NPASS Compound

Natural Product: NPC22531

Natural Product ID	NPC22531
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FITSCHPIOGIYJY-CYBMUJFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	147559
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 38 39 0 0 0 0 0 0 0 0999 V2000 2.3822 0.5815 -2.4936 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3963 0.1693 -1.4842 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 0.3563 -1.8390 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9384 -0.0228 -0.9843 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5869 -0.5858 0.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7467 -0.7872 0.6062 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0229 -1.3922 1.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7401 -0.3950 -0.2759 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1552 -0.5363 0.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7549 0.6702 0.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7884 1.8190 0.0596 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8064 -0.8864 0.9534 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0033 -1.7196 1.8285 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8291 0.0810 0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2266 -0.3793 0.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5789 1.4691 0.9013 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 0.0336 -1.0581 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8189 -1.1768 -1.6295 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1578 -0.2257 -2.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8864 0.6072 -3.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7840 1.5906 -2.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2320 0.8025 -2.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2004 -2.0686 2.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9157 -2.0307 1.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1194 -0.6551 2.7327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2950 -1.4561 0.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 -0.7228 -0.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8019 0.4683 1.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1663 0.8269 1.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 2.4759 0.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5473 -1.1134 -0.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9009 0.5242 0.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2782 -0.8353 1.6801 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4597 1.8946 1.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3284 2.1746 0.0835 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7008 1.4564 1.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7821 0.9051 -1.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7886 -1.9171 -0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 6 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 5 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 14 16 1 0 14 17 1 0 17 18 1 0 8 2 1 0 17 4 1 0 1 19 1 0 1 20 1 0 1 21 1 0 3 22 1 0 7 23 1 0 7 24 1 0 7 25 1 0 9 26 1 0 9 27 1 0 10 28 1 0 10 29 1 0 11 30 1 0 15 31 1 0 15 32 1 0 15 33 1 0 16 34 1 0 16 35 1 0 16 36 1 0 17 37 1 6 18 38 1 0 M END

Standard InCHIKey	FITSCHPIOGIYJY-CYBMUJFWSA-N
Standard InCHI	InChI=1S/C15H20O3/c1-8-7-11-12(9(2)10(8)5-6-16)14(18)15(3,4)13(11)17/h7,13,16-17H,5-6H2,1-4H3/t13-/m1/s1
SMILES	Cc1cc2c(c(C)c1CCO)C(=O)C(C)(C)[C@@H]2O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	248.14	Volume:	266.708 ? Van der Waals volume.
Dense:	0.93	LogP:	2.291 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.303 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.508 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	11.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.842	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.491	Fsp³:	0.533
MCE-18:	50.783 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.057	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.333 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.047 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.362	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.852	MDCK Permeability:	-4.67
Pgp-inhibitor:	0.086	Pgp-substrate:	0.853
PAMPA:	0.989 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.03	30% Bioavailability (F30%):	0.044
50% Bioavailability (F50%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181	MRP1:	0.999
Plasma Protein Binding (PPB):	78.985%	Volume Distribution (VD):	0.203
Fu:	26.054% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.925
OATP1B3 inhibitor:	0.969	BCRP inhibitor:	0.011
BSEP inhibitor:	0.909

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.07	CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.1	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.057
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.262
HLM stability:	0.067 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.187

Half-life (T1/2):

1.297

ADMET: Toxicity

hERG Blockers:	0.068	hERG Blockers (10um):	0.31
Human Hepatotoxicity (H-HT):	0.783	Drug-induced Liver Injury (DILI):	0.617
AMES Toxicity:	0.828	Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.206	Skin Sensitization:	0.983
Carcinogencity:	0.693	Eye Corrosion:	0.026
Eye Irritation:	0.913	Respiratory Toxicity:	0.514
Drug-induced Neurotoxicity:	0.282	Ototoxicity:	0.618
Hematotoxicity:	0.715	Drug-induced Nephrotoxicity:	0.582
Genotoxicity:	0.282	RPMI-8226 Immunitoxicity:	0.181
A549 Cytotoxicity:	0.259	Hek293 Cytotoxicity:	0.281
BCF:	0.681 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.203 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.538 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.879 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006909]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
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]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13087.1	Pteridium aquilinum var. latiusculum	Varieties	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087.1	Pteridium aquilinum var. latiusculum	Varieties	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087.1	Pteridium aquilinum var. latiusculum	Varieties	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	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]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	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	Organism Name	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
Activity	1
IC50	1

Activity Type	# Activity
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2615	Cell line	HEK-293T	Homo sapiens	Activity	=	100.0	%	PMID[28006909]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	183700.0	nM	PMID[28532669]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC22531 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24132
0.1-0.2	25324
0.2-0.3	375
0.3-0.4	10
0.4-0.5	8
0.5-0.6	3
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7805	Intermediate Similarity	NPC31499
0.6087	Remote Similarity	NPC46971
0.6	Remote Similarity	NPC135654
0.6	Remote Similarity	NPC269860
0.6	Remote Similarity	NPC190729
0.6	Remote Similarity	NPC485143
0.5778	Remote Similarity	NPC112903
0.5333	Remote Similarity	NPC159323
0.5217	Remote Similarity	NPC83409

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC22531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4431
0.1-0.2	4685
0.2-0.3	34
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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