NPASS Compound

Structure

NPC24635 OpenBabel07101718242D 41 45 0 0 0 0 0 0 0 0999 V2000 2.5416 -5.3804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -4.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -3.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -3.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -3.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -3.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 41 1 0 0 0 0 3 13 1 0 0 0 0 3 24 2 0 0 0 0 4 14 2 0 0 0 0 4 24 1 0 0 0 0 5 21 3 0 0 0 0 5 24 1 0 0 0 0 6 15 1 0 0 0 0 6 25 2 0 0 0 0 7 16 2 0 0 0 0 7 25 1 0 0 0 0 8 17 2 0 0 0 0 8 26 1 0 0 0 0 9 18 2 0 0 0 0 9 26 1 0 0 0 0 10 19 1 0 0 0 0 10 27 2 0 0 0 0 11 20 2 0 0 0 0 11 27 1 0 0 0 0 12 22 2 0 0 0 0 12 28 1 0 0 0 0 13 29 2 0 0 0 0 14 29 1 0 0 0 0 15 30 2 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 21 34 1 0 0 0 0 22 33 1 0 0 0 0 23 28 1 0 0 0 0 23 37 1 0 0 0 0 25 33 1 0 0 0 0 26 35 2 3 0 0 0 27 35 1 0 0 0 0 28 34 2 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 40 2 0 0 0 0 32 41 1 0 0 0 0 33 36 2 0 0 0 0 34 36 1 0 0 0 0 35 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.19
Volume:	584.925
LogP:	5.793
LogD:	3.35
LogS:	-4.283
# Rotatable Bonds:	6
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	2.981
Fsp3:	0.083
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:	-5.175
MDCK Permeability:	1.1079615433118306e-05
Pgp-inhibitor:	0.923
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	101.51703643798828%
Volume Distribution (VD):	0.247
Pgp-substrate:	0.18306203186511993%

ADMET: Metabolism

CYP1A2-inhibitor:	0.473
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.166
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	5.322
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.944
Carcinogencity:	0.786
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.502

Download Data

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

Natural Product: NPC24635

Natural Product ID:	NPC24635
*Common Name:**	Selaginellin D
IUPAC Name:	4-[(4-ethoxyphenyl)-[3-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethynyl]phenyl]methylidene]cyclohexa-2,5-dien-1-one
Synonyms:	Selaginellin D
Standard InCHIKey:	OTBCTHSGTKXCDG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C36H28O5/c1-2-41-32-19-10-27(11-20-32)35(26-8-17-31(40)18-9-26)36-33(25-6-15-30(39)16-7-25)22-12-28(23-37)34(36)21-5-24-3-13-29(38)14-4-24/h3-4,6-20,22,37-39H,2,23H2,1H3
SMILES:	CCOc1ccc(cc1)C(=C1C=CC(=O)C=C1)c1c(ccc(c1C#Cc1ccc(cc1)O)CO)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1090671
PubChem CID:	46885678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20335035]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29144743]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	5.3	ug.mL-1	PMID[492070]

