NPASS Compound

Structure

NPC35341 OpenBabel07101718192D 39 43 0 0 0 0 0 0 0 0999 V2000 3.3854 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2317 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2317 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 3.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 3.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9545 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 1.6927 -2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9244 2.4432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 1.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 3.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 3.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 1 22 2 0 0 0 0 2 12 2 0 0 0 0 2 22 1 0 0 0 0 3 19 3 0 0 0 0 3 22 1 0 0 0 0 4 13 1 0 0 0 0 4 23 2 0 0 0 0 5 14 2 0 0 0 0 5 23 1 0 0 0 0 6 15 1 0 0 0 0 6 24 2 0 0 0 0 7 16 2 0 0 0 0 7 24 1 0 0 0 0 8 17 2 0 0 0 0 8 25 1 0 0 0 0 9 18 2 0 0 0 0 9 25 1 0 0 0 0 10 20 2 0 0 0 0 10 26 1 0 0 0 0 11 27 2 0 0 0 0 12 27 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 30 1 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 35 1 0 0 0 0 23 31 1 0 0 0 0 24 33 1 0 0 0 0 25 33 2 3 0 0 0 26 32 2 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 39 2 0 0 0 0 31 34 2 0 0 0 0 32 34 1 0 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.16
Volume:	550.333
LogP:	5.105
LogD:	2.976
LogS:	-3.926
# Rotatable Bonds:	4
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	2.998
Fsp3:	0.029
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:	-5.215
MDCK Permeability:	9.675150067778304e-06
Pgp-inhibitor:	0.892
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	101.04076385498047%
Volume Distribution (VD):	-0.019
Pgp-substrate:	0.30986741185188293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.584
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.683
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.583
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	7.131
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.637
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.946
Carcinogencity:	0.761
Eye Corrosion:	0.003
Eye Irritation:	0.934
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC35341

Natural Product ID:	NPC35341
*Common Name:**	Selaginellin
IUPAC Name:	4-[[3-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethynyl]phenyl]-(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
Synonyms:
Standard InCHIKey:	SJSFYXIEVFIZJC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C34H24O5/c35-21-26-10-20-31(23-4-13-28(37)14-5-23)34(32(26)19-3-22-1-11-27(36)12-2-22)33(24-6-15-29(38)16-7-24)25-8-17-30(39)18-9-25/h1-2,4-18,20,35-38H,21H2
SMILES:	OCc1ccc(c(c1C#Cc1ccc(cc1)O)C(=C1C=CC(=O)C=C1)c1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3394769
PubChem CID:	16664188
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
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14158	Selaginella tamariscina	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	3
Ki	2

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4600.0	nM	PMID[526677]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	15900.0	nM	PMID[526678]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	3000.0	nM	PMID[526677]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	13900.0	nM	PMID[526678]
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	1000.0	nM	PMID[526679]

☑ 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 NPC35341 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	304
0.1-0.2	1691
0.2-0.3	3556
0.3-0.4	11750
0.4-0.5	8056
0.5-0.6	9989
0.6-0.7	6578
0.7-0.8	749
0.8-0.85	16
0.85-0.9	2
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283508
0.9583	High Similarity	NPC12824
0.9496	High Similarity	NPC71870
0.9297	High Similarity	NPC35630
0.9084	High Similarity	NPC24635
0.8615	High Similarity	NPC472369
