NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.12
Volume:	281.601
LogP:	3.327
LogD:	3.116
LogS:	-4.308
# Rotatable Bonds:	1
TPSA:	51.83
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.866
Synthetic Accessibility Score:	4.548
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.2315152162045706e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.513
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	92.45372009277344%
Volume Distribution (VD):	1.498
Pgp-substrate:	9.0490140914917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.75
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.179
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.745

ADMET: Excretion

Clearance (CL):	7.713
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.748
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.826
Carcinogencity:	0.829
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC219560

Natural Product ID:	NPC219560
*Common Name:**	Ustusorane C
IUPAC Name:	(7R,9S)-9-methoxy-7-methyl-2-propan-2-ylidene-7,9-dihydro-6H-furo[3,2-h]isochromen-3-one
Synonyms:
Standard InCHIKey:	LJIFRPHOUJGTPG-ABKXIKBNSA-N
Standard InCHI:	InChI=1S/C16H18O4/c1-8(2)14-13(17)11-6-5-10-7-9(3)19-16(18-4)12(10)15(11)20-14/h5-6,9,16H,7H2,1-4H3/t9-,16+/m1/s1
SMILES:	CC(=C1C(=O)c2ccc3C[C@@H](C)O[C@@H](c3c2O1)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078204
PubChem CID:	44557646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277746]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
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]
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]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	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]
NPO28821	Stichopus horrens	Species	Stichopodidae	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]
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]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	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]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	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]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	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]
NPO17304	Sipunculus nudus	Species	Sipunculidae	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]
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]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	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]
NPO14002	Petalostemon purpureum	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]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	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]
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]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	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]

☑ 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

Activity Type	# Activity
Cell Line	3

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[559606]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[559606]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5900.0	nM	PMID[559607]

