NPASS Compound

Structure

CID190298 OpenBabel06191715572D 21 24 0 0 1 0 0 0 0 0999 V2000 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 11 8 1 6 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 6 1 6 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 10 1 6 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.09
Volume:	285.068
LogP:	2.324
LogD:	1.651
LogS:	-3.578
# Rotatable Bonds:	1
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	3.908
Fsp3:	0.294
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:	-4.712
MDCK Permeability:	2.4528277208446525e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	94.68619537353516%
Volume Distribution (VD):	0.728
Pgp-substrate:	2.2959158420562744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.642
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.79
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.839
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	3.885
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.968
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.927
Carcinogencity:	0.28
Eye Corrosion:	0.006
Eye Irritation:	0.109
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC190298

Natural Product ID:	NPC190298
*Common Name:**	Cryptocaryanone A
IUPAC Name:	(3aS,7R,9bR)-7-phenyl-3a,7,8,9b-tetrahydro-1H-furo[3,2-f]chromene-2,9-dione
Synonyms:
Standard InCHIKey:	VISHTIMCJNWYLP-CORIIIEPSA-N
Standard InCHI:	InChI=1S/C17H14O4/c18-12-9-15(10-4-2-1-3-5-10)20-14-7-6-13-11(17(12)14)8-16(19)21-13/h1-7,11,13,15H,8-9H2/t11-,13-,15+/m0/s1
SMILES:	O=C1O[C@@H]2[C@H](C1)C1=C(C=C2)O[C@H](CC1=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223795
PubChem CID:	10356404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
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]
NPO40824	Cryptocarya rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24344605]
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]
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]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	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]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11607	Marrubium parviflorum	Species	Lamiaceae	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]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	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]
NPO1202	Psathyrotes ramosissima	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]
NPO14485	Eriocephalus kingesii	Species	Asteraceae	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]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10936	Andira retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26228	Phymatopteris hastata	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6615	Aplidium solidum	Species	Polyclinidae	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]
NPO12818	Lespedeza maximowiczi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6229	Chenopodiastrum murale	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	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]
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]
NPO14086	Parthenium confertum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	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]
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]
NPO14639	Balanophora polyandra	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13241	Coprosma foetidissima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2075	Zanthoxylum ocumarense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20068	Fusarium striatum	Species	Nectriaceae	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]
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]
NPO1946	Veronica stricta	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8632	Aralia hispida	Species	Araliaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5100.0	nM	PMID[569968]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4300.0	nM	PMID[569968]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	5000.0	nM	PMID[569968]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2500.0	nM	PMID[569968]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	10900.0	nM	PMID[569969]

