NPASS Compound

Structure

CID23046 OpenBabel06191715352D 30 32 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 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -4.3301 -1.5000 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 -5.1962 -2.0000 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 -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 -5.1962 -3.0000 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 -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 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 6 0 0 0 17 24 2 0 0 0 0 17 30 1 0 0 0 0 18 27 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 6 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 22 23 1 1 0 0 0 23 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.21
Volume:	429.044
LogP:	3.681
LogD:	3.272
LogS:	-4.133
# Rotatable Bonds:	7
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.907
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	3.2502954127267e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.789
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	53.74064254760742%
Volume Distribution (VD):	1.491
Pgp-substrate:	40.58915710449219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	6.571
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.955
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.72
Carcinogencity:	0.959
Eye Corrosion:	0.358
Eye Irritation:	0.057
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC23046

Natural Product ID:	NPC23046
*Common Name:**	Ustusolate D
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)-6,6-dimethoxyhexa-2,4-dienoate
Synonyms:	Ustusolate D
Standard InCHIKey:	IHLICQZFMFYTOA-ODJYOQRJSA-N
Standard InCHI:	InChI=1S/C23H32O7/c1-21(2)11-8-12-22(3)19(21)16(13-15-14-29-20(25)23(15,22)26)30-17(24)9-6-7-10-18(27-4)28-5/h6-7,9-10,13,16,18-19,26H,8,11-12,14H2,1-5H3/b9-6+,10-7+/t16-,19+,22+,23+/m1/s1
SMILES:	COC(/C=C/C=C/C(=O)O[C@@H]1C=C2COC(=O)[C@@]2([C@@]2([C@@H]1C(C)(C)CCC2)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080953
PubChem CID:	44557643
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.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	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]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	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]
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]
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]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	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]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	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]
NPO17602	Arbutus menziesii	Species	Ericaceae	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]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	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]
NPO17844	Agaricus integer	Species	Agaricaceae	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]
NPO16695	Fumaria kraliki	Species	Papaveraceae	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]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO18073	Justicia trinervia	Species	Acanthaceae	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]
NPO15004	Artemisia taurica	Species	Asteraceae	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]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	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]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	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]
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]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28319	Ulva prolifera	Species	Ulvaceae	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	2

Activity Type	# Activity
Cell Line	2

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[483352]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[483352]

