NPASS Compound

Structure

CID56448 OpenBabel06191715392D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 2 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 6 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 20 21 1 1 0 0 0 21 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	383.025
LogP:	2.788
LogD:	2.755
LogS:	-4.22
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	4.731
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.704
MDCK Permeability:	1.5416453607031144e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	55.20079040527344%
Volume Distribution (VD):	0.938
Pgp-substrate:	33.160064697265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.545
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.591
CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	2.643
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.681
AMES Toxicity:	0.976
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.609
Skin Sensitization:	0.58
Carcinogencity:	0.963
Eye Corrosion:	0.922
Eye Irritation:	0.628
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC56448

Natural Product ID:	NPC56448
*Common Name:**	Ustusolate E
IUPAC Name:	[(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E)-6-oxohexa-2,4-dienoate
Synonyms:	Ustusolate E
Standard InCHIKey:	NTEIYTQTTHYBTI-BEFOBABASA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-19(2)9-7-10-20(3)17(19)15(27-16(23)8-5-4-6-11-22)12-14-13-26-18(24)21(14,20)25/h4-6,8,11-12,15,17,25H,7,9-10,13H2,1-3H3/b6-4+,8-5+/t15-,17+,20+,21+/m1/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1[C@@H](C=C1COC(=O)[C@]21O)OC(=O)/C=C/C=C/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078135
PubChem CID:	44480472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277746]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19835393]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21261297]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21539300]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21868221]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25679537]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25901993]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[29715021]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO84	Isoberlinia angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18073	Justicia trinervia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14002	Petalostemon purpureum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28319	Ulva prolifera	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14813	Agaricus silvaticus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25550	Buchenavia tetraphylla	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17602	Arbutus menziesii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15748	Hypoxis nyasica	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16695	Fumaria kraliki	Species	Papaveraceae	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	3
IC50	2

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[473489]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	9000.0	nM	PMID[473489]
NPT1864	Cell Line	L5178Y	Mus musculus	EC50	=	0.6	ug.mL-1	PMID[473490]
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	=	7.2	ug.mL-1	PMID[473490]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	=	5.9	ug.mL-1	PMID[473490]

☑ 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 NPC56448 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	200
0.1-0.2	999
0.2-0.3	3395
0.3-0.4	6641
0.4-0.5	12992
0.5-0.6	8806
0.6-0.7	6942
0.7-0.8	2611
0.8-0.85	97
0.85-0.9	5
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC304180
0.9808	High Similarity	NPC179798
0.9623	High Similarity	NPC469454
0.9623	High Similarity	NPC469496
0.9623	High Similarity	NPC469463