☑ 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 NPC190298 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	277
0.1-0.2	1205
0.2-0.3	2656
0.3-0.4	6773
0.4-0.5	11793
0.5-0.6	12908
0.6-0.7	6624
0.7-0.8	445
0.8-0.85	11
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC291419
0.878	High Similarity	NPC60825
0.8571	High Similarity	NPC136994
0.8571	High Similarity	NPC88255
0.8407	Intermediate Similarity	NPC40178
0.8393	Intermediate Similarity	NPC51174
0.8376	Intermediate Similarity	NPC471616
0.8333	Intermediate Similarity	NPC474223
0.8333	Intermediate Similarity	NPC475827
0.8319	Intermediate Similarity	NPC47536
0.8276	Intermediate Similarity	NPC474176
0.822	Intermediate Similarity	NPC149691
0.8182	Intermediate Similarity	NPC474222
0.8182	Intermediate Similarity	NPC475804
0.813	Intermediate Similarity	NPC474159
0.813	Intermediate Similarity	NPC474254
0.8051	Intermediate Similarity	NPC307651
0.8051	Intermediate Similarity	NPC87069
0.7983	Intermediate Similarity	NPC474408
0.7965	Intermediate Similarity	NPC234305
0.7931	Intermediate Similarity	NPC474364
0.7931	Intermediate Similarity	NPC265407
0.7931	Intermediate Similarity	NPC83628
0.792	Intermediate Similarity	NPC51079
0.7917	Intermediate Similarity	NPC135730
0.7899	Intermediate Similarity	NPC477411
0.7899	Intermediate Similarity	NPC196075
0.7886	Intermediate Similarity	NPC289432
0.7886	Intermediate Similarity	NPC988
0.7881	Intermediate Similarity	NPC474689
0.7869	Intermediate Similarity	NPC64340
0.7845	Intermediate Similarity	NPC20485
0.7833	Intermediate Similarity	NPC228936
0.7833	Intermediate Similarity	NPC210092
0.7823	Intermediate Similarity	NPC144547
0.7818	Intermediate Similarity	NPC5472
0.7815	Intermediate Similarity	NPC161611
0.7815	Intermediate Similarity	NPC128368
0.7815	Intermediate Similarity	NPC13784
0.7807	Intermediate Similarity	NPC474365
0.7807	Intermediate Similarity	NPC301943
0.7797	Intermediate Similarity	NPC474157
0.7795	Intermediate Similarity	NPC476033
0.7778	Intermediate Similarity	NPC469636
0.7769	Intermediate Similarity	NPC226093
0.7759	Intermediate Similarity	NPC30594
0.7759	Intermediate Similarity	NPC37622
0.775	Intermediate Similarity	NPC172525
0.7742	Intermediate Similarity	NPC238861
0.7742	Intermediate Similarity	NPC77000
0.7739	Intermediate Similarity	NPC114594
0.7731	Intermediate Similarity	NPC212415
0.7692	Intermediate Similarity	NPC214246
0.7692	Intermediate Similarity	NPC277788
0.7692	Intermediate Similarity	NPC471832
0.768	Intermediate Similarity	NPC50872
0.7679	Intermediate Similarity	NPC270654
0.7672	Intermediate Similarity	NPC209632
0.7667	Intermediate Similarity	NPC272524
0.7656	Intermediate Similarity	NPC476599
0.7656	Intermediate Similarity	NPC79608
0.7652	Intermediate Similarity	NPC89886
0.7652	Intermediate Similarity	NPC60679
0.7647	Intermediate Similarity	NPC210089
0.7636	Intermediate Similarity	NPC77273
0.7632	Intermediate Similarity	NPC42211
0.7627	Intermediate Similarity	NPC469511
0.7623	Intermediate Similarity	NPC216387
0.7611	Intermediate Similarity	NPC225060
0.7607	Intermediate Similarity	NPC477251
0.7603	Intermediate Similarity	NPC308744
0.7603	Intermediate Similarity	NPC474363
0.76	Intermediate Similarity	NPC243059
0.76	Intermediate Similarity	NPC232958
0.76	Intermediate Similarity	NPC473243
0.76	Intermediate Similarity	NPC280827
0.7597	Intermediate Similarity	NPC51292
0.7586	Intermediate Similarity	NPC269644
0.7586	Intermediate Similarity	NPC85977
0.7583	Intermediate Similarity	NPC474314
0.7583	Intermediate Similarity	NPC82899
0.7583	Intermediate Similarity	NPC270699
0.7578	Intermediate Similarity	NPC246166
0.7568	Intermediate Similarity	NPC23453
0.7563	Intermediate Similarity	NPC196246
0.7563	Intermediate Similarity	NPC214067
0.7559	Intermediate Similarity	NPC474283
0.7559	Intermediate Similarity	NPC475692
0.7544	Intermediate Similarity	NPC118343
0.7544	Intermediate Similarity	NPC146351
0.7544	Intermediate Similarity	NPC476042
0.7544	Intermediate Similarity	NPC98911