☑ 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 NPC219560 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	434
0.1-0.2	1572
0.2-0.3	3733
0.3-0.4	9162
0.4-0.5	9852
0.5-0.6	4145
0.6-0.7	7395
0.7-0.8	6275
0.8-0.85	117
0.85-0.9	2
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC228906
0.993	High Similarity	NPC471348
0.993	High Similarity	NPC469416
0.9521	High Similarity	NPC175617
0.9456	High Similarity	NPC471347
0.9456	High Similarity	NPC471349
0.9178	High Similarity	NPC471346
0.9041	High Similarity	NPC469385
0.8944	High Similarity	NPC217914
0.8733	High Similarity	NPC469425
0.8514	High Similarity	NPC477537
0.8491	Intermediate Similarity	NPC216752
0.8481	Intermediate Similarity	NPC65784
0.8397	Intermediate Similarity	NPC470331
0.8389	Intermediate Similarity	NPC477535
0.8375	Intermediate Similarity	NPC101116
0.8375	Intermediate Similarity	NPC146837
0.8375	Intermediate Similarity	NPC212099
0.8375	Intermediate Similarity	NPC278329
0.8367	Intermediate Similarity	NPC232996
0.8365	Intermediate Similarity	NPC313368
0.8364	Intermediate Similarity	NPC470667
0.8364	Intermediate Similarity	NPC186800
0.8355	Intermediate Similarity	NPC474630
0.8344	Intermediate Similarity	NPC473202
0.8311	Intermediate Similarity	NPC477534
0.8299	Intermediate Similarity	NPC470844
0.8291	Intermediate Similarity	NPC155063
0.8288	Intermediate Similarity	NPC477536
0.8272	Intermediate Similarity	NPC178281
0.8269	Intermediate Similarity	NPC318424
0.8258	Intermediate Similarity	NPC88886
0.8258	Intermediate Similarity	NPC104172
0.8247	Intermediate Similarity	NPC471285
0.8232	Intermediate Similarity	NPC191653
0.8224	Intermediate Similarity	NPC471639
0.8224	Intermediate Similarity	NPC471643
0.8221	Intermediate Similarity	NPC178851
0.8217	Intermediate Similarity	NPC473967
0.821	Intermediate Similarity	NPC17432
0.8207	Intermediate Similarity	NPC473271
0.8204	Intermediate Similarity	NPC475233
0.8199	Intermediate Similarity	NPC34376
0.8193	Intermediate Similarity	NPC98776
0.8193	Intermediate Similarity	NPC85368
0.8187	Intermediate Similarity	NPC50430
0.8182	Intermediate Similarity	NPC473927
0.8176	Intermediate Similarity	NPC164244
0.8171	Intermediate Similarity	NPC63470
0.817	Intermediate Similarity	NPC189650
0.817	Intermediate Similarity	NPC184702
0.816	Intermediate Similarity	NPC314653
0.816	Intermediate Similarity	NPC316262
0.8153	Intermediate Similarity	NPC232645
0.8153	Intermediate Similarity	NPC72958
0.8151	Intermediate Similarity	NPC324488
0.8148	Intermediate Similarity	NPC302741
0.8137	Intermediate Similarity	NPC43971
0.8137	Intermediate Similarity	NPC19554
0.8137	Intermediate Similarity	NPC470358
0.8137	Intermediate Similarity	NPC74749
0.8133	Intermediate Similarity	NPC76128
0.8133	Intermediate Similarity	NPC5029
0.8133	Intermediate Similarity	NPC30432
0.8133	Intermediate Similarity	NPC111536
0.8133	Intermediate Similarity	NPC271385
0.8129	Intermediate Similarity	NPC471734
0.8121	Intermediate Similarity	NPC470207
0.8121	Intermediate Similarity	NPC470206
0.8121	Intermediate Similarity	NPC259905
0.8117	Intermediate Similarity	NPC49282
0.8113	Intermediate Similarity	NPC284353
0.8108	Intermediate Similarity	NPC247743
0.8108	Intermediate Similarity	NPC1249
0.8105	Intermediate Similarity	NPC469885
0.8105	Intermediate Similarity	NPC215451
0.8105	Intermediate Similarity	NPC277369
0.8101	Intermediate Similarity	NPC87708
0.8101	Intermediate Similarity	NPC288534
0.8101	Intermediate Similarity	NPC68882
0.8095	Intermediate Similarity	NPC475246
0.8092	Intermediate Similarity	NPC171094
0.8092	Intermediate Similarity	NPC470856
0.8089	Intermediate Similarity	NPC474660
0.8089	Intermediate Similarity	NPC325983
0.8084	Intermediate Similarity	NPC199357
0.8084	Intermediate Similarity	NPC203751
0.8079	Intermediate Similarity	NPC477408
0.8075	Intermediate Similarity	NPC279732
0.8075	Intermediate Similarity	NPC113055
0.8072	Intermediate Similarity	NPC298778
0.8067	Intermediate Similarity	NPC301341
0.8065	Intermediate Similarity	NPC471735
0.8063	Intermediate Similarity	NPC476652
0.8063	Intermediate Similarity	NPC17521
0.8063	Intermediate Similarity	NPC211482
0.8061	Intermediate Similarity	NPC472660
0.8052	Intermediate Similarity	NPC475813
