NPASS Compound

Structure

CID210148 OpenBabel06191716002D 24 29 0 0 1 0 0 0 0 0999 V2000 4.7381 -0.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9610 -0.6194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1843 1.6236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5153 -0.6196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6300 1.6234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5152 1.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6303 -0.1710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6735 0.2779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5275 0.7257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7381 -0.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4070 1.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7381 0.7265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4072 0.2777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1842 -0.1709 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9613 1.1750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2925 -0.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8530 1.1746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2925 0.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8532 0.2774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9611 0.2777 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.1460 -0.4481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.4517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1460 1.0039 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 20 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 8 23 1 0 0 0 0 9 22 1 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 2 1 1 0 0 0 14 20 1 0 0 0 0 15 3 1 1 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.12
Volume:	316.18
LogP:	3.205
LogD:	2.772
LogS:	-4.082
# Rotatable Bonds:	0
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	4.16
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.972
MDCK Permeability:	4.970691952621564e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.828
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	86.02643585205078%
Volume Distribution (VD):	2.401
Pgp-substrate:	6.397460460662842%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	18.921
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.267
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.131
Carcinogencity:	0.945
Eye Corrosion:	0.005
Eye Irritation:	0.026
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC210148

Natural Product ID:	NPC210148
*Common Name:**	Escholtzine
IUPAC Name:	n.a.
Synonyms:	Escholtzine
Standard InCHIKey:	PGINMPJZCWDQNT-GJZGRUSLSA-N
Standard InCHI:	InChI=1S/C19H17NO4/c1-20-14-2-10-4-16-18(23-8-21-16)6-12(10)15(20)3-11-5-17-19(7-13(11)14)24-9-22-17/h4-7,14-15H,2-3,8-9H2,1H3/t14-,15-/m0/s1
SMILES:	CN1[C@H]2Cc3c([C@@H]1Cc1c2cc2OCOc2c1)cc1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481839
PubChem CID:	12304178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002793] Pavine alkaloids

*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]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	twig	n.a.	PMID[16204994]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	Oakham, MA, US	n.a.	PMID[16562853]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17250743]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	leaves	Lai-I, Pingtung County, Taiwan	2005-May	PMID[20704331]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO23033	Cryptocarya laevigata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099003]
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]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4986	Eschscholzia californica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	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]
NPO4986	Eschscholzia californica	Species	Papaveraceae	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]
NPO20068	Fusarium striatum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2075	Zanthoxylum ocumarense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14639	Balanophora polyandra	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23033	Cryptocarya laevigata	Species	Lauraceae	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]
NPO12296	Sphaerechinus granularis	Species	Toxopneustidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1946	Veronica stricta	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16090	Panicum crus-galli	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11607	Marrubium parviflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8632	Aralia hispida	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14344	Trifolium diffusum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15098	Cyttaria johowii	Species	Cyttariaceae	Eukaryota	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]
NPO7878	Lysastrosoma anthosticta	n.a.	n.a.	n.a.	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]
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]
NPO14885	Lilium rubrum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10936	Andira retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7036	Davidsonia pruriens	Species	Cunoniaceae	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]
NPO12818	Lespedeza maximowiczi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4986	Eschscholzia californica	Species	Papaveraceae	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]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5040	Polygonatum polyanthemum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11833	Dyssodia anthemidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14223	Harpullia cupanioides	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12064	Lychnophora pinaster	Species	Asteraceae	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]
NPO14366	Youngia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14086	Parthenium confertum	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]

☑ 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
EC50	1
IC50	6
Ki	1

Activity Type	# Activity
Cell Line	4
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	13400.0	nM	PMID[545742]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8709.0	nM	PMID[545743]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	26130.0	nM	PMID[545743]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26560.0	nM	PMID[545743]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	17030.0	nM	PMID[545743]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	EC50	=	11000.0	nM	PMID[545742]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	=	6000.0	nM	PMID[545742]
NPT2	Others	Unspecified		IC50	=	19800.0	nM	PMID[545743]