☑ 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 NPC24635 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	332
0.1-0.2	1660
0.2-0.3	3738
0.3-0.4	11262
0.4-0.5	7603
0.5-0.6	5005
0.6-0.7	10871
0.7-0.8	2202
0.8-0.85	15
0.85-0.9	4
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC35630
0.9084	High Similarity	NPC35341
0.9084	High Similarity	NPC283508
0.8855	High Similarity	NPC12824
0.8626	High Similarity	NPC71870
0.8271	Intermediate Similarity	NPC103916
0.8156	Intermediate Similarity	NPC189482
0.8148	Intermediate Similarity	NPC251259
0.8112	Intermediate Similarity	NPC472370
0.8074	Intermediate Similarity	NPC131868
0.8058	Intermediate Similarity	NPC428300
0.8043	Intermediate Similarity	NPC28476
0.8043	Intermediate Similarity	NPC133407
0.8042	Intermediate Similarity	NPC141023
0.8042	Intermediate Similarity	NPC184269
0.8	Intermediate Similarity	NPC71465
0.8	Intermediate Similarity	NPC472646
0.7987	Intermediate Similarity	NPC43716
0.7987	Intermediate Similarity	NPC475719
0.7987	Intermediate Similarity	NPC101255
0.7986	Intermediate Similarity	NPC37410
0.7931	Intermediate Similarity	NPC472647
0.7931	Intermediate Similarity	NPC472648
0.7931	Intermediate Similarity	NPC471522
0.7931	Intermediate Similarity	NPC206525
0.7931	Intermediate Similarity	NPC191462
0.7931	Intermediate Similarity	NPC133463
0.7931	Intermediate Similarity	NPC472649
0.7931	Intermediate Similarity	NPC170328
0.7917	Intermediate Similarity	NPC71372
0.7905	Intermediate Similarity	NPC186033
0.7902	Intermediate Similarity	NPC73656
0.7891	Intermediate Similarity	NPC273623
0.7887	Intermediate Similarity	NPC472369
0.7877	Intermediate Similarity	NPC470307
0.7877	Intermediate Similarity	NPC470308
0.7862	Intermediate Similarity	NPC258780
0.7838	Intermediate Similarity	NPC473499
0.7832	Intermediate Similarity	NPC282508
0.7817	Intermediate Similarity	NPC86257
0.7793	Intermediate Similarity	NPC476616
0.7793	Intermediate Similarity	NPC476615
0.7793	Intermediate Similarity	NPC476617
0.7785	Intermediate Similarity	NPC105584
0.7771	Intermediate Similarity	NPC469507
0.7771	Intermediate Similarity	NPC288353
0.777	Intermediate Similarity	NPC221134
0.777	Intermediate Similarity	NPC106055
0.777	Intermediate Similarity	NPC110699
0.7764	Intermediate Similarity	NPC469664
0.7763	Intermediate Similarity	NPC174251
0.7763	Intermediate Similarity	NPC153182
0.7762	Intermediate Similarity	NPC249425
0.7762	Intermediate Similarity	NPC254000
0.7748	Intermediate Similarity	NPC91694
0.7748	Intermediate Similarity	NPC307205
0.7748	Intermediate Similarity	NPC300603
0.7746	Intermediate Similarity	NPC471064
0.7744	Intermediate Similarity	NPC35344
0.7744	Intermediate Similarity	NPC141003
0.7736	Intermediate Similarity	NPC195136
0.7733	Intermediate Similarity	NPC69755
0.773	Intermediate Similarity	NPC304630
0.773	Intermediate Similarity	NPC17837
0.7727	Intermediate Similarity	NPC162976
0.7727	Intermediate Similarity	NPC205501
0.7727	Intermediate Similarity	NPC472837
0.7727	Intermediate Similarity	NPC118000
0.7724	Intermediate Similarity	NPC211352
0.7714	Intermediate Similarity	NPC474532
0.7714	Intermediate Similarity	NPC61685
0.7712	Intermediate Similarity	NPC478163
0.7708	Intermediate Similarity	NPC153019
0.7703	Intermediate Similarity	NPC475104
0.7698	Intermediate Similarity	NPC152946
0.7698	Intermediate Similarity	NPC174977
0.7697	Intermediate Similarity	NPC215678
0.7697	Intermediate Similarity	NPC274454
0.7688	Intermediate Similarity	NPC189552
0.7688	Intermediate Similarity	NPC273467
0.7687	Intermediate Similarity	NPC115861
0.7687	Intermediate Similarity	NPC249817
0.7682	Intermediate Similarity	NPC36732
0.7681	Intermediate Similarity	NPC129176
0.7677	Intermediate Similarity	NPC58310
0.7677	Intermediate Similarity	NPC295977
0.7673	Intermediate Similarity	NPC55443
0.7673	Intermediate Similarity	NPC15815
0.7673	Intermediate Similarity	NPC51760
0.7673	Intermediate Similarity	NPC18699
0.7671	Intermediate Similarity	NPC184677
0.7671	Intermediate Similarity	NPC11266
0.7662	Intermediate Similarity	NPC474556
0.766	Intermediate Similarity	NPC76119
0.766	Intermediate Similarity	NPC232387
0.766	Intermediate Similarity	NPC4286
0.7658	Intermediate Similarity	NPC54830
