NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.07
Volume:	253.163
LogP:	2.563
LogD:	2.503
LogS:	-3.556
# Rotatable Bonds:	2
TPSA:	61.81
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.713
Fsp3:	0.214
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:	-4.659
MDCK Permeability:	3.0054141461732797e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	72.28264617919922%
Volume Distribution (VD):	0.934
Pgp-substrate:	20.366106033325195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.447
CYP2D6-substrate:	0.809
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	7.837
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.376
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.276
Carcinogencity:	0.725
Eye Corrosion:	0.003
Eye Irritation:	0.176
Respiratory Toxicity:	0.758

Download Data

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

Natural Product: NPC264293

Natural Product ID:	NPC264293
*Common Name:**	Khellin
IUPAC Name:	4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one
Synonyms:	Ammivin; Khellin; Khelloyd
Standard InCHIKey:	HSMPDPBYAYSOBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
SMILES:	Cc1cc(=O)c2c(c3ccoc3c(c2o1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL44746
PubChem CID:	3828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones [CHEMONTID:0001735] Furanochromones

*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
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[26091146]
NPO40718	Indian beech tree	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30108931]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22103	Ammi visnaga	Species	Apiaceae	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
AC50	5
IC50	12
Ki	2
Others	55
Potency	27

Activity Type	# Activity
Individual Protein	45
NON-MOLECULAR	5
Organism	19
Others	28
PROTEIN COMPLEX	3
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[510854]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	5011.9	nM	PMID[510856]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PMID[510855]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[510857]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	28183.8	nM	PMID[510855]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	10000.0	nM	PMID[510855]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	5011.9	nM	PMID[510856]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	10000.0	nM	PMID[510856]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	316.2	nM	PMID[510856]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	10000.0	nM	PMID[510856]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	5011.87	nM	PMID[510856]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	5011.87	nM	PMID[510856]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	19.95	nM	PMID[510856]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[510856]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	5489.7	nM	PMID[510856]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[510859]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	7.57	%	PMID[510860]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5700.7	nM	PMID[510861]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[510862]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14319.4	nM	PMID[510861]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	891.3	nM	PMID[510861]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Inhibition	=	92.0	%	PMID[510867]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Inhibition	=	8.0	%	PMID[510867]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	Inhibition	=	5.0	%	PMID[510867]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	Inhibition	=	99.0	%	PMID[510867]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	11.0	%	PMID[510867]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Inhibition	=	12.0	%	PMID[510867]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Inhibition	=	8.0	%	PMID[510867]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Inhibition	=	75.0	%	PMID[510867]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	4020.0	nM	PMID[510867]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Ki	=	3800.0	nM	PMID[510867]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	40.0	nM	PMID[510867]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	Ki	=	31.0	nM	PMID[510867]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	34600.0	nM	PMID[510867]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	10000.0	nM	PMID[510867]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	IC50	>	10000.0	nM	PMID[510867]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	IC50	>	10000.0	nM	PMID[510867]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	10000.0	nM	PMID[510867]
NPT2	Others	Unspecified		T/C	=	1.46	n.a.	PMID[510852]
NPT2	Others	Unspecified		T/C	=	0.37	n.a.	PMID[510852]
NPT2	Others	Unspecified		T/C	=	1.21	n.a.	PMID[510852]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	309000.0	nM	PMID[510853]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	316100.0	nM	PMID[510853]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	PD'2	=	4.46	n.a.	PMID[510853]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	1258.9	nM	PMID[510855]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	8.9	nM	PMID[510855]
NPT2	Others	Unspecified		Potency	=	366.3	nM	PMID[510855]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	147.2	nM	PMID[510855]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[510859]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.3	%	PMID[510860]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	83.15	%	PMID[510863]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	102.23	%	PMID[510863]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	1.0	n.a.	PMID[510864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	0.0	%	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (acute)	=	1.0	n.a.	PMID[510864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (acute)	=	0.0	%	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (cytolytic)	=	1.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (choleostasis)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (severe hepatitis)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (chronic liver disease)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (cirrhosis)	=	0.0	n.a.	PMID[510864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (granulomatous hepatitis)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (association with vascular disease)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (steatosis)	=	0.0	n.a.	PMID[510864]
NPT2	Others	Unspecified		Hepatotoxicity (malignant tumour)	=	0.0	n.a.	PMID[510864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (benign tumour)	=	0.0	n.a.	PMID[510864]
NPT35	Others	n.a.		-log(solubility)	=	4.11	n.a.	PMID[510865]
NPT35	Others	n.a.		-log(solubility)	=	4.51	n.a.	PMID[510865]
NPT35	Others	n.a.		-log(solubility)	=	4.0	n.a.	PMID[510865]
NPT35	Others	n.a.		-log(solubility)	=	4.14	n.a.	PMID[510865]
NPT35	Others	n.a.		-log(solubility)	=	4.01	n.a.	PMID[510865]
NPT35	Others	n.a.		-log(solubility)	=	4.23	n.a.	PMID[510865]
NPT2	Others	Unspecified		AC50	n.a.	707.9	nM	PMID[510866]
NPT21243	SINGLE PROTEIN	Galactocerebrosidase	Homo sapiens	Potency	n.a.	631.0	nM	PMID[510866]
NPT2	Others	Unspecified		Ac50	n.a.	0.7079	uM	PMID[510866]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	15.74	%	PMID[510868]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	13.85	%	PMID[510868]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-6.58	%	PMID[510868]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	20.27	%	PMID[510868]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	5.11	%	PMID[510868]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-0.82	%	PMID[510868]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	-0.57	%	PMID[510868]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition index	=	0.3275	n.a.	PMID[510869]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-17.62	%	PMID[510870]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	21.91	%	PMID[510871]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	11.98	%	PMID[510872]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.11	%	PMID[510873]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.18	%	PMID[510874]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[510875]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[510875]
NPT2	Others	Unspecified		Potency	n.a.	5955.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	7166.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	113.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4064.5	nM	PubChem BioAssay data set

