NPASS Compound

Structure

CID285973 OpenBabel06191716092D 22 25 0 0 0 0 0 0 0 0999 V2000 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 8 2 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 9 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.05
Volume:	282.716
LogP:	2.875
LogD:	2.559
LogS:	-3.867
# Rotatable Bonds:	1
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	2.577
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.752
MDCK Permeability:	1.858633004303556e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.00470733642578%
Volume Distribution (VD):	0.5
Pgp-substrate:	2.3187131881713867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.802
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	10.034
Half-life (T1/2):	0.497

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.601
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.8
Carcinogencity:	0.789
Eye Corrosion:	0.008
Eye Irritation:	0.907
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC285973

Natural Product ID:	NPC285973
*Common Name:**	9-Hydroxy-7-(4-Hydroxyphenyl)-[1,3]Dioxolo[4,5-G]Chromen-8-One
IUPAC Name:	9-hydroxy-7-(4-hydroxyphenyl)-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:
Standard InCHIKey:	NUGRQNBDTZWXTP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2
SMILES:	c1cc(ccc1c1coc2cc3c(c(c2c1=O)O)OCO3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3527329
PubChem CID:	5281779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94679-X]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795841]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22388969]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25204177]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30199256]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040154]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28647	Fleischmannia deborabellae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29071	Anacardium giganteum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28624	Canthium gilfillanii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28328	Cortispongilla barroisi	Species	Malawispongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28672	Ficus cunia	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28761	Tricholoma populinum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22882	Biancaea millettii	Species	Fabaceae	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
Ki	13
Others	37

Activity Type	# Activity
Individual Protein	29
Others	7
Tissue	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	FC	=	48.4	n.a.	PMID[465701]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	Activity	=	138.0	%	PMID[465701]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	Activity	=	151.0	%	PMID[465701]
NPT27	Others	Unspecified		Ki	=	183400.0	nM	PMID[465700]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Vmax	=	0.27	nmol/mg/min	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Km	=	24600.0	nM	PMID[465700]
NPT903	Individual Protein	UDP-glucuronosyltransferase 1-7	Homo sapiens	Km	=	9400.0	nM	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Km	=	70900.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Ki	=	96900.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Vmax	=	0.34	nmol/mg/min	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Ki	=	65300.0	nM	PMID[465700]
NPT699	Individual Protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Vmax	=	1.03	nmol/mg/min	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Vmax	=	0.54	nmol/mg/min	PMID[465700]
NPT903	Individual Protein	UDP-glucuronosyltransferase 1-7	Homo sapiens	Ki	=	101000.0	nM	PMID[465700]
NPT27	Others	Unspecified		Vmax	=	0.28	nmol/mg/min	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Vmax	=	1.0	nmol/mg/min	PMID[465700]