0.7658	Intermediate Similarity	NPC56049
0.7655	Intermediate Similarity	NPC27578
0.7655	Intermediate Similarity	NPC303144
0.7655	Intermediate Similarity	NPC289624
0.7651	Intermediate Similarity	NPC470407
0.7647	Intermediate Similarity	NPC299180
0.7647	Intermediate Similarity	NPC39361
0.7647	Intermediate Similarity	NPC25648
0.7635	Intermediate Similarity	NPC22676
0.7635	Intermediate Similarity	NPC198621
0.7635	Intermediate Similarity	NPC186647
0.7635	Intermediate Similarity	NPC475482
0.7635	Intermediate Similarity	NPC216940
0.7632	Intermediate Similarity	NPC274960
0.7632	Intermediate Similarity	NPC143120
0.7632	Intermediate Similarity	NPC473909
0.7632	Intermediate Similarity	NPC308006
0.7628	Intermediate Similarity	NPC472838
0.7628	Intermediate Similarity	NPC306011
0.7625	Intermediate Similarity	NPC186325
0.7625	Intermediate Similarity	NPC312993
0.7622	Intermediate Similarity	NPC277458
0.7622	Intermediate Similarity	NPC307050
0.7622	Intermediate Similarity	NPC215300
0.7619	Intermediate Similarity	NPC15109
0.7619	Intermediate Similarity	NPC173569
0.7619	Intermediate Similarity	NPC11727
0.7619	Intermediate Similarity	NPC125579
0.7619	Intermediate Similarity	NPC477874
0.7616	Intermediate Similarity	NPC201297
0.7613	Intermediate Similarity	NPC145527
0.7613	Intermediate Similarity	NPC208785
0.7613	Intermediate Similarity	NPC470619
0.7613	Intermediate Similarity	NPC261322
0.7613	Intermediate Similarity	NPC470618
0.7612	Intermediate Similarity	NPC321589
0.761	Intermediate Similarity	NPC257166
0.7603	Intermediate Similarity	NPC138940
0.7603	Intermediate Similarity	NPC470406
0.7603	Intermediate Similarity	NPC469610
0.76	Intermediate Similarity	NPC100482
0.76	Intermediate Similarity	NPC78987
0.76	Intermediate Similarity	NPC277331
0.76	Intermediate Similarity	NPC82336
0.7597	Intermediate Similarity	NPC478018
0.7595	Intermediate Similarity	NPC215203
0.7595	Intermediate Similarity	NPC150908
0.7595	Intermediate Similarity	NPC121649
0.7595	Intermediate Similarity	NPC205026
0.7595	Intermediate Similarity	NPC248739
0.7595	Intermediate Similarity	NPC478161
0.7595	Intermediate Similarity	NPC100049
0.7595	Intermediate Similarity	NPC265624
0.7595	Intermediate Similarity	NPC186227
0.7595	Intermediate Similarity	NPC159707
0.7595	Intermediate Similarity	NPC478159
0.7595	Intermediate Similarity	NPC14606
0.7595	Intermediate Similarity	NPC52611
0.7595	Intermediate Similarity	NPC158027
0.7589	Intermediate Similarity	NPC164014
0.7589	Intermediate Similarity	NPC265413
0.7589	Intermediate Similarity	NPC10154
0.7586	Intermediate Similarity	NPC8899
0.7586	Intermediate Similarity	NPC471517
0.7586	Intermediate Similarity	NPC473309
0.7586	Intermediate Similarity	NPC191395
0.7584	Intermediate Similarity	NPC470209
0.7584	Intermediate Similarity	NPC55947
0.7584	Intermediate Similarity	NPC116742
0.7584	Intermediate Similarity	NPC182249
0.7584	Intermediate Similarity	NPC139243
0.7582	Intermediate Similarity	NPC471524
0.7582	Intermediate Similarity	NPC471523
0.7582	Intermediate Similarity	NPC14468
0.7582	Intermediate Similarity	NPC471473
0.7582	Intermediate Similarity	NPC478019
0.758	Intermediate Similarity	NPC223720
0.758	Intermediate Similarity	NPC115203
0.7578	Intermediate Similarity	NPC472261
0.7578	Intermediate Similarity	NPC18380
0.7574	Intermediate Similarity	NPC19290
0.7571	Intermediate Similarity	NPC30462
0.7571	Intermediate Similarity	NPC255026
0.7571	Intermediate Similarity	NPC150026
0.7569	Intermediate Similarity	NPC471519
0.7569	Intermediate Similarity	NPC471518
0.7568	Intermediate Similarity	NPC475549
0.7568	Intermediate Similarity	NPC141717
0.7568	Intermediate Similarity	NPC265515
0.7568	Intermediate Similarity	NPC120852
0.7566	Intermediate Similarity	NPC475492
0.7564	Intermediate Similarity	NPC473579
0.7564	Intermediate Similarity	NPC475454
0.7564	Intermediate Similarity	NPC475311
0.7564	Intermediate Similarity	NPC118033
0.7564	Intermediate Similarity	NPC473680
0.7564	Intermediate Similarity	NPC475718
0.7562	Intermediate Similarity	NPC51247
0.7562	Intermediate Similarity	NPC324736
0.7562	Intermediate Similarity	NPC195167
0.7562	Intermediate Similarity	NPC177650
0.7552	Intermediate Similarity	NPC186889
0.7552	Intermediate Similarity	NPC473993

