NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.07
Volume:	171.438
LogP:	2.41
LogD:	2.629
LogS:	-3.165
# Rotatable Bonds:	1
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	2.11
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.574
MDCK Permeability:	2.030263203778304e-05
Pgp-inhibitor:	0.281
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.432
Plasma Protein Binding (PPB):	96.14498138427734%
Volume Distribution (VD):	1.147
Pgp-substrate:	4.633333683013916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.996
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.486
CYP2C9-inhibitor:	0.352
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	15.361
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.685
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.692
Carcinogencity:	0.892
Eye Corrosion:	0.689
Eye Irritation:	0.975
Respiratory Toxicity:	0.38

Download Data

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

Natural Product: NPC127326

Natural Product ID:	NPC127326
*Common Name:**	Isosafrole
IUPAC Name:	5-[(E)-prop-1-enyl]-1,3-benzodioxole
Synonyms:	Isosafrole
Standard InCHIKey:	VHVOLFRBFDOUSH-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+
SMILES:	C/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487603
PubChem CID:	637796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662104]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[23376010]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	fruits	Coimbatore, India	2010-JUN	PMID[23691929]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27136692]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12728	Artemisia rupestris	Species	Asteraceae	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
MIC	5
Others	2
Potency	17

Activity Type	# Activity
Individual Protein	14
Organism	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	10000.0	nM	PMID[507336]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[507337]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	707.9	nM	PMID[507336]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	1.8	nM	PMID[507337]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	3.2	nM	PMID[507337]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	7.1	nM	PMID[507337]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PMID[507337]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	1059.1	nM	PMID[507337]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[507336]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[507342]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[507342]
NPT167	Organism	Propionibacterium acnes	Propionibacterium acnes	MIC	=	200.0	ug.mL-1	PMID[507334]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	200.0	ug.mL-1	PMID[507335]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	100.0	ug.mL-1	PMID[507335]
NPT523	Organism	Malassezia furfur	Malassezia furfur	MIC	=	100.0	ug.mL-1	PMID[507335]
NPT2	Others	Unspecified		Potency	=	3264.3	nM	PMID[507336]
NPT2	Others	Unspecified		Potency	=	7943.3	nM	PMID[507338]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7375.3	nM	PMID[507336]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[507336]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	3080000.0	nM	PMID[507341]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	75.01	%	PMID[507343]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	79.83	%	PMID[507343]
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PMID[507342]

☑ 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 NPC127326 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	404
0.1-0.2	2425
0.2-0.3	8520
0.3-0.4	11305
0.4-0.5	4187
0.5-0.6	9913
0.6-0.7	4337
0.7-0.8	1438
0.8-0.85	114
0.85-0.9	42
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC31279
0.9307	High Similarity	NPC310905
0.9307	High Similarity	NPC12714
0.9266	High Similarity	NPC199209
0.9266	High Similarity	NPC33271
0.9266	High Similarity	NPC212643