☑ 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 NPC23046 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	208
0.1-0.2	1054
0.2-0.3	3489
0.3-0.4	6673
0.4-0.5	12448
0.5-0.6	9227
0.6-0.7	6783
0.7-0.8	2665
0.8-0.85	136
0.85-0.9	6
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC469496
0.9537	High Similarity	NPC469454
0.9537	High Similarity	NPC469463
0.9533	High Similarity	NPC304180
0.9533	High Similarity	NPC179798
0.9358	High Similarity	NPC56448
0.9259	High Similarity	NPC5103
0.8889	High Similarity	NPC477125
0.8796	High Similarity	NPC258532
0.8739	High Similarity	NPC235014
0.8624	High Similarity	NPC146731
0.8584	High Similarity	NPC269530
0.8547	High Similarity	NPC48692
0.8475	Intermediate Similarity	NPC473250
0.8455	Intermediate Similarity	NPC296950
0.8421	Intermediate Similarity	NPC321272
0.8421	Intermediate Similarity	NPC328074
0.8421	Intermediate Similarity	NPC317460
0.8421	Intermediate Similarity	NPC470025
0.8407	Intermediate Similarity	NPC119550
0.8403	Intermediate Similarity	NPC473231
0.8378	Intermediate Similarity	NPC252296
0.8362	Intermediate Similarity	NPC471816
0.8348	Intermediate Similarity	NPC470027
0.8348	Intermediate Similarity	NPC157441
0.8348	Intermediate Similarity	NPC471204
0.8333	Intermediate Similarity	NPC17791
0.8319	Intermediate Similarity	NPC316974
0.8306	Intermediate Similarity	NPC471855
0.8305	Intermediate Similarity	NPC476529
0.8305	Intermediate Similarity	NPC474179
0.8305	Intermediate Similarity	NPC475834
0.8305	Intermediate Similarity	NPC475775
0.8304	Intermediate Similarity	NPC184512
0.8291	Intermediate Similarity	NPC473968
0.8264	Intermediate Similarity	NPC470922
0.8261	Intermediate Similarity	NPC12046
0.8261	Intermediate Similarity	NPC194951
0.8246	Intermediate Similarity	NPC316708
0.8235	Intermediate Similarity	NPC107338
0.8235	Intermediate Similarity	NPC109607
0.823	Intermediate Similarity	NPC48548
0.823	Intermediate Similarity	NPC128795
0.823	Intermediate Similarity	NPC135015
0.823	Intermediate Similarity	NPC311223
0.823	Intermediate Similarity	NPC217921
0.823	Intermediate Similarity	NPC470024
0.8226	Intermediate Similarity	NPC213634
0.822	Intermediate Similarity	NPC284707
0.822	Intermediate Similarity	NPC475913
0.8214	Intermediate Similarity	NPC469607
0.8205	Intermediate Similarity	NPC176840
0.8198	Intermediate Similarity	NPC132395
0.8198	Intermediate Similarity	NPC471365
0.8198	Intermediate Similarity	NPC471364
0.8198	Intermediate Similarity	NPC134270
0.8197	Intermediate Similarity	NPC222307
0.819	Intermediate Similarity	NPC25909
0.8182	Intermediate Similarity	NPC67251
0.8174	Intermediate Similarity	NPC470026
0.8174	Intermediate Similarity	NPC188738
0.8167	Intermediate Similarity	NPC473228
0.8167	Intermediate Similarity	NPC470829
0.8165	Intermediate Similarity	NPC23364
0.8158	Intermediate Similarity	NPC112457
0.8158	Intermediate Similarity	NPC40728
0.8151	Intermediate Similarity	NPC305260
0.8151	Intermediate Similarity	NPC270850
0.8151	Intermediate Similarity	NPC122971
0.8148	Intermediate Similarity	NPC311166
0.8145	Intermediate Similarity	NPC473593
0.8145	Intermediate Similarity	NPC471407
0.8142	Intermediate Similarity	NPC88013
0.8142	Intermediate Similarity	NPC187435
0.8142	Intermediate Similarity	NPC125423
0.8142	Intermediate Similarity	NPC67321
0.8142	Intermediate Similarity	NPC109376
0.8136	Intermediate Similarity	NPC98249
0.8136	Intermediate Similarity	NPC13713
0.8136	Intermediate Similarity	NPC473590
0.8136	Intermediate Similarity	NPC53396
0.8136	Intermediate Similarity	NPC469684
0.813	Intermediate Similarity	NPC470780
0.8125	Intermediate Similarity	NPC473207
0.8125	Intermediate Similarity	NPC201880
0.8125	Intermediate Similarity	NPC81567
0.8125	Intermediate Similarity	NPC264867
0.8125	Intermediate Similarity	NPC470321
0.812	Intermediate Similarity	NPC181145
0.812	Intermediate Similarity	NPC474181
0.8108	Intermediate Similarity	NPC295791
0.8108	Intermediate Similarity	NPC238397
0.8108	Intermediate Similarity	NPC471363
0.8108	Intermediate Similarity	NPC235369
