NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	3.511
LogD:	2.562
LogS:	-3.44
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	2.698
Fsp3:	0.133
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:	-4.898
MDCK Permeability:	9.246232366422191e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.715
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	89.78883361816406%
Volume Distribution (VD):	0.729
Pgp-substrate:	11.322283744812012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.364
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.709
CYP2D6-substrate:	0.843
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	4.32
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.497
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.891
Carcinogencity:	0.05
Eye Corrosion:	0.01
Eye Irritation:	0.934
Respiratory Toxicity:	0.421

Download Data

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

Natural Product: NPC7943

Natural Product ID:	NPC7943
*Common Name:**	Rubrofusarin
IUPAC Name:	5,6-dihydroxy-8-methoxy-2-methylbenzo[g]chromen-4-one
Synonyms:	Rubrofusarin
Standard InCHIKey:	FPNKCZKRICBAKG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c1-7-3-10(16)14-12(20-7)5-8-4-9(19-2)6-11(17)13(8)15(14)18/h3-6,17-18H,1-2H3
SMILES:	Cc1cc(=O)c2c(cc3cc(cc(c3c2O)O)OC)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475086
PubChem CID:	72537
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO22786	Senna obliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987063]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21109	Cassia quinquangula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21109	Cassia quinquangula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21109	Cassia quinquangula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22786	Senna obliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	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
MIC	1
Others	3

Activity Type	# Activity
NON-MOLECULAR	1
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.0	ug.mL-1	PMID[544213]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	99.0	%	PMID[544213]
NPT27	Others	Unspecified		CC50	=	1019600.0	nM	PMID[544214]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56200.0	nM	PMID[544214]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	18.1	n.a.	PMID[544214]
NPT2	Others	Unspecified		IC50	=	162.04	ug.mL-1	PMID[544215]
NPT35	Others	n.a.		IC50	=	3.03	ug.mL-1	PMID[544215]

