0.8772	High Similarity	NPC286074
0.8772	High Similarity	NPC472619
0.8735	High Similarity	NPC20530
0.8735	High Similarity	NPC146636
0.8735	High Similarity	NPC215917
0.8735	High Similarity	NPC10754
0.8729	High Similarity	NPC470195
0.8729	High Similarity	NPC470196
0.8729	High Similarity	NPC470200
0.8729	High Similarity	NPC470194
0.8729	High Similarity	NPC470197
0.8729	High Similarity	NPC316274
0.8729	High Similarity	NPC282474
0.8729	High Similarity	NPC470198
0.8729	High Similarity	NPC470193
0.8728	High Similarity	NPC476311
0.8728	High Similarity	NPC476229
0.8728	High Similarity	NPC476152
0.8713	High Similarity	NPC472622
0.8708	High Similarity	NPC282636
0.8708	High Similarity	NPC294863
0.8698	High Similarity	NPC472059
0.8693	High Similarity	NPC475161
0.8693	High Similarity	NPC477860
0.8678	High Similarity	NPC162248
0.8671	High Similarity	NPC477529
0.8671	High Similarity	NPC476159
0.8663	High Similarity	NPC102810
0.8663	High Similarity	NPC473096
0.8663	High Similarity	NPC5319
0.8663	High Similarity	NPC326877
0.8663	High Similarity	NPC177480
0.8663	High Similarity	NPC476216
0.8663	High Similarity	NPC473095
0.8655	High Similarity	NPC85047
0.8655	High Similarity	NPC17274
0.8655	High Similarity	NPC469394
0.8655	High Similarity	NPC472621
0.8655	High Similarity	NPC120857
0.8647	High Similarity	NPC63438
0.8647	High Similarity	NPC472053
0.8644	High Similarity	NPC475656
0.8644	High Similarity	NPC475148
0.8639	High Similarity	NPC3629
0.8636	High Similarity	NPC84494
0.8636	High Similarity	NPC245059
0.8636	High Similarity	NPC473607
0.8631	High Similarity	NPC186113
0.8631	High Similarity	NPC125969
0.8623	High Similarity	NPC164427
0.8619	High Similarity	NPC314459
0.8619	High Similarity	NPC470199
0.8614	High Similarity	NPC209760
0.8614	High Similarity	NPC100134
0.8613	High Similarity	NPC74559
0.8606	High Similarity	NPC207346
0.8606	High Similarity	NPC46564
0.8605	High Similarity	NPC225419
0.8605	High Similarity	NPC292233
0.8605	High Similarity	NPC473094
0.8596	High Similarity	NPC75574
0.8596	High Similarity	NPC472057
0.8596	High Similarity	NPC472051
0.8588	High Similarity	NPC470452
0.8588	High Similarity	NPC470453
0.8588	High Similarity	NPC470448
0.8588	High Similarity	NPC473022
0.8588	High Similarity	NPC164047
0.8587	High Similarity	NPC131405
0.858	High Similarity	NPC233978
0.858	High Similarity	NPC471976
0.8571	High Similarity	NPC63105
0.8563	High Similarity	NPC237560
0.8563	High Similarity	NPC473113
0.8563	High Similarity	NPC217706
0.8563	High Similarity	NPC48579
0.8563	High Similarity	NPC118128
0.8563	High Similarity	NPC259710
0.8563	High Similarity	NPC207809
0.8563	High Similarity	NPC315619
0.8563	High Similarity	NPC477958
0.8563	High Similarity	NPC111341
0.8563	High Similarity	NPC304207
0.8563	High Similarity	NPC476169
0.8563	High Similarity	NPC304745
0.8555	High Similarity	NPC476146
0.8555	High Similarity	NPC158329
0.8555	High Similarity	NPC75141
0.8555	High Similarity	NPC41598
0.8555	High Similarity	NPC20734
0.8555	High Similarity	NPC246274
0.8555	High Similarity	NPC40089
0.8555	High Similarity	NPC55422
0.8555	High Similarity	NPC47634
0.8554	High Similarity	NPC475790
0.8554	High Similarity	NPC217149
0.8554	High Similarity	NPC216035
0.8554	High Similarity	NPC210597
0.8554	High Similarity	NPC138288
0.8547	High Similarity	NPC471213
0.8547	High Similarity	NPC62444
0.8547	High Similarity	NPC87583
0.8547	High Similarity	NPC476255
0.8538	High Similarity	NPC469395
0.8537	High Similarity	NPC191634
0.8531	High Similarity	NPC244903
0.8531	High Similarity	NPC473729
0.8529	High Similarity	NPC97812
0.8529	High Similarity	NPC476929
0.8523	High Similarity	NPC475246
0.8523	High Similarity	NPC46958
0.8523	High Similarity	NPC98943
0.8521	High Similarity	NPC474373
0.8514	High Similarity	NPC213052
0.8514	High Similarity	NPC470335
0.8514	High Similarity	NPC73899
0.8514	High Similarity	NPC17105
0.8514	High Similarity	NPC474276
0.8514	High Similarity	NPC147363
0.8514	High Similarity	NPC470336
0.8506	High Similarity	NPC313304
0.8506	High Similarity	NPC175429
0.8506	High Similarity	NPC138990
0.8506	High Similarity	NPC313717
0.8506	High Similarity	NPC277532
0.8506	High Similarity	NPC103307
0.8506	High Similarity	NPC476196
0.8506	High Similarity	NPC209550
0.8506	High Similarity	NPC315306
0.8503	High Similarity	NPC180301
0.8503	High Similarity	NPC293286
0.8503	High Similarity	NPC236756
0.8503	High Similarity	NPC268193
0.8503	High Similarity	NPC311579
0.8503	High Similarity	NPC326592