☑ 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 NPC264293 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	573
0.1-0.2	2263
0.2-0.3	5906
0.3-0.4	11916
0.4-0.5	5066
0.5-0.6	4712
0.6-0.7	5890
0.7-0.8	4491
0.8-0.85	1293
0.85-0.9	530
0.9-0.95	48
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC179464
0.9551	High Similarity	NPC78612
0.9551	High Similarity	NPC234536
0.9494	High Similarity	NPC210460
0.9494	High Similarity	NPC155264
0.9494	High Similarity	NPC67450
0.9494	High Similarity	NPC193881
0.949	High Similarity	NPC65846
0.9359	High Similarity	NPC33320
0.9299	High Similarity	NPC243509
0.9241	High Similarity	NPC216092
0.9236	High Similarity	NPC250076
0.9202	High Similarity	NPC62640
0.9198	High Similarity	NPC144288
0.9167	High Similarity	NPC233776
0.9145	High Similarity	NPC190572
0.9103	High Similarity	NPC41719
0.9091	High Similarity	NPC107244
0.9085	High Similarity	NPC233956
0.908	High Similarity	NPC190351
0.908	High Similarity	NPC281835
0.9068	High Similarity	NPC173149
0.9068	High Similarity	NPC179015
0.9038	High Similarity	NPC38361
0.9038	High Similarity	NPC130015
0.903	High Similarity	NPC224165
0.903	High Similarity	NPC53917
0.9018	High Similarity	NPC41853
0.8963	High Similarity	NPC28042
0.8957	High Similarity	NPC167479
0.8957	High Similarity	NPC241820
0.8944	High Similarity	NPC193998
0.8931	High Similarity	NPC19097
0.8916	High Similarity	NPC66804
0.891	High Similarity	NPC135303
0.891	High Similarity	NPC148423
0.8889	High Similarity	NPC263092
0.8889	High Similarity	NPC1755
0.8889	High Similarity	NPC1706
0.8889	High Similarity	NPC59295
0.8889	High Similarity	NPC39305
0.8882	High Similarity	NPC27220
0.8855	High Similarity	NPC72455
0.8854	High Similarity	NPC98028
0.8848	High Similarity	NPC51404
0.8846	High Similarity	NPC69752
0.8839	High Similarity	NPC117463
0.8839	High Similarity	NPC198427
0.8834	High Similarity	NPC36320
0.8834	High Similarity	NPC38914
0.8834	High Similarity	NPC187923
0.8827	High Similarity	NPC238995
0.8795	High Similarity	NPC157522
0.879	High Similarity	NPC201547
0.879	High Similarity	NPC259058
0.8786	High Similarity	NPC60848
0.8782	High Similarity	NPC306788
0.8774	High Similarity	NPC231013
0.8773	High Similarity	NPC15819
0.8758	High Similarity	NPC16935
0.875	High Similarity	NPC45131
0.8743	High Similarity	NPC65885
0.8743	High Similarity	NPC277510
0.8742	High Similarity	NPC472408
0.8742	High Similarity	NPC128961
0.8734	High Similarity	NPC472407
0.8727	High Similarity	NPC247973
0.8726	High Similarity	NPC181250
0.8726	High Similarity	NPC88445
0.872	High Similarity	NPC45449
0.8718	High Similarity	NPC304443
0.8718	High Similarity	NPC74539
0.8718	High Similarity	NPC299923
0.8718	High Similarity	NPC205522
0.8712	High Similarity	NPC272722
0.8704	High Similarity	NPC298093
0.869	High Similarity	NPC289244
0.8679	High Similarity	NPC263676
0.8679	High Similarity	NPC166201
0.8679	High Similarity	NPC253872
0.8671	High Similarity	NPC472406
0.8671	High Similarity	NPC191104
0.8667	High Similarity	NPC472895
0.8662	High Similarity	NPC10304
0.8662	High Similarity	NPC63256
0.8654	High Similarity	NPC110639
0.8654	High Similarity	NPC106461
0.8654	High Similarity	NPC216314
0.8654	High Similarity	NPC14958
0.8654	High Similarity	NPC215932
0.8654	High Similarity	NPC310259
0.8654	High Similarity	NPC120924
0.8654	High Similarity	NPC40818
0.8654	High Similarity	NPC195919
0.865	High Similarity	NPC188486
0.865	High Similarity	NPC258331
0.865	High Similarity	NPC109238
