NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.04
Volume:	209.781
LogP:	1.971
LogD:	2.324
LogS:	-3.557
# Rotatable Bonds:	1
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.505
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	3.1867632060311735e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	79.68633270263672%
Volume Distribution (VD):	0.917
Pgp-substrate:	14.914276123046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.547
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.803
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	12.973
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.844
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.308
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.236
Skin Sensitization:	0.185
Carcinogencity:	0.906
Eye Corrosion:	0.007
Eye Irritation:	0.081
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC179464

Natural Product ID:	NPC179464
*Common Name:**	Sphondin
IUPAC Name:	6-methoxyfuro[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	DLCJNIBLOSKIQW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H8O4/c1-14-9-6-7-2-3-10(13)16-11(7)8-4-5-15-12(8)9/h2-6H,1H3
SMILES:	COc1cc2ccc(=O)oc2c2ccoc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1452868
PubChem CID:	108104
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO2060	Garcinia parvifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12494345]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[27019553]
NPO40718	Indian beech tree	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30108931]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31381	Auricularia auricula	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11015	Zanthoxylum echinocarpum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11015	Zanthoxylum echinocarpum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31381	Auricularia auricula	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9075.2	Peucedanum govanianum (wall) benth ex c. b. clarke var. bicolo wolff	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10614	Pinus krempfii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2060	Garcinia parvifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9090	Patrinia villosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12210	Hypoxylon sclerophaeum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6521	Quercus sessilis	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11846	Ulosa spongia	Species	Dictyonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11015	Zanthoxylum echinocarpum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9329	Acanthus montanus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2815	Schenkia spicata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8827	Kniphofia tuckii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8564	Cornicularia normoerica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7487	Antidesma membranaceum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12569	Trixis inula	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
Others	3
Potency	23

Activity Type	# Activity
Individual Protein	21
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	2511.9	nM	PMID[470526]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	6309.6	nM	PMID[470526]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[470527]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[470526]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[470526]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	22387.2	nM	PMID[470527]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3981.1	nM	PMID[470526]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[470526]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	259.3	nM	PMID[470527]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[470527]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	316.2	nM	PMID[470527]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[470527]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Inhibition	=	67.0	%	PMID[470529]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000.0	nM	PMID[470526]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	12589.3	nM	PMID[470527]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	31622.8	nM	PMID[470526]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[470527]
NPT2	Others	Unspecified		Potency	=	8199.5	nM	PMID[470527]
NPT2	Others	Unspecified		Potency	=	316.2	nM	PMID[470526]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4653.5	nM	PMID[470527]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[470527]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	56234.1	nM	PMID[470527]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[470527]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	126.97	%	PMID[470528]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	102.52	%	PMID[470528]

