NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.13
Volume:	240.622
LogP:	2.75
LogD:	2.208
LogS:	-4.047
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	3.154
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.5
MDCK Permeability:	1.8194341464550234e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.361

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937
Plasma Protein Binding (PPB):	90.20438385009766%
Volume Distribution (VD):	0.959
Pgp-substrate:	10.5867338180542%

ADMET: Metabolism

CYP1A2-inhibitor:	0.844
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	8.684
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.407
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.409
Skin Sensitization:	0.224
Carcinogencity:	0.509
Eye Corrosion:	0.007
Eye Irritation:	0.504
Respiratory Toxicity:	0.546

Download Data

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

Natural Product: NPC83409

Natural Product ID:	NPC83409
*Common Name:**	(2R)-6-(2-Hydroxyethyl)-2,5,7-Trimethyl-2,3-Dihydroinden-1-One
IUPAC Name:	(2R)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one
Synonyms:
Standard InCHIKey:	SJNCSXMTBXDZQA-SECBINFHSA-N
Standard InCHI:	InChI=1S/C14H18O2/c1-8-6-11-7-9(2)14(16)13(11)10(3)12(8)4-5-15/h6,9,15H,4-5,7H2,1-3H3/t9-/m1/s1
SMILES:	Cc1cc2C[C@@H](C)C(=O)c2c(C)c1CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1728959
PubChem CID:	115049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*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
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89285-7]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO6424	Populus sieboldii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933880]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19739599]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO5299	Raspailia agminata	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087018]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[23157017]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23157017]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	Chinese liverworts	n.a.	PMID[24491225]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[305622]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO3534	Ajuga lupulina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759163]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7164	Calystegia hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7164	Calystegia hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5894	Ipomoea hederifolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7056	Pedinophyllum interruptum	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11567	Picradeniopsis absinthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13236	Viguiera multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26205	Leucopaxillus eucalyptorum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13019	Emericella dentata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7868	Xeromphis obovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5299	Raspailia agminata	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1741	Purshia tridentata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1890	Lidbeckia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3694	Solanum callium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12517	Tylophora cordifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15182	Ampelocera ruizii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15376	Gentiana ramosa	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13340	Cymbochasma borysthenica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12650	Aralia mandshurica	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27787	Pseudocentrotus depressus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6424	Populus sieboldii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15726	Rudbeckia subtomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8866	Papaver atlanticum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16170	Xerula longipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17685	Crotalaria naragutensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8611	Cornutia grandifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7164	Calystegia hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12294	Kydia calycina	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14580	Heliotropium strigosum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2312	Encephalosphaera lasiandra	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10624	Solidago wrightii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15306	Smilax japonica	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9155	Kageneckia angustifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7673	Astragalus quisqualis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13360	Passiflora racemosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3534	Ajuga lupulina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15818	Lycianthes marlipoensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14630	Boronia ramosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	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	1
Potency	6

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	580.5	nM	PMID[464089]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[464089]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[464089]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	50100.0	nM	PMID[464090]
NPT2	Others	Unspecified		Potency	n.a.	231.1	nM	PMID[464089]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[464089]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[464089]

