NPASS Compound

Structure

NPC71870 OpenBabel07101718292D 36 40 0 0 0 0 0 0 0 0999 V2000 2.5347 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0694 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0694 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9512 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 -5.9143 2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 25 2 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 31 2 0 0 0 0 9 12 3 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 10 23 2 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 24 2 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 27 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 28 2 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 27 32 2 3 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 36 2 0 0 0 0 31 33 1 0 0 0 0 32 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.16
Volume:	515.456
LogP:	5.931
LogD:	3.618
LogS:	-4.471
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	2.752
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168
MDCK Permeability:	1.2720260201604106e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	101.13640594482422%
Volume Distribution (VD):	0.352
Pgp-substrate:	0.16702984273433685%

ADMET: Metabolism

CYP1A2-inhibitor:	0.627
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.452
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.822
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	4.794
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.52
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.951
Carcinogencity:	0.533
Eye Corrosion:	0.004
Eye Irritation:	0.952
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC71870

Natural Product ID:	NPC71870
*Common Name:**	Selaginellin
IUPAC Name:	4-[[2-(4-hydroxyphenyl)-6-[2-(4-hydroxyphenyl)ethynyl]phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-one
Synonyms:	Selaginellin
Standard InCHIKey:	JOEMXJKVASNPSW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C33H22O3/c34-28-17-10-23(11-18-28)9-12-26-7-4-8-31(24-13-19-29(35)20-14-24)33(26)32(25-5-2-1-3-6-25)27-15-21-30(36)22-16-27/h1-8,10-11,13-22,34-35H
SMILES:	O=C1C=CC(=C(c2c(cccc2c2ccc(cc2)O)C#Cc2ccc(cc2)O)c2ccccc2)C=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1089785
PubChem CID:	46885722
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
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1.2	ug.mL-1	PMID[469799]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.6	ug.mL-1	PMID[469799]

☑ 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 NPC71870 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	321
0.1-0.2	1934
0.2-0.3	4213
0.3-0.4	12884
0.4-0.5	6530
0.5-0.6	10564
0.6-0.7	5536
0.7-0.8	693
0.8-0.85	15
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC12824
0.9496	High Similarity	NPC35341
0.9496	High Similarity	NPC283508
0.8828	High Similarity	NPC35630
0.8626	High Similarity	NPC24635
0.8475	Intermediate Similarity	NPC321589
0.8407	Intermediate Similarity	NPC135784
0.84	Intermediate Similarity	NPC164014
0.8347	Intermediate Similarity	NPC299180
0.8319	Intermediate Similarity	NPC322239
0.8264	Intermediate Similarity	NPC261973
0.8235	Intermediate Similarity	NPC228988
0.8154	Intermediate Similarity	NPC472369
0.8151	Intermediate Similarity	NPC95716
0.8087	Intermediate Similarity	NPC168829
0.8083	Intermediate Similarity	NPC46940
0.8053	Intermediate Similarity	NPC201967
0.8051	Intermediate Similarity	NPC11554
0.8034	Intermediate Similarity	NPC271274
0.8017	Intermediate Similarity	NPC715
0.8017	Intermediate Similarity	NPC288411
0.7983	Intermediate Similarity	NPC314187
0.7982	Intermediate Similarity	NPC130193
0.7949	Intermediate Similarity	NPC138942
0.7934	Intermediate Similarity	NPC286222