0.9524	High Similarity	NPC5103
0.9358	High Similarity	NPC23046
0.9143	High Similarity	NPC477125
0.9048	High Similarity	NPC258532
0.8868	High Similarity	NPC146731
0.8692	High Similarity	NPC296950
0.8649	High Similarity	NPC269530
0.8482	Intermediate Similarity	NPC476801
0.8468	Intermediate Similarity	NPC235014
0.844	Intermediate Similarity	NPC469607
0.844	Intermediate Similarity	NPC1679
0.8435	Intermediate Similarity	NPC284707
0.8407	Intermediate Similarity	NPC471204
0.8396	Intermediate Similarity	NPC23364
0.8393	Intermediate Similarity	NPC188738
0.8348	Intermediate Similarity	NPC98249
0.8348	Intermediate Similarity	NPC53396
0.8348	Intermediate Similarity	NPC469684
0.8333	Intermediate Similarity	NPC295791
0.8333	Intermediate Similarity	NPC235369
0.8318	Intermediate Similarity	NPC174314
0.8304	Intermediate Similarity	NPC478211
0.8304	Intermediate Similarity	NPC210005
0.8288	Intermediate Similarity	NPC89171
0.8288	Intermediate Similarity	NPC306265
0.8288	Intermediate Similarity	NPC476802
0.8261	Intermediate Similarity	NPC176840
0.8261	Intermediate Similarity	NPC179626
0.8261	Intermediate Similarity	NPC478216
0.8261	Intermediate Similarity	NPC477509
0.8261	Intermediate Similarity	NPC270478
0.8246	Intermediate Similarity	NPC25909
0.8246	Intermediate Similarity	NPC474271
0.8235	Intermediate Similarity	NPC67251
0.823	Intermediate Similarity	NPC132790
0.823	Intermediate Similarity	NPC97939
0.823	Intermediate Similarity	NPC100329
0.823	Intermediate Similarity	NPC247031
0.822	Intermediate Similarity	NPC473250
0.8214	Intermediate Similarity	NPC474243
0.8214	Intermediate Similarity	NPC141350
0.8214	Intermediate Similarity	NPC469370
0.8205	Intermediate Similarity	NPC475775
0.8205	Intermediate Similarity	NPC270850
0.8205	Intermediate Similarity	NPC305260
0.8205	Intermediate Similarity	NPC476529
0.8198	Intermediate Similarity	NPC67321
0.8198	Intermediate Similarity	NPC144854
0.8198	Intermediate Similarity	NPC3316
0.8198	Intermediate Similarity	NPC187435
0.819	Intermediate Similarity	NPC473590
0.819	Intermediate Similarity	NPC477129
0.819	Intermediate Similarity	NPC477130
0.819	Intermediate Similarity	NPC473968
0.8182	Intermediate Similarity	NPC470297
0.8174	Intermediate Similarity	NPC474181
0.8167	Intermediate Similarity	NPC470922
0.8167	Intermediate Similarity	NPC24651
0.8165	Intermediate Similarity	NPC31058
0.8165	Intermediate Similarity	NPC273005
0.8165	Intermediate Similarity	NPC469606
0.8158	Intermediate Similarity	NPC126691
0.8158	Intermediate Similarity	NPC472002
0.8158	Intermediate Similarity	NPC236217
0.8151	Intermediate Similarity	NPC473231
0.8142	Intermediate Similarity	NPC253906
0.8142	Intermediate Similarity	NPC286880
0.8136	Intermediate Similarity	NPC474585
0.8136	Intermediate Similarity	NPC107338
0.8136	Intermediate Similarity	NPC475885
0.8136	Intermediate Similarity	NPC109607
0.8125	Intermediate Similarity	NPC37628
0.8125	Intermediate Similarity	NPC154608
0.8125	Intermediate Similarity	NPC192813
0.8125	Intermediate Similarity	NPC275539
0.8125	Intermediate Similarity	NPC277017
0.8125	Intermediate Similarity	NPC189075
0.8125	Intermediate Similarity	NPC476479
0.812	Intermediate Similarity	NPC153440
0.8103	Intermediate Similarity	NPC474734
0.8103	Intermediate Similarity	NPC190286
0.8099	Intermediate Similarity	NPC181999
0.8095	Intermediate Similarity	NPC475912
0.8091	Intermediate Similarity	NPC156681
0.8091	Intermediate Similarity	NPC23584
0.8091	Intermediate Similarity	NPC159533
0.8091	Intermediate Similarity	NPC475871
0.8091	Intermediate Similarity	NPC475945
0.8087	Intermediate Similarity	NPC477126
0.8087	Intermediate Similarity	NPC49451
0.8087	Intermediate Similarity	NPC51978
0.8087	Intermediate Similarity	NPC475966
0.8083	Intermediate Similarity	NPC469789
0.8073	Intermediate Similarity	NPC474742
0.807	Intermediate Similarity	NPC469656