0.8647	High Similarity	NPC104682
0.8642	High Similarity	NPC104459
0.8642	High Similarity	NPC195832
0.8642	High Similarity	NPC257914
0.8642	High Similarity	NPC238405
0.8642	High Similarity	NPC196879
0.8639	High Similarity	NPC8127
0.8639	High Similarity	NPC49667
0.8634	High Similarity	NPC248299
0.8634	High Similarity	NPC180340
0.8634	High Similarity	NPC472461
0.8631	High Similarity	NPC310794
0.8625	High Similarity	NPC279930
0.8625	High Similarity	NPC244371
0.8625	High Similarity	NPC186507
0.8623	High Similarity	NPC131866
0.8623	High Similarity	NPC476641
0.8608	High Similarity	NPC238366
0.8599	High Similarity	NPC85233
0.8598	High Similarity	NPC219861
0.8598	High Similarity	NPC312056
0.8598	High Similarity	NPC273021
0.8598	High Similarity	NPC302741
0.8598	High Similarity	NPC81679
0.8598	High Similarity	NPC18284
0.8598	High Similarity	NPC84515
0.859	High Similarity	NPC136278
0.859	High Similarity	NPC246903
0.859	High Similarity	NPC471590
0.8589	High Similarity	NPC131557
0.8589	High Similarity	NPC246478
0.858	High Similarity	NPC287243
0.858	High Similarity	NPC476981
0.8571	High Similarity	NPC189960
0.8571	High Similarity	NPC276059
0.8571	High Similarity	NPC230619
0.8571	High Similarity	NPC478238
0.8571	High Similarity	NPC54098
0.8571	High Similarity	NPC250769
0.8571	High Similarity	NPC278010
0.8571	High Similarity	NPC241774
0.8571	High Similarity	NPC34725
0.8571	High Similarity	NPC32557
0.8571	High Similarity	NPC475964
0.8571	High Similarity	NPC295608
0.8571	High Similarity	NPC284353
0.8571	High Similarity	NPC122623
0.8563	High Similarity	NPC152477
0.8562	High Similarity	NPC148497
0.8562	High Similarity	NPC292460
0.8562	High Similarity	NPC301123
0.8562	High Similarity	NPC40033
0.8562	High Similarity	NPC60211
0.8562	High Similarity	NPC153008
0.8562	High Similarity	NPC134677
0.8554	High Similarity	NPC277480
0.8553	High Similarity	NPC157944
0.8553	High Similarity	NPC189270
0.8553	High Similarity	NPC5840
0.8553	High Similarity	NPC474274
0.8553	High Similarity	NPC29638
0.8547	High Similarity	NPC8927
0.8547	High Similarity	NPC228209
0.8545	High Similarity	NPC470459
0.8545	High Similarity	NPC132054
0.8544	High Similarity	NPC476342
0.8537	High Similarity	NPC165549
0.8535	High Similarity	NPC302408
0.8535	High Similarity	NPC283002
0.8526	High Similarity	NPC113089
0.8526	High Similarity	NPC23955
0.8526	High Similarity	NPC182842
0.8521	High Similarity	NPC82217
0.8521	High Similarity	NPC216842
0.8521	High Similarity	NPC476640
0.8519	High Similarity	NPC257277
0.8519	High Similarity	NPC245546
0.8519	High Similarity	NPC178854
0.8519	High Similarity	NPC266960
0.8519	High Similarity	NPC43243
0.8519	High Similarity	NPC303255
0.8509	High Similarity	NPC478213
0.8509	High Similarity	NPC131725
0.8509	High Similarity	NPC280937
0.8509	High Similarity	NPC476289
0.8509	High Similarity	NPC86485
0.8509	High Similarity	NPC473664
0.8503	High Similarity	NPC95715
0.8503	High Similarity	NPC186392
0.85	High Similarity	NPC149614
0.85	High Similarity	NPC116604
0.8494	Intermediate Similarity	NPC291110
0.8494	Intermediate Similarity	NPC470457
0.8494	Intermediate Similarity	NPC37183
0.8485	Intermediate Similarity	NPC475144
0.848	Intermediate Similarity	NPC77179
0.848	Intermediate Similarity	NPC23553
0.848	Intermediate Similarity	NPC221820
0.8476	Intermediate Similarity	NPC169
0.8476	Intermediate Similarity	NPC476980
0.8471	Intermediate Similarity	NPC165512
0.8471	Intermediate Similarity	NPC290304
0.8471	Intermediate Similarity	NPC236327