0.792	Intermediate Similarity	NPC93071
0.7917	Intermediate Similarity	NPC296683
0.7881	Intermediate Similarity	NPC69332
0.7881	Intermediate Similarity	NPC95178
0.7881	Intermediate Similarity	NPC29989
0.7863	Intermediate Similarity	NPC96024
0.7852	Intermediate Similarity	NPC472370
0.7833	Intermediate Similarity	NPC88141
0.782	Intermediate Similarity	NPC72669
0.782	Intermediate Similarity	NPC474517
0.7812	Intermediate Similarity	NPC176208
0.7807	Intermediate Similarity	NPC292730
0.7807	Intermediate Similarity	NPC82664
0.7807	Intermediate Similarity	NPC132271
0.7807	Intermediate Similarity	NPC216520
0.7805	Intermediate Similarity	NPC195922
0.7803	Intermediate Similarity	NPC86257
0.7788	Intermediate Similarity	NPC151715
0.7778	Intermediate Similarity	NPC126002
0.7778	Intermediate Similarity	NPC68269
0.7769	Intermediate Similarity	NPC13482
0.775	Intermediate Similarity	NPC262365
0.7742	Intermediate Similarity	NPC322197
0.7739	Intermediate Similarity	NPC32674
0.7734	Intermediate Similarity	NPC120545
0.7734	Intermediate Similarity	NPC154696
0.7731	Intermediate Similarity	NPC70843
0.7721	Intermediate Similarity	NPC283088
0.7719	Intermediate Similarity	NPC26244
0.7717	Intermediate Similarity	NPC103916
0.7714	Intermediate Similarity	NPC19631
0.7714	Intermediate Similarity	NPC239136
0.7712	Intermediate Similarity	NPC8931
0.7712	Intermediate Similarity	NPC261573
0.7712	Intermediate Similarity	NPC120693
0.7705	Intermediate Similarity	NPC470355
0.7705	Intermediate Similarity	NPC297657
0.7704	Intermediate Similarity	NPC475457
0.7704	Intermediate Similarity	NPC475627
0.7704	Intermediate Similarity	NPC18982
0.7704	Intermediate Similarity	NPC475346
0.7692	Intermediate Similarity	NPC51015
0.7687	Intermediate Similarity	NPC244699
0.7686	Intermediate Similarity	NPC58865
0.768	Intermediate Similarity	NPC471936
0.768	Intermediate Similarity	NPC471668
0.7674	Intermediate Similarity	NPC91478
0.7674	Intermediate Similarity	NPC71094
0.7672	Intermediate Similarity	NPC92730
0.7669	Intermediate Similarity	NPC276238
0.7656	Intermediate Similarity	NPC259703
0.7656	Intermediate Similarity	NPC131868
0.7656	Intermediate Similarity	NPC32322
0.7652	Intermediate Similarity	NPC473388
0.7647	Intermediate Similarity	NPC472262
0.7647	Intermediate Similarity	NPC161964
0.7647	Intermediate Similarity	NPC287604
0.7647	Intermediate Similarity	NPC303141
0.7647	Intermediate Similarity	NPC243677
0.7642	Intermediate Similarity	NPC250323
0.7627	Intermediate Similarity	NPC470202
0.7623	Intermediate Similarity	NPC44732
0.7623	Intermediate Similarity	NPC141782
0.7623	Intermediate Similarity	NPC21162
0.7611	Intermediate Similarity	NPC45040
0.7609	Intermediate Similarity	NPC474110
0.7609	Intermediate Similarity	NPC44960
0.7609	Intermediate Similarity	NPC62272
0.7603	Intermediate Similarity	NPC470039
0.7597	Intermediate Similarity	NPC251259
0.7594	Intermediate Similarity	NPC471064
0.7594	Intermediate Similarity	NPC48248
0.7591	Intermediate Similarity	NPC43353
0.7586	Intermediate Similarity	NPC225464
0.7583	Intermediate Similarity	NPC54765
0.7583	Intermediate Similarity	NPC188677
0.7578	Intermediate Similarity	NPC318552
0.7578	Intermediate Similarity	NPC190501
0.7578	Intermediate Similarity	NPC99734
0.7576	Intermediate Similarity	NPC254492
0.7576	Intermediate Similarity	NPC71610
0.7576	Intermediate Similarity	NPC145659
0.7576	Intermediate Similarity	NPC9292
0.7574	Intermediate Similarity	NPC225051
0.7565	Intermediate Similarity	NPC274678
0.7563	Intermediate Similarity	NPC327811
0.7563	Intermediate Similarity	NPC254965
0.7561	Intermediate Similarity	NPC260323
0.7561	Intermediate Similarity	NPC151537
0.7561	Intermediate Similarity	NPC308689
0.7561	Intermediate Similarity	NPC176279
0.7561	Intermediate Similarity	NPC322753