☑ 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 NPC210148 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	290
0.1-0.2	1696
0.2-0.3	8872
0.3-0.4	9144
0.4-0.5	7941
0.5-0.6	10966
0.6-0.7	2826
0.7-0.8	600
0.8-0.85	204
0.85-0.9	125
0.9-0.95	24
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233029
0.966	High Similarity	NPC31311
0.966	High Similarity	NPC234392
0.9592	High Similarity	NPC138487
0.9592	High Similarity	NPC216459
0.9592	High Similarity	NPC41178
0.9583	High Similarity	NPC475959
0.953	High Similarity	NPC477080
0.9527	High Similarity	NPC146288
0.94	High Similarity	NPC111485
0.9371	High Similarity	NPC128019
0.9371	High Similarity	NPC476567
0.9371	High Similarity	NPC136860
0.9156	High Similarity	NPC276944
0.9156	High Similarity	NPC238530
0.9156	High Similarity	NPC232514
0.9116	High Similarity	NPC210437
0.9116	High Similarity	NPC51957
0.9116	High Similarity	NPC16107
0.9116	High Similarity	NPC106295
0.9116	High Similarity	NPC476144
0.9097	High Similarity	NPC474915
0.9097	High Similarity	NPC188163
0.9097	High Similarity	NPC213206
0.9097	High Similarity	NPC328750
0.9073	High Similarity	NPC78733
0.9054	High Similarity	NPC7467
0.9038	High Similarity	NPC210918
0.9028	High Similarity	NPC314682
0.8961	High Similarity	NPC306902
0.8961	High Similarity	NPC160298
0.8961	High Similarity	NPC232924
0.8961	High Similarity	NPC477559
0.8961	High Similarity	NPC266753
0.8951	High Similarity	NPC7018
0.8947	High Similarity	NPC93593
0.8947	High Similarity	NPC76079
0.894	High Similarity	NPC148898
0.8933	High Similarity	NPC151895
0.8933	High Similarity	NPC97221
0.8933	High Similarity	NPC220858
0.8933	High Similarity	NPC223125
0.8933	High Similarity	NPC88249
0.8933	High Similarity	NPC192768
0.891	High Similarity	NPC167546
0.891	High Similarity	NPC16805
0.891	High Similarity	NPC302527
0.8896	High Similarity	NPC106786
0.8854	High Similarity	NPC476432
0.8854	High Similarity	NPC24264
0.8846	High Similarity	NPC59567
0.8816	High Similarity	NPC223124
0.8812	High Similarity	NPC2314
0.8797	High Similarity	NPC247389
0.879	High Similarity	NPC225774
0.8734	High Similarity	NPC219341
0.8725	High Similarity	NPC185838
0.8718	High Similarity	NPC215829
0.8718	High Similarity	NPC97072
0.8701	High Similarity	NPC276588
0.8701	High Similarity	NPC2413
0.8701	High Similarity	NPC39701
0.8701	High Similarity	NPC204828
0.8701	High Similarity	NPC295691
0.8701	High Similarity	NPC127674
0.8701	High Similarity	NPC189266
0.8701	High Similarity	NPC80129
0.8701	High Similarity	NPC469817
0.8701	High Similarity	NPC249797
0.8701	High Similarity	NPC187022
0.8701	High Similarity	NPC207757
0.8701	High Similarity	NPC278799
0.8701	High Similarity	NPC54379
0.8701	High Similarity	NPC184026
0.8701	High Similarity	NPC172765
0.8701	High Similarity	NPC193949
0.8701	High Similarity	NPC5238
0.8701	High Similarity	NPC110416
0.8679	High Similarity	NPC298979
0.8679	High Similarity	NPC474324
0.8679	High Similarity	NPC57812
0.8679	High Similarity	NPC100566
0.8675	High Similarity	NPC135538
0.8675	High Similarity	NPC24233
0.8675	High Similarity	NPC428
0.8675	High Similarity	NPC130941
0.8675	High Similarity	NPC147390
0.8675	High Similarity	NPC476571
0.8675	High Similarity	NPC246587
0.865	High Similarity	NPC118633
0.865	High Similarity	NPC294790
0.865	High Similarity	NPC148693
0.8645	High Similarity	NPC25084
0.8645	High Similarity	NPC247639
0.8634	High Similarity	NPC19520
0.8634	High Similarity	NPC149090
0.8634	High Similarity	NPC65403
0.8627	High Similarity	NPC476568
0.8625	High Similarity	NPC266176
0.8625	High Similarity	NPC82533
0.8625	High Similarity	NPC290759
0.8625	High Similarity	NPC475845
0.8625	High Similarity	NPC158148
0.8625	High Similarity	NPC241055