NPT699	Individual Protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	CL	=	99900.0	mL.min-1.g-1	PMID[465700]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	CL	=	53300.0	mL.min-1.g-1	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	CL	=	27200.0	mL.min-1.g-1	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	CL	=	20200.0	mL.min-1.g-1	PMID[465700]
NPT903	Individual Protein	UDP-glucuronosyltransferase 1-7	Homo sapiens	CL	=	3900.0	mL.min-1.g-1	PMID[465700]
NPT27	Others	Unspecified		CL	=	71800.0	mL.min-1.g-1	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	CL	=	51000.0	mL.min-1.g-1	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	CL	=	48500.0	mL.min-1.g-1	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Vmax	=	0.14	nmol/mg/min	PMID[465700]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Ki	=	534000.0	nM	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Ki	=	8500.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Km	=	9800.0	nM	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Vmax	=	1.37	nmol/mg/min	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Vmax	=	0.67	nmol/mg/min	PMID[465700]
NPT903	Individual Protein	UDP-glucuronosyltransferase 1-7	Homo sapiens	Vmax	=	0.04	nmol/mg/min	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Ki	=	22600.0	nM	PMID[465700]
NPT27	Others	Unspecified		Km	=	16800.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Vmax	=	0.43	nmol/mg/min	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Km	=	34000.0	nM	PMID[465700]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Km	=	5000.0	nM	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Vmax	=	1.33	nmol/mg/min	PMID[465700]
NPT27	Others	Unspecified		Vmax	=	4.87	nmol/mg/min	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Km	=	32900.0	nM	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Km	=	87500.0	nM	PMID[465700]
NPT699	Individual Protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Km	=	10300.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Km	=	64700.0	nM	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Km	=	124500.0	nM	PMID[465700]
NPT27	Others	Unspecified		Km	=	88600.0	nM	PMID[465700]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Ki	=	14100.0	nM	PMID[465700]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Ki	=	23400.0	nM	PMID[465700]
NPT699	Individual Protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Ki	=	121300.0	nM	PMID[465700]
NPT626	Tissue	Liver microsome	Homo sapiens	Ki	=	50900.0	nM	PMID[465700]
NPT587	Tissue	Liver microsome	Rattus norvegicus	Ki	=	44700.0	nM	PMID[465700]
NPT27	Others	Unspecified		Ki	=	49100.0	nM	PMID[465700]

☑ 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 NPC285973 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	558
0.1-0.2	2117
0.2-0.3	5153
0.3-0.4	11156
0.4-0.5	6179
0.5-0.6	4023
0.6-0.7	5243
0.7-0.8	5086
0.8-0.85	1814
0.85-0.9	1068
0.9-0.95	286
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC225624
0.9934	High Similarity	NPC260640
0.9934	High Similarity	NPC295009
0.9803	High Similarity	NPC62518
0.9803	High Similarity	NPC215375
0.9737	High Similarity	NPC167595
0.9603	High Similarity	NPC104728
0.9603	High Similarity	NPC35544
0.9551	High Similarity	NPC470178
0.9548	High Similarity	NPC162668
0.9536	High Similarity	NPC288316
0.9474	High Similarity	NPC291802
0.9474	High Similarity	NPC148497
0.9474	High Similarity	NPC209487
0.9474	High Similarity	NPC269451
0.9474	High Similarity	NPC35763
0.9474	High Similarity	NPC181209
0.9474	High Similarity	NPC216769
0.9474	High Similarity	NPC245382
0.9474	High Similarity	NPC100263
0.9474	High Similarity	NPC131266
0.9474	High Similarity	NPC153008
0.9474	High Similarity	NPC100971
0.9474	High Similarity	NPC121522
0.9412	High Similarity	NPC124714
0.9412	High Similarity	NPC478213
0.9408	High Similarity	NPC19980
0.9408	High Similarity	NPC45291
0.9371	High Similarity	NPC42892
0.9351	High Similarity	NPC39184
0.9342	High Similarity	NPC156953
0.9342	High Similarity	NPC10467
0.9338	High Similarity	NPC218490
0.9286	High Similarity	NPC57211
0.9286	High Similarity	NPC250557
0.9281	High Similarity	NPC279061
0.9281	High Similarity	NPC262623
