NPASS Compound

Structure

CID189960 OpenBabel06191715572D 24 26 0 0 0 0 0 0 0 0999 V2000 -4.3301 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 1.7321 3.0000 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 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 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 2.0000 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 -0.8660 1.5000 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 0.5000 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 -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 -1.7321 3.0000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 10 2 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 19 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 17 2 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	3.15
LogD:	2.935
LogS:	-4.149
# Rotatable Bonds:	4
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.263
Fsp3:	0.167
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:	-4.736
MDCK Permeability:	2.8575394026120193e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	86.04573822021484%
Volume Distribution (VD):	0.812
Pgp-substrate:	12.706459999084473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.271
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	4.556
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.641
Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.336
Carcinogencity:	0.192
Eye Corrosion:	0.004
Eye Irritation:	0.452
Respiratory Toxicity:	0.221

Download Data

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

Natural Product: NPC189960

Natural Product ID:	NPC189960
*Common Name:**	3,7,8-Trimethoxy-5-Hydroxyflavone
IUPAC Name:	5-hydroxy-3,7,8-trimethoxy-2-phenylchromen-4-one
Synonyms:
Standard InCHIKey:	GMKBLHXKYVSJSF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-21-12-9-11(19)13-14(20)18(23-3)15(10-7-5-4-6-8-10)24-17(13)16(12)22-2/h4-9,19H,1-3H3
SMILES:	COc1cc(c2c(=O)c(c(c3ccccc3)oc2c1OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223851
PubChem CID:	21632881
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-O-methylated flavonoids

*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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14510597]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	twig	n.a.	PMID[16204994]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17547459]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	culture broth	n.a.	n.a.	PMID[17547459]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	leaves	Lai-I, Pingtung County, Taiwan	2005-May	PMID[20704331]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7916271]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11607	Marrubium parviflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15098	Cyttaria johowii	Species	Cyttariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23454	Aplidium lobatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14344	Trifolium diffusum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7878	Lysastrosoma anthosticta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1202	Psathyrotes ramosissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6241	Girgensohnia oppositiflora	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26060	Ammodendron longiracemosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14485	Eriocephalus kingesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14885	Lilium rubrum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14996	Lobelia syphilitica	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7036	Davidsonia pruriens	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23699	Salvia nemorosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10936	Andira retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12818	Lespedeza maximowiczi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3521	Geranium collinum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26228	Phymatopteris hastata	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5040	Polygonatum polyanthemum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6229	Chenopodiastrum murale	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6615	Aplidium solidum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11833	Dyssodia anthemidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26663	Polyalthia fragrans	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2770	Pyropolyporus fomentarius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14223	Harpullia cupanioides	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2075	Zanthoxylum ocumarense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14366	Youngia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25018	Pterocaulon lanatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12064	Lychnophora pinaster	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13241	Coprosma foetidissima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14639	Balanophora polyandra	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20068	Fusarium striatum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14086	Parthenium confertum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16090	Panicum crus-galli	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12296	Sphaerechinus granularis	Species	Toxopneustidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13755	Gonotheca helianthoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8632	Aralia hispida	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22159	Anaphalis velutina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1946	Veronica stricta	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25297	Rosellinia necatrix	Species	Xylariaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[492808]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[492808]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[492808]

☑ 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 NPC189960 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	466
0.1-0.2	2031
0.2-0.3	5270
0.3-0.4	11360
0.4-0.5	5723
0.5-0.6	3948
0.6-0.7	5264
0.7-0.8	4680
0.8-0.85	2007
0.85-0.9	1181
0.9-0.95	540
0.95-1	227