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 NPC264293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	1065
0.2-0.3	2020
0.3-0.4	2802
0.4-0.5	1609
0.5-0.6	808
0.6-0.7	241
0.7-0.8	96
0.8-0.85	13
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1247	Approved
0.9359	High Similarity	NPD919	Approved
0.8718	High Similarity	NPD920	Approved
0.8704	High Similarity	NPD5494	Approved
0.859	High Similarity	NPD642	Clinical (unspecified phase)
0.8519	High Similarity	NPD3882	Suspended
0.8462	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD3926	Phase 2
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8282	Intermediate Similarity	NPD2801	Approved
0.8269	Intermediate Similarity	NPD1243	Approved
0.811	Intermediate Similarity	NPD1934	Approved
0.8075	Intermediate Similarity	NPD1512	Approved
0.8061	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD2796	Approved
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1511	Approved
0.795	Intermediate Similarity	NPD6799	Approved
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7849	Intermediate Similarity	NPD6166	Phase 2
0.7849	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7075	Discontinued
0.7799	Intermediate Similarity	NPD1471	Phase 3
0.7798	Intermediate Similarity	NPD5402	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7673	Intermediate Similarity	NPD1510	Phase 2
0.7665	Intermediate Similarity	NPD4380	Phase 2
0.764	Intermediate Similarity	NPD7808	Phase 3
0.764	Intermediate Similarity	NPD1549	Phase 2
0.7633	Intermediate Similarity	NPD7819	Suspended
0.763	Intermediate Similarity	NPD6232	Discontinued
0.7627	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD7411	Suspended
0.76	Intermediate Similarity	NPD7473	Discontinued
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7251	Discontinued
0.7578	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2403	Approved
0.7532	Intermediate Similarity	NPD1240	Approved
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2800	Approved
0.7472	Intermediate Similarity	NPD7472	Approved
0.7472	Intermediate Similarity	NPD7074	Phase 3
0.747	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5401	Approved
0.7442	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1607	Approved
0.7399	Intermediate Similarity	NPD3749	Approved
0.7399	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5403	Approved
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD447	Suspended
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7362	Intermediate Similarity	NPD2344	Approved
0.736	Intermediate Similarity	NPD2163	Approved
0.7356	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7317	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD2935	Discontinued
0.7301	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD6959	Discontinued
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3748	Approved
0.7238	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3226	Approved
0.7191	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2309	Approved
0.7167	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD230	Phase 1
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD5242	Approved
0.7081	Intermediate Similarity	NPD2313	Discontinued
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6808	Phase 2
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7037	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3750	Approved
0.7021	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5353	Approved
0.6983	Remote Similarity	NPD7199	Phase 2