0.8387	Intermediate Similarity	NPC299180
0.8361	Intermediate Similarity	NPC321589
0.8295	Intermediate Similarity	NPC164014
0.8211	Intermediate Similarity	NPC322239
0.8162	Intermediate Similarity	NPC472370
0.813	Intermediate Similarity	NPC228988
0.8016	Intermediate Similarity	NPC261973
0.8015	Intermediate Similarity	NPC475346
0.8015	Intermediate Similarity	NPC475627
0.8015	Intermediate Similarity	NPC18982
0.8015	Intermediate Similarity	NPC475457
0.8	Intermediate Similarity	NPC71094
0.7984	Intermediate Similarity	NPC46940
0.7983	Intermediate Similarity	NPC135784
0.792	Intermediate Similarity	NPC715
0.7903	Intermediate Similarity	NPC95716
0.7886	Intermediate Similarity	NPC314187
0.7852	Intermediate Similarity	NPC86257
0.7829	Intermediate Similarity	NPC93071
0.7823	Intermediate Similarity	NPC44732
0.7812	Intermediate Similarity	NPC477136
0.7805	Intermediate Similarity	NPC262365
0.7805	Intermediate Similarity	NPC11554
0.7795	Intermediate Similarity	NPC35797
0.7795	Intermediate Similarity	NPC192948
0.7778	Intermediate Similarity	NPC96024
0.777	Intermediate Similarity	NPC283088
0.7769	Intermediate Similarity	NPC103916
0.7762	Intermediate Similarity	NPC19631
0.7762	Intermediate Similarity	NPC239136
0.7761	Intermediate Similarity	NPC71610
0.776	Intermediate Similarity	NPC308689
0.7744	Intermediate Similarity	NPC474532
0.7737	Intermediate Similarity	NPC72669
0.7737	Intermediate Similarity	NPC474517
0.7737	Intermediate Similarity	NPC93015
0.7734	Intermediate Similarity	NPC219112
0.7734	Intermediate Similarity	NPC38893
0.7734	Intermediate Similarity	NPC477137
0.7734	Intermediate Similarity	NPC308311
0.7731	Intermediate Similarity	NPC130193
0.7727	Intermediate Similarity	NPC174977
0.7727	Intermediate Similarity	NPC176208
0.7717	Intermediate Similarity	NPC285350
0.7717	Intermediate Similarity	NPC195922
0.7717	Intermediate Similarity	NPC268160
0.7714	Intermediate Similarity	NPC249817
0.7698	Intermediate Similarity	NPC287604
0.7698	Intermediate Similarity	NPC11266
0.7698	Intermediate Similarity	NPC472262
0.7698	Intermediate Similarity	NPC161964
0.7692	Intermediate Similarity	NPC151197
0.7692	Intermediate Similarity	NPC126002
0.7692	Intermediate Similarity	NPC182240
0.7686	Intermediate Similarity	NPC168829
0.768	Intermediate Similarity	NPC296683
0.7674	Intermediate Similarity	NPC172219
0.7674	Intermediate Similarity	NPC304510
0.7669	Intermediate Similarity	NPC471187
0.7664	Intermediate Similarity	NPC27659
0.766	Intermediate Similarity	NPC475482
0.766	Intermediate Similarity	NPC216940
0.766	Intermediate Similarity	NPC22676
0.766	Intermediate Similarity	NPC62272
0.766	Intermediate Similarity	NPC198621
0.7656	Intermediate Similarity	NPC147179
0.7652	Intermediate Similarity	NPC154696
0.7652	Intermediate Similarity	NPC251259
0.7647	Intermediate Similarity	NPC201967
0.7647	Intermediate Similarity	NPC48248
0.7647	Intermediate Similarity	NPC471064
0.7643	Intermediate Similarity	NPC477874
0.7643	Intermediate Similarity	NPC173569
0.7642	Intermediate Similarity	NPC271274
0.7639	Intermediate Similarity	NPC469520
0.7634	Intermediate Similarity	NPC473136
0.7626	Intermediate Similarity	NPC52407
0.7626	Intermediate Similarity	NPC225051
0.7623	Intermediate Similarity	NPC288411
0.7619	Intermediate Similarity	NPC470355
0.7619	Intermediate Similarity	NPC290194
0.7615	Intermediate Similarity	NPC471671
0.7612	Intermediate Similarity	NPC181334
0.7612	Intermediate Similarity	NPC265413
0.7612	Intermediate Similarity	NPC10154
0.7609	Intermediate Similarity	NPC244699
0.7609	Intermediate Similarity	NPC471851
0.7606	Intermediate Similarity	NPC116742
0.7606	Intermediate Similarity	NPC139243
0.7606	Intermediate Similarity	NPC182249
0.7603	Intermediate Similarity	NPC7686
0.7603	Intermediate Similarity	NPC40258
0.7603	Intermediate Similarity	NPC91461
0.76	Intermediate Similarity	NPC88141
0.76	Intermediate Similarity	NPC58865
0.7597	Intermediate Similarity	NPC92
0.7597	Intermediate Similarity	NPC308828
