NPASS Compound

Structure

CID19721 OpenBabel06191715342D 23 25 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 5 2 0 0 0 0 1 8 1 0 0 0 0 2 5 1 0 0 0 0 2 9 2 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 5 1 1 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.05
Volume:	294.193
LogP:	0.11
LogD:	-0.313
LogS:	-2.312
# Rotatable Bonds:	1
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	3.718
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.338
MDCK Permeability:	3.938849204132566e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	87.42156219482422%
Volume Distribution (VD):	0.595
Pgp-substrate:	13.104990005493164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.538
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	8.145
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.389
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.95
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.909
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC19721

Natural Product ID:	NPC19721
*Common Name:**	(2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-Trihydroxyphenyl)-2,3-Dihydrochromen-4-One
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	KJXSIXMJHKAJOD-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m0/s1
SMILES:	c1c(cc(c(c1O)O)O)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3348861
PubChem CID:	161557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins [CHEMONTID:0001594] Epigallocatechins

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[11824572]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12033510]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713398]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO2449	Alangium grisolleoides	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124751]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124775]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562825]
NPO30996	Ampelopsis cantoniensis	Species	Vitaceae	Eukaryota	n.a.	root	n.a.	PMID[17059013]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791473]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21082802]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28165740]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	Pericarp	n.a.	n.a.	PMID[9748380]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30276	Ampelopsis grossedentata	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5490	Rhododendron cinnabarinum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5490	Rhododendron cinnabarinum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29193	Nekemias grossedentata	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5490	Rhododendron cinnabarinum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30276	Ampelopsis grossedentata	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26958	Uvaria griffithii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20659	Aplysia parvula	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29193	Nekemias grossedentata	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2107	Leycesteria formosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20994	Cryptocarya alba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2449	Alangium grisolleoides	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16729	Annella reticulata	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18373	Chromodoris lochi	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6667	Zephyranthes sulphurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12887	Brevibacterium linens	Species	Brevibacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2403	Glochidion sumatranum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18208	Streptomyces thermoviolaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2373	Popillia japonica	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8843	Epipactis palustris	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	16
Others	8
Potency	2

Activity Type	# Activity
Cell Line	8
Individual Protein	1
NON-MOLECULAR	2
ORGANISM	3
Others	3
SINGLE PROTEIN	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	172.04	%	PMID[537689]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	109.58	%	PMID[537689]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[537689]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[537689]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	32660.0	nM	PMID[537689]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	96.97	%	PMID[537689]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[537689]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	>	10000.0	nM	PMID[537689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	5304.5	nM	PMID[537687]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	13324.4	nM	PMID[537687]
NPT2	Others	Unspecified		IC50	=	633900.0	nM	PMID[537688]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	12800.0	nM	PMID[537690]
NPT2	Others	Unspecified		IC50	=	25300.0	nM	PMID[537690]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-1.32	%	PMID[537691]
NPT21994	SINGLE PROTEIN	Synaptojanin-1	Homo sapiens	IC50	<=	15900.0	nM	PMID[537692]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	3170.0	nM	PMID[537692]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	3170.0	nM	PMID[537693]
NPT21994	SINGLE PROTEIN	Synaptojanin-1	Homo sapiens	IC50	<=	15900.0	nM	PMID[537693]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	3170.0	nM	PMID[537694]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	100.06	%	PMID[537695]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	IC50	=	180.0	nM	PMID[537695]
NPT22753	SINGLE PROTEIN	Replicase polyprotein 1ab	Middle East respiratory syndrome-related coronavirus (isolate UnitedKingdom/H123990006/2012) (Betacoronavirus England 1) (Humancoronavirus EMC)	IC50	>	10000.0	nM	PMID[537695]
NPT22753	SINGLE PROTEIN	Replicase polyprotein 1ab	Middle East respiratory syndrome-related coronavirus (isolate UnitedKingdom/H123990006/2012) (Betacoronavirus England 1) (Humancoronavirus EMC)	Inhibition	=	18.0	%	PMID[537695]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.16	%	PMID[537696]
NPT2	Others	Unspecified		IC50	=	22000.0	nM	PMID[537697]

