Natural Product: NPC217176

Natural Product IDNPC217176
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Kokusaginine
IUPAC Name 4,6,7-trimethoxyfuro[2,3-b]quinoline
Synonyms Kokusaginine
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL278779
PubChem CID 10227
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0002374] Furanoquinolines

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

  Chemical Representations

Standard InCHIKey JBRXRVFXQIKPEA-UHFFFAOYSA-N
Standard InCHI InChI=1S/C14H13NO4/c1-16-11-6-9-10(7-12(11)17-2)15-14-8(4-5-19-14)13(9)18-3/h4-7H,1-3H3/p+1
SMILES COc1cc2c(cc1OC)[nH+]c1c(cco1)c2OC

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   259.08 Volume:   255.37
?
Van der Waals volume.
Dense:   1.015 LogP:   2.579
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.816
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.257
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   15.0
TPSA:   53.72
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.723 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.39 Fsp3:   0.214
MCE-18:   16.0
?
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:   0.073 Fluc inhibitor:   0.3
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.871
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.176
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.104 Promiscuous compounds:   0.401

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.604 MDCK Permeability:   -4.629
Pgp-inhibitor:   0.485 Pgp-substrate:   0.035
PAMPA:   0.036
?
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):   0.107
20% Bioavailability (F20%):   0.193 30% Bioavailability (F30%):   0.06
50% Bioavailability (F50%):   0.559

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.01 MRP1:   0.953
Plasma Protein Binding (PPB):   88.311% Volume Distribution (VD):   0.012
Fu: 11.463%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.994
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.967
BSEP inhibitor:   0.99

ADMET: Metabolism

CYP1A2-inhibitor:   0.99 CYP1A2-substrate:   0.206
CYP2C19-inhibitor:   0.861 CYP2C19-substrate:   0.072
CYP2C9-inhibitor:   0.897 CYP2C9-substrate:   0.005
CYP2D6-inhibitor:   0.998 CYP2D6-substrate:   0.54
CYP3A4-inhibitor:   0.979 CYP3A4-substrate:   0.031
CYP2B6-substrate:   0.578 CYP2C8-inhibitor:   0.603
HLM stability:   0.076
?
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):  6.803 Half-life (T1/2):  1.822

