NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	184.13
Volume:	220.405
LogP:	5.142
LogD:	4.267
LogS:	-6.092
# Rotatable Bonds:	1
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	1.658
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.545
MDCK Permeability:	1.770268863765523e-05
Pgp-inhibitor:	0.735
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.266
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	97.0793228149414%
Volume Distribution (VD):	0.882
Pgp-substrate:	2.033267021179199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.261
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.526

ADMET: Excretion

Clearance (CL):	8.017
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.344
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.152
Carcinogencity:	0.578
Eye Corrosion:	0.669
Eye Irritation:	0.991
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC22760

Natural Product ID:	NPC22760
*Common Name:**	Chamazulene
IUPAC Name:	7-ethyl-1,4-dimethylazulene
Synonyms:	Chamazulene
Standard InCHIKey:	GXGJIOMUZAGVEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
SMILES:	CCc1ccc(c2c(c1)c(C)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495665
PubChem CID:	10719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762792]
NPO17534	Uvaria chamae	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[15217292]
NPO12907	Hypericum carinatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921431]
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	Eukaryota	essential oil	n.a.	n.a.	PMID[16933870]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[25051625]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	Bark	n.a.	n.a.	PMID[28290698]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[8158164]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158164]
NPO17534	Uvaria chamae	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[845713]
NPO19246	Skimmia laureola	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO23177	Achillea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27984	Achillea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17534	Uvaria chamae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19246	Skimmia laureola	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23177	Achillea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17534	Uvaria chamae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27984	Achillea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19246	Skimmia laureola	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29083	Matricaria chamomilla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30415	Lindera aggregate	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31274	Lindera strychnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30745	Chrysanthemum morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23177	Achillea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27984	Achillea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27984	Achillea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19748	Aspergillus phoenicis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21477	Euryops rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17534	Uvaria chamae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO542	Artemisia absinthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28772	Polygonum mite	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13840	Streptomyces incarnatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20602	Trichomanes reniforme	Species	Hymenophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17743	Solanum aculeatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23177	Achillea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20180	Rabdosia loxothyrsa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12907	Hypericum carinatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11665	Kloeckera brevis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19246	Skimmia laureola	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20253	Eucalyptus decorticans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10235	Castanopsis eyrei	Species	Fagaceae	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