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32557
0.9932	High Similarity	NPC178854
0.9932	High Similarity	NPC86485
0.9866	High Similarity	NPC110070
0.9866	High Similarity	NPC203891
0.9866	High Similarity	NPC101830
0.9864	High Similarity	NPC301123
0.98	High Similarity	NPC261004
0.98	High Similarity	NPC22472
0.98	High Similarity	NPC176300
0.98	High Similarity	NPC19687
0.98	High Similarity	NPC105242
0.98	High Similarity	NPC4481
0.98	High Similarity	NPC204854
0.98	High Similarity	NPC288669
0.98	High Similarity	NPC143828
0.98	High Similarity	NPC7846
0.98	High Similarity	NPC18607
0.98	High Similarity	NPC25495
0.98	High Similarity	NPC9609
0.98	High Similarity	NPC115798
0.98	High Similarity	NPC18772
0.98	High Similarity	NPC191459
0.98	High Similarity	NPC300943
0.98	High Similarity	NPC152166
0.98	High Similarity	NPC130894
0.98	High Similarity	NPC253634
0.9799	High Similarity	NPC43243
0.9799	High Similarity	NPC266960
0.9799	High Similarity	NPC292107
0.9799	High Similarity	NPC245546
0.9799	High Similarity	NPC49824
0.9797	High Similarity	NPC246204
0.9796	High Similarity	NPC236769
0.9796	High Similarity	NPC226973
0.9796	High Similarity	NPC208043
0.9733	High Similarity	NPC305663
0.9733	High Similarity	NPC287979
0.9733	High Similarity	NPC235215
0.9733	High Similarity	NPC93376
0.9733	High Similarity	NPC78302
0.9733	High Similarity	NPC75215
0.9733	High Similarity	NPC224137
0.9733	High Similarity	NPC227192
0.9733	High Similarity	NPC189179
0.9733	High Similarity	NPC7973
0.9733	High Similarity	NPC29841
0.9733	High Similarity	NPC176665
0.9733	High Similarity	NPC163524
0.9733	High Similarity	NPC472438
0.9732	High Similarity	NPC201451
0.9732	High Similarity	NPC26227
0.9732	High Similarity	NPC44079
0.973	High Similarity	NPC134677
0.9728	High Similarity	NPC50728
0.9728	High Similarity	NPC166753
0.9728	High Similarity	NPC306821
0.9669	High Similarity	NPC193842
0.9667	High Similarity	NPC55619
0.9667	High Similarity	NPC100916
0.9667	High Similarity	NPC265511
0.9667	High Similarity	NPC200388
0.9667	High Similarity	NPC268161
0.9667	High Similarity	NPC474520
0.9667	High Similarity	NPC98661
0.9667	High Similarity	NPC247017
0.9664	High Similarity	NPC270620
0.9664	High Similarity	NPC69394
0.9664	High Similarity	NPC183878
0.9664	High Similarity	NPC22519
0.9664	High Similarity	NPC255350
0.9664	High Similarity	NPC179126
0.9664	High Similarity	NPC145379
0.9664	High Similarity	NPC78326
0.9664	High Similarity	NPC236223
0.9664	High Similarity	NPC274327
0.9664	High Similarity	NPC231018
0.9664	High Similarity	NPC47781
0.9664	High Similarity	NPC160951
0.9664	High Similarity	NPC176775
0.9662	High Similarity	NPC308451
0.9662	High Similarity	NPC76376
0.966	High Similarity	NPC328119
0.966	High Similarity	NPC69752
0.966	High Similarity	NPC159103
0.9605	High Similarity	NPC246478
0.96	High Similarity	NPC214138
0.96	High Similarity	NPC196439
0.96	High Similarity	NPC138360
0.96	High Similarity	NPC92659
0.96	High Similarity	NPC50715
0.96	High Similarity	NPC183597
0.96	High Similarity	NPC4455
0.96	High Similarity	NPC213622
0.96	High Similarity	NPC2476
0.96	High Similarity	NPC280339
0.96	High Similarity	NPC167815
0.96	High Similarity	NPC201136
0.96	High Similarity	NPC163780
0.96	High Similarity	NPC20830