0.8503	High Similarity	NPC109594
0.8503	High Similarity	NPC248793
0.8503	High Similarity	NPC203080
0.8503	High Similarity	NPC112701
0.8497	Intermediate Similarity	NPC8965
0.8497	Intermediate Similarity	NPC234497
0.8497	Intermediate Similarity	NPC470341
0.8497	Intermediate Similarity	NPC472058
0.8497	Intermediate Similarity	NPC223413
0.8497	Intermediate Similarity	NPC105414
0.8497	Intermediate Similarity	NPC63470
0.8497	Intermediate Similarity	NPC324522
0.8494	Intermediate Similarity	NPC471677
0.8494	Intermediate Similarity	NPC474021
0.8494	Intermediate Similarity	NPC262038
0.8494	Intermediate Similarity	NPC319910
0.8494	Intermediate Similarity	NPC278476
0.8494	Intermediate Similarity	NPC474023
0.8494	Intermediate Similarity	NPC262039
0.8494	Intermediate Similarity	NPC295650
0.8494	Intermediate Similarity	NPC254412
0.8488	Intermediate Similarity	NPC475979
0.8488	Intermediate Similarity	NPC62261
0.8488	Intermediate Similarity	NPC189689
0.848	Intermediate Similarity	NPC472402
0.848	Intermediate Similarity	NPC475106
0.848	Intermediate Similarity	NPC259834
0.8475	Intermediate Similarity	NPC470334
0.8471	Intermediate Similarity	NPC472055
0.8466	Intermediate Similarity	NPC68381
0.8466	Intermediate Similarity	NPC199533
0.8466	Intermediate Similarity	NPC470454
0.8466	Intermediate Similarity	NPC3718
0.8462	Intermediate Similarity	NPC282390
0.8462	Intermediate Similarity	NPC246466

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 NPC469345 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
0.8683	High Similarity	NPD7075	Discontinued
0.8663	High Similarity	NPD7804	Clinical (unspecified phase)
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.85	High Similarity	NPD7879	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6801	Discontinued
0.8343	Intermediate Similarity	NPD5402	Approved
0.8314	Intermediate Similarity	NPD6959	Discontinued
0.8284	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6166	Phase 2
0.8258	Intermediate Similarity	NPD7808	Phase 3
0.8235	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7473	Discontinued
0.8214	Intermediate Similarity	NPD4380	Phase 2
0.8212	Intermediate Similarity	NPD8312	Approved
0.8212	Intermediate Similarity	NPD8313	Approved
0.8202	Intermediate Similarity	NPD7251	Discontinued
0.8177	Intermediate Similarity	NPD8150	Discontinued
0.8156	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6797	Phase 2
0.8144	Intermediate Similarity	NPD5403	Approved
0.8101	Intermediate Similarity	NPD6559	Discontinued
0.809	Intermediate Similarity	NPD7074	Phase 3
0.8081	Intermediate Similarity	NPD7768	Phase 2
0.8077	Intermediate Similarity	NPD8434	Phase 2
0.807	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7054	Approved
0.8034	Intermediate Similarity	NPD5844	Phase 1
0.8024	Intermediate Similarity	NPD5401	Approved
0.8024	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7989	Intermediate Similarity	NPD7472	Approved
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD3751	Discontinued
0.7964	Intermediate Similarity	NPD6799	Approved
0.7958	Intermediate Similarity	NPD7435	Discontinued
0.7953	Intermediate Similarity	NPD7411	Suspended
0.7943	Intermediate Similarity	NPD5494	Approved
0.7907	Intermediate Similarity	NPD1934	Approved
0.7874	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7874	Approved
0.7784	Intermediate Similarity	NPD3750	Approved
0.7772	Intermediate Similarity	NPD7698	Approved
0.7772	Intermediate Similarity	NPD7696	Phase 3
0.7772	Intermediate Similarity	NPD7697	Approved
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7766	Intermediate Similarity	NPD7783	Phase 2
0.7766	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1465	Phase 2
0.7759	Intermediate Similarity	NPD8455	Phase 2
0.7759	Intermediate Similarity	NPD2801	Approved
0.7755	Intermediate Similarity	NPD8151	Discontinued
0.7753	Intermediate Similarity	NPD3787	Discontinued
0.7732	Intermediate Similarity	NPD8320	Phase 1
0.7732	Intermediate Similarity	NPD8319	Approved
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3749	Approved
0.7711	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6778	Approved
0.7708	Intermediate Similarity	NPD6777	Approved
0.7708	Intermediate Similarity	NPD6776	Approved
0.7708	Intermediate Similarity	NPD6781	Approved
0.7708	Intermediate Similarity	NPD6782	Approved
0.7708	Intermediate Similarity	NPD6780	Approved
0.7708	Intermediate Similarity	NPD6779	Approved
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD7701	Phase 2