0.9276	High Similarity	NPC40290
0.9276	High Similarity	NPC139293
0.9276	High Similarity	NPC264550
0.9276	High Similarity	NPC333691
0.9276	High Similarity	NPC69430
0.9276	High Similarity	NPC195763
0.9276	High Similarity	NPC200060
0.9276	High Similarity	NPC264289
0.9276	High Similarity	NPC142876
0.9272	High Similarity	NPC188074
0.9272	High Similarity	NPC125449
0.925	High Similarity	NPC76482
0.9241	High Similarity	NPC469575
0.9226	High Similarity	NPC18954
0.9226	High Similarity	NPC130589
0.9226	High Similarity	NPC134287
0.9226	High Similarity	NPC478238
0.9221	High Similarity	NPC52623
0.9216	High Similarity	NPC239363
0.9216	High Similarity	NPC234152
0.9211	High Similarity	NPC194653
0.9211	High Similarity	NPC287395
0.9211	High Similarity	NPC183655
0.9211	High Similarity	NPC139364
0.9211	High Similarity	NPC80710
0.9211	High Similarity	NPC203747
0.9211	High Similarity	NPC254702
0.9202	High Similarity	NPC472607
0.9198	High Similarity	NPC205076
0.9198	High Similarity	NPC307518
0.9198	High Similarity	NPC48773
0.9193	High Similarity	NPC471287
0.9177	High Similarity	NPC470756
0.9161	High Similarity	NPC471981
0.915	High Similarity	NPC92722
0.915	High Similarity	NPC102003
0.9136	High Similarity	NPC471416
0.9136	High Similarity	NPC212748
0.9136	High Similarity	NPC105511
0.9136	High Similarity	NPC224462
0.9136	High Similarity	NPC34287
0.913	High Similarity	NPC45618
0.913	High Similarity	NPC58716
0.913	High Similarity	NPC471288
0.913	High Similarity	NPC146792
0.9125	High Similarity	NPC165720
0.9119	High Similarity	NPC81679
0.9114	High Similarity	NPC269906
0.9108	High Similarity	NPC78103
0.9108	High Similarity	NPC474990
0.9108	High Similarity	NPC210084
0.9108	High Similarity	NPC99597
0.9103	High Similarity	NPC20830
0.9103	High Similarity	NPC2928
0.9103	High Similarity	NPC213622
0.9103	High Similarity	NPC256612
0.9097	High Similarity	NPC156222
0.9097	High Similarity	NPC239128
0.9097	High Similarity	NPC187498
0.9097	High Similarity	NPC188203
0.9097	High Similarity	NPC241498
0.9097	High Similarity	NPC301323
0.9097	High Similarity	NPC212678
0.9097	High Similarity	NPC198826
0.9097	High Similarity	NPC83508
0.9097	High Similarity	NPC100887
0.9097	High Similarity	NPC256283
0.9097	High Similarity	NPC293183
0.9097	High Similarity	NPC25270
0.9097	High Similarity	NPC120163
0.9097	High Similarity	NPC292460
0.9097	High Similarity	NPC71334
0.9097	High Similarity	NPC222830
0.9097	High Similarity	NPC275836
0.9097	High Similarity	NPC131624
0.9097	High Similarity	NPC275722
0.9097	High Similarity	NPC57030
0.9097	High Similarity	NPC162313
0.9091	High Similarity	NPC45873
0.9085	High Similarity	NPC15329
0.9085	High Similarity	NPC131451
0.908	High Similarity	NPC235575
0.908	High Similarity	NPC223375
0.908	High Similarity	NPC475825
0.9079	High Similarity	NPC12377
0.9079	High Similarity	NPC143903
0.9079	High Similarity	NPC88345
0.9079	High Similarity	NPC226987
0.9074	High Similarity	NPC58053
0.9074	High Similarity	NPC186807
0.9074	High Similarity	NPC170675
0.9074	High Similarity	NPC201292
0.9074	High Similarity	NPC226294
0.9074	High Similarity	NPC471457
0.9074	High Similarity	NPC105025
0.9074	High Similarity	NPC93337
0.9074	High Similarity	NPC112755
0.9074	High Similarity	NPC475942
0.9074	High Similarity	NPC469931
0.9074	High Similarity	NPC45638
0.9073	High Similarity	NPC38065
0.9073	High Similarity	NPC242893
0.9068	High Similarity	NPC113093
0.9068	High Similarity	NPC254306
0.9062	High Similarity	NPC110257
0.9062	High Similarity	NPC88043
0.9057	High Similarity	NPC94155
0.9057	High Similarity	NPC471290
0.9045	High Similarity	NPC235165
0.9045	High Similarity	NPC255106
0.9045	High Similarity	NPC472916
0.9038	High Similarity	NPC280937
0.9038	High Similarity	NPC206238
0.9038	High Similarity	NPC271779
0.9038	High Similarity	NPC176775
0.9038	High Similarity	NPC167091
0.9038	High Similarity	NPC183878
0.9038	High Similarity	NPC145379
0.9038	High Similarity	NPC255350
0.9038	High Similarity	NPC88645
0.9038	High Similarity	NPC274327
0.9038	High Similarity	NPC231018