☑ 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 NPC7943 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	443
0.1-0.2	1969
0.2-0.3	4292
0.3-0.4	11223
0.4-0.5	6899
0.5-0.6	3880
0.6-0.7	5348
0.7-0.8	4751
0.8-0.85	2179
0.85-0.9	1477
0.9-0.95	215
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22005
1.0	High Similarity	NPC123202
0.9929	High Similarity	NPC7025
0.9929	High Similarity	NPC256672
0.9929	High Similarity	NPC27221
0.9859	High Similarity	NPC100985
0.9859	High Similarity	NPC158338
0.9859	High Similarity	NPC97029
0.9859	High Similarity	NPC65589
0.9859	High Similarity	NPC97028
0.9859	High Similarity	NPC288036
0.9653	High Similarity	NPC325983
0.9643	High Similarity	NPC182255
0.9643	High Similarity	NPC94076
0.9589	High Similarity	NPC210942
0.9589	High Similarity	NPC329844
0.9589	High Similarity	NPC169990
0.9586	High Similarity	NPC232645
0.9586	High Similarity	NPC72958
0.9586	High Similarity	NPC258249
0.9586	High Similarity	NPC149526
0.9586	High Similarity	NPC474417
0.9574	High Similarity	NPC84266
0.9521	High Similarity	NPC87708
0.9517	High Similarity	NPC202595
0.9507	High Similarity	NPC189650
0.9452	High Similarity	NPC478148
0.9444	High Similarity	NPC34802
0.9437	High Similarity	NPC310340
0.9433	High Similarity	NPC275734
0.9388	High Similarity	NPC154683
0.9388	High Similarity	NPC40356
0.9324	High Similarity	NPC214632
0.9315	High Similarity	NPC291049
0.9315	High Similarity	NPC10027
0.9315	High Similarity	NPC233267
0.9315	High Similarity	NPC329933
0.9315	High Similarity	NPC65775
0.931	High Similarity	NPC190648
0.931	High Similarity	NPC118027
0.931	High Similarity	NPC289042
0.931	High Similarity	NPC56433
0.931	High Similarity	NPC312929
0.931	High Similarity	NPC126767
0.931	High Similarity	NPC245584
0.9272	High Similarity	NPC186325
0.9257	High Similarity	NPC175978
0.9257	High Similarity	NPC217447
0.9247	High Similarity	NPC105415
0.9241	High Similarity	NPC267509
0.9236	High Similarity	NPC19896
0.9225	High Similarity	NPC18260
0.9225	High Similarity	NPC78913
0.9214	High Similarity	NPC242712
0.9211	High Similarity	NPC273467
0.9211	High Similarity	NPC66288
0.9211	High Similarity	NPC189552
0.9205	High Similarity	NPC177650
0.92	High Similarity	NPC180924
0.9189	High Similarity	NPC133856
0.9184	High Similarity	NPC269420
0.9178	High Similarity	NPC259632
0.9178	High Similarity	NPC71055
0.9172	High Similarity	NPC32470
0.9161	High Similarity	NPC241100
0.9161	High Similarity	NPC159275
0.9155	High Similarity	NPC201395
0.9155	High Similarity	NPC57380
0.915	High Similarity	NPC294965
0.9145	High Similarity	NPC312993
0.9143	High Similarity	NPC125920
0.9139	High Similarity	NPC96342
0.9139	High Similarity	NPC164110
0.9139	High Similarity	NPC212967
0.9139	High Similarity	NPC246647
0.9128	High Similarity	NPC273483
0.9122	High Similarity	NPC290954
0.9122	High Similarity	NPC158866
0.9122	High Similarity	NPC294646
0.9122	High Similarity	NPC227122
0.9122	High Similarity	NPC470568
0.9122	High Similarity	NPC255641
0.9122	High Similarity	NPC119929
0.9122	High Similarity	NPC147735
0.9116	High Similarity	NPC37139
0.911	High Similarity	NPC24136
0.911	High Similarity	NPC196114
0.911	High Similarity	NPC163846
0.911	High Similarity	NPC473927
0.911	High Similarity	NPC187282
0.911	High Similarity	NPC225173
0.911	High Similarity	NPC290133
0.9103	High Similarity	NPC11700
0.9097	High Similarity	NPC282300
0.9097	High Similarity	NPC110969
0.9091	High Similarity	NPC216978