0.807	Intermediate Similarity	NPC474846
0.807	Intermediate Similarity	NPC317107
0.807	Intermediate Similarity	NPC469655
0.8067	Intermediate Similarity	NPC46570
0.8056	Intermediate Similarity	NPC216478
0.8056	Intermediate Similarity	NPC222303
0.8053	Intermediate Similarity	NPC478210
0.8051	Intermediate Similarity	NPC5292
0.8051	Intermediate Similarity	NPC156745
0.8051	Intermediate Similarity	NPC268958
0.8051	Intermediate Similarity	NPC236918
0.8036	Intermediate Similarity	NPC78966
0.8036	Intermediate Similarity	NPC230541
0.8036	Intermediate Similarity	NPC133422
0.8036	Intermediate Similarity	NPC110496
0.8036	Intermediate Similarity	NPC284732
0.8034	Intermediate Similarity	NPC176513
0.8034	Intermediate Similarity	NPC470775
0.8034	Intermediate Similarity	NPC474518
0.8033	Intermediate Similarity	NPC476008
0.8019	Intermediate Similarity	NPC469491
0.8018	Intermediate Similarity	NPC220964
0.8018	Intermediate Similarity	NPC474741
0.8018	Intermediate Similarity	NPC475676
0.8017	Intermediate Similarity	NPC305044
0.8017	Intermediate Similarity	NPC8369
0.8017	Intermediate Similarity	NPC145238
0.8017	Intermediate Similarity	NPC265290
0.8017	Intermediate Similarity	NPC476729
0.8	Intermediate Similarity	NPC474516
0.8	Intermediate Similarity	NPC474747
0.8	Intermediate Similarity	NPC107493
0.8	Intermediate Similarity	NPC303697
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC317687
0.8	Intermediate Similarity	NPC312833
0.8	Intermediate Similarity	NPC149371
0.8	Intermediate Similarity	NPC11956
0.8	Intermediate Similarity	NPC473596
0.8	Intermediate Similarity	NPC302146
0.7983	Intermediate Similarity	NPC79579
0.7983	Intermediate Similarity	NPC48692
0.7983	Intermediate Similarity	NPC329080
0.7983	Intermediate Similarity	NPC185876
0.7983	Intermediate Similarity	NPC19336
0.7983	Intermediate Similarity	NPC472759
0.7982	Intermediate Similarity	NPC37116
0.7982	Intermediate Similarity	NPC471413
0.7982	Intermediate Similarity	NPC47024
0.7967	Intermediate Similarity	NPC236999
0.7966	Intermediate Similarity	NPC478205
0.7966	Intermediate Similarity	NPC470776
0.7966	Intermediate Similarity	NPC21326
0.7966	Intermediate Similarity	NPC251310
0.7966	Intermediate Similarity	NPC472760
0.7966	Intermediate Similarity	NPC108581
0.7966	Intermediate Similarity	NPC478206
0.7965	Intermediate Similarity	NPC264819
0.7963	Intermediate Similarity	NPC70145
0.7963	Intermediate Similarity	NPC91695
0.7963	Intermediate Similarity	NPC208094
0.7951	Intermediate Similarity	NPC293112
0.7951	Intermediate Similarity	NPC477745
0.7949	Intermediate Similarity	NPC148458
0.7949	Intermediate Similarity	NPC96312
0.7949	Intermediate Similarity	NPC40632
0.7949	Intermediate Similarity	NPC470628
0.7949	Intermediate Similarity	NPC474046
0.7949	Intermediate Similarity	NPC251236
0.7949	Intermediate Similarity	NPC259306
0.7949	Intermediate Similarity	NPC328374
0.7949	Intermediate Similarity	NPC207217
0.7946	Intermediate Similarity	NPC478208
0.7946	Intermediate Similarity	NPC472645
0.7946	Intermediate Similarity	NPC472749
0.7946	Intermediate Similarity	NPC472751
0.7946	Intermediate Similarity	NPC102352
0.7944	Intermediate Similarity	NPC14961
0.7944	Intermediate Similarity	NPC295347
0.7944	Intermediate Similarity	NPC270013
0.7944	Intermediate Similarity	NPC36954
0.7934	Intermediate Similarity	NPC91693
0.7934	Intermediate Similarity	NPC265557
0.7934	Intermediate Similarity	NPC18945
0.7934	Intermediate Similarity	NPC120724
0.7934	Intermediate Similarity	NPC105926
0.7931	Intermediate Similarity	NPC478212
0.7931	Intermediate Similarity	NPC101400
0.7931	Intermediate Similarity	NPC101965
0.7928	Intermediate Similarity	NPC99266
0.7928	Intermediate Similarity	NPC474775
0.7928	Intermediate Similarity	NPC475321
0.7928	Intermediate Similarity	NPC472755
0.7928	Intermediate Similarity	NPC472747