0.7561	Intermediate Similarity	NPC268388
0.7557	Intermediate Similarity	NPC199273
0.7544	Intermediate Similarity	NPC181709
0.7538	Intermediate Similarity	NPC255026
0.7538	Intermediate Similarity	NPC174977
0.7538	Intermediate Similarity	NPC120172
0.7535	Intermediate Similarity	NPC296752
0.7521	Intermediate Similarity	NPC132078
0.7521	Intermediate Similarity	NPC78119
0.7521	Intermediate Similarity	NPC151477
0.7521	Intermediate Similarity	NPC51333
0.7521	Intermediate Similarity	NPC216468
0.752	Intermediate Similarity	NPC268160
0.752	Intermediate Similarity	NPC285350
0.752	Intermediate Similarity	NPC107240
0.752	Intermediate Similarity	NPC249270
0.7519	Intermediate Similarity	NPC176130
0.7519	Intermediate Similarity	NPC84672
0.7519	Intermediate Similarity	NPC72667
0.7519	Intermediate Similarity	NPC78364
0.7519	Intermediate Similarity	NPC216216
0.7519	Intermediate Similarity	NPC69424
0.7519	Intermediate Similarity	NPC428300
0.7518	Intermediate Similarity	NPC50924
0.75	Intermediate Similarity	NPC133407
0.75	Intermediate Similarity	NPC42657
0.75	Intermediate Similarity	NPC182240
0.75	Intermediate Similarity	NPC176893
0.75	Intermediate Similarity	NPC28476
0.7482	Intermediate Similarity	NPC245923
0.7481	Intermediate Similarity	NPC27659
0.748	Intermediate Similarity	NPC278652
0.748	Intermediate Similarity	NPC183700
0.748	Intermediate Similarity	NPC116842
0.748	Intermediate Similarity	NPC477136
0.748	Intermediate Similarity	NPC222905
0.7478	Intermediate Similarity	NPC76938
0.7478	Intermediate Similarity	NPC128062
0.7464	Intermediate Similarity	NPC173569
0.7464	Intermediate Similarity	NPC477874
0.7462	Intermediate Similarity	NPC295034
0.746	Intermediate Similarity	NPC23402
0.746	Intermediate Similarity	NPC35797
0.746	Intermediate Similarity	NPC192948
0.746	Intermediate Similarity	NPC147179
0.7459	Intermediate Similarity	NPC95344
0.7458	Intermediate Similarity	NPC211885
0.7458	Intermediate Similarity	NPC225506
0.7458	Intermediate Similarity	NPC213730
0.7447	Intermediate Similarity	NPC225243
0.7445	Intermediate Similarity	NPC53896
0.7445	Intermediate Similarity	NPC473665
0.7444	Intermediate Similarity	NPC15837
0.7442	Intermediate Similarity	NPC473136
0.7442	Intermediate Similarity	NPC69006
0.744	Intermediate Similarity	NPC141003
0.744	Intermediate Similarity	NPC35344
0.7438	Intermediate Similarity	NPC21594
0.7436	Intermediate Similarity	NPC156313
0.7436	Intermediate Similarity	NPC77492
0.7429	Intermediate Similarity	NPC20210
0.7426	Intermediate Similarity	NPC18798
0.7424	Intermediate Similarity	NPC265413
0.7424	Intermediate Similarity	NPC10154
0.7424	Intermediate Similarity	NPC474766
0.7424	Intermediate Similarity	NPC97578
0.7424	Intermediate Similarity	NPC474532
0.7422	Intermediate Similarity	NPC328694
0.7417	Intermediate Similarity	NPC238696
0.7414	Intermediate Similarity	NPC32714
0.7413	Intermediate Similarity	NPC451542
0.7413	Intermediate Similarity	NPC295712
0.7413	Intermediate Similarity	NPC474203
0.7413	Intermediate Similarity	NPC313047
0.741	Intermediate Similarity	NPC474813
0.741	Intermediate Similarity	NPC249817
0.741	Intermediate Similarity	NPC155211
0.7407	Intermediate Similarity	NPC34414
0.7407	Intermediate Similarity	NPC470747
0.7407	Intermediate Similarity	NPC99731
0.7407	Intermediate Similarity	NPC146647
0.7407	Intermediate Similarity	NPC171460
0.7405	Intermediate Similarity	NPC282577

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 NPC71870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	1058
0.2-0.3	1088
0.3-0.4	2991
0.4-0.5	2110
0.5-0.6	1244
0.6-0.7	287
0.7-0.8	29
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
0.7826	Intermediate Similarity	NPD3020	Approved
0.7815	Intermediate Similarity	NPD2342	Discontinued
0.7719	Intermediate Similarity	NPD2859	Approved