☑ 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 NPC83409 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	210
0.1-0.2	997
0.2-0.3	2398
0.3-0.4	8135
0.4-0.5	16170
0.5-0.6	11746
0.6-0.7	2635
0.7-0.8	357
0.8-0.85	33
0.85-0.9	12
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185763
0.97	High Similarity	NPC112903
0.9406	High Similarity	NPC37914
0.875	High Similarity	NPC133302
0.8716	High Similarity	NPC274839
0.8596	High Similarity	NPC18785
0.8558	High Similarity	NPC247976
0.8545	High Similarity	NPC476357
0.8519	High Similarity	NPC265513
0.8396	Intermediate Similarity	NPC471186
0.8364	Intermediate Similarity	NPC470253
0.8349	Intermediate Similarity	NPC474057
0.8318	Intermediate Similarity	NPC100767
0.8273	Intermediate Similarity	NPC292834
0.8246	Intermediate Similarity	NPC318173
0.8224	Intermediate Similarity	NPC172483
0.8214	Intermediate Similarity	NPC215419
0.8174	Intermediate Similarity	NPC476645
0.8158	Intermediate Similarity	NPC323440
0.8158	Intermediate Similarity	NPC222968
0.8158	Intermediate Similarity	NPC80605
0.8125	Intermediate Similarity	NPC196673
0.8037	Intermediate Similarity	NPC274443
0.8037	Intermediate Similarity	NPC329556
0.8036	Intermediate Similarity	NPC143768
0.7982	Intermediate Similarity	NPC94751
0.7982	Intermediate Similarity	NPC142326
0.7982	Intermediate Similarity	NPC9274
0.7965	Intermediate Similarity	NPC471721
0.7963	Intermediate Similarity	NPC329282
0.7946	Intermediate Similarity	NPC471188
0.7946	Intermediate Similarity	NPC66208
0.7946	Intermediate Similarity	NPC471189
0.7944	Intermediate Similarity	NPC244427
0.7944	Intermediate Similarity	NPC222390
0.7941	Intermediate Similarity	NPC133461
0.7909	Intermediate Similarity	NPC249811
0.7895	Intermediate Similarity	NPC474095
0.7895	Intermediate Similarity	NPC186933
0.789	Intermediate Similarity	NPC134120
0.7881	Intermediate Similarity	NPC472981
0.7876	Intermediate Similarity	NPC93287
0.7864	Intermediate Similarity	NPC153885
0.7864	Intermediate Similarity	NPC314690
0.7863	Intermediate Similarity	NPC472708
0.7843	Intermediate Similarity	NPC86670
0.7843	Intermediate Similarity	NPC70940
0.7843	Intermediate Similarity	NPC274455
0.78	Intermediate Similarity	NPC164526
0.78	Intermediate Similarity	NPC160339
0.78	Intermediate Similarity	NPC307
0.7798	Intermediate Similarity	NPC315794
0.7788	Intermediate Similarity	NPC186128
0.7788	Intermediate Similarity	NPC238219
0.7778	Intermediate Similarity	NPC304873
0.7778	Intermediate Similarity	NPC25458
0.7778	Intermediate Similarity	NPC320891
0.7759	Intermediate Similarity	NPC469843
0.7748	Intermediate Similarity	NPC211439
0.7742	Intermediate Similarity	NPC82712
0.7727	Intermediate Similarity	NPC471133
0.7724	Intermediate Similarity	NPC478162
0.7724	Intermediate Similarity	NPC478165
0.7719	Intermediate Similarity	NPC242957
0.7719	Intermediate Similarity	NPC206414
0.7719	Intermediate Similarity	NPC287055
0.7719	Intermediate Similarity	NPC306977
0.7714	Intermediate Similarity	NPC260233
0.7712	Intermediate Similarity	NPC202015
0.7692	Intermediate Similarity	NPC323420
0.7692	Intermediate Similarity	NPC155232
0.7686	Intermediate Similarity	NPC328107
0.7686	Intermediate Similarity	NPC318067
0.7685	Intermediate Similarity	NPC225079
0.7685	Intermediate Similarity	NPC289117
0.7679	Intermediate Similarity	NPC318327
0.7672	Intermediate Similarity	NPC135730
0.767	Intermediate Similarity	NPC173413
0.7664	Intermediate Similarity	NPC317280
0.7664	Intermediate Similarity	NPC329387
0.7658	Intermediate Similarity	NPC85560
0.7658	Intermediate Similarity	NPC244933
0.7652	Intermediate Similarity	NPC326664
0.7647	Intermediate Similarity	NPC153308
0.7647	Intermediate Similarity	NPC329064
0.7642	Intermediate Similarity	NPC261947
0.7636	Intermediate Similarity	NPC56168
0.7632	Intermediate Similarity	NPC280789
0.7627	Intermediate Similarity	NPC472697
0.7627	Intermediate Similarity	NPC472698
0.7593	Intermediate Similarity	NPC217621
0.7589	Intermediate Similarity	NPC203732
0.7586	Intermediate Similarity	NPC93181
0.7586	Intermediate Similarity	NPC217111
0.7586	Intermediate Similarity	NPC228936
0.757	Intermediate Similarity	NPC265220
0.757	Intermediate Similarity	NPC239185