0.7544	Intermediate Similarity	NPC472318
0.7541	Intermediate Similarity	NPC474685
0.7522	Intermediate Similarity	NPC249912
0.7522	Intermediate Similarity	NPC92754
0.7522	Intermediate Similarity	NPC276775
0.7521	Intermediate Similarity	NPC269457
0.7519	Intermediate Similarity	NPC470818
0.75	Intermediate Similarity	NPC152812
0.75	Intermediate Similarity	NPC305912
0.75	Intermediate Similarity	NPC1082
0.75	Intermediate Similarity	NPC475691
0.75	Intermediate Similarity	NPC61651
0.75	Intermediate Similarity	NPC167504
0.75	Intermediate Similarity	NPC472704
0.75	Intermediate Similarity	NPC138798
0.7481	Intermediate Similarity	NPC469930
0.748	Intermediate Similarity	NPC210531
0.7479	Intermediate Similarity	NPC10251
0.7479	Intermediate Similarity	NPC269023
0.7479	Intermediate Similarity	NPC281604
0.7479	Intermediate Similarity	NPC17417
0.7479	Intermediate Similarity	NPC99846
0.7478	Intermediate Similarity	NPC70624
0.746	Intermediate Similarity	NPC476225
0.7458	Intermediate Similarity	NPC119271
0.7458	Intermediate Similarity	NPC329705
0.7458	Intermediate Similarity	NPC474111
0.7456	Intermediate Similarity	NPC35448
0.7456	Intermediate Similarity	NPC78701
0.7456	Intermediate Similarity	NPC179411
0.7444	Intermediate Similarity	NPC469499
0.7444	Intermediate Similarity	NPC477412
0.7444	Intermediate Similarity	NPC196979
0.7444	Intermediate Similarity	NPC475569
0.7444	Intermediate Similarity	NPC470977
0.7444	Intermediate Similarity	NPC470976
0.7442	Intermediate Similarity	NPC472694
0.7442	Intermediate Similarity	NPC295664
0.7442	Intermediate Similarity	NPC472693
0.744	Intermediate Similarity	NPC293424
0.7438	Intermediate Similarity	NPC79496
0.7431	Intermediate Similarity	NPC304760
0.7422	Intermediate Similarity	NPC223351
0.7422	Intermediate Similarity	NPC472703
0.7417	Intermediate Similarity	NPC273837
0.7417	Intermediate Similarity	NPC251854
0.7417	Intermediate Similarity	NPC93084
0.7414	Intermediate Similarity	NPC45613
0.7405	Intermediate Similarity	NPC268607
0.7398	Intermediate Similarity	NPC474095
0.7398	Intermediate Similarity	NPC470764
0.7395	Intermediate Similarity	NPC56493
0.7395	Intermediate Similarity	NPC156648
0.7391	Intermediate Similarity	NPC325497
0.7391	Intermediate Similarity	NPC187566
0.7391	Intermediate Similarity	NPC203925
0.7387	Intermediate Similarity	NPC119631
0.7381	Intermediate Similarity	NPC201284
0.7377	Intermediate Similarity	NPC265002
0.7368	Intermediate Similarity	NPC2989
0.7368	Intermediate Similarity	NPC470278
0.7368	Intermediate Similarity	NPC183348
0.7368	Intermediate Similarity	NPC282230
0.7368	Intermediate Similarity	NPC475478
0.7364	Intermediate Similarity	NPC173443
0.7364	Intermediate Similarity	NPC220893
0.736	Intermediate Similarity	NPC325295
0.736	Intermediate Similarity	NPC76308
0.7353	Intermediate Similarity	NPC309056
0.735	Intermediate Similarity	NPC82426
0.735	Intermediate Similarity	NPC91820
0.7345	Intermediate Similarity	NPC130398
0.7339	Intermediate Similarity	NPC89377
0.7339	Intermediate Similarity	NPC96625
0.7333	Intermediate Similarity	NPC203486
0.7333	Intermediate Similarity	NPC475282
0.7333	Intermediate Similarity	NPC329913
0.7328	Intermediate Similarity	NPC169913
0.7328	Intermediate Similarity	NPC472706
0.7323	Intermediate Similarity	NPC470585
0.7319	Intermediate Similarity	NPC477904
0.7319	Intermediate Similarity	NPC183270
0.7317	Intermediate Similarity	NPC153053
0.7313	Intermediate Similarity	NPC15083
0.7313	Intermediate Similarity	NPC472394
0.7313	Intermediate Similarity	NPC471880
0.7311	Intermediate Similarity	NPC474376
0.7311	Intermediate Similarity	NPC37115
0.7311	Intermediate Similarity	NPC472315
0.7311	Intermediate Similarity	NPC475203
0.7311	Intermediate Similarity	NPC472316
0.7304	Intermediate Similarity	NPC145052
0.7295	Intermediate Similarity	NPC234376
0.7295	Intermediate Similarity	NPC158282
0.7293	Intermediate Similarity	NPC147561
0.7293	Intermediate Similarity	NPC42234
0.7293	Intermediate Similarity	NPC66246
0.7293	Intermediate Similarity	NPC170546
0.7288	Intermediate Similarity	NPC171831
0.7288	Intermediate Similarity	NPC242913
0.7288	Intermediate Similarity	NPC280616