0.8052	Intermediate Similarity	NPC470932
0.8052	Intermediate Similarity	NPC477409
0.805	Intermediate Similarity	NPC279930
0.8047	Intermediate Similarity	NPC5671
0.8039	Intermediate Similarity	NPC471640
0.8039	Intermediate Similarity	NPC297985
0.8039	Intermediate Similarity	NPC471644
0.8038	Intermediate Similarity	NPC470380
0.8038	Intermediate Similarity	NPC23253
0.8037	Intermediate Similarity	NPC310603
0.8037	Intermediate Similarity	NPC125991
0.8036	Intermediate Similarity	NPC68381
0.8036	Intermediate Similarity	NPC3718
0.8036	Intermediate Similarity	NPC146803
0.8027	Intermediate Similarity	NPC477412
0.8027	Intermediate Similarity	NPC279596
0.8026	Intermediate Similarity	NPC11566
0.8025	Intermediate Similarity	NPC78944
0.8025	Intermediate Similarity	NPC306978
0.8013	Intermediate Similarity	NPC259685
0.8013	Intermediate Similarity	NPC137296
0.8013	Intermediate Similarity	NPC52106
0.8013	Intermediate Similarity	NPC71055
0.8012	Intermediate Similarity	NPC246274
0.8012	Intermediate Similarity	NPC96342
0.8012	Intermediate Similarity	NPC212967
0.8012	Intermediate Similarity	NPC246647
0.8012	Intermediate Similarity	NPC310206
0.8012	Intermediate Similarity	NPC470606
0.8012	Intermediate Similarity	NPC175477
0.8012	Intermediate Similarity	NPC164110
0.8012	Intermediate Similarity	NPC177742
0.8012	Intermediate Similarity	NPC222455
0.8	Intermediate Similarity	NPC114257
0.8	Intermediate Similarity	NPC299149
0.8	Intermediate Similarity	NPC471923
0.8	Intermediate Similarity	NPC475923
0.8	Intermediate Similarity	NPC298071
0.8	Intermediate Similarity	NPC153578
0.8	Intermediate Similarity	NPC277710
0.8	Intermediate Similarity	NPC474044
0.7988	Intermediate Similarity	NPC278419
0.7988	Intermediate Similarity	NPC46958
0.7988	Intermediate Similarity	NPC132054
0.7988	Intermediate Similarity	NPC91288
0.7988	Intermediate Similarity	NPC102053
0.7988	Intermediate Similarity	NPC471286
0.7988	Intermediate Similarity	NPC156635
0.7988	Intermediate Similarity	NPC66087
0.7988	Intermediate Similarity	NPC289876
0.7988	Intermediate Similarity	NPC179198
0.7987	Intermediate Similarity	NPC154683
0.7987	Intermediate Similarity	NPC271681
0.7987	Intermediate Similarity	NPC34965
0.7987	Intermediate Similarity	NPC24232
0.7987	Intermediate Similarity	NPC477961
0.7987	Intermediate Similarity	NPC167663
0.7987	Intermediate Similarity	NPC40356
0.7987	Intermediate Similarity	NPC477960
0.7987	Intermediate Similarity	NPC183536
0.7987	Intermediate Similarity	NPC477962
0.7976	Intermediate Similarity	NPC213052
0.7975	Intermediate Similarity	NPC473466
0.7975	Intermediate Similarity	NPC158866
0.7975	Intermediate Similarity	NPC472780
0.7975	Intermediate Similarity	NPC472783
0.7964	Intermediate Similarity	NPC477571
0.7964	Intermediate Similarity	NPC313717
0.7964	Intermediate Similarity	NPC477572
0.7964	Intermediate Similarity	NPC315306
0.7964	Intermediate Similarity	NPC477573
0.7963	Intermediate Similarity	NPC470607
0.7962	Intermediate Similarity	NPC37139
0.7959	Intermediate Similarity	NPC183348
0.7959	Intermediate Similarity	NPC282230
0.7953	Intermediate Similarity	NPC477860
0.7953	Intermediate Similarity	NPC475161
0.7952	Intermediate Similarity	NPC48640
0.7952	Intermediate Similarity	NPC150131
0.7952	Intermediate Similarity	NPC473531
0.7952	Intermediate Similarity	NPC149244
0.7952	Intermediate Similarity	NPC475453
0.795	Intermediate Similarity	NPC301897
0.795	Intermediate Similarity	NPC180924
0.7949	Intermediate Similarity	NPC470357
0.7949	Intermediate Similarity	NPC469758
0.7947	Intermediate Similarity	NPC284184
0.7941	Intermediate Similarity	NPC47191
0.7939	Intermediate Similarity	NPC279768
0.7937	Intermediate Similarity	NPC185103
0.7937	Intermediate Similarity	NPC301233
0.7937	Intermediate Similarity	NPC169990
0.7937	Intermediate Similarity	NPC210942
0.7937	Intermediate Similarity	NPC193200
0.7937	Intermediate Similarity	NPC472799
0.7937	Intermediate Similarity	NPC135522
0.7935	Intermediate Similarity	NPC471451
0.7935	Intermediate Similarity	NPC42540
0.7935	Intermediate Similarity	NPC151607
0.7935	Intermediate Similarity	NPC89664
0.7935	Intermediate Similarity	NPC274085
0.7933	Intermediate Similarity	NPC298900