0.757	Intermediate Similarity	NPC156021
0.7565	Intermediate Similarity	NPC13784
0.7549	Intermediate Similarity	NPC322387
0.7547	Intermediate Similarity	NPC172925
0.7541	Intermediate Similarity	NPC85511
0.7538	Intermediate Similarity	NPC156393
0.7524	Intermediate Similarity	NPC188844
0.7524	Intermediate Similarity	NPC1682
0.7523	Intermediate Similarity	NPC136810
0.7523	Intermediate Similarity	NPC472879
0.7523	Intermediate Similarity	NPC264728
0.7523	Intermediate Similarity	NPC128248
0.7523	Intermediate Similarity	NPC469481
0.7523	Intermediate Similarity	NPC473325
0.7523	Intermediate Similarity	NPC133809
0.7521	Intermediate Similarity	NPC269923
0.7521	Intermediate Similarity	NPC167323
0.75	Intermediate Similarity	NPC988
0.75	Intermediate Similarity	NPC277277
0.75	Intermediate Similarity	NPC49994
0.75	Intermediate Similarity	NPC470585
0.75	Intermediate Similarity	NPC77000
0.75	Intermediate Similarity	NPC238861
0.75	Intermediate Similarity	NPC67377
0.75	Intermediate Similarity	NPC229242
0.75	Intermediate Similarity	NPC75724
0.75	Intermediate Similarity	NPC241851
0.75	Intermediate Similarity	NPC289432
0.75	Intermediate Similarity	NPC134882
0.75	Intermediate Similarity	NPC105709
0.748	Intermediate Similarity	NPC152525
0.748	Intermediate Similarity	NPC12818
0.748	Intermediate Similarity	NPC68756
0.7478	Intermediate Similarity	NPC218855
0.7477	Intermediate Similarity	NPC219573
0.7477	Intermediate Similarity	NPC249067
0.7477	Intermediate Similarity	NPC185208
0.7476	Intermediate Similarity	NPC157778
0.7459	Intermediate Similarity	NPC282577
0.7458	Intermediate Similarity	NPC212891
0.7458	Intermediate Similarity	NPC158157
0.7453	Intermediate Similarity	NPC289883
0.744	Intermediate Similarity	NPC51448
0.744	Intermediate Similarity	NPC115797
0.7438	Intermediate Similarity	NPC144547
0.7438	Intermediate Similarity	NPC190971
0.7436	Intermediate Similarity	NPC470764
0.7429	Intermediate Similarity	NPC110704
0.7429	Intermediate Similarity	NPC284475
0.7417	Intermediate Similarity	NPC204784
0.7411	Intermediate Similarity	NPC105899
0.7407	Intermediate Similarity	NPC253423
0.7407	Intermediate Similarity	NPC226041
0.7407	Intermediate Similarity	NPC289201
0.7404	Intermediate Similarity	NPC113307
0.7402	Intermediate Similarity	NPC72915
0.7398	Intermediate Similarity	NPC228739
0.7398	Intermediate Similarity	NPC472704
0.7391	Intermediate Similarity	NPC133308
0.7391	Intermediate Similarity	NPC95126
0.7391	Intermediate Similarity	NPC475002
0.7391	Intermediate Similarity	NPC137315
0.7391	Intermediate Similarity	NPC210089
0.7387	Intermediate Similarity	NPC255676
0.7379	Intermediate Similarity	NPC43945
0.7374	Intermediate Similarity	NPC17408
0.7374	Intermediate Similarity	NPC285716
0.7364	Intermediate Similarity	NPC109514
0.7364	Intermediate Similarity	NPC476993
0.7364	Intermediate Similarity	NPC203486
0.7364	Intermediate Similarity	NPC112552
0.7358	Intermediate Similarity	NPC59677
0.7355	Intermediate Similarity	NPC472679
0.7355	Intermediate Similarity	NPC472680
0.7355	Intermediate Similarity	NPC232958
0.7353	Intermediate Similarity	NPC252067
0.735	Intermediate Similarity	NPC130591
0.735	Intermediate Similarity	NPC234637
0.7344	Intermediate Similarity	NPC471851
0.7339	Intermediate Similarity	NPC199273
0.7339	Intermediate Similarity	NPC234890
0.7339	Intermediate Similarity	NPC74507
0.7339	Intermediate Similarity	NPC120393
0.7333	Intermediate Similarity	NPC58872
0.7323	Intermediate Similarity	NPC49272
0.7321	Intermediate Similarity	NPC472221
0.7321	Intermediate Similarity	NPC472222
0.7317	Intermediate Similarity	NPC472703
0.7317	Intermediate Similarity	NPC65627
0.7315	Intermediate Similarity	NPC469893
0.7308	Intermediate Similarity	NPC23894
0.7308	Intermediate Similarity	NPC474659
0.7302	Intermediate Similarity	NPC19432
0.73	Intermediate Similarity	NPC145053
0.7295	Intermediate Similarity	NPC476234
0.7288	Intermediate Similarity	NPC221275
0.7288	Intermediate Similarity	NPC306740
0.728	Intermediate Similarity	NPC123506
0.728	Intermediate Similarity	NPC236405
0.728	Intermediate Similarity	NPC131799
0.7273	Intermediate Similarity	NPC221825
0.7273	Intermediate Similarity	NPC473767
0.7265	Intermediate Similarity	NPC471481