0.8103	Intermediate Similarity	NPC476801
0.8103	Intermediate Similarity	NPC236217
0.8095	Intermediate Similarity	NPC478151
0.8087	Intermediate Similarity	NPC210005
0.8087	Intermediate Similarity	NPC478211
0.8087	Intermediate Similarity	NPC83005
0.8083	Intermediate Similarity	NPC474585
0.8083	Intermediate Similarity	NPC475885
0.8073	Intermediate Similarity	NPC98112
0.807	Intermediate Similarity	NPC224660
0.807	Intermediate Similarity	NPC189075
0.807	Intermediate Similarity	NPC476479
0.807	Intermediate Similarity	NPC177524
0.807	Intermediate Similarity	NPC275539
0.807	Intermediate Similarity	NPC219900
0.807	Intermediate Similarity	NPC392
0.8067	Intermediate Similarity	NPC473828
0.8067	Intermediate Similarity	NPC153440
0.8067	Intermediate Similarity	NPC234522
0.8067	Intermediate Similarity	NPC473617
0.8065	Intermediate Similarity	NPC473888
0.8065	Intermediate Similarity	NPC270109
0.8053	Intermediate Similarity	NPC218158
0.8053	Intermediate Similarity	NPC127609
0.8053	Intermediate Similarity	NPC472749
0.8053	Intermediate Similarity	NPC172867
0.8053	Intermediate Similarity	NPC472751
0.8051	Intermediate Similarity	NPC477509
0.8051	Intermediate Similarity	NPC478216
0.8051	Intermediate Similarity	NPC270478
0.8051	Intermediate Similarity	NPC470628
0.8051	Intermediate Similarity	NPC474046
0.8051	Intermediate Similarity	NPC474734
0.8051	Intermediate Similarity	NPC179626
0.8051	Intermediate Similarity	NPC190286
0.8051	Intermediate Similarity	NPC259306
0.8049	Intermediate Similarity	NPC181999
0.8036	Intermediate Similarity	NPC475889
0.8036	Intermediate Similarity	NPC472747
0.8036	Intermediate Similarity	NPC23584
0.8036	Intermediate Similarity	NPC7644
0.8036	Intermediate Similarity	NPC127933
0.8036	Intermediate Similarity	NPC7613
0.8036	Intermediate Similarity	NPC472750
0.8034	Intermediate Similarity	NPC51978
0.8034	Intermediate Similarity	NPC474410
0.8034	Intermediate Similarity	NPC474271
0.8034	Intermediate Similarity	NPC293658
0.8034	Intermediate Similarity	NPC477126
0.8034	Intermediate Similarity	NPC264153
0.8034	Intermediate Similarity	NPC75167
0.8034	Intermediate Similarity	NPC311592
0.8033	Intermediate Similarity	NPC469789
0.8033	Intermediate Similarity	NPC41129
0.8031	Intermediate Similarity	NPC471234
0.8017	Intermediate Similarity	NPC202051
0.8017	Intermediate Similarity	NPC317107
0.8017	Intermediate Similarity	NPC100329
0.8017	Intermediate Similarity	NPC46570
0.8017	Intermediate Similarity	NPC247031
0.8017	Intermediate Similarity	NPC132790
0.8017	Intermediate Similarity	NPC204731
0.8017	Intermediate Similarity	NPC97939
0.8016	Intermediate Similarity	NPC478152
0.8016	Intermediate Similarity	NPC478150
0.8016	Intermediate Similarity	NPC478153
0.8016	Intermediate Similarity	NPC155529
0.8016	Intermediate Similarity	NPC478154
0.8	Intermediate Similarity	NPC5292
0.8	Intermediate Similarity	NPC236918
0.8	Intermediate Similarity	NPC141350
0.8	Intermediate Similarity	NPC206618
0.8	Intermediate Similarity	NPC268958
0.8	Intermediate Similarity	NPC469370
0.8	Intermediate Similarity	NPC156745
0.7984	Intermediate Similarity	NPC596
0.7984	Intermediate Similarity	NPC152091
0.7984	Intermediate Similarity	NPC295885
0.7984	Intermediate Similarity	NPC42399
0.7984	Intermediate Similarity	NPC140045
0.7982	Intermediate Similarity	NPC110496
0.7982	Intermediate Similarity	NPC293512
0.7982	Intermediate Similarity	NPC3316
0.7982	Intermediate Similarity	NPC144854
0.7969	Intermediate Similarity	NPC158350
0.7967	Intermediate Similarity	NPC145238
0.7967	Intermediate Similarity	NPC8369
0.7967	Intermediate Similarity	NPC476729
0.7967	Intermediate Similarity	NPC24651
0.7966	Intermediate Similarity	NPC470919
0.7966	Intermediate Similarity	NPC265290
0.7966	Intermediate Similarity	NPC475163
0.7966	Intermediate Similarity	NPC305044
0.7966	Intermediate Similarity	NPC469877
0.7965	Intermediate Similarity	NPC475676
0.7965	Intermediate Similarity	NPC472748
0.7965	Intermediate Similarity	NPC220964