0.9091	High Similarity	NPC220062
0.9091	High Similarity	NPC301217
0.9091	High Similarity	NPC303633
0.9091	High Similarity	NPC55018
0.9091	High Similarity	NPC53181
0.9091	High Similarity	NPC165172
0.9091	High Similarity	NPC96565
0.9091	High Similarity	NPC217186
0.9091	High Similarity	NPC270837
0.9079	High Similarity	NPC55443
0.9079	High Similarity	NPC18699
0.9079	High Similarity	NPC85121
0.9078	High Similarity	NPC60667
0.9073	High Similarity	NPC146211
0.9071	High Similarity	NPC108113
0.9071	High Similarity	NPC93756
0.9067	High Similarity	NPC135522
0.9067	High Similarity	NPC178964
0.9067	High Similarity	NPC93552
0.9067	High Similarity	NPC280530
0.9067	High Similarity	NPC95842
0.9067	High Similarity	NPC193200
0.906	High Similarity	NPC470569
0.9054	High Similarity	NPC473978
0.9054	High Similarity	NPC474052
0.9048	High Similarity	NPC125801
0.9041	High Similarity	NPC311741
0.9041	High Similarity	NPC216538
0.9041	High Similarity	NPC224714
0.9041	High Similarity	NPC234629
0.9041	High Similarity	NPC134621
0.9041	High Similarity	NPC273538
0.9041	High Similarity	NPC271288
0.9034	High Similarity	NPC73028
0.9034	High Similarity	NPC473042
0.9034	High Similarity	NPC226636
0.9034	High Similarity	NPC11561
0.9034	High Similarity	NPC1534
0.9032	High Similarity	NPC469664
0.9028	High Similarity	NPC172986
0.9028	High Similarity	NPC220106
0.9028	High Similarity	NPC182421
0.9028	High Similarity	NPC270883
0.9028	High Similarity	NPC150522
0.9028	High Similarity	NPC261227
0.9021	High Similarity	NPC131130
0.902	High Similarity	NPC470810
0.9014	High Similarity	NPC47815
0.9014	High Similarity	NPC29353
0.9014	High Similarity	NPC194281
0.9014	High Similarity	NPC124784
0.9014	High Similarity	NPC234133
0.9014	High Similarity	NPC193792
0.9014	High Similarity	NPC231772
0.9014	High Similarity	NPC174999
0.9014	High Similarity	NPC473887
0.9014	High Similarity	NPC127447
0.9013	High Similarity	NPC263483
0.9013	High Similarity	NPC201127
0.9013	High Similarity	NPC272196
0.9013	High Similarity	NPC268360
0.9013	High Similarity	NPC44199
0.9007	High Similarity	NPC226656
0.9007	High Similarity	NPC66508
0.9007	High Similarity	NPC254351
0.9007	High Similarity	NPC149618
0.9007	High Similarity	NPC89625
0.9007	High Similarity	NPC148938
0.9	High Similarity	NPC142527
0.9	High Similarity	NPC45934
0.9	High Similarity	NPC271681
0.8993	High Similarity	NPC295036
0.8993	High Similarity	NPC470107
0.8993	High Similarity	NPC472633
0.8993	High Similarity	NPC37348
0.8993	High Similarity	NPC150928
0.8986	High Similarity	NPC5537
0.898	High Similarity	NPC473132
0.898	High Similarity	NPC477955
0.898	High Similarity	NPC237208
0.898	High Similarity	NPC130176
0.898	High Similarity	NPC124729
0.898	High Similarity	NPC99454
0.898	High Similarity	NPC178343
0.898	High Similarity	NPC306488
0.898	High Similarity	NPC470676
0.898	High Similarity	NPC473135
0.898	High Similarity	NPC5820
0.8973	High Similarity	NPC212932
0.8973	High Similarity	NPC9117
0.8973	High Similarity	NPC166138
0.8973	High Similarity	NPC95123
0.8973	High Similarity	NPC106985
0.8973	High Similarity	NPC158874
0.8973	High Similarity	NPC475201
0.8973	High Similarity	NPC190637
0.8973	High Similarity	NPC24821
0.8973	High Similarity	NPC293053
0.8973	High Similarity	NPC66404
0.8973	High Similarity	NPC18585
0.8973	High Similarity	NPC219915
0.8968	High Similarity	NPC197168
0.8966	High Similarity	NPC213322
0.8966	High Similarity	NPC147688