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 NPC24635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	1066
0.2-0.3	1284
0.3-0.4	2651
0.4-0.5	2004
0.5-0.6	1179
0.6-0.7	599
0.7-0.8	73
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
0.7905	Intermediate Similarity	NPD7003	Approved
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4060	Phase 1
0.7622	Intermediate Similarity	NPD4908	Phase 1
0.7613	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4626	Approved
0.7578	Intermediate Similarity	NPD6959	Discontinued
0.7547	Intermediate Similarity	NPD7768	Phase 2
0.7536	Intermediate Similarity	NPD1651	Approved
0.7536	Intermediate Similarity	NPD5691	Approved
0.7534	Intermediate Similarity	NPD4140	Approved
0.7532	Intermediate Similarity	NPD6273	Approved
0.7517	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4625	Phase 3
0.7439	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8166	Discontinued
0.7432	Intermediate Similarity	NPD6353	Approved
0.7417	Intermediate Similarity	NPD7037	Approved
0.7407	Intermediate Similarity	NPD5535	Approved
0.7394	Intermediate Similarity	NPD6583	Phase 3
0.7394	Intermediate Similarity	NPD6582	Phase 2
0.7394	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7458	Discontinued
0.7361	Intermediate Similarity	NPD6584	Phase 3
0.7361	Intermediate Similarity	NPD4624	Approved
0.7343	Intermediate Similarity	NPD1283	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD5327	Phase 3
0.7267	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1611	Approved
0.7248	Intermediate Similarity	NPD5735	Approved
0.7246	Intermediate Similarity	NPD7157	Approved
0.7239	Intermediate Similarity	NPD2684	Approved
0.7237	Intermediate Similarity	NPD2346	Discontinued
0.7234	Intermediate Similarity	NPD6516	Phase 2
0.7234	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1241	Discontinued
0.7222	Intermediate Similarity	NPD8651	Approved
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7205	Intermediate Similarity	NPD8455	Phase 2
0.7202	Intermediate Similarity	NPD5844	Phase 1
0.7193	Intermediate Similarity	NPD8313	Approved
0.7193	Intermediate Similarity	NPD8312	Approved
0.7184	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2979	Phase 3
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.7162	Intermediate Similarity	NPD7294	Phase 1
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1610	Phase 2
0.7133	Intermediate Similarity	NPD1281	Approved
0.7124	Intermediate Similarity	NPD2344	Approved
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7095	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD968	Approved
0.7089	Intermediate Similarity	NPD4319	Phase 2
0.7083	Intermediate Similarity	NPD3972	Approved
0.7081	Intermediate Similarity	NPD7411	Suspended
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7067	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3620	Phase 2
0.7067	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD4476	Approved
0.7059	Intermediate Similarity	NPD5451	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7055	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD3268	Approved
0.7047	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD2342	Discontinued
0.7025	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5124	Phase 1
0.7013	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7773	Phase 2
0.7	Intermediate Similarity	NPD7265	Discontinued
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD3748	Approved
0.6986	Remote Similarity	NPD1876	Approved
0.698	Remote Similarity	NPD7008	Discontinued
0.6974	Remote Similarity	NPD4097	Suspended
0.6972	Remote Similarity	NPD6580	Approved
0.6972	Remote Similarity	NPD1548	Phase 1
0.6972	Remote Similarity	NPD6581	Approved
0.6972	Remote Similarity	NPD3091	Approved
0.697	Remote Similarity	NPD3749	Approved
0.6968	Remote Similarity	NPD2424	Discontinued
0.6963	Remote Similarity	NPD3134	Approved