0.7963	Intermediate Similarity	NPC88507
0.7963	Intermediate Similarity	NPC477129
0.7963	Intermediate Similarity	NPC477130
0.7963	Intermediate Similarity	NPC469491
0.7951	Intermediate Similarity	NPC107493
0.7951	Intermediate Similarity	NPC287236
0.7949	Intermediate Similarity	NPC472002
0.7949	Intermediate Similarity	NPC317687
0.7949	Intermediate Similarity	NPC222834

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 NPC23046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1261
0.2-0.3	3381
0.3-0.4	2702
0.4-0.5	977
0.5-0.6	381
0.6-0.7	220
0.7-0.8	48
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
0.807	Intermediate Similarity	NPD6686	Approved
0.7869	Intermediate Similarity	NPD8513	Phase 3
0.7869	Intermediate Similarity	NPD8515	Approved
0.7869	Intermediate Similarity	NPD8517	Approved
0.7869	Intermediate Similarity	NPD8516	Approved
0.7661	Intermediate Similarity	NPD6370	Approved
0.7638	Intermediate Similarity	NPD7736	Approved
0.7619	Intermediate Similarity	NPD7507	Approved
0.7581	Intermediate Similarity	NPD7503	Approved
0.7541	Intermediate Similarity	NPD7115	Discovery
0.754	Intermediate Similarity	NPD7492	Approved
0.7522	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.7462	Intermediate Similarity	NPD7260	Phase 2
0.746	Intermediate Similarity	NPD8328	Phase 3
0.7442	Intermediate Similarity	NPD7319	Approved
0.7438	Intermediate Similarity	NPD4632	Approved
0.7422	Intermediate Similarity	NPD7078	Approved
0.7422	Intermediate Similarity	NPD8293	Discontinued
0.7417	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6009	Approved
0.7373	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6319	Approved
0.7355	Intermediate Similarity	NPD6882	Approved
0.7355	Intermediate Similarity	NPD8297	Approved
0.7311	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6899	Approved
0.7311	Intermediate Similarity	NPD6881	Approved
0.7302	Intermediate Similarity	NPD6015	Approved
0.7302	Intermediate Similarity	NPD6016	Approved
0.7287	Intermediate Similarity	NPD8074	Phase 3
0.7273	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6649	Approved
0.7258	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5988	Approved
0.7232	Intermediate Similarity	NPD5778	Approved
0.7232	Intermediate Similarity	NPD5779	Approved
0.7227	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD6059	Approved
0.719	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6883	Approved
0.719	Intermediate Similarity	NPD7102	Approved
0.719	Intermediate Similarity	NPD7290	Approved
0.719	Intermediate Similarity	NPD6371	Approved
0.7155	Intermediate Similarity	NPD6648	Approved
0.7155	Intermediate Similarity	NPD7640	Approved
0.7155	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6845	Suspended
0.7143	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7131	Intermediate Similarity	NPD6847	Approved
0.7131	Intermediate Similarity	NPD8130	Phase 1
0.7131	Intermediate Similarity	NPD6869	Approved
0.7131	Intermediate Similarity	NPD6617	Approved
0.7107	Intermediate Similarity	NPD6372	Approved
0.7107	Intermediate Similarity	NPD6013	Approved
0.7107	Intermediate Similarity	NPD6373	Approved
0.7107	Intermediate Similarity	NPD6014	Approved
0.7107	Intermediate Similarity	NPD6012	Approved
0.7094	Intermediate Similarity	NPD5344	Discontinued
0.7073	Intermediate Similarity	NPD6053	Discontinued
0.7069	Intermediate Similarity	NPD7638	Approved
0.7064	Intermediate Similarity	NPD1694	Approved
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7059	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD46	Approved
0.7054	Intermediate Similarity	NPD6698	Approved
0.7054	Intermediate Similarity	NPD7604	Phase 2
0.7054	Intermediate Similarity	NPD7838	Discovery
0.7034	Intermediate Similarity	NPD5211	Phase 2
0.7031	Intermediate Similarity	NPD5983	Phase 2
0.7031	Intermediate Similarity	NPD8033	Approved
0.7025	Intermediate Similarity	NPD7320	Approved
0.7025	Intermediate Similarity	NPD6011	Approved
0.7008	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8294	Approved