0.7288	Intermediate Similarity	NPC31786
0.7286	Intermediate Similarity	NPC104956
0.728	Intermediate Similarity	NPC128249
0.7279	Intermediate Similarity	NPC212207
0.7279	Intermediate Similarity	NPC37065
0.7273	Intermediate Similarity	NPC223807
0.7273	Intermediate Similarity	NPC174099

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 NPC190298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	812
0.2-0.3	1276
0.3-0.4	2742
0.4-0.5	2473
0.5-0.6	1236
0.6-0.7	354
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7949	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2067	Discontinued
0.7742	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3266	Approved
0.7656	Intermediate Similarity	NPD3267	Approved
0.7586	Intermediate Similarity	NPD5909	Discontinued
0.7544	Intermediate Similarity	NPD1238	Approved
0.7479	Intermediate Similarity	NPD2182	Approved
0.7398	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD3268	Approved
0.7288	Intermediate Similarity	NPD164	Approved
0.7209	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6085	Phase 2
0.7197	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1282	Approved
0.7177	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6858	Approved
0.7097	Intermediate Similarity	NPD7094	Approved
0.7077	Intermediate Similarity	NPD6287	Discontinued
0.7068	Intermediate Similarity	NPD2798	Approved
0.7068	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6647	Phase 2
0.7037	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2797	Approved
0.6985	Remote Similarity	NPD3764	Approved
0.6984	Remote Similarity	NPD2629	Approved
0.6978	Remote Similarity	NPD2569	Approved
0.6978	Remote Similarity	NPD2567	Approved
0.6963	Remote Similarity	NPD6832	Phase 2
0.6957	Remote Similarity	NPD1202	Approved
0.695	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7798	Approved
0.694	Remote Similarity	NPD5647	Approved
0.6929	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD7033	Discontinued
0.6923	Remote Similarity	NPD17	Approved
0.6905	Remote Similarity	NPD6010	Discontinued
0.6899	Remote Similarity	NPD1894	Discontinued
0.6894	Remote Similarity	NPD6637	Approved
0.6885	Remote Similarity	NPD3134	Approved
0.688	Remote Similarity	NPD969	Suspended
0.6879	Remote Similarity	NPD2796	Approved
0.6864	Remote Similarity	NPD9495	Approved
0.686	Remote Similarity	NPD1237	Approved
0.6853	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3673	Approved
0.6842	Remote Similarity	NPD3672	Approved
0.6838	Remote Similarity	NPD1989	Approved
0.6835	Remote Similarity	NPD6355	Discontinued
0.6831	Remote Similarity	NPD2346	Discontinued
0.6831	Remote Similarity	NPD1471	Phase 3
0.6828	Remote Similarity	NPD7236	Approved
0.6809	Remote Similarity	NPD3748	Approved
0.6807	Remote Similarity	NPD2066	Phase 3
0.6803	Remote Similarity	NPD5048	Discontinued
0.6797	Remote Similarity	NPD4198	Discontinued
0.6791	Remote Similarity	NPD1876	Approved
0.6791	Remote Similarity	NPD3225	Approved
0.6786	Remote Similarity	NPD9259	Approved
0.6786	Remote Similarity	NPD9257	Approved
0.6777	Remote Similarity	NPD1929	Approved
0.6777	Remote Similarity	NPD1930	Approved
0.6777	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9545	Approved
0.6767	Remote Similarity	NPD1608	Approved
0.6763	Remote Similarity	NPD4307	Phase 2
0.6757	Remote Similarity	NPD920	Approved
0.6744	Remote Similarity	NPD9493	Approved
0.6742	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6798	Discontinued
0.6735	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5926	Approved
0.6718	Remote Similarity	NPD5585	Approved
0.6714	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1358	Approved
0.6693	Remote Similarity	NPD5535	Approved
0.6692	Remote Similarity	NPD1281	Approved
0.6692	Remote Similarity	NPD2347	Approved
0.6691	Remote Similarity	NPD8032	Phase 2
0.6691	Remote Similarity	NPD1019	Discontinued
0.669	Remote Similarity	NPD1510	Phase 2
0.669	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5889	Approved
0.6689	Remote Similarity	NPD5890	Approved
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD9697	Approved
0.6667	Remote Similarity	NPD5667	Approved