0.7928	Intermediate Similarity	NPC254202
0.7928	Intermediate Similarity	NPC473624
0.7928	Intermediate Similarity	NPC472750
0.7928	Intermediate Similarity	NPC120321
0.7928	Intermediate Similarity	NPC4620
0.7925	Intermediate Similarity	NPC476300

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 NPC56448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1219
0.2-0.3	3356
0.3-0.4	2724
0.4-0.5	1050
0.5-0.6	342
0.6-0.7	229
0.7-0.8	56
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
0.7727	Intermediate Similarity	NPD4225	Approved
0.7627	Intermediate Similarity	NPD4632	Approved
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7541	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD7260	Phase 2
0.75	Intermediate Similarity	NPD6686	Approved
0.7436	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5697	Approved
0.7414	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8297	Approved
0.7381	Intermediate Similarity	NPD7507	Approved
0.7373	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6899	Approved
0.735	Intermediate Similarity	NPD6881	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD8515	Approved
0.7339	Intermediate Similarity	NPD8517	Approved
0.7339	Intermediate Similarity	NPD8513	Phase 3
0.7339	Intermediate Similarity	NPD8516	Approved
0.7311	Intermediate Similarity	NPD6650	Approved
0.7311	Intermediate Similarity	NPD6649	Approved
0.7302	Intermediate Similarity	NPD7492	Approved
0.7295	Intermediate Similarity	NPD6009	Approved
0.7288	Intermediate Similarity	NPD6014	Approved
0.7288	Intermediate Similarity	NPD6012	Approved
0.7288	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD1694	Approved
0.7258	Intermediate Similarity	NPD6054	Approved
0.7244	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD6883	Approved
0.7227	Intermediate Similarity	NPD7102	Approved
0.7227	Intermediate Similarity	NPD6371	Approved
0.7227	Intermediate Similarity	NPD7290	Approved
0.7217	Intermediate Similarity	NPD5211	Phase 2
0.7209	Intermediate Similarity	NPD7319	Approved
0.7203	Intermediate Similarity	NPD6011	Approved
0.72	Intermediate Similarity	NPD5983	Phase 2
0.72	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD6015	Approved
0.7193	Intermediate Similarity	NPD6648	Approved
0.7193	Intermediate Similarity	NPD7640	Approved
0.7193	Intermediate Similarity	NPD7639	Approved
0.7188	Intermediate Similarity	NPD7078	Approved
0.7182	Intermediate Similarity	NPD7983	Approved
0.7179	Intermediate Similarity	NPD6675	Approved
0.7179	Intermediate Similarity	NPD6402	Approved
0.7179	Intermediate Similarity	NPD7128	Approved
0.7179	Intermediate Similarity	NPD5739	Approved
0.7179	Intermediate Similarity	NPD6008	Approved
0.7176	Intermediate Similarity	NPD6845	Suspended
0.7167	Intermediate Similarity	NPD6847	Approved
0.7167	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8130	Phase 1
0.7167	Intermediate Similarity	NPD6869	Approved
0.7167	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5344	Discontinued
0.7119	Intermediate Similarity	NPD5701	Approved
0.7119	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7107	Intermediate Similarity	NPD6882	Approved
0.7105	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7638	Approved
0.7094	Intermediate Similarity	NPD5141	Approved
0.7091	Intermediate Similarity	NPD46	Approved
0.7091	Intermediate Similarity	NPD6698	Approved
0.7091	Intermediate Similarity	NPD7838	Discovery
0.7087	Intermediate Similarity	NPD7604	Phase 2
0.7083	Intermediate Similarity	NPD4634	Approved
0.7063	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD7320	Approved
0.7054	Intermediate Similarity	NPD8074	Phase 3
0.7054	Intermediate Similarity	NPD5282	Discontinued
0.7043	Intermediate Similarity	NPD5286	Approved
0.7043	Intermediate Similarity	NPD4696	Approved
0.7043	Intermediate Similarity	NPD5285	Approved