0.7719	Intermediate Similarity	NPD2860	Approved
0.7632	Intermediate Similarity	NPD2934	Approved
0.7632	Intermediate Similarity	NPD2933	Approved
0.7609	Intermediate Similarity	NPD5405	Approved
0.7609	Intermediate Similarity	NPD5406	Approved
0.7609	Intermediate Similarity	NPD5404	Approved
0.7609	Intermediate Similarity	NPD5408	Approved
0.7578	Intermediate Similarity	NPD3019	Approved
0.7578	Intermediate Similarity	NPD2286	Discontinued
0.7578	Intermediate Similarity	NPD2932	Approved
0.7578	Intermediate Similarity	NPD4059	Approved
0.7442	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7003	Approved
0.7364	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7390	Discontinued
0.736	Intermediate Similarity	NPD7635	Approved
0.7328	Intermediate Similarity	NPD1201	Approved
0.7328	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3091	Approved
0.7273	Intermediate Similarity	NPD8166	Discontinued
0.7258	Intermediate Similarity	NPD3022	Approved
0.7258	Intermediate Similarity	NPD3021	Approved
0.7239	Intermediate Similarity	NPD1470	Approved
0.7231	Intermediate Similarity	NPD4093	Discontinued
0.7226	Intermediate Similarity	NPD3764	Approved
0.7119	Intermediate Similarity	NPD1809	Phase 2
0.7111	Intermediate Similarity	NPD1164	Approved
0.7094	Intermediate Similarity	NPD845	Approved
0.7068	Intermediate Similarity	NPD3092	Approved
0.7045	Intermediate Similarity	NPD4626	Approved
0.7042	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3023	Approved
0.6992	Remote Similarity	NPD3026	Approved
0.6985	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5951	Approved
0.697	Remote Similarity	NPD3025	Approved
0.697	Remote Similarity	NPD1651	Approved
0.697	Remote Similarity	NPD3024	Approved
0.6963	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4624	Approved
0.6923	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3095	Discontinued
0.6899	Remote Similarity	NPD2234	Approved
0.6899	Remote Similarity	NPD2229	Approved
0.6899	Remote Similarity	NPD2228	Approved
0.6885	Remote Similarity	NPD1242	Phase 1
0.6861	Remote Similarity	NPD3094	Phase 2
0.6857	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD111	Approved
0.6833	Remote Similarity	NPD844	Approved
0.6829	Remote Similarity	NPD846	Approved
0.6829	Remote Similarity	NPD940	Approved
0.6809	Remote Similarity	NPD6663	Approved
0.6803	Remote Similarity	NPD3750	Approved
0.6791	Remote Similarity	NPD4589	Approved
0.6788	Remote Similarity	NPD1283	Approved
0.6786	Remote Similarity	NPD5156	Approved
0.6786	Remote Similarity	NPD7008	Discontinued
0.6786	Remote Similarity	NPD5155	Approved
0.6777	Remote Similarity	NPD288	Approved
0.6774	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5303	Approved
0.6767	Remote Similarity	NPD5304	Approved
0.6765	Remote Similarity	NPD4878	Approved
0.6761	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3028	Approved
0.6742	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7768	Phase 2
0.6719	Remote Similarity	NPD4750	Phase 3
0.6719	Remote Similarity	NPD1792	Phase 2
0.6719	Remote Similarity	NPD5451	Approved
0.6716	Remote Similarity	NPD5691	Approved
0.6715	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3594	Approved
0.6714	Remote Similarity	NPD4908	Phase 1
0.6714	Remote Similarity	NPD3595	Approved
0.6714	Remote Similarity	NPD2605	Approved
0.6714	Remote Similarity	NPD2606	Approved
0.6692	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD1751	Approved
0.6667	Remote Similarity	NPD7037	Approved
0.6646	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3845	Phase 1
0.6599	Remote Similarity	NPD2344	Approved
0.6594	Remote Similarity	NPD6583	Phase 3
0.6594	Remote Similarity	NPD1669	Approved
0.6594	Remote Similarity	NPD6582	Phase 2
0.6591	Remote Similarity	NPD497	Approved
0.6579	Remote Similarity	NPD6273	Approved