0.6953	Remote Similarity	NPD8377	Approved
0.6947	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5701	Approved
0.6917	Remote Similarity	NPD5141	Approved
0.6911	Remote Similarity	NPD4634	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.688	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD5282	Discontinued
0.6864	Remote Similarity	NPD5285	Approved
0.6864	Remote Similarity	NPD4696	Approved
0.6864	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD6411	Approved
0.6838	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6083	Phase 2
0.681	Remote Similarity	NPD5695	Phase 3
0.6794	Remote Similarity	NPD7830	Approved
0.6794	Remote Similarity	NPD7829	Approved
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6399	Phase 3
0.678	Remote Similarity	NPD5696	Approved
0.6757	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5224	Approved
0.675	Remote Similarity	NPD5226	Approved
0.675	Remote Similarity	NPD4633	Approved
0.675	Remote Similarity	NPD5225	Approved
0.6744	Remote Similarity	NPD7101	Approved
0.6744	Remote Similarity	NPD7100	Approved
0.672	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6033	Approved
0.6696	Remote Similarity	NPD5281	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD5284	Approved
0.6695	Remote Similarity	NPD4755	Approved
0.6695	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD5174	Approved
0.6694	Remote Similarity	NPD5175	Approved
0.6692	Remote Similarity	NPD8451	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7641	Discontinued
0.6642	Remote Similarity	NPD8448	Approved
0.6641	Remote Similarity	NPD6274	Approved
0.6641	Remote Similarity	NPD6921	Approved
0.6641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8342	Approved
0.6617	Remote Similarity	NPD8340	Approved
0.6617	Remote Similarity	NPD8341	Approved
0.6617	Remote Similarity	NPD8299	Approved
0.6612	Remote Similarity	NPD7632	Discontinued
0.661	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5222	Approved
0.661	Remote Similarity	NPD5221	Approved
0.6609	Remote Similarity	NPD5785	Approved
0.6589	Remote Similarity	NPD6317	Approved
0.6583	Remote Similarity	NPD4700	Approved
0.6581	Remote Similarity	NPD7748	Approved
0.6579	Remote Similarity	NPD6672	Approved
0.6579	Remote Similarity	NPD5737	Approved
0.6555	Remote Similarity	NPD5173	Approved
0.6552	Remote Similarity	NPD5694	Approved
0.6552	Remote Similarity	NPD6050	Approved
0.6552	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD6079	Approved
0.6541	Remote Similarity	NPD7642	Approved
0.6541	Remote Similarity	NPD6067	Discontinued
0.6538	Remote Similarity	NPD6314	Approved
0.6538	Remote Similarity	NPD6313	Approved
0.6525	Remote Similarity	NPD4629	Approved
0.6525	Remote Similarity	NPD5210	Approved
0.6522	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6868	Approved
0.65	Remote Similarity	NPD7799	Discontinued
0.6496	Remote Similarity	NPD8391	Approved
0.6496	Remote Similarity	NPD8392	Approved
0.6496	Remote Similarity	NPD5956	Approved
0.6496	Remote Similarity	NPD8390	Approved
0.6491	Remote Similarity	NPD3573	Approved
0.6491	Remote Similarity	NPD7524	Approved
0.648	Remote Similarity	NPD4729	Approved
0.648	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD4697	Phase 3
0.6466	Remote Similarity	NPD5692	Phase 3
0.6466	Remote Similarity	NPD5207	Approved
0.6441	Remote Similarity	NPD7900	Approved
0.6441	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD5279	Phase 3
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6391	Remote Similarity	NPD6909	Approved
0.6391	Remote Similarity	NPD6908	Approved
0.6391	Remote Similarity	NPD8444	Approved
0.6387	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1695	Approved
0.6379	Remote Similarity	NPD6904	Approved
0.6379	Remote Similarity	NPD6080	Approved
0.6379	Remote Similarity	NPD5328	Approved
0.6379	Remote Similarity	NPD6673	Approved
0.6379	Remote Similarity	NPD4753	Phase 2
0.6378	Remote Similarity	NPD5250	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