0.9174	High Similarity	NPC111225
0.9126	High Similarity	NPC292792
0.9099	High Similarity	NPC119949
0.9099	High Similarity	NPC69670
0.9018	High Similarity	NPC344161
0.8929	High Similarity	NPC57501
0.8868	High Similarity	NPC227894
0.8868	High Similarity	NPC258171
0.886	High Similarity	NPC80241
0.886	High Similarity	NPC193484
0.886	High Similarity	NPC114845
0.886	High Similarity	NPC301641
0.8783	High Similarity	NPC256167
0.8716	High Similarity	NPC245552
0.8707	High Similarity	NPC249788
0.8704	High Similarity	NPC246358
0.8704	High Similarity	NPC36108
0.8704	High Similarity	NPC7097
0.8704	High Similarity	NPC233731
0.8632	High Similarity	NPC283170
0.8632	High Similarity	NPC191768
0.8632	High Similarity	NPC92869
0.8632	High Similarity	NPC300955
0.8624	High Similarity	NPC179309
0.8624	High Similarity	NPC137685
0.8621	High Similarity	NPC211231
0.8559	High Similarity	NPC170583
0.8559	High Similarity	NPC152186
0.8559	High Similarity	NPC303522
0.8559	High Similarity	NPC85830
0.8559	High Similarity	NPC182147
0.8559	High Similarity	NPC207541
0.8559	High Similarity	NPC246133
0.8559	High Similarity	NPC71105
0.8559	High Similarity	NPC17348
0.8545	High Similarity	NPC156840
0.8545	High Similarity	NPC139617
0.8545	High Similarity	NPC257124
0.8545	High Similarity	NPC8547
0.8545	High Similarity	NPC203924
0.8545	High Similarity	NPC173746
0.8545	High Similarity	NPC78918
0.8545	High Similarity	NPC55300
0.8532	High Similarity	NPC165386
0.8487	Intermediate Similarity	NPC251466
0.8487	Intermediate Similarity	NPC274356
0.8487	Intermediate Similarity	NPC156944
0.8482	Intermediate Similarity	NPC294941
0.8468	Intermediate Similarity	NPC165646
0.8417	Intermediate Similarity	NPC286683
0.8417	Intermediate Similarity	NPC99798
0.8417	Intermediate Similarity	NPC100129
0.8417	Intermediate Similarity	NPC191302
0.8417	Intermediate Similarity	NPC41331
0.8417	Intermediate Similarity	NPC177167
0.8417	Intermediate Similarity	NPC291449
0.8417	Intermediate Similarity	NPC157740
0.8417	Intermediate Similarity	NPC64948
0.8417	Intermediate Similarity	NPC158737
0.8393	Intermediate Similarity	NPC165106
0.8393	Intermediate Similarity	NPC204120
0.8347	Intermediate Similarity	NPC246974
0.8347	Intermediate Similarity	NPC158471
0.8347	Intermediate Similarity	NPC147247
0.8347	Intermediate Similarity	NPC165128
0.8347	Intermediate Similarity	NPC57119
0.8347	Intermediate Similarity	NPC226862
0.8333	Intermediate Similarity	NPC213711
0.8333	Intermediate Similarity	NPC40352
0.8333	Intermediate Similarity	NPC473960
0.8317	Intermediate Similarity	NPC8002
0.8317	Intermediate Similarity	NPC99886
0.8317	Intermediate Similarity	NPC259134
0.8317	Intermediate Similarity	NPC177844
0.8279	Intermediate Similarity	NPC228769
0.8279	Intermediate Similarity	NPC476748
0.8279	Intermediate Similarity	NPC470633
0.825	Intermediate Similarity	NPC120066
0.8246	Intermediate Similarity	NPC475815
0.8246	Intermediate Similarity	NPC47194
0.8246	Intermediate Similarity	NPC473264
0.8235	Intermediate Similarity	NPC71853
0.8214	Intermediate Similarity	NPC195873
0.8211	Intermediate Similarity	NPC63574
0.8211	Intermediate Similarity	NPC275950
0.8211	Intermediate Similarity	NPC233224
0.8211	Intermediate Similarity	NPC271208
0.8197	Intermediate Similarity	NPC469977
0.819	Intermediate Similarity	NPC164706
0.819	Intermediate Similarity	NPC159916
0.819	Intermediate Similarity	NPC277460
0.819	Intermediate Similarity	NPC70744
0.819	Intermediate Similarity	NPC107588
0.819	Intermediate Similarity	NPC137537
0.819	Intermediate Similarity	NPC124916
0.819	Intermediate Similarity	NPC272471
0.819	Intermediate Similarity	NPC205502
0.8174	Intermediate Similarity	NPC268317
0.8174	Intermediate Similarity	NPC123948
0.8174	Intermediate Similarity	NPC221049
0.8174	Intermediate Similarity	NPC81067
0.8174	Intermediate Similarity	NPC9341
0.8155	Intermediate Similarity	NPC321956
0.8145	Intermediate Similarity	NPC476345
0.8145	Intermediate Similarity	NPC227160