0.6962	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7041	Phase 2
0.6962	Remote Similarity	NPD7390	Discontinued
0.6948	Remote Similarity	NPD2935	Discontinued
0.6948	Remote Similarity	NPD2531	Phase 2
0.6948	Remote Similarity	NPD2438	Suspended
0.6946	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD3496	Discontinued
0.6943	Remote Similarity	NPD2309	Approved
0.6937	Remote Similarity	NPD7427	Discontinued
0.6933	Remote Similarity	NPD2313	Discontinued
0.6928	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4536	Approved
0.6928	Remote Similarity	NPD4538	Approved
0.6923	Remote Similarity	NPD6674	Discontinued
0.6923	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1669	Approved
0.6918	Remote Similarity	NPD4749	Approved
0.6914	Remote Similarity	NPD4380	Phase 2
0.6914	Remote Similarity	NPD7028	Phase 2
0.6912	Remote Similarity	NPD1358	Approved
0.6908	Remote Similarity	NPD6355	Discontinued
0.6903	Remote Similarity	NPD5762	Approved
0.6903	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5763	Approved
0.6901	Remote Similarity	NPD5536	Phase 2
0.6894	Remote Similarity	NPD3020	Approved
0.689	Remote Similarity	NPD5929	Approved
0.6883	Remote Similarity	NPD4108	Discontinued
0.6883	Remote Similarity	NPD4308	Phase 3
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6671	Approved
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3019	Approved
0.6875	Remote Similarity	NPD4059	Approved
0.6875	Remote Similarity	NPD2286	Discontinued
0.6875	Remote Similarity	NPD2932	Approved
0.6871	Remote Similarity	NPD6696	Suspended
0.6867	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1549	Phase 2
0.6857	Remote Similarity	NPD5283	Phase 1
0.6857	Remote Similarity	NPD1398	Phase 1
0.6853	Remote Similarity	NPD1894	Discontinued
0.6846	Remote Similarity	NPD5736	Approved
0.6831	Remote Similarity	NPD7340	Approved
0.6829	Remote Similarity	NPD7577	Discontinued
0.6828	Remote Similarity	NPD3847	Discontinued
0.6826	Remote Similarity	NPD5709	Phase 3
0.6813	Remote Similarity	NPD7447	Phase 1
0.6813	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3443	Approved
0.6806	Remote Similarity	NPD3444	Approved
0.6806	Remote Similarity	NPD3445	Approved
0.6805	Remote Similarity	NPD6232	Discontinued
0.6797	Remote Similarity	NPD4340	Discontinued
0.6795	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6002	Phase 3
0.6795	Remote Similarity	NPD6005	Phase 3
0.6795	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6004	Phase 3
0.6795	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2860	Approved
0.6794	Remote Similarity	NPD2859	Approved
0.6792	Remote Similarity	NPD6815	Approved
0.6792	Remote Similarity	NPD6666	Approved
0.6792	Remote Similarity	NPD6667	Approved
0.6792	Remote Similarity	NPD7440	Discontinued
0.6788	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4666	Phase 3
0.6786	Remote Similarity	NPD7635	Approved
0.6786	Remote Similarity	NPD821	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6782	Remote Similarity	NPD6559	Discontinued
0.6781	Remote Similarity	NPD422	Phase 1
0.6781	Remote Similarity	NPD3092	Approved
0.6781	Remote Similarity	NPD1535	Discovery
0.6781	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3691	Phase 2
0.6779	Remote Similarity	NPD3690	Phase 2
0.6779	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2798	Approved
0.6774	Remote Similarity	NPD1510	Phase 2
0.6774	Remote Similarity	NPD5588	Approved
0.6774	Remote Similarity	NPD5960	Phase 3
0.6766	Remote Similarity	NPD7833	Phase 2
0.6766	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7831	Phase 2
0.6766	Remote Similarity	NPD7075	Discontinued
0.6759	Remote Similarity	NPD3095	Discontinued
0.6757	Remote Similarity	NPD3225	Approved
0.6755	Remote Similarity	NPD6179	Discontinued
0.6755	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3027	Phase 3

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