☑ 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 NPC179464 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	590
0.1-0.2	2371
0.2-0.3	6075
0.3-0.4	11478
0.4-0.5	5581
0.5-0.6	4756
0.6-0.7	5765
0.7-0.8	4701
0.8-0.85	1127
0.85-0.9	207
0.9-0.95	34
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC234536
0.9935	High Similarity	NPC78612
0.9872	High Similarity	NPC193881
0.9872	High Similarity	NPC155264
0.9872	High Similarity	NPC210460
0.9872	High Similarity	NPC67450
0.974	High Similarity	NPC33320
0.9677	High Similarity	NPC243509
0.9615	High Similarity	NPC216092
0.9615	High Similarity	NPC264293
0.9563	High Similarity	NPC144288
0.9448	High Similarity	NPC107244
0.9444	High Similarity	NPC233956
0.9441	High Similarity	NPC281835
0.9434	High Similarity	NPC173149
0.9434	High Similarity	NPC179015
0.9387	High Similarity	NPC224165
0.9387	High Similarity	NPC53917
0.9226	High Similarity	NPC98028
0.9207	High Similarity	NPC72455
0.9202	High Similarity	NPC51404
0.913	High Similarity	NPC15819
0.913	High Similarity	NPC65846
0.9097	High Similarity	NPC88445
0.9091	High Similarity	NPC74539
0.9091	High Similarity	NPC304443
0.9038	High Similarity	NPC191104
0.8987	High Similarity	NPC186507
0.8976	High Similarity	NPC62640
0.8961	High Similarity	NPC246903
0.8931	High Similarity	NPC250769
0.8931	High Similarity	NPC276059
0.8931	High Similarity	NPC278010
0.8931	High Similarity	NPC122623
0.8931	High Similarity	NPC34725
0.8931	High Similarity	NPC295608
0.8931	High Similarity	NPC241774
0.8916	High Similarity	NPC475964
0.8882	High Similarity	NPC250076
0.8875	High Similarity	NPC257277
0.8868	High Similarity	NPC131725
0.8841	High Similarity	NPC187923
0.8839	High Similarity	NPC208584
0.8831	High Similarity	NPC51146
0.8831	High Similarity	NPC166858
0.8831	High Similarity	NPC313036
0.8827	High Similarity	NPC169
0.882	High Similarity	NPC19097
0.8812	High Similarity	NPC233776
0.8795	High Similarity	NPC41853
0.879	High Similarity	NPC266743
0.8782	High Similarity	NPC190572
0.878	High Similarity	NPC1755
0.878	High Similarity	NPC263092
0.878	High Similarity	NPC39305
0.878	High Similarity	NPC59295
0.878	High Similarity	NPC1706
0.8773	High Similarity	NPC14822
0.8766	High Similarity	NPC27220
0.875	High Similarity	NPC41719
0.8743	High Similarity	NPC190351
0.8742	High Similarity	NPC472535
0.8742	High Similarity	NPC474388
0.8742	High Similarity	NPC474170
0.8735	High Similarity	NPC167479
0.8734	High Similarity	NPC69752
0.8728	High Similarity	NPC73703
0.8727	High Similarity	NPC36320
0.8726	High Similarity	NPC117463
0.872	High Similarity	NPC238995
0.8712	High Similarity	NPC49009
0.8712	High Similarity	NPC303210
0.8712	High Similarity	NPC239270
0.8712	High Similarity	NPC95472
0.8704	High Similarity	NPC269495
0.8698	High Similarity	NPC66804
0.8696	High Similarity	NPC471746
0.8688	High Similarity	NPC38361
0.8688	High Similarity	NPC130015
0.8679	High Similarity	NPC177839
0.8679	High Similarity	NPC259058
0.8679	High Similarity	NPC155882
0.8679	High Similarity	NPC201547
0.8675	High Similarity	NPC472895
0.8667	High Similarity	NPC132054
0.8662	High Similarity	NPC231013
0.865	High Similarity	NPC257914
0.865	High Similarity	NPC238405
0.865	High Similarity	NPC16935
0.865	High Similarity	NPC104459
0.8645	High Similarity	NPC254010
0.8642	High Similarity	NPC45131
0.8642	High Similarity	NPC19860
0.8639	High Similarity	NPC65885
0.8636	High Similarity	NPC262635
0.8634	High Similarity	NPC244371
0.8634	High Similarity	NPC279930
0.8634	High Similarity	NPC472408
0.8634	High Similarity	NPC128961
0.8631	High Similarity	NPC28042
0.8625	High Similarity	NPC198615
0.8625	High Similarity	NPC474663
0.8623	High Similarity	NPC247973
0.8623	High Similarity	NPC241820
0.8616	High Similarity	NPC181250
0.8614	High Similarity	NPC280893
0.8614	High Similarity	NPC45449
0.8608	High Similarity	NPC299923
0.8608	High Similarity	NPC205522
0.8606	High Similarity	NPC302741
0.8606	High Similarity	NPC273021
0.8606	High Similarity	NPC193998
0.8606	High Similarity	NPC18284
0.8606	High Similarity	NPC272722
0.8598	High Similarity	NPC298093
0.8598	High Similarity	NPC131557
0.8596	High Similarity	NPC98546
0.8589	High Similarity	NPC270044
0.858	High Similarity	NPC478238
0.858	High Similarity	NPC284353
0.858	High Similarity	NPC157522
0.8571	High Similarity	NPC153008
0.8571	High Similarity	NPC148497
0.8571	High Similarity	NPC292460
0.8571	High Similarity	NPC166201
0.8563	High Similarity	NPC298071
0.8563	High Similarity	NPC323137
0.8562	High Similarity	NPC29056
0.8562	High Similarity	NPC148423
0.8562	High Similarity	NPC135303
0.8553	High Similarity	NPC63256
0.8553	High Similarity	NPC10304