0.8145	Intermediate Similarity	NPC192255
0.8145	Intermediate Similarity	NPC82111
0.813	Intermediate Similarity	NPC470706
0.812	Intermediate Similarity	NPC37858
0.8119	Intermediate Similarity	NPC206876
0.8103	Intermediate Similarity	NPC164386
0.8103	Intermediate Similarity	NPC304208
0.8103	Intermediate Similarity	NPC120075
0.8103	Intermediate Similarity	NPC52464
0.8103	Intermediate Similarity	NPC259638
0.8103	Intermediate Similarity	NPC293619
0.8103	Intermediate Similarity	NPC39793
0.8103	Intermediate Similarity	NPC185738
0.8103	Intermediate Similarity	NPC280001
0.808	Intermediate Similarity	NPC147616
0.808	Intermediate Similarity	NPC252833
0.808	Intermediate Similarity	NPC97316
0.808	Intermediate Similarity	NPC104077
0.808	Intermediate Similarity	NPC106739
0.808	Intermediate Similarity	NPC219671
0.808	Intermediate Similarity	NPC7744
0.808	Intermediate Similarity	NPC259742
0.808	Intermediate Similarity	NPC227002
0.808	Intermediate Similarity	NPC471505
0.8073	Intermediate Similarity	NPC12987
0.8073	Intermediate Similarity	NPC474603
0.8067	Intermediate Similarity	NPC57268
0.8067	Intermediate Similarity	NPC126935
0.8067	Intermediate Similarity	NPC312713
0.8067	Intermediate Similarity	NPC172676
0.8067	Intermediate Similarity	NPC65933
0.8067	Intermediate Similarity	NPC216929
0.8065	Intermediate Similarity	NPC173308
0.8065	Intermediate Similarity	NPC134764
0.8065	Intermediate Similarity	NPC477694
0.8065	Intermediate Similarity	NPC184814
0.8065	Intermediate Similarity	NPC181079
0.8065	Intermediate Similarity	NPC477705
0.8065	Intermediate Similarity	NPC171550
0.8051	Intermediate Similarity	NPC222175
0.8051	Intermediate Similarity	NPC2058
0.8051	Intermediate Similarity	NPC202474
0.8049	Intermediate Similarity	NPC302378
0.8034	Intermediate Similarity	NPC255675
0.8034	Intermediate Similarity	NPC474214
0.8034	Intermediate Similarity	NPC470626
0.8034	Intermediate Similarity	NPC474040
0.8017	Intermediate Similarity	NPC193067
0.8016	Intermediate Similarity	NPC6836
0.8016	Intermediate Similarity	NPC266848
0.8016	Intermediate Similarity	NPC471390
0.8016	Intermediate Similarity	NPC25821
0.8016	Intermediate Similarity	NPC282477
0.8016	Intermediate Similarity	NPC136750
0.8016	Intermediate Similarity	NPC58585
0.8016	Intermediate Similarity	NPC284855
0.8016	Intermediate Similarity	NPC196937
0.8016	Intermediate Similarity	NPC169973
0.8016	Intermediate Similarity	NPC471391
0.8016	Intermediate Similarity	NPC473463
0.8016	Intermediate Similarity	NPC205915
0.8	Intermediate Similarity	NPC217574
0.8	Intermediate Similarity	NPC471581
0.8	Intermediate Similarity	NPC477706
0.8	Intermediate Similarity	NPC318862
0.7984	Intermediate Similarity	NPC307110
0.7984	Intermediate Similarity	NPC270849
0.7984	Intermediate Similarity	NPC248355
0.7984	Intermediate Similarity	NPC166040
0.7984	Intermediate Similarity	NPC26653
0.7983	Intermediate Similarity	NPC471877
0.7983	Intermediate Similarity	NPC267064
0.7983	Intermediate Similarity	NPC204466
0.7966	Intermediate Similarity	NPC181969
0.7966	Intermediate Similarity	NPC299406
0.7966	Intermediate Similarity	NPC135961
0.7966	Intermediate Similarity	NPC474320
0.7966	Intermediate Similarity	NPC475961
0.7966	Intermediate Similarity	NPC254625
0.7966	Intermediate Similarity	NPC311595
0.7966	Intermediate Similarity	NPC24474
0.7966	Intermediate Similarity	NPC308217
0.7966	Intermediate Similarity	NPC320987
0.7966	Intermediate Similarity	NPC310338
0.7966	Intermediate Similarity	NPC15805
0.7966	Intermediate Similarity	NPC281298
0.7966	Intermediate Similarity	NPC20674
0.7953	Intermediate Similarity	NPC470881
0.7953	Intermediate Similarity	NPC170779

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 NPC127326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	1138
0.2-0.3	1985
0.3-0.4	2676
0.4-0.5	1622
0.5-0.6	946
0.6-0.7	393
0.7-0.8	49
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9099	High Similarity	NPD1357	Approved
0.8696	High Similarity	NPD3705	Approved