0.7597	Intermediate Similarity	NPC471668
0.7597	Intermediate Similarity	NPC469663
0.7594	Intermediate Similarity	NPC255026
0.7594	Intermediate Similarity	NPC91478
0.7591	Intermediate Similarity	NPC276238
0.7591	Intermediate Similarity	NPC470747
0.7586	Intermediate Similarity	NPC296752
0.7586	Intermediate Similarity	NPC478164
0.7583	Intermediate Similarity	NPC216468
0.7583	Intermediate Similarity	NPC78119
0.7583	Intermediate Similarity	NPC51333
0.7583	Intermediate Similarity	NPC132078
0.7578	Intermediate Similarity	NPC12656
0.7578	Intermediate Similarity	NPC473137
0.7576	Intermediate Similarity	NPC259703
0.7576	Intermediate Similarity	NPC32322
0.7576	Intermediate Similarity	NPC131868
0.7574	Intermediate Similarity	NPC428300
0.7571	Intermediate Similarity	NPC50924
0.7571	Intermediate Similarity	NPC202225
0.7561	Intermediate Similarity	NPC138942
0.7559	Intermediate Similarity	NPC250323
0.7559	Intermediate Similarity	NPC286222
0.7557	Intermediate Similarity	NPC469644
0.7552	Intermediate Similarity	NPC470617
0.7552	Intermediate Similarity	NPC470616
0.7552	Intermediate Similarity	NPC473591
0.7552	Intermediate Similarity	NPC155192
0.7552	Intermediate Similarity	NPC271494
0.7551	Intermediate Similarity	NPC314437
0.7541	Intermediate Similarity	NPC68269
0.754	Intermediate Similarity	NPC132720
0.754	Intermediate Similarity	NPC183700
0.754	Intermediate Similarity	NPC133308
0.7537	Intermediate Similarity	NPC198014
0.7536	Intermediate Similarity	NPC199253
0.7536	Intermediate Similarity	NPC136588
0.7535	Intermediate Similarity	NPC71465
0.7535	Intermediate Similarity	NPC472646
0.7535	Intermediate Similarity	NPC245923
0.7534	Intermediate Similarity	NPC477913
0.7521	Intermediate Similarity	NPC213730
0.7519	Intermediate Similarity	NPC120545
0.7519	Intermediate Similarity	NPC23402
0.7519	Intermediate Similarity	NPC31936
0.7518	Intermediate Similarity	NPC43353
0.7518	Intermediate Similarity	NPC37410
0.7517	Intermediate Similarity	NPC477221
0.7517	Intermediate Similarity	NPC85310
0.7517	Intermediate Similarity	NPC477209
0.75	Intermediate Similarity	NPC69006
0.75	Intermediate Similarity	NPC70843
0.75	Intermediate Similarity	NPC78307
0.75	Intermediate Similarity	NPC254492
0.75	Intermediate Similarity	NPC29989
0.75	Intermediate Similarity	NPC471930
0.75	Intermediate Similarity	NPC27518
0.75	Intermediate Similarity	NPC145659
0.75	Intermediate Similarity	NPC471935
0.75	Intermediate Similarity	NPC471929
0.75	Intermediate Similarity	NPC304110
0.75	Intermediate Similarity	NPC53896
0.75	Intermediate Similarity	NPC95178
0.75	Intermediate Similarity	NPC9292
0.75	Intermediate Similarity	NPC314048
0.75	Intermediate Similarity	NPC225243
0.75	Intermediate Similarity	NPC69332
0.75	Intermediate Similarity	NPC472801
0.7483	Intermediate Similarity	NPC478160
0.7481	Intermediate Similarity	NPC469609
0.7481	Intermediate Similarity	NPC199273
0.7481	Intermediate Similarity	NPC48342
0.7481	Intermediate Similarity	NPC154030
0.7481	Intermediate Similarity	NPC474766
0.7481	Intermediate Similarity	NPC164649
0.748	Intermediate Similarity	NPC176279
0.748	Intermediate Similarity	NPC297657
0.748	Intermediate Similarity	NPC323810
0.748	Intermediate Similarity	NPC151537
0.748	Intermediate Similarity	NPC260323
0.748	Intermediate Similarity	NPC177576
0.7466	Intermediate Similarity	NPC451542
0.7466	Intermediate Similarity	NPC295712
0.7466	Intermediate Similarity	NPC474203
0.7466	Intermediate Similarity	NPC313047
0.7465	Intermediate Similarity	NPC133463
0.7465	Intermediate Similarity	NPC206525
0.7465	Intermediate Similarity	NPC475549
0.7465	Intermediate Similarity	NPC472648
0.7465	Intermediate Similarity	NPC155211
0.7465	Intermediate Similarity	NPC472649
0.7465	Intermediate Similarity	NPC472647
0.7465	Intermediate Similarity	NPC191462
0.7465	Intermediate Similarity	NPC474813
0.7465	Intermediate Similarity	NPC170328
0.7464	Intermediate Similarity	NPC34414