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 NPC219560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	962
0.2-0.3	1652
0.3-0.4	2678
0.4-0.5	1954
0.5-0.6	1035
0.6-0.7	367
0.7-0.8	136
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.805	Intermediate Similarity	NPD7819	Suspended
0.8013	Intermediate Similarity	NPD2346	Discontinued
0.7976	Intermediate Similarity	NPD6559	Discontinued
0.7937	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD2533	Approved
0.7874	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD2796	Approved
0.7805	Intermediate Similarity	NPD5494	Approved
0.7799	Intermediate Similarity	NPD3226	Approved
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7075	Discontinued
0.7778	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD1471	Phase 3
0.7778	Intermediate Similarity	NPD8313	Approved
0.7744	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD6799	Approved
0.7683	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6801	Discontinued
0.7651	Intermediate Similarity	NPD6959	Discontinued
0.7633	Intermediate Similarity	NPD3818	Discontinued
0.7622	Intermediate Similarity	NPD3882	Suspended
0.7607	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1243	Approved
0.7562	Intermediate Similarity	NPD920	Approved
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7545	Intermediate Similarity	NPD1247	Approved
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7455	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5402	Approved
0.7455	Intermediate Similarity	NPD3817	Phase 2
0.7453	Intermediate Similarity	NPD5403	Approved
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1933	Approved
0.745	Intermediate Similarity	NPD2798	Approved
0.7446	Intermediate Similarity	NPD7435	Discontinued
0.7442	Intermediate Similarity	NPD7074	Phase 3
0.7438	Intermediate Similarity	NPD5401	Approved
0.7438	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3748	Approved
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5710	Approved
0.7396	Intermediate Similarity	NPD5711	Approved
0.7389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7384	Intermediate Similarity	NPD7054	Approved
0.7372	Intermediate Similarity	NPD1551	Phase 2
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD2313	Discontinued
0.7353	Intermediate Similarity	NPD3926	Phase 2
0.7351	Intermediate Similarity	NPD7698	Approved
0.7351	Intermediate Similarity	NPD7696	Phase 3
0.7351	Intermediate Similarity	NPD7697	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2800	Approved
0.7342	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7472	Approved
0.7333	Intermediate Similarity	NPD1934	Approved
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3751	Discontinued
0.7326	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD7871	Phase 2
0.7312	Intermediate Similarity	NPD7870	Phase 2
0.7296	Intermediate Similarity	NPD4628	Phase 3
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3787	Discontinued
0.7293	Intermediate Similarity	NPD6535	Approved
0.7293	Intermediate Similarity	NPD6534	Approved
0.729	Intermediate Similarity	NPD1607	Approved
0.7262	Intermediate Similarity	NPD3749	Approved
0.726	Intermediate Similarity	NPD5691	Approved
0.7255	Intermediate Similarity	NPD411	Approved
0.7251	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7215	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7874	Approved
0.7209	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6166	Phase 2
0.7209	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7768	Phase 2
0.7197	Intermediate Similarity	NPD1510	Phase 2
0.7196	Intermediate Similarity	NPD7701	Phase 2
0.7193	Intermediate Similarity	NPD6232	Discontinued
0.7188	Intermediate Similarity	NPD3750	Approved
0.7181	Intermediate Similarity	NPD9717	Approved
0.7174	Intermediate Similarity	NPD7700	Phase 2
0.7174	Intermediate Similarity	NPD7699	Phase 2
0.7169	Intermediate Similarity	NPD5889	Approved
0.7169	Intermediate Similarity	NPD5890	Approved
0.7168	Intermediate Similarity	NPD7473	Discontinued
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1240	Approved
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD1651	Approved
0.7112	Intermediate Similarity	NPD6823	Phase 2
0.7107	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6005	Phase 3
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD6004	Phase 3
0.7107	Intermediate Similarity	NPD6002	Phase 3
0.7107	Intermediate Similarity	NPD5763	Approved
0.7095	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD7801	Approved
0.7073	Intermediate Similarity	NPD1512	Approved
0.7073	Intermediate Similarity	NPD6273	Approved
0.7067	Intermediate Similarity	NPD3972	Approved
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7049	Intermediate Similarity	NPD6213	Phase 3
0.7049	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6212	Phase 3
0.7044	Intermediate Similarity	NPD5406	Approved
0.7044	Intermediate Similarity	NPD2438	Suspended
0.7044	Intermediate Similarity	NPD5404	Approved
0.7044	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD5408	Approved
0.7043	Intermediate Similarity	NPD8285	Discontinued
0.7041	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD3267	Approved
0.7039	Intermediate Similarity	NPD1203	Approved
0.7037	Intermediate Similarity	NPD8320	Phase 1
0.7037	Intermediate Similarity	NPD8319	Approved
0.7035	Intermediate Similarity	NPD7199	Phase 2
0.7029	Intermediate Similarity	NPD7177	Discontinued
0.7024	Intermediate Similarity	NPD37	Approved
0.7019	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD6585	Discontinued
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD1281	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4967	Phase 2
0.6982	Remote Similarity	NPD8455	Phase 2
0.6982	Remote Similarity	NPD2801	Approved
0.6981	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7033	Discontinued
0.6981	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4626	Approved
0.698	Remote Similarity	NPD1778	Approved
0.6974	Remote Similarity	NPD1876	Approved
0.6968	Remote Similarity	NPD4625	Phase 3
0.6968	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1241	Discontinued
0.6961	Remote Similarity	NPD8434	Phase 2
0.6957	Remote Similarity	NPD2897	Discontinued
0.6954	Remote Similarity	NPD1608	Approved
0.6951	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1511	Approved
0.6943	Remote Similarity	NPD4060	Phase 1
0.6933	Remote Similarity	NPD3887	Approved
0.6933	Remote Similarity	NPD2309	Approved
0.6932	Remote Similarity	NPD7799	Discontinued
0.6928	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6234	Discontinued
0.6914	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2403	Approved
0.6914	Remote Similarity	NPD2654	Approved
0.6911	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7783	Phase 2
0.6907	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4868	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