0.9038	High Similarity	NPC292214
0.9038	High Similarity	NPC160951
0.9038	High Similarity	NPC244371
0.9038	High Similarity	NPC22519
0.9038	High Similarity	NPC69394
0.9038	High Similarity	NPC47781
0.9032	High Similarity	NPC251110
0.9032	High Similarity	NPC256406
0.903	High Similarity	NPC257714
0.9026	High Similarity	NPC17286
0.9026	High Similarity	NPC296197
0.9026	High Similarity	NPC259713
0.9026	High Similarity	NPC216318
0.902	High Similarity	NPC93034
0.902	High Similarity	NPC119660
0.9018	High Similarity	NPC22195
0.9018	High Similarity	NPC183357
0.9018	High Similarity	NPC245014
0.9018	High Similarity	NPC282987
0.9018	High Similarity	NPC72249
0.9018	High Similarity	NPC21190
0.9018	High Similarity	NPC44558
0.9018	High Similarity	NPC474434
0.9018	High Similarity	NPC84265
0.9013	High Similarity	NPC224687
0.9012	High Similarity	NPC45400
0.9012	High Similarity	NPC135345
0.9012	High Similarity	NPC229729
0.9006	High Similarity	NPC470773
0.8994	High Similarity	NPC476980
0.8987	High Similarity	NPC258644
0.8987	High Similarity	NPC472914
0.8987	High Similarity	NPC474836
0.8987	High Similarity	NPC245758
0.8987	High Similarity	NPC222814
0.8987	High Similarity	NPC470402
0.8987	High Similarity	NPC472911
0.8987	High Similarity	NPC96167
0.8987	High Similarity	NPC475267
0.8987	High Similarity	NPC472910
0.8987	High Similarity	NPC156057

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 NPC285973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	481
0.1-0.2	997
0.2-0.3	2083
0.3-0.4	2676
0.4-0.5	1634
0.5-0.6	859
0.6-0.7	278
0.7-0.8	104
0.8-0.85	23
0.85-0.9	11
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9371	High Similarity	NPD3818	Discontinued
0.9038	High Similarity	NPD2801	Approved
0.8855	High Similarity	NPD4338	Clinical (unspecified phase)
0.8854	High Similarity	NPD1934	Approved
0.8805	High Similarity	NPD3882	Suspended
0.8727	High Similarity	NPD7054	Approved
0.8701	High Similarity	NPD1511	Approved
0.8675	High Similarity	NPD7074	Phase 3
0.8675	High Similarity	NPD7472	Approved
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.859	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8543	High Similarity	NPD1510	Phase 2
0.8512	High Similarity	NPD6797	Phase 2
0.8462	Intermediate Similarity	NPD7251	Discontinued
0.8418	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5494	Approved
0.8412	Intermediate Similarity	NPD7808	Phase 3
0.8395	Intermediate Similarity	NPD3817	Phase 2
0.8375	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD943	Approved
0.8204	Intermediate Similarity	NPD6232	Discontinued
0.8166	Intermediate Similarity	NPD7473	Discontinued
0.8158	Intermediate Similarity	NPD1240	Approved
0.8144	Intermediate Similarity	NPD1247	Approved
0.8141	Intermediate Similarity	NPD1549	Phase 2
0.814	Intermediate Similarity	NPD6559	Discontinued
0.8077	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8038	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7964	Intermediate Similarity	NPD7075	Discontinued
0.7939	Intermediate Similarity	NPD37	Approved
0.7921	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD919	Approved
0.7914	Intermediate Similarity	NPD1653	Approved
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7898	Intermediate Similarity	NPD2796	Approved
0.7892	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6799	Approved
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD230	Phase 1
0.7861	Intermediate Similarity	NPD5844	Phase 1
0.7853	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6801	Discontinued
0.7824	Intermediate Similarity	NPD7199	Phase 2
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7798	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD7819	Suspended
0.7751	Intermediate Similarity	NPD3749	Approved
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD2532	Approved
0.773	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2533	Approved
0.7727	Intermediate Similarity	NPD7685	Pre-registration
0.7722	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD3750	Approved