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	1490.0	nM	PMID[538061]

☑ 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 NPC22760 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	1053
0.1-0.2	3838
0.2-0.3	16507
0.3-0.4	16767
0.4-0.5	3654
0.5-0.6	633
0.6-0.7	174
0.7-0.8	40
0.8-0.85	26
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC297358
0.9524	High Similarity	NPC264470
0.8551	High Similarity	NPC263385
0.831	Intermediate Similarity	NPC1901
0.8209	Intermediate Similarity	NPC21211
0.8209	Intermediate Similarity	NPC113670
0.8182	Intermediate Similarity	NPC135924
0.8182	Intermediate Similarity	NPC210849
0.8116	Intermediate Similarity	NPC267443
0.8088	Intermediate Similarity	NPC32312
0.8088	Intermediate Similarity	NPC198023
0.8088	Intermediate Similarity	NPC155172
0.806	Intermediate Similarity	NPC29680
0.8	Intermediate Similarity	NPC212114
0.8	Intermediate Similarity	NPC65873
0.8	Intermediate Similarity	NPC120441
0.8	Intermediate Similarity	NPC300345
0.7971	Intermediate Similarity	NPC178527
0.7941	Intermediate Similarity	NPC88566
0.7941	Intermediate Similarity	NPC45756
0.791	Intermediate Similarity	NPC238023
0.791	Intermediate Similarity	NPC150196
0.791	Intermediate Similarity	NPC248705
0.791	Intermediate Similarity	NPC246588
0.791	Intermediate Similarity	NPC54368
0.791	Intermediate Similarity	NPC310758
0.7887	Intermediate Similarity	NPC139416
0.7887	Intermediate Similarity	NPC473206
0.7887	Intermediate Similarity	NPC213570
0.7887	Intermediate Similarity	NPC246822
0.7846	Intermediate Similarity	NPC269586
0.7846	Intermediate Similarity	NPC198841
0.7826	Intermediate Similarity	NPC291066
0.7794	Intermediate Similarity	NPC66517
0.7794	Intermediate Similarity	NPC22786
0.7778	Intermediate Similarity	NPC251490
0.7763	Intermediate Similarity	NPC255345
0.7761	Intermediate Similarity	NPC147062
0.7692	Intermediate Similarity	NPC277704
0.7692	Intermediate Similarity	NPC149436
0.7671	Intermediate Similarity	NPC158028
0.7671	Intermediate Similarity	NPC280135
0.7671	Intermediate Similarity	NPC135433
0.7671	Intermediate Similarity	NPC87099
0.7671	Intermediate Similarity	NPC226999
0.7671	Intermediate Similarity	NPC39799
0.7671	Intermediate Similarity	NPC193578
0.7671	Intermediate Similarity	NPC1008
0.7612	Intermediate Similarity	NPC8235
0.7612	Intermediate Similarity	NPC36357
0.7612	Intermediate Similarity	NPC64270
0.7612	Intermediate Similarity	NPC114327
0.7606	Intermediate Similarity	NPC6107
0.7536	Intermediate Similarity	NPC71009
0.7534	Intermediate Similarity	NPC72670
0.75	Intermediate Similarity	NPC169110
0.7465	Intermediate Similarity	NPC113837
0.7465	Intermediate Similarity	NPC289915
0.7368	Intermediate Similarity	NPC307195
0.7333	Intermediate Similarity	NPC54269
0.7286	Intermediate Similarity	NPC200745
0.7237	Intermediate Similarity	NPC258492
0.7237	Intermediate Similarity	NPC96835
0.7215	Intermediate Similarity	NPC159661
0.7125	Intermediate Similarity	NPC315216
0.7105	Intermediate Similarity	NPC212463
0.7079	Intermediate Similarity	NPC261947
0.6988	Remote Similarity	NPC133162
0.6986	Remote Similarity	NPC36440
0.6962	Remote Similarity	NPC3190
0.6962	Remote Similarity	NPC249018
0.6944	Remote Similarity	NPC50266
0.6933	Remote Similarity	NPC200936
0.6901	Remote Similarity	NPC45255
0.6875	Remote Similarity	NPC245896
0.6875	Remote Similarity	NPC66270
0.6875	Remote Similarity	NPC103488
0.6835	Remote Similarity	NPC110264
0.6824	Remote Similarity	NPC243166
0.68	Remote Similarity	NPC311343
0.6782	Remote Similarity	NPC113307
0.6761	Remote Similarity	NPC147578
0.6753	Remote Similarity	NPC74458
0.675	Remote Similarity	NPC9796
0.675	Remote Similarity	NPC298023
0.6711	Remote Similarity	NPC5324
0.6711	Remote Similarity	NPC98880
0.6709	Remote Similarity	NPC276699
0.6709	Remote Similarity	NPC189371
0.6707	Remote Similarity	NPC50063
0.6707	Remote Similarity	NPC285716
0.6707	Remote Similarity	NPC157055
0.6707	Remote Similarity	NPC17408