0.96	High Similarity	NPC128863
0.96	High Similarity	NPC227325
0.96	High Similarity	NPC146165
0.96	High Similarity	NPC256612
0.9597	High Similarity	NPC187498
0.9597	High Similarity	NPC198826
0.9597	High Similarity	NPC162313
0.9597	High Similarity	NPC301323
0.9597	High Similarity	NPC100887
0.9597	High Similarity	NPC57030
0.9597	High Similarity	NPC212678
0.9597	High Similarity	NPC222830
0.9597	High Similarity	NPC239128
0.9597	High Similarity	NPC293183
0.9597	High Similarity	NPC25270
0.9597	High Similarity	NPC279989
0.9597	High Similarity	NPC256283
0.9597	High Similarity	NPC83508
0.9597	High Similarity	NPC241498
0.9597	High Similarity	NPC188203
0.9597	High Similarity	NPC71334
0.9597	High Similarity	NPC156222
0.9597	High Similarity	NPC275836
0.9597	High Similarity	NPC275722
0.9597	High Similarity	NPC131624
0.9597	High Similarity	NPC82325
0.9597	High Similarity	NPC120163
0.9595	High Similarity	NPC219330
0.9595	High Similarity	NPC259058
0.9595	High Similarity	NPC201547
0.9592	High Similarity	NPC261548
0.9592	High Similarity	NPC195202
0.9539	High Similarity	NPC195832
0.9539	High Similarity	NPC152904
0.9533	High Similarity	NPC472915
0.9533	High Similarity	NPC280937
0.9533	High Similarity	NPC250822
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC162351
0.9533	High Similarity	NPC276409
0.9533	High Similarity	NPC75279
0.953	High Similarity	NPC252933
0.953	High Similarity	NPC125062
0.953	High Similarity	NPC200740
0.953	High Similarity	NPC54394
0.953	High Similarity	NPC225731
0.953	High Similarity	NPC117579
0.9527	High Similarity	NPC181250
0.9524	High Similarity	NPC12200
0.9524	High Similarity	NPC62536
0.9524	High Similarity	NPC33265
0.9474	High Similarity	NPC476981
0.9474	High Similarity	NPC470402
0.947	High Similarity	NPC208197
0.947	High Similarity	NPC472909
0.947	High Similarity	NPC37392
0.9467	High Similarity	NPC142540
0.9467	High Similarity	NPC27208
0.9467	High Similarity	NPC39732
0.9467	High Similarity	NPC123886
0.9467	High Similarity	NPC60972
0.9467	High Similarity	NPC55205
0.9463	High Similarity	NPC149127
0.9463	High Similarity	NPC188871
0.9463	High Similarity	NPC184136
0.9463	High Similarity	NPC286342
0.9456	High Similarity	NPC110639
0.9456	High Similarity	NPC310259
0.9456	High Similarity	NPC14958
0.9456	High Similarity	NPC40818
0.9456	High Similarity	NPC106461
0.9456	High Similarity	NPC215932
0.9419	High Similarity	NPC470459
0.9408	High Similarity	NPC303255
0.9408	High Similarity	NPC472916
0.94	High Similarity	NPC262623
0.94	High Similarity	NPC149614
0.94	High Similarity	NPC133953
0.94	High Similarity	NPC50403
0.94	High Similarity	NPC260895
0.94	High Similarity	NPC28274
0.9396	High Similarity	NPC48479
0.9396	High Similarity	NPC195351
0.9396	High Similarity	NPC87125
0.9396	High Similarity	NPC270465
0.9396	High Similarity	NPC137062
0.9396	High Similarity	NPC183950
0.9396	High Similarity	NPC296197
0.9396	High Similarity	NPC216318
0.9396	High Similarity	NPC177298
0.9396	High Similarity	NPC52005
0.9396	High Similarity	NPC287101
0.9396	High Similarity	NPC259713
0.9396	High Similarity	NPC223579
0.9396	High Similarity	NPC17286
0.9392	High Similarity	NPC85233
0.9392	High Similarity	NPC93034
0.9392	High Similarity	NPC299923
0.9392	High Similarity	NPC119660
0.9392	High Similarity	NPC205522