0.7464	Intermediate Similarity	NPC146647

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 NPC35341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	1068
0.2-0.3	1146
0.3-0.4	2895
0.4-0.5	2151
0.5-0.6	1286
0.6-0.7	302
0.7-0.8	25
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
0.792	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2342	Discontinued
0.766	Intermediate Similarity	NPD5406	Approved
0.766	Intermediate Similarity	NPD5408	Approved
0.766	Intermediate Similarity	NPD5405	Approved
0.766	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD2286	Discontinued
0.7481	Intermediate Similarity	NPD3091	Approved
0.7448	Intermediate Similarity	NPD8166	Discontinued
0.7448	Intermediate Similarity	NPD7003	Approved
0.7438	Intermediate Similarity	NPD3020	Approved
0.7415	Intermediate Similarity	NPD7390	Discontinued
0.7368	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4059	Approved
0.7368	Intermediate Similarity	NPD3019	Approved
0.7368	Intermediate Similarity	NPD2932	Approved
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7287	Intermediate Similarity	NPD7635	Approved
0.7259	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD2933	Approved
0.725	Intermediate Similarity	NPD2934	Approved
0.7248	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3095	Discontinued
0.7174	Intermediate Similarity	NPD3094	Phase 2
0.7174	Intermediate Similarity	NPD1470	Approved
0.7132	Intermediate Similarity	NPD1201	Approved
0.712	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD5736	Approved
0.7054	Intermediate Similarity	NPD3021	Approved
0.7054	Intermediate Similarity	NPD3022	Approved
0.7042	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD1651	Approved
0.7037	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7008	Discontinued
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7458	Discontinued
0.6934	Remote Similarity	NPD3026	Approved
0.6934	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5951	Approved
0.6912	Remote Similarity	NPD4093	Discontinued
0.6912	Remote Similarity	NPD3025	Approved
0.6912	Remote Similarity	NPD5691	Approved
0.6912	Remote Similarity	NPD3024	Approved
0.6906	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4624	Approved
0.6875	Remote Similarity	NPD6663	Approved
0.6857	Remote Similarity	NPD1283	Approved
0.6832	Remote Similarity	NPD6959	Discontinued
0.6828	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1164	Approved
0.6809	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7768	Phase 2
0.6783	Remote Similarity	NPD4908	Phase 1
0.6774	Remote Similarity	NPD844	Approved
0.6774	Remote Similarity	NPD1809	Phase 2
0.6753	Remote Similarity	NPD6273	Approved
0.6748	Remote Similarity	NPD845	Approved
0.6733	Remote Similarity	NPD7037	Approved
0.672	Remote Similarity	NPD288	Approved
0.6712	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD405	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4750	Phase 3
0.6645	Remote Similarity	NPD3750	Approved
0.6644	Remote Similarity	NPD7743	Approved
0.6644	Remote Similarity	NPD7742	Approved
0.6643	Remote Similarity	NPD1281	Approved
0.6622	Remote Similarity	NPD6353	Approved
0.6621	Remote Similarity	NPD5156	Approved
0.6621	Remote Similarity	NPD5155	Approved
0.6621	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4625	Phase 3
0.6619	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8131	Suspended
0.6601	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2979	Phase 3
0.6599	Remote Similarity	NPD3620	Phase 2
0.6596	Remote Similarity	NPD4878	Approved
0.6596	Remote Similarity	NPD3972	Approved
0.6593	Remote Similarity	NPD496	Approved
0.6593	Remote Similarity	NPD2229	Approved
0.6593	Remote Similarity	NPD498	Approved
0.6593	Remote Similarity	NPD2234	Approved
0.6593	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2228	Approved
0.6593	Remote Similarity	NPD495	Approved
0.6588	Remote Similarity	NPD8313	Approved
0.6588	Remote Similarity	NPD8312	Approved