0.6667	Remote Similarity	NPC200624
0.6667	Remote Similarity	NPC285679
0.6667	Remote Similarity	NPC224544
0.6629	Remote Similarity	NPC475023
0.6629	Remote Similarity	NPC475059
0.6627	Remote Similarity	NPC231986
0.6627	Remote Similarity	NPC242628
0.6623	Remote Similarity	NPC229235
0.6623	Remote Similarity	NPC95289
0.6588	Remote Similarity	NPC95429
0.6585	Remote Similarity	NPC272260
0.6582	Remote Similarity	NPC112609
0.6582	Remote Similarity	NPC122327
0.6582	Remote Similarity	NPC113000
0.6579	Remote Similarity	NPC82770
0.6579	Remote Similarity	NPC78954
0.6579	Remote Similarity	NPC239931
0.6556	Remote Similarity	NPC475057
0.6548	Remote Similarity	NPC230068
0.6543	Remote Similarity	NPC290638
0.6538	Remote Similarity	NPC326200
0.6538	Remote Similarity	NPC208302
0.6506	Remote Similarity	NPC328178
0.6506	Remote Similarity	NPC184030
0.6506	Remote Similarity	NPC164449
0.6494	Remote Similarity	NPC169222
0.6494	Remote Similarity	NPC16190
0.6494	Remote Similarity	NPC235059
0.6463	Remote Similarity	NPC137847
0.6463	Remote Similarity	NPC76455
0.6456	Remote Similarity	NPC271437
0.6456	Remote Similarity	NPC244738
0.6447	Remote Similarity	NPC52330
0.6437	Remote Similarity	NPC148231
0.6429	Remote Similarity	NPC133050
0.642	Remote Similarity	NPC139658
0.642	Remote Similarity	NPC271642
0.6395	Remote Similarity	NPC267704
0.6386	Remote Similarity	NPC139901
0.6386	Remote Similarity	NPC151405
0.6375	Remote Similarity	NPC208075
0.6375	Remote Similarity	NPC108218
0.6374	Remote Similarity	NPC314690
0.6353	Remote Similarity	NPC121478
0.6353	Remote Similarity	NPC73637
0.6344	Remote Similarity	NPC21959
0.6341	Remote Similarity	NPC329318
0.6341	Remote Similarity	NPC98269
0.6341	Remote Similarity	NPC179726
0.6341	Remote Similarity	NPC325662
0.6333	Remote Similarity	NPC58872
0.6329	Remote Similarity	NPC155429
0.6322	Remote Similarity	NPC475710
0.6322	Remote Similarity	NPC474354
0.631	Remote Similarity	NPC95868
0.631	Remote Similarity	NPC477703
0.631	Remote Similarity	NPC190567
0.6308	Remote Similarity	NPC11150
0.6296	Remote Similarity	NPC98976
0.6279	Remote Similarity	NPC477770
0.6279	Remote Similarity	NPC119677
0.6277	Remote Similarity	NPC251579
0.6277	Remote Similarity	NPC133135
0.6265	Remote Similarity	NPC285470
0.6265	Remote Similarity	NPC36342
0.6265	Remote Similarity	NPC2785
0.6264	Remote Similarity	NPC79917
0.625	Remote Similarity	NPC474211
0.6235	Remote Similarity	NPC145053
0.6235	Remote Similarity	NPC273033
0.6235	Remote Similarity	NPC12936
0.622	Remote Similarity	NPC175393
0.6207	Remote Similarity	NPC304538
0.6207	Remote Similarity	NPC168855
0.6203	Remote Similarity	NPC219246
0.619	Remote Similarity	NPC170484
0.619	Remote Similarity	NPC469894
0.619	Remote Similarity	NPC300205
0.618	Remote Similarity	NPC69057
0.618	Remote Similarity	NPC60408
0.6163	Remote Similarity	NPC103387
0.6163	Remote Similarity	NPC283012
0.6163	Remote Similarity	NPC14326
0.6163	Remote Similarity	NPC323103
0.6163	Remote Similarity	NPC475199
0.6154	Remote Similarity	NPC181786
0.6154	Remote Similarity	NPC277277
0.6146	Remote Similarity	NPC7435
0.6145	Remote Similarity	NPC3672
0.6145	Remote Similarity	NPC287790
0.6145	Remote Similarity	NPC245966
0.6136	Remote Similarity	NPC99482
0.6136	Remote Similarity	NPC252067
0.6118	Remote Similarity	NPC71664
0.6118	Remote Similarity	NPC164086
0.6118	Remote Similarity	NPC121800
0.61	Remote Similarity	NPC472700
0.61	Remote Similarity	NPC472699
0.6098	Remote Similarity	NPC32203
0.6098	Remote Similarity	NPC206800
0.6092	Remote Similarity	NPC273758
0.6092	Remote Similarity	NPC44830
0.6092	Remote Similarity	NPC270507
0.6092	Remote Similarity	NPC39600
0.6092	Remote Similarity	NPC104070
0.6092	Remote Similarity	NPC197581
0.6092	Remote Similarity	NPC172984

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 NPC22760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	898
0.1-0.2	852
0.2-0.3	3288
0.3-0.4	2844
0.4-0.5	892
0.5-0.6	290
0.6-0.7	77
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9844	High Similarity	NPD1673	Approved
0.8209	Intermediate Similarity	NPD675	Discontinued
0.7875	Intermediate Similarity	NPD1697	Approved