0.6575	Remote Similarity	NPD2799	Discontinued
0.6571	Remote Similarity	NPD6584	Phase 3
0.6571	Remote Similarity	NPD2798	Approved
0.6569	Remote Similarity	NPD1281	Approved
0.6567	Remote Similarity	NPD7610	Discontinued
0.6562	Remote Similarity	NPD6959	Discontinued
0.6562	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6353	Approved
0.6544	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2935	Discontinued
0.6528	Remote Similarity	NPD4140	Approved
0.6525	Remote Similarity	NPD4208	Discontinued
0.6525	Remote Similarity	NPD3635	Approved
0.6525	Remote Similarity	NPD3637	Approved
0.6525	Remote Similarity	NPD3636	Approved
0.6522	Remote Similarity	NPD3972	Approved
0.6515	Remote Similarity	NPD496	Approved
0.6515	Remote Similarity	NPD498	Approved
0.6515	Remote Similarity	NPD495	Approved
0.6515	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1929	Approved
0.6508	Remote Similarity	NPD1930	Approved
0.6508	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2797	Approved
0.649	Remote Similarity	NPD3300	Phase 2
0.6484	Remote Similarity	NPD1444	Approved
0.6484	Remote Similarity	NPD1445	Approved
0.6478	Remote Similarity	NPD3749	Approved
0.6475	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5819	Phase 2
0.6463	Remote Similarity	NPD7742	Approved
0.6463	Remote Similarity	NPD3748	Approved
0.6463	Remote Similarity	NPD7743	Approved
0.6458	Remote Similarity	NPD8032	Phase 2
0.6457	Remote Similarity	NPD1237	Approved
0.6456	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2194	Approved
0.6454	Remote Similarity	NPD2195	Approved
0.6449	Remote Similarity	NPD1610	Phase 2
0.6447	Remote Similarity	NPD2421	Approved
0.6447	Remote Similarity	NPD2420	Approved
0.6447	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7041	Phase 2
0.6444	Remote Similarity	NPD5536	Phase 2
0.6438	Remote Similarity	NPD4097	Suspended
0.6438	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6966	Discovery
0.6434	Remote Similarity	NPD7095	Approved
0.6433	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2309	Approved
0.6424	Remote Similarity	NPD8131	Suspended
0.6423	Remote Similarity	NPD6516	Phase 2
0.6423	Remote Similarity	NPD5846	Approved
0.6414	Remote Similarity	NPD3620	Phase 2
0.6414	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD943	Approved
0.641	Remote Similarity	NPD7028	Phase 2
0.6408	Remote Similarity	NPD4212	Discontinued
0.6408	Remote Similarity	NPD2861	Phase 2
0.6397	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7330	Discontinued
0.6392	Remote Similarity	NPD8455	Phase 2
0.6391	Remote Similarity	NPD1241	Discontinued
0.6391	Remote Similarity	NPD5283	Phase 1
0.6389	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3268	Approved
0.6389	Remote Similarity	NPD2313	Discontinued
0.6383	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4103	Phase 2
0.6377	Remote Similarity	NPD3847	Discontinued
0.6377	Remote Similarity	NPD4879	Approved
0.6376	Remote Similarity	NPD7266	Discontinued
0.6376	Remote Similarity	NPD4726	Approved
0.6376	Remote Similarity	NPD2346	Discontinued
0.6376	Remote Similarity	NPD4725	Approved
0.6376	Remote Similarity	NPD4721	Approved
0.6364	Remote Similarity	NPD4207	Discontinued
0.6357	Remote Similarity	NPD968	Approved
0.6357	Remote Similarity	NPD4659	Approved
0.6357	Remote Similarity	NPD5327	Phase 3
0.6357	Remote Similarity	NPD3134	Approved
0.6352	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1510	Phase 2
0.6343	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7451	Discontinued
0.6331	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1611	Approved
0.6328	Remote Similarity	NPD9608	Approved
0.6328	Remote Similarity	NPD9610	Approved
0.6323	Remote Similarity	NPD7427	Discontinued
0.6319	Remote Similarity	NPD5952	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data