0.6562	Remote Similarity	NPD3028	Approved
0.6562	Remote Similarity	NPD1242	Phase 1
0.6562	Remote Similarity	NPD8455	Phase 2
0.6556	Remote Similarity	NPD7266	Discontinued
0.6552	Remote Similarity	NPD3594	Approved
0.6552	Remote Similarity	NPD2605	Approved
0.6552	Remote Similarity	NPD3595	Approved
0.6552	Remote Similarity	NPD2606	Approved
0.6549	Remote Similarity	NPD6582	Phase 2
0.6549	Remote Similarity	NPD6583	Phase 3
0.6541	Remote Similarity	NPD5451	Approved
0.6538	Remote Similarity	NPD1237	Approved
0.6536	Remote Similarity	NPD4628	Phase 3
0.6528	Remote Similarity	NPD6584	Phase 3
0.6522	Remote Similarity	NPD7610	Discontinued
0.6522	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5535	Approved
0.6516	Remote Similarity	NPD7041	Phase 2
0.6516	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD940	Approved
0.6512	Remote Similarity	NPD846	Approved
0.651	Remote Similarity	NPD4097	Suspended
0.6503	Remote Similarity	NPD1876	Approved
0.65	Remote Similarity	NPD4589	Approved
0.65	Remote Similarity	NPD6516	Phase 2
0.65	Remote Similarity	NPD5846	Approved
0.65	Remote Similarity	NPD1751	Approved
0.65	Remote Similarity	NPD111	Approved
0.649	Remote Similarity	NPD2935	Discontinued
0.6488	Remote Similarity	NPD5844	Phase 1
0.6483	Remote Similarity	NPD4208	Discontinued
0.6478	Remote Similarity	NPD7028	Phase 2
0.6478	Remote Similarity	NPD4380	Phase 2
0.6475	Remote Similarity	NPD5303	Approved
0.6475	Remote Similarity	NPD5304	Approved
0.6471	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4103	Phase 2
0.6452	Remote Similarity	NPD3300	Phase 2
0.6447	Remote Similarity	NPD2346	Discontinued
0.6443	Remote Similarity	NPD5735	Approved
0.6434	Remote Similarity	NPD1669	Approved
0.6434	Remote Similarity	NPD5327	Phase 3
0.6434	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4659	Approved
0.6433	Remote Similarity	NPD4319	Phase 2
0.6429	Remote Similarity	NPD3400	Discontinued
0.6429	Remote Similarity	NPD7177	Discontinued
0.6424	Remote Similarity	NPD2799	Discontinued
0.6424	Remote Similarity	NPD1510	Phase 2
0.6419	Remote Similarity	NPD6405	Approved
0.6419	Remote Similarity	NPD6407	Approved
0.6418	Remote Similarity	NPD1792	Phase 2
0.6408	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1611	Approved
0.6408	Remote Similarity	NPD1610	Phase 2
0.6403	Remote Similarity	NPD5536	Phase 2
0.64	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7843	Approved
0.6395	Remote Similarity	NPD6966	Discovery
0.6389	Remote Similarity	NPD8651	Approved
0.6386	Remote Similarity	NPD6232	Discontinued
0.6383	Remote Similarity	NPD5126	Approved
0.6383	Remote Similarity	NPD7725	Approved
0.6383	Remote Similarity	NPD5125	Phase 3
0.6383	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2438	Suspended
0.6382	Remote Similarity	NPD2531	Phase 2
0.6377	Remote Similarity	NPD4198	Discontinued
0.6377	Remote Similarity	NPD7157	Approved
0.637	Remote Similarity	NPD3637	Approved
0.637	Remote Similarity	NPD2861	Phase 2
0.637	Remote Similarity	NPD3636	Approved
0.637	Remote Similarity	NPD3635	Approved
0.6369	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7473	Discontinued
0.6369	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3638	Discontinued
0.6358	Remote Similarity	NPD7819	Suspended
0.6358	Remote Similarity	NPD7097	Phase 1
0.6357	Remote Similarity	NPD7741	Discontinued
0.6351	Remote Similarity	NPD7294	Phase 1
0.6351	Remote Similarity	NPD6798	Discontinued
0.635	Remote Similarity	NPD5283	Phase 1
0.635	Remote Similarity	NPD1241	Discontinued
0.6346	Remote Similarity	NPD3845	Phase 1
0.6343	Remote Similarity	NPD2684	Approved
0.6343	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3749	Approved
0.634	Remote Similarity	NPD2344	Approved
0.6338	Remote Similarity	NPD3847	Discontinued
0.6335	Remote Similarity	NPD7411	Suspended
0.6319	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD968	Approved
0.6316	Remote Similarity	NPD3748	Approved

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