0.7342	Intermediate Similarity	NPD3979	Approved
0.7342	Intermediate Similarity	NPD3981	Approved
0.7125	Intermediate Similarity	NPD3904	Approved
0.7125	Intermediate Similarity	NPD3903	Approved
0.7083	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4635	Approved
0.6988	Remote Similarity	NPD3429	Approved
0.6988	Remote Similarity	NPD3427	Approved
0.6974	Remote Similarity	NPD294	Approved
0.6974	Remote Similarity	NPD292	Approved
0.6933	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3035	Approved
0.675	Remote Similarity	NPD4144	Approved
0.675	Remote Similarity	NPD4147	Approved
0.6747	Remote Similarity	NPD4170	Approved
0.6747	Remote Similarity	NPD4169	Approved
0.6747	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3346	Approved
0.6705	Remote Similarity	NPD3344	Approved
0.6667	Remote Similarity	NPD4000	Phase 3
0.6667	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2001	Discontinued
0.6628	Remote Similarity	NPD4406	Approved
0.6628	Remote Similarity	NPD4409	Approved
0.6627	Remote Similarity	NPD4027	Approved
0.6627	Remote Similarity	NPD4026	Approved
0.6588	Remote Similarity	NPD4544	Approved
0.6588	Remote Similarity	NPD5178	Approved
0.6585	Remote Similarity	NPD590	Approved
0.6585	Remote Similarity	NPD1475	Approved
0.6585	Remote Similarity	NPD589	Approved
0.6582	Remote Similarity	NPD9591	Approved
0.6582	Remote Similarity	NPD9593	Approved
0.6582	Remote Similarity	NPD9590	Approved
0.6582	Remote Similarity	NPD9588	Approved
0.6582	Remote Similarity	NPD80	Approved
0.6582	Remote Similarity	NPD9589	Approved
0.6582	Remote Similarity	NPD9594	Approved
0.6582	Remote Similarity	NPD9592	Approved
0.6552	Remote Similarity	NPD3428	Approved
0.6552	Remote Similarity	NPD3426	Approved
0.6506	Remote Similarity	NPD914	Suspended
0.6506	Remote Similarity	NPD1617	Discontinued
0.6506	Remote Similarity	NPD260	Discontinued
0.6477	Remote Similarity	NPD3345	Approved
0.6463	Remote Similarity	NPD9564	Approved
0.6463	Remote Similarity	NPD9563	Approved
0.6463	Remote Similarity	NPD79	Approved
0.6456	Remote Similarity	NPD9728	Phase 1
0.6437	Remote Similarity	NPD4636	Approved
0.6386	Remote Similarity	NPD1053	Approved
0.6386	Remote Similarity	NPD1052	Approved
0.6386	Remote Similarity	NPD1051	Approved
0.6375	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1508	Approved
0.6364	Remote Similarity	NPD2002	Discontinued
0.6364	Remote Similarity	NPD4145	Approved
0.6364	Remote Similarity	NPD4146	Approved
0.6344	Remote Similarity	NPD1738	Approved
0.6341	Remote Similarity	NPD603	Approved
0.6322	Remote Similarity	NPD2205	Approved
0.6322	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2208	Approved
0.631	Remote Similarity	NPD5372	Approved
0.631	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5371	Approved
0.6292	Remote Similarity	NPD5675	Discontinued
0.6279	Remote Similarity	NPD3971	Phase 1
0.6279	Remote Similarity	NPD1185	Approved
0.6265	Remote Similarity	NPD293	Approved
0.6265	Remote Similarity	NPD295	Approved
0.6265	Remote Similarity	NPD296	Approved
0.6264	Remote Similarity	NPD4543	Discontinued
0.625	Remote Similarity	NPD3099	Discontinued
0.6235	Remote Similarity	NPD942	Approved
0.6222	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2539	Approved
0.6207	Remote Similarity	NPD2538	Approved
0.6196	Remote Similarity	NPD4405	Approved
0.6196	Remote Similarity	NPD4408	Approved
0.6196	Remote Similarity	NPD4407	Approved
0.618	Remote Similarity	NPD1087	Approved
0.617	Remote Similarity	NPD1843	Approved
0.6154	Remote Similarity	NPD5915	Approved
0.6154	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5916	Discontinued
0.6129	Remote Similarity	NPD4542	Approved
0.6129	Remote Similarity	NPD4545	Approved
0.6111	Remote Similarity	NPD1101	Approved
0.6098	Remote Similarity	NPD9716	Approved
0.6092	Remote Similarity	NPD831	Approved
0.6092	Remote Similarity	NPD263	Approved
0.6092	Remote Similarity	NPD830	Approved
0.6092	Remote Similarity	NPD423	Phase 3
0.6092	Remote Similarity	NPD262	Approved
0.6071	Remote Similarity	NPD225	Approved
0.6071	Remote Similarity	NPD9397	Approved
0.6071	Remote Similarity	NPD9393	Approved