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 NPC189960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	445
0.1-0.2	1015
0.2-0.3	1841
0.3-0.4	2663
0.4-0.5	1718
0.5-0.6	963
0.6-0.7	342
0.7-0.8	108
0.8-0.85	32
0.85-0.9	16
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD2801	Approved
0.9281	High Similarity	NPD3882	Suspended
0.9216	High Similarity	NPD3817	Phase 2
0.9195	High Similarity	NPD1512	Approved
0.9085	High Similarity	NPD1934	Approved
0.906	High Similarity	NPD1511	Approved
0.9	High Similarity	NPD4378	Clinical (unspecified phase)
0.8957	High Similarity	NPD4338	Clinical (unspecified phase)
0.8903	High Similarity	NPD2393	Clinical (unspecified phase)
0.8875	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD6167	Clinical (unspecified phase)
0.8727	High Similarity	NPD7808	Phase 3
0.872	High Similarity	NPD6797	Phase 2
0.8667	High Similarity	NPD7251	Discontinued
0.865	High Similarity	NPD3818	Discontinued
0.8625	High Similarity	NPD5494	Approved
0.8608	High Similarity	NPD5402	Approved
0.8598	High Similarity	NPD7054	Approved
0.8571	High Similarity	NPD1247	Approved
0.8562	High Similarity	NPD6799	Approved
0.8545	High Similarity	NPD7472	Approved
0.85	High Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8355	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1240	Approved
0.8242	Intermediate Similarity	NPD3926	Phase 2
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.8221	Intermediate Similarity	NPD919	Approved
0.8165	Intermediate Similarity	NPD5403	Approved
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD1607	Approved
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7819	Suspended
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5401	Approved
0.8037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD943	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD447	Suspended
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD2800	Approved
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7751	Intermediate Similarity	NPD3787	Discontinued
0.7748	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6190	Approved
0.7727	Intermediate Similarity	NPD230	Phase 1
0.7725	Intermediate Similarity	NPD3749	Approved
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7701	Intermediate Similarity	NPD6559	Discontinued
0.7682	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7662	Intermediate Similarity	NPD1613	Approved
0.7662	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1933	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD920	Approved
0.7595	Intermediate Similarity	NPD2344	Approved
0.7582	Intermediate Similarity	NPD3027	Phase 3
0.758	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD1653	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD6099	Approved
0.7515	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7458	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2403	Approved
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7452	Intermediate Similarity	NPD6651	Approved
0.7451	Intermediate Similarity	NPD9494	Approved
0.7443	Intermediate Similarity	NPD5953	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7286	Phase 2
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7381	Intermediate Similarity	NPD37	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7299	Intermediate Similarity	NPD5242	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD4908	Phase 1
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2798	Approved
0.7257	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7212	Intermediate Similarity	NPD4357	Discontinued
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD2797	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5353	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3225	Approved
0.7124	Intermediate Similarity	NPD9269	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7115	Intermediate Similarity	NPD2861	Phase 2
0.7107	Intermediate Similarity	NPD4060	Phase 1
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7086	Intermediate Similarity	NPD9268	Approved
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7079	Intermediate Similarity	NPD2163	Approved
0.7079	Intermediate Similarity	NPD7228	Approved
0.7078	Intermediate Similarity	NPD2983	Phase 2
0.7078	Intermediate Similarity	NPD2982	Phase 2
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.7066	Intermediate Similarity	NPD3146	Approved
0.7066	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7025	Intermediate Similarity	NPD4625	Phase 3
0.7025	Intermediate Similarity	NPD7095	Approved
0.7024	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4361	Phase 2
0.7021	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2981	Phase 2
0.7013	Intermediate Similarity	NPD1481	Phase 2
0.6994	Remote Similarity	NPD4288	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3887	Approved
0.6987	Remote Similarity	NPD1470	Approved

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