☑ 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 NPC19721 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	459
0.1-0.2	1810
0.2-0.3	4666
0.3-0.4	10593
0.4-0.5	7013
0.5-0.6	3748
0.6-0.7	4776
0.7-0.8	5410
0.8-0.85	2603
0.85-0.9	1310
0.9-0.95	276
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC36835
0.9863	High Similarity	NPC260491
0.9863	High Similarity	NPC9743
0.9863	High Similarity	NPC246162
0.9863	High Similarity	NPC240476
0.9863	High Similarity	NPC61506
0.9797	High Similarity	NPC250922
0.9796	High Similarity	NPC256346
0.9796	High Similarity	NPC27532
0.9796	High Similarity	NPC325028
0.9796	High Similarity	NPC246328
0.9664	High Similarity	NPC201837
0.9664	High Similarity	NPC320825
0.9664	High Similarity	NPC13858
0.9664	High Similarity	NPC326037
0.9655	High Similarity	NPC21835
0.9603	High Similarity	NPC470326
0.96	High Similarity	NPC52530
0.9589	High Similarity	NPC294852
0.9589	High Similarity	NPC321011
0.9589	High Similarity	NPC218569
0.9589	High Similarity	NPC188679
0.9539	High Similarity	NPC471499
0.9539	High Similarity	NPC289771
0.9536	High Similarity	NPC22192
0.9533	High Similarity	NPC471500
0.953	High Similarity	NPC141212
0.9524	High Similarity	NPC183959
0.9524	High Similarity	NPC1612
0.9474	High Similarity	NPC471744
0.9474	High Similarity	NPC263449
0.9474	High Similarity	NPC282009
0.9474	High Similarity	NPC287328
0.9474	High Similarity	NPC470183
0.947	High Similarity	NPC471515
0.947	High Similarity	NPC471479
0.9463	High Similarity	NPC219582
0.9463	High Similarity	NPC236637
0.9463	High Similarity	NPC302950
0.9452	High Similarity	NPC169749
0.9412	High Similarity	NPC112418
0.9412	High Similarity	NPC308992
0.9408	High Similarity	NPC53545
0.9408	High Similarity	NPC117418
0.9404	High Similarity	NPC474638
0.94	High Similarity	NPC18727
0.9396	High Similarity	NPC133953
0.9396	High Similarity	NPC28274
0.9396	High Similarity	NPC204515
0.9396	High Similarity	NPC50403
0.9384	High Similarity	NPC208176
0.9384	High Similarity	NPC62290
0.9384	High Similarity	NPC49130
0.9384	High Similarity	NPC4152
0.9384	High Similarity	NPC142731
0.9384	High Similarity	NPC279417
0.9384	High Similarity	NPC306607
0.9384	High Similarity	NPC326506
0.9355	High Similarity	NPC7688
0.9355	High Similarity	NPC72787
0.9355	High Similarity	NPC58223
0.9355	High Similarity	NPC7154
0.9355	High Similarity	NPC36916
0.9355	High Similarity	NPC36
0.9355	High Similarity	NPC125039
0.9351	High Similarity	NPC471745
0.9351	High Similarity	NPC211107
0.9346	High Similarity	NPC472630
0.9346	High Similarity	NPC472631
0.9342	High Similarity	NPC67876
0.9342	High Similarity	NPC472598
0.9342	High Similarity	NPC474055
0.9338	High Similarity	NPC477503
0.9338	High Similarity	NPC470327
0.9338	High Similarity	NPC45849
0.9338	High Similarity	NPC200761
0.9338	High Similarity	NPC321779
0.9333	High Similarity	NPC123886
0.9333	High Similarity	NPC106976
0.9329	High Similarity	NPC338131
0.9324	High Similarity	NPC3036
0.9324	High Similarity	NPC119059
0.932	High Similarity	NPC148011
0.932	High Similarity	NPC1940
0.932	High Similarity	NPC20791
0.932	High Similarity	NPC179271
0.9295	High Similarity	NPC471213
0.929	High Similarity	NPC472625
0.9286	High Similarity	NPC472634
0.9286	High Similarity	NPC26326
0.9286	High Similarity	NPC173137
0.9286	High Similarity	NPC142252
0.9286	High Similarity	NPC158188
0.9281	High Similarity	NPC55738
0.9276	High Similarity	NPC470328
0.9276	High Similarity	NPC209614