0.6071	Remote Similarity	NPD227	Approved
0.6067	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1693	Approved
0.6047	Remote Similarity	NPD472	Approved
0.6044	Remote Similarity	NPD771	Phase 3
0.6023	Remote Similarity	NPD785	Approved
0.6	Remote Similarity	NPD1989	Approved
0.6	Remote Similarity	NPD781	Approved
0.6	Remote Similarity	NPD5963	Phase 2
0.6	Remote Similarity	NPD3093	Approved
0.6	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6	Remote Similarity	NPD507	Approved
0.6	Remote Similarity	NPD780	Approved
0.6	Remote Similarity	NPD3457	Approved
0.6	Remote Similarity	NPD508	Approved
0.6	Remote Similarity	NPD5964	Phase 2
0.6	Remote Similarity	NPD3458	Approved
0.6	Remote Similarity	NPD783	Approved
0.6	Remote Similarity	NPD782	Approved
0.6	Remote Similarity	NPD3456	Approved
0.598	Remote Similarity	NPD8010	Approved
0.598	Remote Similarity	NPD8009	Approved
0.5978	Remote Similarity	NPD3672	Approved
0.5978	Remote Similarity	NPD1086	Approved
0.5978	Remote Similarity	NPD4728	Approved
0.5978	Remote Similarity	NPD1090	Approved
0.5978	Remote Similarity	NPD1089	Approved
0.5978	Remote Similarity	NPD3673	Approved
0.5957	Remote Similarity	NPD3980	Approved
0.5957	Remote Similarity	NPD1563	Approved
0.5957	Remote Similarity	NPD3982	Approved
0.5957	Remote Similarity	NPD2878	Approved
0.5955	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5597	Approved
0.5938	Remote Similarity	NPD5598	Approved
0.5938	Remote Similarity	NPD713	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5630	Phase 1
0.5914	Remote Similarity	NPD2997	Approved
0.5914	Remote Similarity	NPD1239	Approved
0.5914	Remote Similarity	NPD3000	Approved
0.5914	Remote Similarity	NPD7609	Phase 3
0.5914	Remote Similarity	NPD2998	Approved
0.5909	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5554	Approved
0.5895	Remote Similarity	NPD4094	Approved
0.587	Remote Similarity	NPD800	Approved
0.587	Remote Similarity	NPD5347	Phase 2
0.587	Remote Similarity	NPD5346	Phase 2
0.5862	Remote Similarity	NPD226	Approved
0.5851	Remote Similarity	NPD1088	Approved
0.5851	Remote Similarity	NPD7631	Approved
0.5843	Remote Similarity	NPD9395	Approved
0.5833	Remote Similarity	NPD6472	Discontinued
0.5833	Remote Similarity	NPD2005	Discontinued
0.5833	Remote Similarity	NPD2895	Discontinued
0.5833	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4793	Discontinued
0.5824	Remote Similarity	NPD650	Approved
0.5816	Remote Similarity	NPD4737	Phase 2
0.5814	Remote Similarity	NPD9490	Approved
0.5789	Remote Similarity	NPD845	Approved
0.5789	Remote Similarity	NPD735	Approved
0.5789	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD736	Approved
0.5789	Remote Similarity	NPD1409	Phase 3
0.5784	Remote Similarity	NPD3459	Approved
0.5773	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD1564	Approved
0.5773	Remote Similarity	NPD4657	Approved
0.5773	Remote Similarity	NPD1565	Approved
0.5773	Remote Similarity	NPD4655	Approved
0.5773	Remote Similarity	NPD1566	Phase 3
0.5765	Remote Similarity	NPD9294	Approved
0.5761	Remote Similarity	NPD531	Approved
0.5745	Remote Similarity	NPD517	Discontinued
0.5745	Remote Similarity	NPD530	Approved
0.573	Remote Similarity	NPD9491	Approved
0.5729	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD2655	Approved
0.5729	Remote Similarity	NPD2656	Approved
0.5729	Remote Similarity	NPD4814	Discontinued
0.5729	Remote Similarity	NPD688	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6049	Phase 2
0.5727	Remote Similarity	NPD5569	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4117	Approved
0.5714	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5832	Phase 3
0.57	Remote Similarity	NPD2841	Approved
0.5699	Remote Similarity	NPD1629	Approved
0.5699	Remote Similarity	NPD1628	Approved
0.5684	Remote Similarity	NPD752	Approved
0.567	Remote Similarity	NPD2859	Approved
0.567	Remote Similarity	NPD2860	Approved
0.5657	Remote Similarity	NPD4008	Approved
0.5657	Remote Similarity	NPD4007	Approved
0.5657	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3020	Approved
0.5652	Remote Similarity	NPD506	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