0.8618	High Similarity	NPC92541
0.8618	High Similarity	NPC219162
0.8616	High Similarity	NPC86144
0.8616	High Similarity	NPC304659
0.8609	High Similarity	NPC191376
0.8609	High Similarity	NPC321505
0.8609	High Similarity	NPC179825
0.8608	High Similarity	NPC320104
0.8571	High Similarity	NPC474708
0.8571	High Similarity	NPC75958
0.8571	High Similarity	NPC6152
0.8571	High Similarity	NPC311991
0.8562	High Similarity	NPC181653
0.8562	High Similarity	NPC190332
0.8553	High Similarity	NPC231198
0.8553	High Similarity	NPC247972
0.8553	High Similarity	NPC168409
0.8535	High Similarity	NPC216816
0.8531	High Similarity	NPC160193
0.8528	High Similarity	NPC128560
0.8528	High Similarity	NPC199465
0.8528	High Similarity	NPC229166
0.8519	High Similarity	NPC225597
0.8519	High Similarity	NPC477640
0.8519	High Similarity	NPC470739
0.8509	High Similarity	NPC58766
0.8509	High Similarity	NPC475686
0.8506	High Similarity	NPC81733
0.8506	High Similarity	NPC326316
0.8506	High Similarity	NPC476579
0.8494	Intermediate Similarity	NPC299990
0.8494	Intermediate Similarity	NPC73492
0.8491	Intermediate Similarity	NPC189470
0.8487	Intermediate Similarity	NPC95075
0.8487	Intermediate Similarity	NPC144863
0.8487	Intermediate Similarity	NPC253883
0.8487	Intermediate Similarity	NPC476151
0.8487	Intermediate Similarity	NPC90844
0.8477	Intermediate Similarity	NPC130926
0.8462	Intermediate Similarity	NPC325871
0.8462	Intermediate Similarity	NPC99659
0.8457	Intermediate Similarity	NPC474475
0.8428	Intermediate Similarity	NPC24954
0.8424	Intermediate Similarity	NPC114364
0.8424	Intermediate Similarity	NPC320223
0.8415	Intermediate Similarity	NPC187678
0.8415	Intermediate Similarity	NPC304675
0.8378	Intermediate Similarity	NPC253429
0.8377	Intermediate Similarity	NPC207824
0.8377	Intermediate Similarity	NPC477565
0.8377	Intermediate Similarity	NPC60538
0.8377	Intermediate Similarity	NPC103379
0.8375	Intermediate Similarity	NPC475393
0.8367	Intermediate Similarity	NPC11147
0.8364	Intermediate Similarity	NPC287588
0.8364	Intermediate Similarity	NPC237044
0.8364	Intermediate Similarity	NPC474470
0.8354	Intermediate Similarity	NPC476572
0.8344	Intermediate Similarity	NPC244112
0.8343	Intermediate Similarity	NPC477259
0.8343	Intermediate Similarity	NPC169387
0.8333	Intermediate Similarity	NPC37272
0.8323	Intermediate Similarity	NPC284183
0.8323	Intermediate Similarity	NPC24465
0.8323	Intermediate Similarity	NPC4138
0.8323	Intermediate Similarity	NPC121275
0.8313	Intermediate Similarity	NPC15919
0.8313	Intermediate Similarity	NPC474325
0.8312	Intermediate Similarity	NPC59907
0.8312	Intermediate Similarity	NPC37144
0.8291	Intermediate Similarity	NPC186063
0.8274	Intermediate Similarity	NPC116284
0.8274	Intermediate Similarity	NPC275132
0.8274	Intermediate Similarity	NPC248642
0.8272	Intermediate Similarity	NPC264850
0.8272	Intermediate Similarity	NPC250846
0.8272	Intermediate Similarity	NPC240841
0.8272	Intermediate Similarity	NPC476002
0.8272	Intermediate Similarity	NPC268503
0.8272	Intermediate Similarity	NPC317272
0.8272	Intermediate Similarity	NPC42549
0.8272	Intermediate Similarity	NPC13916
0.8272	Intermediate Similarity	NPC256012
0.8269	Intermediate Similarity	NPC277669
0.8269	Intermediate Similarity	NPC76213
0.8264	Intermediate Similarity	NPC172403
0.8263	Intermediate Similarity	NPC258695
0.8263	Intermediate Similarity	NPC474745
0.8263	Intermediate Similarity	NPC126284
0.8263	Intermediate Similarity	NPC27887
0.8263	Intermediate Similarity	NPC244554
0.8263	Intermediate Similarity	NPC470879
0.8261	Intermediate Similarity	NPC233650
0.8246	Intermediate Similarity	NPC281581
0.8235	Intermediate Similarity	NPC145304
0.8232	Intermediate Similarity	NPC152212