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 NPC83409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	905
0.2-0.3	1373
0.3-0.4	2937
0.4-0.5	2402
0.5-0.6	1110
0.6-0.7	203
0.7-0.8	40
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD4141	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1693	Approved
0.8037	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1929	Approved
0.8037	Intermediate Similarity	NPD1930	Approved
0.7925	Intermediate Similarity	NPD2066	Phase 3
0.7845	Intermediate Similarity	NPD7610	Discontinued
0.7843	Intermediate Similarity	NPD1089	Approved
0.7843	Intermediate Similarity	NPD1086	Approved
0.7843	Intermediate Similarity	NPD1090	Approved
0.7778	Intermediate Similarity	NPD7009	Phase 2
0.7745	Intermediate Similarity	NPD800	Approved
0.7692	Intermediate Similarity	NPD1088	Approved
0.7586	Intermediate Similarity	NPD5951	Approved
0.7583	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD3495	Discontinued
0.7549	Intermediate Similarity	NPD1087	Approved
0.7547	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD1508	Approved
0.7524	Intermediate Similarity	NPD7631	Approved
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1237	Approved
0.7455	Intermediate Similarity	NPD1932	Approved
0.7453	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7609	Phase 3
0.7379	Intermediate Similarity	NPD650	Approved
0.7368	Intermediate Similarity	NPD2329	Discontinued
0.7315	Intermediate Similarity	NPD1843	Approved
0.7304	Intermediate Similarity	NPD1317	Discontinued
0.7265	Intermediate Similarity	NPD6858	Approved
0.7265	Intermediate Similarity	NPD7094	Approved
0.7264	Intermediate Similarity	NPD1239	Approved
0.7248	Intermediate Similarity	NPD1566	Phase 3
0.7248	Intermediate Similarity	NPD1564	Approved
0.7248	Intermediate Similarity	NPD1565	Approved
0.7241	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7961	Discontinued
0.7188	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD9491	Approved
0.7156	Intermediate Similarity	NPD1989	Approved
0.7097	Intermediate Similarity	NPD5618	Discontinued
0.7087	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6647	Phase 2
0.708	Intermediate Similarity	NPD5765	Approved
0.7073	Intermediate Similarity	NPD2932	Approved
0.7073	Intermediate Similarity	NPD3019	Approved
0.7054	Intermediate Similarity	NPD7008	Discontinued
0.7043	Intermediate Similarity	NPD6685	Approved
0.7016	Intermediate Similarity	NPD4879	Approved
0.7	Intermediate Similarity	NPD4766	Approved
0.6992	Remote Similarity	NPD1245	Approved
0.6972	Remote Similarity	NPD1563	Approved
0.6961	Remote Similarity	NPD226	Approved
0.6935	Remote Similarity	NPD2345	Approved
0.693	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1876	Approved
0.6923	Remote Similarity	NPD2182	Approved
0.6917	Remote Similarity	NPD2652	Approved
0.6917	Remote Similarity	NPD2650	Approved
0.6916	Remote Similarity	NPD5347	Phase 2
0.6916	Remote Similarity	NPD5346	Phase 2
0.6891	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9495	Approved
0.687	Remote Similarity	NPD164	Approved
0.686	Remote Similarity	NPD1246	Approved
0.686	Remote Similarity	NPD2629	Approved
0.6855	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9256	Approved
0.6852	Remote Similarity	NPD9258	Approved
0.6852	Remote Similarity	NPD3673	Approved
0.6852	Remote Similarity	NPD3672	Approved
0.685	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7236	Approved
0.6825	Remote Similarity	NPD1201	Approved
0.6822	Remote Similarity	NPD6085	Phase 2
0.6822	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3317	Approved
0.6796	Remote Similarity	NPD942	Approved
0.6774	Remote Similarity	NPD4479	Discontinued
0.6772	Remote Similarity	NPD4878	Approved
0.6769	Remote Similarity	NPD7084	Phase 3
0.6765	Remote Similarity	NPD9490	Approved
0.6746	Remote Similarity	NPD3023	Approved
0.6746	Remote Similarity	NPD3026	Approved
0.6729	Remote Similarity	NPD4793	Discontinued
0.672	Remote Similarity	NPD3025	Approved
0.672	Remote Similarity	NPD3024	Approved
0.6713	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD1101	Approved
0.6667	Remote Similarity	NPD8165	Discontinued
0.6667	Remote Similarity	NPD1283	Approved