0.8545	High Similarity	NPD228	Approved
0.8393	Intermediate Similarity	NPD5283	Phase 1
0.8145	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD5536	Phase 2
0.7857	Intermediate Similarity	NPD1358	Approved
0.7812	Intermediate Similarity	NPD2492	Phase 1
0.7705	Intermediate Similarity	NPD2981	Phase 2
0.7642	Intermediate Similarity	NPD2982	Phase 2
0.7642	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD2983	Phase 2
0.7632	Intermediate Similarity	NPD2684	Approved
0.7611	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD9296	Approved
0.7442	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD9494	Approved
0.7402	Intermediate Similarity	NPD3018	Phase 2
0.7391	Intermediate Similarity	NPD290	Approved
0.7373	Intermediate Similarity	NPD7843	Approved
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD776	Approved
0.7333	Intermediate Similarity	NPD709	Approved
0.7333	Intermediate Similarity	NPD7157	Approved
0.7313	Intermediate Similarity	NPD1375	Discontinued
0.7302	Intermediate Similarity	NPD2922	Phase 1
0.7299	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1182	Approved
0.7288	Intermediate Similarity	NPD1137	Approved
0.7288	Intermediate Similarity	NPD1139	Approved
0.7287	Intermediate Similarity	NPD3027	Phase 3
0.7287	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5451	Approved
0.7265	Intermediate Similarity	NPD556	Approved
0.7257	Intermediate Similarity	NPD291	Approved
0.7236	Intermediate Similarity	NPD5691	Approved
0.7231	Intermediate Similarity	NPD3144	Approved
0.7231	Intermediate Similarity	NPD5718	Phase 2
0.7231	Intermediate Similarity	NPD5109	Approved
0.7231	Intermediate Similarity	NPD5111	Phase 2
0.7231	Intermediate Similarity	NPD5110	Phase 2
0.7231	Intermediate Similarity	NPD3145	Approved
0.7227	Intermediate Similarity	NPD1138	Approved
0.7214	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4626	Approved
0.7176	Intermediate Similarity	NPD2674	Phase 3
0.7121	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3620	Phase 2
0.7097	Intermediate Similarity	NPD1651	Approved
0.7083	Intermediate Similarity	NPD821	Approved
0.7083	Intermediate Similarity	NPD5535	Approved
0.7068	Intermediate Similarity	NPD3657	Discovery
0.7064	Intermediate Similarity	NPD9365	Approved
0.7063	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD1091	Approved
0.7025	Intermediate Similarity	NPD1241	Discontinued
0.7015	Intermediate Similarity	NPD2653	Approved
0.7009	Intermediate Similarity	NPD968	Approved
0.7008	Intermediate Similarity	NPD1840	Phase 2
0.7007	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1558	Phase 1
0.6985	Remote Similarity	NPD2161	Phase 2
0.6981	Remote Similarity	NPD111	Approved
0.6975	Remote Similarity	NPD3021	Approved
0.6975	Remote Similarity	NPD3022	Approved
0.6963	Remote Similarity	NPD6896	Approved
0.6963	Remote Similarity	NPD6895	Approved
0.696	Remote Similarity	NPD5585	Approved
0.6957	Remote Similarity	NPD4236	Phase 3
0.6957	Remote Similarity	NPD4237	Approved
0.6953	Remote Similarity	NPD5327	Phase 3
0.695	Remote Similarity	NPD4739	Approved
0.6947	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD9697	Approved
0.6918	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2977	Approved
0.6918	Remote Similarity	NPD2978	Approved
0.6912	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6671	Approved
0.6906	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4110	Phase 3
0.6905	Remote Similarity	NPD1778	Approved
0.6899	Remote Similarity	NPD1283	Approved
0.6881	Remote Similarity	NPD9295	Approved
0.6871	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1613	Approved
0.6861	Remote Similarity	NPD3539	Phase 1
0.685	Remote Similarity	NPD3496	Discontinued
0.6849	Remote Similarity	NPD37	Approved
0.6838	Remote Similarity	NPD6111	Discontinued
0.6835	Remote Similarity	NPD6674	Discontinued
0.6822	Remote Similarity	NPD1669	Approved
0.6822	Remote Similarity	NPD3685	Discontinued
0.6822	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD447	Suspended