0.6643	Remote Similarity	NPD2979	Phase 3
0.6642	Remote Similarity	NPD9717	Approved
0.6642	Remote Similarity	NPD3972	Approved
0.6624	Remote Similarity	NPD6808	Phase 2
0.6622	Remote Similarity	NPD5401	Approved
0.6621	Remote Similarity	NPD1243	Approved
0.6618	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD694	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1693	Approved
0.6606	Remote Similarity	NPD9490	Approved
0.66	Remote Similarity	NPD7239	Suspended
0.6599	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2344	Approved
0.6597	Remote Similarity	NPD6005	Phase 3
0.6597	Remote Similarity	NPD6004	Phase 3
0.6597	Remote Similarity	NPD6002	Phase 3
0.6596	Remote Similarity	NPD4618	Approved
0.6596	Remote Similarity	NPD1933	Approved
0.6596	Remote Similarity	NPD4622	Approved
0.6591	Remote Similarity	NPD5691	Approved
0.6587	Remote Similarity	NPD5236	Approved
0.6587	Remote Similarity	NPD5240	Approved
0.6587	Remote Similarity	NPD5237	Approved
0.6587	Remote Similarity	NPD5239	Approved
0.6587	Remote Similarity	NPD5235	Approved
0.6579	Remote Similarity	NPD1087	Approved
0.6579	Remote Similarity	NPD7411	Suspended
0.6575	Remote Similarity	NPD8166	Discontinued
0.6575	Remote Similarity	NPD4628	Phase 3
0.6575	Remote Similarity	NPD3750	Approved
0.6573	Remote Similarity	NPD4308	Phase 3
0.6571	Remote Similarity	NPD6233	Phase 2
0.6569	Remote Similarity	NPD2788	Approved
0.6557	Remote Similarity	NPD1932	Approved
0.6554	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD9256	Approved
0.6552	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1549	Phase 2
0.6552	Remote Similarity	NPD9258	Approved
0.6547	Remote Similarity	NPD6039	Approved
0.6544	Remote Similarity	NPD1283	Approved
0.6544	Remote Similarity	NPD2198	Approved
0.6544	Remote Similarity	NPD2199	Approved
0.6538	Remote Similarity	NPD3317	Approved
0.6535	Remote Similarity	NPD2201	Approved
0.6533	Remote Similarity	NPD5403	Approved
0.6531	Remote Similarity	NPD3887	Approved
0.6528	Remote Similarity	NPD2935	Discontinued
0.6528	Remote Similarity	NPD2438	Suspended
0.6518	Remote Similarity	NPD9491	Approved
0.6513	Remote Similarity	NPD6585	Discontinued
0.6512	Remote Similarity	NPD2652	Approved
0.6512	Remote Similarity	NPD2650	Approved
0.651	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD9261	Approved
0.6504	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5688	Approved
0.6503	Remote Similarity	NPD5689	Approved
0.65	Remote Similarity	NPD1296	Phase 2
0.65	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3847	Discontinued
0.6493	Remote Similarity	NPD3496	Discontinued
0.6486	Remote Similarity	NPD226	Approved
0.6483	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6685	Approved
0.6475	Remote Similarity	NPD2614	Approved
0.6471	Remote Similarity	NPD4359	Approved
0.6467	Remote Similarity	NPD6273	Approved
0.6466	Remote Similarity	NPD1651	Approved
0.6466	Remote Similarity	NPD800	Approved
0.6463	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4110	Phase 3
0.6462	Remote Similarity	NPD5951	Approved
0.646	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7305	Phase 1
0.6454	Remote Similarity	NPD6663	Approved
0.6454	Remote Similarity	NPD4062	Phase 3
0.6452	Remote Similarity	NPD5402	Approved
0.6452	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1535	Discovery
0.6444	Remote Similarity	NPD2612	Approved
0.6444	Remote Similarity	NPD2611	Approved
0.6444	Remote Similarity	NPD2608	Approved
0.6444	Remote Similarity	NPD4215	Approved
0.6444	Remote Similarity	NPD2610	Approved
0.6444	Remote Similarity	NPD3131	Approved
0.6444	Remote Similarity	NPD4217	Approved
0.6444	Remote Similarity	NPD4218	Approved
0.6444	Remote Similarity	NPD2609	Approved
0.6444	Remote Similarity	NPD4216	Approved
0.6444	Remote Similarity	NPD3132	Approved
0.6443	Remote Similarity	NPD6799	Approved
0.6439	Remote Similarity	NPD6065	Approved
0.6438	Remote Similarity	NPD5958	Discontinued
0.6433	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6801	Discontinued
0.6424	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2309	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