0.768	Intermediate Similarity	NPD3818	Discontinued
0.768	Intermediate Similarity	NPD7228	Approved
0.7665	Intermediate Similarity	NPD1549	Phase 2
0.7644	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.763	Intermediate Similarity	NPD3226	Approved
0.7604	Intermediate Similarity	NPD7699	Phase 2
0.7604	Intermediate Similarity	NPD7700	Phase 2
0.7602	Intermediate Similarity	NPD2532	Approved
0.7602	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD2534	Approved
0.7588	Intermediate Similarity	NPD7801	Approved
0.7574	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1512	Approved
0.7545	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6823	Phase 2
0.7448	Intermediate Similarity	NPD6534	Approved
0.7448	Intermediate Similarity	NPD6535	Approved
0.7442	Intermediate Similarity	NPD1511	Approved
0.744	Intermediate Similarity	NPD1551	Phase 2
0.744	Intermediate Similarity	NPD2796	Approved
0.7427	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD920	Approved
0.7412	Intermediate Similarity	NPD2800	Approved
0.741	Intermediate Similarity	NPD6355	Discontinued
0.7401	Intermediate Similarity	NPD37	Approved
0.7389	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD919	Approved
0.7381	Intermediate Similarity	NPD1510	Phase 2
0.7374	Intermediate Similarity	NPD4965	Approved
0.7374	Intermediate Similarity	NPD4966	Approved
0.7374	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5953	Discontinued
0.7351	Intermediate Similarity	NPD7286	Phase 2
0.7349	Intermediate Similarity	NPD4060	Phase 1
0.7345	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7240	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1247	Approved
0.7305	Intermediate Similarity	NPD5124	Phase 1
0.7305	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1607	Approved
0.7262	Intermediate Similarity	NPD6651	Approved
0.7246	Intermediate Similarity	NPD1240	Approved
0.7241	Intermediate Similarity	NPD7390	Discontinued
0.7235	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD6100	Approved
0.7232	Intermediate Similarity	NPD7458	Discontinued
0.7229	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3926	Phase 2
0.7228	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6190	Approved
0.7219	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6233	Phase 2
0.7174	Intermediate Similarity	NPD5711	Approved
0.7174	Intermediate Similarity	NPD5710	Approved
0.7174	Intermediate Similarity	NPD7229	Phase 3
0.7168	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7129	Intermediate Similarity	NPD7584	Approved
0.7121	Intermediate Similarity	NPD8285	Discontinued
0.712	Intermediate Similarity	NPD8127	Discontinued
0.712	Intermediate Similarity	NPD7199	Phase 2
0.711	Intermediate Similarity	NPD1243	Approved
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7108	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5762	Approved
0.7093	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD4360	Phase 2
0.7092	Intermediate Similarity	NPD4363	Phase 3
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8404	Phase 2
0.7066	Intermediate Similarity	NPD4625	Phase 3
0.7062	Intermediate Similarity	NPD6273	Approved
0.7041	Intermediate Similarity	NPD1613	Approved
0.7041	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5408	Approved
0.7035	Intermediate Similarity	NPD5405	Approved
0.7035	Intermediate Similarity	NPD5404	Approved
0.7035	Intermediate Similarity	NPD5406	Approved
0.7024	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7985	Registered
0.7021	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8366	Approved
0.7014	Intermediate Similarity	NPD7907	Approved
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2403	Approved
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2344	Approved
0.6991	Remote Similarity	NPD8067	Phase 3
0.6983	Remote Similarity	NPD1653	Approved
0.698	Remote Similarity	NPD7680	Approved
0.6977	Remote Similarity	NPD7033	Discontinued
0.6971	Remote Similarity	NPD7930	Approved
0.6971	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8166	Discontinued
0.6966	Remote Similarity	NPD5049	Phase 3
0.6964	Remote Similarity	NPD7095	Approved
0.6963	Remote Similarity	NPD8368	Discontinued
0.6954	Remote Similarity	NPD6213	Phase 3
0.6954	Remote Similarity	NPD6212	Phase 3
0.6954	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2424	Discontinued
0.695	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4288	Approved
0.6936	Remote Similarity	NPD2438	Suspended

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