0.9276	High Similarity	NPC278778
0.9276	High Similarity	NPC235165
0.9276	High Similarity	NPC291878
0.9276	High Similarity	NPC35038
0.9276	High Similarity	NPC255106
0.9276	High Similarity	NPC472626
0.9276	High Similarity	NPC195796
0.9272	High Similarity	NPC213896
0.9272	High Similarity	NPC298692
0.9272	High Similarity	NPC192083
0.9272	High Similarity	NPC162351
0.9272	High Similarity	NPC74924
0.9272	High Similarity	NPC58382
0.9267	High Similarity	NPC252933
0.9267	High Similarity	NPC54394
0.9267	High Similarity	NPC200740
0.9267	High Similarity	NPC125062
0.9262	High Similarity	NPC87125
0.9262	High Similarity	NPC105512
0.9262	High Similarity	NPC270465
0.9257	High Similarity	NPC51443
0.9257	High Similarity	NPC211466
0.9257	High Similarity	NPC74881
0.9257	High Similarity	NPC44721
0.9257	High Similarity	NPC122828
0.9257	High Similarity	NPC95864
0.9257	High Similarity	NPC3779
0.9257	High Similarity	NPC40086
0.9257	High Similarity	NPC176869
0.9257	High Similarity	NPC476182
0.9247	High Similarity	NPC175013
0.9241	High Similarity	NPC182421
0.9236	High Similarity	NPC160156
0.9236	High Similarity	NPC92565
0.9236	High Similarity	NPC260266
0.9231	High Similarity	NPC277205
0.9231	High Similarity	NPC55786
0.9231	High Similarity	NPC470457
0.9231	High Similarity	NPC240431
0.9231	High Similarity	NPC19388
0.9231	High Similarity	NPC475888
0.9226	High Similarity	NPC127782
0.9226	High Similarity	NPC472635
0.9226	High Similarity	NPC300537
0.9221	High Similarity	NPC101731
0.9221	High Similarity	NPC174953
0.9216	High Similarity	NPC223787
0.9216	High Similarity	NPC475267
0.9216	High Similarity	NPC474836
0.9216	High Similarity	NPC27337
0.9216	High Similarity	NPC474208
0.9216	High Similarity	NPC48208
0.9216	High Similarity	NPC291508
0.9216	High Similarity	NPC156057
0.9216	High Similarity	NPC162869
0.9216	High Similarity	NPC210084
0.9216	High Similarity	NPC99597
0.9211	High Similarity	NPC67396
0.9205	High Similarity	NPC472912
0.9205	High Similarity	NPC27208
0.9205	High Similarity	NPC279989
0.9205	High Similarity	NPC199100
0.9205	High Similarity	NPC101996
0.9205	High Similarity	NPC180234
0.9205	High Similarity	NPC120537
0.9205	High Similarity	NPC82325
0.9205	High Similarity	NPC55205
0.9205	High Similarity	NPC260979
0.92	High Similarity	NPC286342
0.92	High Similarity	NPC29231
0.92	High Similarity	NPC188871
0.92	High Similarity	NPC77858
0.92	High Similarity	NPC219330
0.92	High Similarity	NPC61620
0.92	High Similarity	NPC62042
0.92	High Similarity	NPC149127
0.9195	High Similarity	NPC194856
0.9195	High Similarity	NPC196277
0.9195	High Similarity	NPC120464
0.9195	High Similarity	NPC43669
0.9195	High Similarity	NPC276930
0.9195	High Similarity	NPC272721
0.9184	High Similarity	NPC279121
0.9177	High Similarity	NPC52382
0.9177	High Similarity	NPC270578
0.9172	High Similarity	NPC197285
0.9172	High Similarity	NPC179950
0.9172	High Similarity	NPC277174
0.9172	High Similarity	NPC73855
0.9172	High Similarity	NPC118284
0.9172	High Similarity	NPC281131
0.9172	High Similarity	NPC135599
0.9172	High Similarity	NPC56077
0.9172	High Similarity	NPC253662
0.9172	High Similarity	NPC328940
0.9172	High Similarity	NPC308404
0.9172	High Similarity	NPC274618
0.9172	High Similarity	NPC145038
0.9172	High Similarity	NPC88789
0.9172	High Similarity	NPC21100
0.9172	High Similarity	NPC276222
0.9172	High Similarity	NPC113968
0.9167	High Similarity	NPC470459
0.9167	High Similarity	NPC41301