0.7701	Intermediate Similarity	NPD3751	Discontinued
0.7701	Intermediate Similarity	NPD7228	Approved
0.7665	Intermediate Similarity	NPD7411	Suspended
0.7636	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD5403	Approved
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5401	Approved
0.7613	Intermediate Similarity	NPD3027	Phase 3
0.7597	Intermediate Similarity	NPD9494	Approved
0.758	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7548	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6190	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD2800	Approved
0.7529	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7423	Intermediate Similarity	NPD1243	Approved
0.7419	Intermediate Similarity	NPD2798	Approved
0.7414	Intermediate Similarity	NPD6959	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD3748	Approved
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD9269	Phase 2
0.7384	Intermediate Similarity	NPD7768	Phase 2
0.7348	Intermediate Similarity	NPD8313	Approved
0.7348	Intermediate Similarity	NPD8312	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7317	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.724	Intermediate Similarity	NPD7698	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.7238	Intermediate Similarity	NPD7240	Approved
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5242	Approved
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD2309	Approved
0.7213	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7182	Intermediate Similarity	NPD5953	Discontinued
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7173	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7286	Phase 2
0.716	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD1203	Approved
0.7128	Intermediate Similarity	NPD7584	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7124	Intermediate Similarity	NPD9268	Approved
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5006	Approved
0.7098	Intermediate Similarity	NPD5005	Approved
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.7073	Intermediate Similarity	NPD2799	Discontinued
0.7071	Intermediate Similarity	NPD7801	Approved
0.7068	Intermediate Similarity	NPD7699	Phase 2
0.7068	Intermediate Similarity	NPD7700	Phase 2
0.7052	Intermediate Similarity	NPD6385	Approved
0.7052	Intermediate Similarity	NPD6386	Approved
0.7041	Intermediate Similarity	NPD7390	Discontinued
0.7041	Intermediate Similarity	NPD4357	Discontinued
0.7029	Intermediate Similarity	NPD5353	Approved
0.7025	Intermediate Similarity	NPD1470	Approved
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7028	Phase 2
0.6987	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7783	Phase 2
0.6985	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4420	Approved
0.697	Remote Similarity	NPD7033	Discontinued
0.6952	Remote Similarity	NPD8150	Discontinued
0.6948	Remote Similarity	NPD1548	Phase 1
0.6947	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6213	Phase 3
0.6947	Remote Similarity	NPD6212	Phase 3
0.6943	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD6099	Approved
0.6927	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6844	Discontinued
0.6912	Remote Similarity	NPD2899	Discontinued
0.6901	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6832	Phase 2
0.6889	Remote Similarity	NPD7229	Phase 3
0.6888	Remote Similarity	NPD7680	Approved
0.6883	Remote Similarity	NPD5536	Phase 2
0.6879	Remote Similarity	NPD1201	Approved
0.6879	Remote Similarity	NPD3705	Approved
0.6879	Remote Similarity	NPD1610	Phase 2
0.6878	Remote Similarity	NPD4287	Approved
0.6875	Remote Similarity	NPD8455	Phase 2
0.6867	Remote Similarity	NPD4308	Phase 3
0.6864	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD9545	Approved
0.6836	Remote Similarity	NPD4288	Approved
0.6835	Remote Similarity	NPD9717	Approved
0.6832	Remote Similarity	NPD2861	Phase 2
0.6832	Remote Similarity	NPD3018	Phase 2
0.6828	Remote Similarity	NPD7549	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