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 NPC210148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	776
0.2-0.3	1062
0.3-0.4	1906
0.4-0.5	2753
0.5-0.6	1700
0.6-0.7	601
0.7-0.8	144
0.8-0.85	16
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9116	High Similarity	NPD4584	Approved
0.9097	High Similarity	NPD4664	Clinical (unspecified phase)
0.8701	High Similarity	NPD7298	Approved
0.8533	High Similarity	NPD5084	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD3641	Approved
0.8497	Intermediate Similarity	NPD3640	Phase 3
0.8497	Intermediate Similarity	NPD3639	Approved
0.8387	Intermediate Similarity	NPD4017	Approved
0.8355	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4773	Phase 2
0.828	Intermediate Similarity	NPD4772	Phase 2
0.8151	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6030	Approved
0.8141	Intermediate Similarity	NPD6031	Approved
0.8098	Intermediate Similarity	NPD6107	Approved
0.8072	Intermediate Similarity	NPD8252	Approved
0.8072	Intermediate Similarity	NPD8251	Approved
0.8072	Intermediate Similarity	NPD8099	Discontinued
0.8049	Intermediate Similarity	NPD4166	Phase 2
0.8037	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD8156	Discontinued
0.8013	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD5718	Phase 2
0.7949	Intermediate Similarity	NPD3124	Discontinued
0.7939	Intermediate Similarity	NPD4010	Discontinued
0.7919	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7281	Phase 3
0.7895	Intermediate Similarity	NPD7280	Phase 3
0.7865	Intermediate Similarity	NPD4420	Approved
0.7821	Intermediate Similarity	NPD5241	Discontinued
0.7811	Intermediate Similarity	NPD5313	Approved
0.7811	Intermediate Similarity	NPD5312	Approved
0.7771	Intermediate Similarity	NPD7802	Discontinued
0.7746	Intermediate Similarity	NPD8053	Approved
0.7746	Intermediate Similarity	NPD8054	Approved
0.7744	Intermediate Similarity	NPD6788	Approved
0.7738	Intermediate Similarity	NPD4481	Phase 3
0.773	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6895	Approved
0.7712	Intermediate Similarity	NPD6896	Approved
0.7697	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7831	Phase 2
0.7697	Intermediate Similarity	NPD7833	Phase 2
0.7692	Intermediate Similarity	NPD5006	Approved
0.7692	Intermediate Similarity	NPD5005	Approved
0.7647	Intermediate Similarity	NPD2492	Phase 1
0.7633	Intermediate Similarity	NPD2898	Approved
0.7622	Intermediate Similarity	NPD2978	Approved
0.7622	Intermediate Similarity	NPD2977	Approved
0.7619	Intermediate Similarity	NPD3051	Approved
0.7616	Intermediate Similarity	NPD6297	Approved
0.7588	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5977	Approved
0.7576	Intermediate Similarity	NPD5978	Approved
0.7574	Intermediate Similarity	NPD2970	Approved
0.7574	Intermediate Similarity	NPD2969	Approved
0.7529	Intermediate Similarity	NPD27	Approved
0.7529	Intermediate Similarity	NPD2489	Approved
0.7516	Intermediate Similarity	NPD3110	Approved
0.7516	Intermediate Similarity	NPD3109	Approved
0.7515	Intermediate Similarity	NPD6071	Discontinued
0.7485	Intermediate Similarity	NPD5604	Discontinued
0.7485	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2563	Approved
0.747	Intermediate Similarity	NPD2560	Approved
0.7469	Intermediate Similarity	NPD4727	Phase 1
0.7453	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6851	Approved
0.7443	Intermediate Similarity	NPD6853	Approved
0.7401	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7110	Phase 1
0.7394	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2420	Approved
0.7391	Intermediate Similarity	NPD2421	Approved
0.7368	Intermediate Similarity	NPD6687	Approved
0.7368	Intermediate Similarity	NPD6688	Approved
0.7363	Intermediate Similarity	NPD5582	Discontinued
0.7356	Intermediate Similarity	NPD3885	Approved
0.7349	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6618	Phase 2
0.7338	Intermediate Similarity	NPD4474	Approved
0.7338	Intermediate Similarity	NPD4475	Approved
0.733	Intermediate Similarity	NPD3816	Phase 1
0.733	Intermediate Similarity	NPD3815	Phase 1
0.7329	Intermediate Similarity	NPD3845	Phase 1
0.7329	Intermediate Similarity	NPD7124	Phase 2
0.7318	Intermediate Similarity	NPD3349	Phase 2
0.7312	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4859	Phase 1