0.6636	Remote Similarity	NPD9259	Approved
0.6636	Remote Similarity	NPD9257	Approved
0.6615	Remote Similarity	NPD1470	Approved
0.6613	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6912	Phase 3
0.6589	Remote Similarity	NPD5159	Phase 2
0.6589	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5157	Phase 1
0.6587	Remote Similarity	NPD1651	Approved
0.6581	Remote Similarity	NPD5909	Discontinued
0.6573	Remote Similarity	NPD6273	Approved
0.6567	Remote Similarity	NPD6663	Approved
0.6552	Remote Similarity	NPD2196	Discontinued
0.6538	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1238	Approved
0.6518	Remote Similarity	NPD1202	Approved
0.6515	Remote Similarity	NPD5736	Approved
0.6508	Remote Similarity	NPD7741	Discontinued
0.6508	Remote Similarity	NPD3091	Approved
0.6504	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5279	Phase 3
0.6475	Remote Similarity	NPD9508	Approved
0.6466	Remote Similarity	NPD7055	Discontinued
0.646	Remote Similarity	NPD6049	Phase 2
0.646	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4814	Discontinued
0.6454	Remote Similarity	NPD7003	Approved
0.6452	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7305	Phase 1
0.6449	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4233	Approved
0.6446	Remote Similarity	NPD4234	Approved
0.6446	Remote Similarity	NPD2067	Discontinued
0.6434	Remote Similarity	NPD2610	Approved
0.6434	Remote Similarity	NPD4216	Approved
0.6434	Remote Similarity	NPD3132	Approved
0.6434	Remote Similarity	NPD4215	Approved
0.6434	Remote Similarity	NPD6287	Discontinued
0.6434	Remote Similarity	NPD2608	Approved
0.6434	Remote Similarity	NPD4217	Approved
0.6434	Remote Similarity	NPD4218	Approved
0.6434	Remote Similarity	NPD2611	Approved
0.6434	Remote Similarity	NPD1281	Approved
0.6434	Remote Similarity	NPD3131	Approved
0.6434	Remote Similarity	NPD2609	Approved
0.6434	Remote Similarity	NPD2612	Approved
0.6429	Remote Similarity	NPD6065	Approved
0.6422	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2648	Phase 3
0.641	Remote Similarity	NPD2193	Phase 2
0.6406	Remote Similarity	NPD3095	Discontinued
0.6406	Remote Similarity	NPD4199	Phase 3
0.6389	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1677	Discontinued
0.6385	Remote Similarity	NPD3972	Approved
0.6372	Remote Similarity	NPD1409	Phase 3
0.6372	Remote Similarity	NPD3719	Approved
0.6372	Remote Similarity	NPD3718	Approved
0.6372	Remote Similarity	NPD845	Approved
0.6371	Remote Similarity	NPD6010	Discontinued
0.6371	Remote Similarity	NPD7076	Approved
0.6371	Remote Similarity	NPD7077	Approved
0.6371	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD2346	Discontinued
0.6349	Remote Similarity	NPD3797	Approved
0.6327	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2798	Approved
0.6316	Remote Similarity	NPD4980	Approved
0.6308	Remote Similarity	NPD3092	Approved
0.6304	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3666	Approved
0.6296	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD6966	Discovery
0.6296	Remote Similarity	NPD4786	Approved
0.6296	Remote Similarity	NPD3665	Phase 1
0.6294	Remote Similarity	NPD7295	Approved
0.6293	Remote Similarity	NPD253	Approved
0.6291	Remote Similarity	NPD7057	Phase 3
0.6291	Remote Similarity	NPD7058	Phase 2
0.629	Remote Similarity	NPD5277	Phase 2
0.629	Remote Similarity	NPD7635	Approved
0.629	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1574	Approved
0.6286	Remote Similarity	NPD5405	Approved
0.6286	Remote Similarity	NPD5408	Approved
0.6286	Remote Similarity	NPD5406	Approved
0.6286	Remote Similarity	NPD5404	Approved
0.6279	Remote Similarity	NPD5125	Phase 3
0.6279	Remote Similarity	NPD5126	Approved
0.6279	Remote Similarity	NPD5306	Approved
0.6279	Remote Similarity	NPD5305	Approved
0.6279	Remote Similarity	NPD4626	Approved
0.6279	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3667	Approved
0.626	Remote Similarity	NPD3644	Approved
0.626	Remote Similarity	NPD3643	Approved
0.626	Remote Similarity	NPD3642	Approved
0.625	Remote Similarity	NPD2197	Approved
0.625	Remote Similarity	NPD1018	Approved
0.625	Remote Similarity	NPD3798	Phase 3

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