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 NPC7943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	1035
0.2-0.3	1580
0.3-0.4	2672
0.4-0.5	1845
0.5-0.6	1046
0.6-0.7	367
0.7-0.8	123
0.8-0.85	43
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD4378	Clinical (unspecified phase)
0.8961	High Similarity	NPD6959	Discontinued
0.8889	High Similarity	NPD970	Clinical (unspecified phase)
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8816	High Similarity	NPD7819	Suspended
0.8811	High Similarity	NPD1510	Phase 2
0.8803	High Similarity	NPD1607	Approved
0.8759	High Similarity	NPD1549	Phase 2
0.8716	High Similarity	NPD1511	Approved
0.8693	High Similarity	NPD2393	Clinical (unspecified phase)
0.8681	High Similarity	NPD1509	Clinical (unspecified phase)
0.8662	High Similarity	NPD1240	Approved
0.8658	High Similarity	NPD7410	Clinical (unspecified phase)
0.86	High Similarity	NPD1512	Approved
0.8544	High Similarity	NPD6232	Discontinued
0.8533	High Similarity	NPD2532	Approved
0.8533	High Similarity	NPD2534	Approved
0.8533	High Similarity	NPD2533	Approved
0.8516	High Similarity	NPD8443	Clinical (unspecified phase)
0.8514	High Similarity	NPD3750	Approved
0.8506	High Similarity	NPD1934	Approved
0.85	High Similarity	NPD7473	Discontinued
0.8493	Intermediate Similarity	NPD2796	Approved
0.8452	Intermediate Similarity	NPD2801	Approved
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD7390	Discontinued
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD2800	Approved
0.8322	Intermediate Similarity	NPD1243	Approved
0.8312	Intermediate Similarity	NPD3226	Approved
0.8291	Intermediate Similarity	NPD7075	Discontinued
0.8291	Intermediate Similarity	NPD3749	Approved
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD6100	Approved
0.8243	Intermediate Similarity	NPD6099	Approved
0.8228	Intermediate Similarity	NPD7768	Phase 2
0.8217	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2346	Discontinued
0.8176	Intermediate Similarity	NPD3748	Approved
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8153	Intermediate Similarity	NPD6801	Discontinued
0.8141	Intermediate Similarity	NPD6599	Discontinued
0.8113	Intermediate Similarity	NPD3882	Suspended
0.8069	Intermediate Similarity	NPD4625	Phase 3
0.8065	Intermediate Similarity	NPD920	Approved
0.8063	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD3817	Phase 2
0.8039	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1465	Phase 2
0.7987	Intermediate Similarity	NPD6799	Approved
0.7963	Intermediate Similarity	NPD5494	Approved
0.7961	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2344	Approved
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6651	Approved
0.7908	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD919	Approved
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.7887	Intermediate Similarity	NPD1201	Approved
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5711	Approved
0.7866	Intermediate Similarity	NPD5710	Approved
0.7844	Intermediate Similarity	NPD7054	Approved
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.7805	Intermediate Similarity	NPD1247	Approved
0.7798	Intermediate Similarity	NPD7472	Approved
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7793	Intermediate Similarity	NPD1470	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2313	Discontinued
0.7763	Intermediate Similarity	NPD5405	Approved
0.7763	Intermediate Similarity	NPD5408	Approved
0.7763	Intermediate Similarity	NPD5404	Approved
0.7763	Intermediate Similarity	NPD5406	Approved
0.7751	Intermediate Similarity	NPD6797	Phase 2
0.7742	Intermediate Similarity	NPD2309	Approved
0.7736	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1283	Approved
0.7706	Intermediate Similarity	NPD7251	Discontinued
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7677	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1651	Approved
0.7671	Intermediate Similarity	NPD1203	Approved
0.7661	Intermediate Similarity	NPD7808	Phase 3
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5953	Discontinued
0.7639	Intermediate Similarity	NPD1610	Phase 2
0.761	Intermediate Similarity	NPD5403	Approved
0.7607	Intermediate Similarity	NPD5402	Approved
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7597	Intermediate Similarity	NPD1471	Phase 3
0.7595	Intermediate Similarity	NPD5401	Approved
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1608	Approved
0.7582	Intermediate Similarity	NPD4308	Phase 3
0.7564	Intermediate Similarity	NPD7003	Approved
0.7558	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7229	Phase 3
0.7534	Intermediate Similarity	NPD4749	Approved
0.7533	Intermediate Similarity	NPD3268	Approved
0.7533	Intermediate Similarity	NPD411	Approved
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1281	Approved
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD4288	Approved
0.7471	Intermediate Similarity	NPD7177	Discontinued
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD9717	Approved
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2797	Approved
0.743	Intermediate Similarity	NPD4360	Phase 2
0.743	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD230	Phase 1
0.7379	Intermediate Similarity	NPD17	Approved
0.7375	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7347	Intermediate Similarity	NPD3972	Approved
0.7341	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.732	Intermediate Similarity	NPD4307	Phase 2
0.7315	Intermediate Similarity	NPD1164	Approved
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7303	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD4287	Approved
0.7303	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7284	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD447	Suspended
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.726	Intermediate Similarity	NPD4626	Approved
0.7248	Intermediate Similarity	NPD3225	Approved
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD2979	Phase 3
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7186	Intermediate Similarity	NPD2296	Approved
0.7184	Intermediate Similarity	NPD1729	Discontinued
0.717	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1611	Approved
0.7161	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5124	Phase 1
0.7158	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1876	Approved
0.7123	Intermediate Similarity	NPD9545	Approved
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7697	Approved
0.7112	Intermediate Similarity	NPD7698	Approved
0.7112	Intermediate Similarity	NPD7435	Discontinued
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9493	Approved
0.7103	Intermediate Similarity	NPD405	Clinical (unspecified phase)

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