0.7301	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7598	Phase 2
0.7268	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5177	Phase 3
0.725	Intermediate Similarity	NPD4236	Phase 3
0.725	Intermediate Similarity	NPD4237	Approved
0.7248	Intermediate Similarity	NPD3705	Approved
0.7247	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8095	Phase 1
0.7239	Intermediate Similarity	NPD1424	Approved
0.7237	Intermediate Similarity	NPD7247	Discontinued
0.7229	Intermediate Similarity	NPD6875	Approved
0.7229	Intermediate Similarity	NPD6876	Approved
0.7225	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7906	Approved
0.7222	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7291	Discontinued
0.7219	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4108	Discontinued
0.7212	Intermediate Similarity	NPD4210	Discontinued
0.7205	Intermediate Similarity	NPD6748	Discontinued
0.7205	Intermediate Similarity	NPD5754	Discontinued
0.7193	Intermediate Similarity	NPD5677	Discontinued
0.7191	Intermediate Similarity	NPD2971	Approved
0.7191	Intermediate Similarity	NPD7311	Approved
0.7191	Intermediate Similarity	NPD7312	Approved
0.7191	Intermediate Similarity	NPD7310	Approved
0.7191	Intermediate Similarity	NPD2968	Approved
0.7191	Intermediate Similarity	NPD7313	Approved
0.7188	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4055	Discovery
0.7169	Intermediate Similarity	NPD4005	Discontinued
0.7152	Intermediate Similarity	NPD5976	Discontinued
0.7151	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3060	Approved
0.7124	Intermediate Similarity	NPD7905	Discontinued
0.712	Intermediate Similarity	NPD6493	Phase 3
0.7115	Intermediate Similarity	NPD2674	Phase 3
0.7112	Intermediate Similarity	NPD5457	Discontinued
0.7104	Intermediate Similarity	NPD7296	Approved
0.7103	Intermediate Similarity	NPD5283	Phase 1
0.7099	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4578	Approved
0.7095	Intermediate Similarity	NPD4577	Approved
0.7089	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4663	Approved
0.7063	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3920	Phase 2
0.7059	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4098	Discontinued
0.7051	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3384	Approved
0.7041	Intermediate Similarity	NPD3383	Approved
0.7041	Intermediate Similarity	NPD3382	Approved
0.7041	Intermediate Similarity	NPD5720	Discontinued
0.7039	Intermediate Similarity	NPD1421	Approved
0.7039	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1420	Approved
0.7039	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7400	Phase 3
0.7033	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3763	Approved
0.7019	Intermediate Similarity	NPD1375	Discontinued
0.7018	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2120	Phase 2
0.7011	Intermediate Similarity	NPD3922	Approved
0.7011	Intermediate Similarity	NPD3921	Approved
0.7011	Intermediate Similarity	NPD3923	Approved
0.7011	Intermediate Similarity	NPD3924	Approved
0.7006	Intermediate Similarity	NPD5600	Discontinued
0.7	Intermediate Similarity	NPD2667	Approved
0.7	Intermediate Similarity	NPD1753	Discontinued
0.7	Intermediate Similarity	NPD5773	Approved
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5772	Approved
0.6994	Remote Similarity	NPD6331	Phase 2
0.6982	Remote Similarity	NPD6386	Approved
0.6982	Remote Similarity	NPD6385	Approved
0.6981	Remote Similarity	NPD2653	Approved
0.6957	Remote Similarity	NPD2161	Phase 2
0.6957	Remote Similarity	NPD2490	Approved
0.6957	Remote Similarity	NPD2488	Approved
0.6954	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3983	Phase 3
0.6952	Remote Similarity	NPD7034	Discontinued
0.6952	Remote Similarity	NPD5564	Approved
0.6946	Remote Similarity	NPD2122	Discontinued
0.6943	Remote Similarity	NPD5110	Phase 2
0.6943	Remote Similarity	NPD3145	Approved
0.6943	Remote Similarity	NPD5111	Phase 2
0.6943	Remote Similarity	NPD5109	Approved
0.6943	Remote Similarity	NPD3144	Approved
0.6937	Remote Similarity	NPD6111	Discontinued
0.6937	Remote Similarity	NPD7119	Phase 2
0.6935	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1669	Approved
0.6928	Remote Similarity	NPD4123	Phase 3

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