0.6812	Remote Similarity	NPD3540	Phase 1
0.6806	Remote Similarity	NPD1653	Approved
0.6794	Remote Similarity	NPD4624	Approved
0.6788	Remote Similarity	NPD4108	Discontinued
0.6786	Remote Similarity	NPD6331	Phase 2
0.6774	Remote Similarity	NPD6387	Discontinued
0.6772	Remote Similarity	NPD2667	Approved
0.6772	Remote Similarity	NPD5846	Approved
0.6772	Remote Similarity	NPD6516	Phase 2
0.6772	Remote Similarity	NPD17	Approved
0.6772	Remote Similarity	NPD2668	Approved
0.6767	Remote Similarity	NPD7095	Approved
0.6763	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7153	Discontinued
0.6763	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2808	Discontinued
0.6761	Remote Similarity	NPD5297	Approved
0.6741	Remote Similarity	NPD4060	Phase 1
0.6726	Remote Similarity	NPD2933	Approved
0.6726	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2934	Approved
0.6724	Remote Similarity	NPD1242	Phase 1
0.672	Remote Similarity	NPD3596	Phase 2
0.6719	Remote Similarity	NPD3847	Discontinued
0.6718	Remote Similarity	NPD987	Approved
0.6714	Remote Similarity	NPD3060	Approved
0.6714	Remote Similarity	NPD4162	Approved
0.6711	Remote Similarity	NPD4965	Approved
0.6711	Remote Similarity	NPD4966	Approved
0.6711	Remote Similarity	NPD4967	Phase 2
0.6692	Remote Similarity	NPD4359	Approved
0.6691	Remote Similarity	NPD7266	Discontinued
0.669	Remote Similarity	NPD4210	Discontinued
0.6667	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD9379	Approved
0.6667	Remote Similarity	NPD9377	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD5604	Discontinued
0.6667	Remote Similarity	NPD844	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6645	Remote Similarity	NPD7199	Phase 2
0.6643	Remote Similarity	NPD4357	Discontinued
0.6641	Remote Similarity	NPD1876	Approved
0.6641	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD3020	Approved
0.6623	Remote Similarity	NPD6234	Discontinued
0.6622	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5241	Discontinued
0.6618	Remote Similarity	NPD4140	Approved
0.6617	Remote Similarity	NPD1712	Approved
0.6617	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2861	Phase 2
0.6615	Remote Similarity	NPD1608	Approved
0.6615	Remote Similarity	NPD2232	Approved
0.6615	Remote Similarity	NPD2230	Approved
0.6615	Remote Similarity	NPD2233	Approved
0.6614	Remote Similarity	NPD6580	Approved
0.6614	Remote Similarity	NPD6581	Approved
0.6614	Remote Similarity	NPD1548	Phase 1
0.6614	Remote Similarity	NPD1894	Discontinued
0.6609	Remote Similarity	NPD288	Approved
0.6597	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3146	Approved
0.6597	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1817	Approved
0.6591	Remote Similarity	NPD1820	Approved
0.6591	Remote Similarity	NPD1819	Approved
0.6591	Remote Similarity	NPD1818	Approved
0.6585	Remote Similarity	NPD969	Suspended
0.6581	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7124	Phase 2
0.6573	Remote Similarity	NPD5058	Phase 3
0.6569	Remote Similarity	NPD6355	Discontinued
0.6569	Remote Similarity	NPD5735	Approved
0.6565	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1420	Approved
0.6565	Remote Similarity	NPD1421	Approved
0.6562	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.656	Remote Similarity	NPD593	Approved
0.656	Remote Similarity	NPD595	Approved
0.6558	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD3532	Approved
0.6544	Remote Similarity	NPD3531	Approved
0.6544	Remote Similarity	NPD8032	Phase 2
0.6544	Remote Similarity	NPD3530	Approved
0.6541	Remote Similarity	NPD558	Phase 2
0.6538	Remote Similarity	NPD422	Phase 1
0.6538	Remote Similarity	NPD1610	Phase 2
0.6522	Remote Similarity	NPD2157	Approved
0.6522	Remote Similarity	NPD6653	Approved
0.6515	Remote Similarity	NPD8651	Approved
0.6512	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD2557	Approved
0.6504	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2219	Phase 1

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