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 NPC19721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	957
0.2-0.3	2000
0.3-0.4	2547
0.4-0.5	1694
0.5-0.6	932
0.6-0.7	420
0.7-0.8	118
0.8-0.85	31
0.85-0.9	13
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD1934	Approved
0.9355	High Similarity	NPD6167	Clinical (unspecified phase)
0.9355	High Similarity	NPD6166	Phase 2
0.9355	High Similarity	NPD6168	Clinical (unspecified phase)
0.932	High Similarity	NPD1512	Approved
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9184	High Similarity	NPD1511	Approved
0.8944	High Similarity	NPD6797	Phase 2
0.8904	High Similarity	NPD1552	Clinical (unspecified phase)
0.8904	High Similarity	NPD1550	Clinical (unspecified phase)
0.8903	High Similarity	NPD3882	Suspended
0.8903	High Similarity	NPD4868	Clinical (unspecified phase)
0.8896	High Similarity	NPD2801	Approved
0.8889	High Similarity	NPD7251	Discontinued
0.8882	High Similarity	NPD7074	Phase 3
0.8875	High Similarity	NPD3818	Discontinued
0.8844	High Similarity	NPD1549	Phase 2
0.8839	High Similarity	NPD3817	Phase 2
0.8834	High Similarity	NPD4338	Clinical (unspecified phase)
0.8824	High Similarity	NPD4380	Phase 2
0.882	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7472	Approved
0.8726	High Similarity	NPD7075	Discontinued
0.8726	High Similarity	NPD4381	Clinical (unspecified phase)
0.872	High Similarity	NPD7808	Phase 3
0.8712	High Similarity	NPD7993	Clinical (unspecified phase)
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8493	Intermediate Similarity	NPD1613	Approved
0.8493	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6801	Discontinued
0.8418	Intermediate Similarity	NPD1465	Phase 2
0.8365	Intermediate Similarity	NPD5402	Approved
0.8312	Intermediate Similarity	NPD6799	Approved
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD5494	Approved
0.8269	Intermediate Similarity	NPD5403	Approved
0.8258	Intermediate Similarity	NPD5401	Approved
0.825	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD943	Approved
0.8243	Intermediate Similarity	NPD1240	Approved
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2796	Approved
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD1607	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8063	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.787	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7834	Intermediate Similarity	NPD6190	Approved
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7771	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3787	Discontinued
0.7711	Intermediate Similarity	NPD3749	Approved
0.7707	Intermediate Similarity	NPD2800	Approved
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD37	Approved
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3748	Approved
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD4967	Phase 2
0.744	Intermediate Similarity	NPD4966	Approved
0.7438	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6651	Approved
0.7434	Intermediate Similarity	NPD9494	Approved
0.7432	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8313	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.7394	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7372	Intermediate Similarity	NPD1933	Approved
0.7362	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2344	Approved
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7345	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.733	Intermediate Similarity	NPD5953	Discontinued
0.7312	Intermediate Similarity	NPD6780	Approved
0.7312	Intermediate Similarity	NPD6777	Approved
0.7312	Intermediate Similarity	NPD6776	Approved
0.7312	Intermediate Similarity	NPD6779	Approved
0.7312	Intermediate Similarity	NPD6778	Approved
0.7312	Intermediate Similarity	NPD6781	Approved
0.7312	Intermediate Similarity	NPD6782	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD2313	Discontinued
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD2346	Discontinued
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7228	Intermediate Similarity	NPD4363	Phase 3
0.7228	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7286	Phase 2
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2309	Approved
0.7173	Intermediate Similarity	NPD7584	Approved
0.7171	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7125	Intermediate Similarity	NPD2799	Discontinued
0.7118	Intermediate Similarity	NPD8455	Phase 2
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7697	Approved
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5353	Approved
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7047	Intermediate Similarity	NPD7701	Phase 2
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6535	Approved
0.7043	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD422	Phase 1
0.7039	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD2424	Discontinued
0.6989	Remote Similarity	NPD5242	Approved
0.6981	Remote Similarity	NPD4060	Phase 1
0.6974	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7874	Approved
0.697	Remote Similarity	NPD2354	Approved
0.6968	Remote Similarity	NPD1470	Approved
0.6966	Remote Similarity	NPD2163	Approved
0.6962	Remote Similarity	NPD3268	Approved
0.6962	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD411	Approved
0.6951	Remote Similarity	NPD2654	Approved
0.6948	Remote Similarity	NPD4749	Approved
0.6946	Remote Similarity	NPD4661	Approved
0.6946	Remote Similarity	NPD4662	Approved
0.6939	Remote Similarity	NPD7801	Approved
0.6939	Remote Similarity	NPD7783	Phase 2
0.6939	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5124	Phase 1
0.6933	Remote Similarity	NPD1471	Phase 3
0.6931	Remote Similarity	NPD7700	Phase 2
0.6931	Remote Similarity	NPD7699	Phase 2

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