0.6991	Remote Similarity	NPD5695	Phase 3
0.6984	Remote Similarity	NPD6059	Approved
0.6981	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6336	Discontinued
0.6957	Remote Similarity	NPD5696	Approved
0.6953	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD4755	Approved
0.687	Remote Similarity	NPD6083	Phase 2
0.687	Remote Similarity	NPD6084	Phase 2
0.6864	Remote Similarity	NPD5175	Approved
0.6864	Remote Similarity	NPD5174	Approved
0.6838	Remote Similarity	NPD5223	Approved
0.6838	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD6399	Phase 3
0.68	Remote Similarity	NPD6274	Approved
0.6797	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5222	Approved
0.6783	Remote Similarity	NPD5221	Approved
0.6772	Remote Similarity	NPD7101	Approved
0.6772	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD4700	Approved
0.6748	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6317	Approved
0.6746	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7637	Suspended
0.6726	Remote Similarity	NPD5693	Phase 1
0.6726	Remote Similarity	NPD5694	Approved
0.6724	Remote Similarity	NPD7902	Approved
0.6724	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6693	Remote Similarity	NPD6335	Approved
0.6693	Remote Similarity	NPD6313	Approved
0.6693	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD5785	Approved
0.6637	Remote Similarity	NPD5207	Approved
0.6637	Remote Similarity	NPD5692	Phase 3
0.6609	Remote Similarity	NPD7748	Approved
0.6607	Remote Similarity	NPD6672	Approved
0.6607	Remote Similarity	NPD5737	Approved
0.6579	Remote Similarity	NPD6079	Approved
0.6579	Remote Similarity	NPD6050	Approved
0.6577	Remote Similarity	NPD5279	Phase 3
0.6562	Remote Similarity	NPD7327	Approved
0.6562	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD1695	Approved
0.6549	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD8033	Approved
0.6535	Remote Similarity	NPD6868	Approved
0.6532	Remote Similarity	NPD5248	Approved
0.6532	Remote Similarity	NPD5251	Approved
0.6532	Remote Similarity	NPD5247	Approved
0.6532	Remote Similarity	NPD5249	Phase 3
0.6532	Remote Similarity	NPD5250	Approved
0.6518	Remote Similarity	NPD7524	Approved
0.6512	Remote Similarity	NPD7516	Approved
0.6504	Remote Similarity	NPD5128	Approved
0.6493	Remote Similarity	NPD6033	Approved
0.6486	Remote Similarity	NPD1696	Phase 3
0.6481	Remote Similarity	NPD4695	Discontinued
0.648	Remote Similarity	NPD5215	Approved
0.648	Remote Similarity	NPD5217	Approved
0.648	Remote Similarity	NPD5216	Approved
0.6475	Remote Similarity	NPD4767	Approved
0.6475	Remote Similarity	NPD4768	Approved
0.6466	Remote Similarity	NPD8451	Approved
0.6466	Remote Similarity	NPD7900	Approved
0.6466	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8294	Approved
0.6462	Remote Similarity	NPD8377	Approved
0.6452	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4754	Approved
0.6435	Remote Similarity	NPD7515	Phase 2
0.6434	Remote Similarity	NPD7641	Discontinued
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD4694	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5690	Phase 2
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD4623	Approved
0.6429	Remote Similarity	NPD4519	Discontinued
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD5280	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6418	Remote Similarity	NPD8448	Approved
0.6412	Remote Similarity	NPD8380	Approved
0.6412	Remote Similarity	NPD8379	Approved
0.6412	Remote Similarity	NPD8335	Approved
0.6412	Remote Similarity	NPD8296	Approved
0.6412	Remote Similarity	NPD6909	Approved
0.6412	Remote Similarity	NPD8378	Approved
0.6412	Remote Similarity	NPD6908	Approved
0.641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6673	Approved
0.6404	Remote Similarity	NPD5328	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