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6279	Approved
0.6971	Remote Similarity	NPD6280	Approved
0.6964	Remote Similarity	NPD2654	Approved
0.6957	Remote Similarity	NPD5953	Discontinued
0.6957	Remote Similarity	NPD6832	Phase 2
0.6952	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2346	Discontinued
0.694	Remote Similarity	NPD7286	Phase 2
0.6928	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6385	Approved
0.6914	Remote Similarity	NPD6386	Approved
0.6901	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1613	Approved
0.6875	Remote Similarity	NPD37	Approved
0.6868	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4967	Phase 2
0.6854	Remote Similarity	NPD4966	Approved
0.6854	Remote Similarity	NPD4965	Approved
0.6852	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5711	Approved
0.6851	Remote Similarity	NPD7229	Phase 3
0.6851	Remote Similarity	NPD5710	Approved
0.6839	Remote Similarity	NPD1653	Approved
0.6832	Remote Similarity	NPD1019	Discontinued
0.6824	Remote Similarity	NPD4628	Phase 3
0.6812	Remote Similarity	NPD7907	Approved
0.6811	Remote Similarity	NPD1729	Discontinued
0.6807	Remote Similarity	NPD6651	Approved
0.6804	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1241	Discontinued
0.679	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4107	Approved
0.6784	Remote Similarity	NPD3887	Approved
0.6784	Remote Similarity	NPD6190	Approved
0.6778	Remote Similarity	NPD6234	Discontinued
0.677	Remote Similarity	NPD3267	Approved
0.677	Remote Similarity	NPD3266	Approved
0.6768	Remote Similarity	NPD1296	Phase 2
0.6763	Remote Similarity	NPD3146	Approved
0.6763	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2353	Approved
0.6746	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5761	Phase 2
0.6742	Remote Similarity	NPD5760	Phase 2
0.6731	Remote Similarity	NPD5536	Phase 2
0.6724	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5889	Approved
0.6723	Remote Similarity	NPD5890	Approved
0.6715	Remote Similarity	NPD4111	Phase 1
0.6715	Remote Similarity	NPD4665	Approved
0.6709	Remote Similarity	NPD17	Approved
0.6707	Remote Similarity	NPD3027	Phase 3
0.6704	Remote Similarity	NPD2296	Approved
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6687	Remote Similarity	NPD9717	Approved
0.6685	Remote Similarity	NPD6844	Discontinued
0.6683	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD4482	Phase 3
0.6649	Remote Similarity	NPD6765	Approved
0.6649	Remote Similarity	NPD6764	Approved
0.6647	Remote Similarity	NPD6355	Discontinued
0.6633	Remote Similarity	NPD3057	Approved
0.6627	Remote Similarity	NPD6233	Phase 2
0.6626	Remote Similarity	NPD2798	Approved
0.6611	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7390	Discontinued
0.6608	Remote Similarity	NPD2424	Discontinued
0.66	Remote Similarity	NPD7697	Approved
0.66	Remote Similarity	NPD7698	Approved
0.66	Remote Similarity	NPD7696	Phase 3
0.6596	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2354	Approved
0.6587	Remote Similarity	NPD4307	Phase 2
0.6585	Remote Similarity	NPD3018	Phase 2
0.6584	Remote Similarity	NPD1608	Approved
0.6584	Remote Similarity	NPD3972	Approved
0.6582	Remote Similarity	NPD4361	Phase 2
0.6582	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4287	Approved
0.6573	Remote Similarity	NPD6585	Discontinued
0.6571	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7870	Phase 2
0.6567	Remote Similarity	NPD7871	Phase 2
0.6566	Remote Similarity	NPD3268	Approved
0.6566	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6798	Discontinued

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