0.8545	High Similarity	NPC188486
0.8544	High Similarity	NPC40818
0.8544	High Similarity	NPC215932
0.8544	High Similarity	NPC120924
0.8544	High Similarity	NPC106461
0.8544	High Similarity	NPC14958
0.8544	High Similarity	NPC195919
0.8544	High Similarity	NPC110639
0.8544	High Similarity	NPC216314
0.8544	High Similarity	NPC310259
0.8538	High Similarity	NPC8127
0.8538	High Similarity	NPC49667
0.8537	High Similarity	NPC15764
0.8537	High Similarity	NPC196879
0.8537	High Similarity	NPC195832
0.8529	High Similarity	NPC310794
0.8529	High Similarity	NPC261471
0.8528	High Similarity	NPC180340
0.8528	High Similarity	NPC472461
0.8528	High Similarity	NPC248299
0.8521	High Similarity	NPC476641
0.8521	High Similarity	NPC131866
0.8519	High Similarity	NPC478213
0.8509	High Similarity	NPC473732
0.8503	High Similarity	NPC279768
0.8503	High Similarity	NPC475369
0.8503	High Similarity	NPC38914
0.85	High Similarity	NPC474648
0.85	High Similarity	NPC238366
0.8494	Intermediate Similarity	NPC312056
0.8494	Intermediate Similarity	NPC81679
0.8494	Intermediate Similarity	NPC84515
0.8494	Intermediate Similarity	NPC108767
0.8491	Intermediate Similarity	NPC198427
0.8491	Intermediate Similarity	NPC85233
0.8488	Intermediate Similarity	NPC297807
0.8485	Intermediate Similarity	NPC246478
0.8485	Intermediate Similarity	NPC477164
0.8485	Intermediate Similarity	NPC139876
0.8481	Intermediate Similarity	NPC471590
0.8481	Intermediate Similarity	NPC136278
0.848	Intermediate Similarity	NPC290304
0.848	Intermediate Similarity	NPC287243
0.848	Intermediate Similarity	NPC236327
0.8476	Intermediate Similarity	NPC310206
0.8476	Intermediate Similarity	NPC258644
0.8476	Intermediate Similarity	NPC476981
0.8475	Intermediate Similarity	NPC60848
0.8471	Intermediate Similarity	NPC230619
0.8471	Intermediate Similarity	NPC54098
0.8466	Intermediate Similarity	NPC32557
0.8466	Intermediate Similarity	NPC189960
0.8462	Intermediate Similarity	NPC280493
0.8462	Intermediate Similarity	NPC470856
0.8462	Intermediate Similarity	NPC211309
0.8462	Intermediate Similarity	NPC152477
0.8457	Intermediate Similarity	NPC301123
0.8457	Intermediate Similarity	NPC68882
0.8457	Intermediate Similarity	NPC40033
0.8457	Intermediate Similarity	NPC60211
0.8457	Intermediate Similarity	NPC134677
0.8457	Intermediate Similarity	NPC475116
0.8452	Intermediate Similarity	NPC277480
0.8447	Intermediate Similarity	NPC189270
0.8447	Intermediate Similarity	NPC5840
0.8443	Intermediate Similarity	NPC470459
0.8443	Intermediate Similarity	NPC110257
0.8442	Intermediate Similarity	NPC474274

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 NPC179464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1072
0.2-0.3	2198
0.3-0.4	2695
0.4-0.5	1585
0.5-0.6	750
0.6-0.7	242
0.7-0.8	89
0.8-0.85	15
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.974	High Similarity	NPD919	Approved
0.9615	High Similarity	NPD1247	Approved
0.9091	High Similarity	NPD920	Approved
0.8961	High Similarity	NPD642	Clinical (unspecified phase)
0.8831	High Similarity	NPD643	Clinical (unspecified phase)
0.8636	High Similarity	NPD1243	Approved
0.8598	High Similarity	NPD5494	Approved
0.858	High Similarity	NPD3817	Phase 2
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD3926	Phase 2
0.8187	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8057	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7075	Discontinued
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8024	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7977	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD1512	Approved
0.7964	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7862	Intermediate Similarity	NPD2796	Approved
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7853	Intermediate Similarity	NPD1511	Approved
0.7849	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7473	Discontinued
0.7759	Intermediate Similarity	NPD6166	Phase 2
0.7759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD447	Suspended
0.7719	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD5401	Approved
0.7661	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.764	Intermediate Similarity	NPD6797	Phase 2
0.7633	Intermediate Similarity	NPD7411	Suspended
0.7605	Intermediate Similarity	NPD5403	Approved
0.7598	Intermediate Similarity	NPD7251	Discontinued
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD1510	Phase 2
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD1549	Phase 2
0.7546	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.7528	Intermediate Similarity	NPD7054	Approved
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7074	Phase 3
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1471	Phase 3
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3748	Approved
0.7444	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1240	Approved
0.7414	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2800	Approved
0.7391	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7768	Phase 2
0.7346	Intermediate Similarity	NPD1607	Approved
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3226	Approved
0.7303	Intermediate Similarity	NPD5242	Approved
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7263	Intermediate Similarity	NPD2403	Approved
0.7256	Intermediate Similarity	NPD2799	Discontinued
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3750	Approved
0.7234	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD943	Approved
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5353	Approved
0.7191	Intermediate Similarity	NPD7199	Phase 2
0.7191	Intermediate Similarity	NPD6959	Discontinued
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.717	Intermediate Similarity	NPD1019	Discontinued
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7151	Intermediate Similarity	NPD1653	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD6386	Approved
0.7126	Intermediate Similarity	NPD6385	Approved
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2309	Approved
0.7099	Intermediate Similarity	NPD1296	Phase 2
0.7088	Intermediate Similarity	NPD2163	Approved
0.7086	Intermediate Similarity	NPD37	Approved
0.7072	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD4966	Approved
0.7062	Intermediate Similarity	NPD4967	Phase 2
0.7056	Intermediate Similarity	NPD3787	Discontinued
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD6808	Phase 2
0.7056	Intermediate Similarity	NPD5711	Approved
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7048	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4628	Phase 3
0.7035	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9717	Approved
0.7019	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3887	Approved
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6234	Discontinued
0.6977	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3146	Approved
0.6974	Remote Similarity	NPD4107	Approved
0.6964	Remote Similarity	NPD2353	Approved
0.6964	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD17	Approved
0.6939	Remote Similarity	NPD4482	Phase 3
0.6909	Remote Similarity	NPD4307	Phase 2
0.6898	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3267	Approved
0.6894	Remote Similarity	NPD3266	Approved
0.6893	Remote Similarity	NPD6279	Approved
0.6893	Remote Similarity	NPD6280	Approved
0.689	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.689	Remote Similarity	NPD411	Approved
0.6888	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2654	Approved
0.6869	Remote Similarity	NPD7435	Discontinued
0.6867	Remote Similarity	NPD6355	Discontinued
0.6859	Remote Similarity	NPD4287	Approved
0.6855	Remote Similarity	NPD422	Phase 1
0.6848	Remote Similarity	NPD6233	Phase 2
0.6845	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1608	Approved
0.6807	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1613	Approved
0.6802	Remote Similarity	NPD2354	Approved
0.6788	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD9268	Approved
0.6768	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.676	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6764	Approved
0.6755	Remote Similarity	NPD6765	Approved
0.6754	Remote Similarity	NPD8150	Discontinued
0.675	Remote Similarity	NPD1611	Approved
0.6746	Remote Similarity	NPD7907	Approved
0.6746	Remote Similarity	NPD7033	Discontinued
0.6746	Remote Similarity	NPD4308	Phase 3
0.6744	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5049	Phase 3
0.6742	Remote Similarity	NPD5889	Approved
0.6742	Remote Similarity	NPD5890	Approved
0.6738	Remote Similarity	NPD1729	Discontinued
0.6734	Remote Similarity	NPD5006	Approved
0.6734	Remote Similarity	NPD5005	Approved
0.6726	Remote Similarity	NPD6651	Approved
0.6721	Remote Similarity	NPD8127	Discontinued
0.672	Remote Similarity	NPD7549	Discontinued
0.672	Remote Similarity	NPD7228	Approved
0.6717	Remote Similarity	NPD6779	Approved
0.6717	Remote Similarity	NPD6776	Approved
0.6717	Remote Similarity	NPD6780	Approved
0.6717	Remote Similarity	NPD6781	Approved
0.6717	Remote Similarity	NPD6782	Approved
0.6717	Remote Similarity	NPD6777	Approved
0.6717	Remote Similarity	NPD6778	Approved
0.671	Remote Similarity	NPD1241	Discontinued
0.6708	Remote Similarity	NPD9269	Phase 2
0.6707	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4060	Phase 1
0.6687	Remote Similarity	NPD3268	Approved
0.6686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1652	Phase 2
0.6685	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8312	Approved
0.6684	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD7875	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