ADMET: Toxicity

hERG Blockers:  0.163 hERG Blockers (10um):  0.52
Human Hepatotoxicity (H-HT):  0.583 Drug-induced Liver Injury (DILI):  0.73
AMES Toxicity:  0.561 Rat Oral Acute Toxicity:  0.562
Maximum Recommended Daily Dose:  0.622 Skin Sensitization:  0.207
Carcinogencity:  0.785 Eye Corrosion:  0.021
Eye Irritation:  0.897 Respiratory Toxicity:  0.749
Drug-induced Neurotoxicity:  0.651 Ototoxicity:  0.319
Hematotoxicity:  0.515 Drug-induced Nephrotoxicity:  0.375
Genotoxicity:  0.586 RPMI-8226 Immunitoxicity:  0.114
A549 Cytotoxicity:  0.14 Hek293 Cytotoxicity:  0.304
BCF:   1.364
?
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:   3.337
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.33
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.789
?
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
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1042/BA20070200]
NPO25892 Tricleocarpa fragilis Species Galaxauraceae Eukaryota n.a. n.a. n.a. PMID[10691711]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11575945]
NPO26262 Strychnos potatorum Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[12398531]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota leaves n.a. n.a. PMID[12568545]
NPO29436 Vepris punctata Species Rutaceae Eukaryota wood Madagascar rainforest n.a. PMID[12713408]
NPO29436 Vepris punctata Species Rutaceae Eukaryota wood Madagascar Rainforest n.a. PMID[15165160]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[15568765]
NPO10019 Ilex oblonga Species Aquifoliaceae Eukaryota n.a. leaf n.a. PMID[17329884]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[18163582]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[18950230]
NPO26797 Laurencia glandulifera Species Rhodomelaceae Eukaryota n.a. the island of Crete in the south Aegean Sea n.a. PMID[19138151]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19191562]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota Whole Plants n.a. n.a. PMID[28093914]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[32141299]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[36786362]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[37029634]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[37049761]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27010 Halosaccion ramentaceum Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26797 Laurencia glandulifera Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3659 Limonium bicolor Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13941 Aeollanthus buchnerianus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29436 Vepris punctata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21284 Cynoglossum viridiflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15500 Aconitum volubile Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26557 Daphne tangutica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6501 Glycosmis cochinchinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10019 Ilex oblonga Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26262 Strychnos potatorum Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25892 Tricleocarpa fragilis Species Galaxauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31182 Melicope sp Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28560 Sarcomelicope glauca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29814 Haplophyllum Genus Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29973 Orixa sp Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30055 Evodia sp. Species n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28920 Haplophyllum sp. Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28560 Sarcomelicope glauca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26557 Daphne tangutica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24610 Melicope sp. Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17586 Evodia sp. Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10699 Orixa sp. Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26447 Cassia singueana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26557 Daphne tangutica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25400 Derris malaccensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13941 Aeollanthus buchnerianus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20206 Oricia suaveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26557 Daphne tangutica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26262 Strychnos potatorum Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21284 Cynoglossum viridiflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20279 Parmelia damaziana Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19166 Helianthus niveus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10019 Ilex oblonga Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26400 Boronia anemonifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1833 Erigeron acris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26317 Cladosporium phlei Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15142 Echium plantagineum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28560 Sarcomelicope glauca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15500 Aconitum volubile Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16406 Leptospermum recurvum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25892 Tricleocarpa fragilis Species Galaxauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25650 Dacrydium fonkii Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16000 Cetorhinus maximus Species Alopiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27010 Halosaccion ramentaceum Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1568 Allium ramosum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6501 Glycosmis cochinchinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26797 Laurencia glandulifera Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18997 Hernandia sonora Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3659 Limonium bicolor Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26447 Cassia singueana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23886 Pachysandra axillaris Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29436 Vepris punctata Species Rutaceae 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1213 Individual protein Voltage-gated potassium channel subunit Kv1.3 Mus musculus BK = 51.0 % PMID[11312924]
NPT1213 Individual protein Voltage-gated potassium channel subunit Kv1.3 Mus musculus IC50 = 49000.0 nM PMID[11312924]
NPT1213 Individual protein Voltage-gated potassium channel subunit Kv1.3 Mus musculus S = 4.1 n.a. PMID[11312924]
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 9200.0 nM PubChem BioAssay data set
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 6309.6 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT160 Individual protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 281.8 nM PubChem BioAssay data set
NPT63 Individual protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 89125.1 nM PubChem BioAssay data set
NPT920 Individual protein Alpha-synuclein Homo sapiens Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT518 Protein complex Tubulin Homo sapiens IC50 = 820.0 nM PMID[29903663]
NPT518 Protein complex Tubulin Homo sapiens Inhibition = 92.0 % PMID[29903663]
NPT518 Protein complex Tubulin Homo sapiens Inhibition = 98.0 % PMID[29903663]
NPT536 Nucleic acid microRNA 21 Homo sapiens Potency = 16481.6 nM PubChem BioAssay data set
NPT49 Individual protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 2818.4 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1212 Cell line N1E-115 Mus musculus BK = 22.0 % PMID[11312924]
NPT1212 Cell line N1E-115 Mus musculus BNa = 0.0 % PMID[11312924]
NPT1212 Cell line N1E-115 Mus musculus IC50 = 200000.0 nM PMID[11312924]
NPT179 Cell line A2780 Homo sapiens IC50 = 3.5 ug.mL-1 PMID[12713408]
NPT71 Cell line HEK293 Homo sapiens Potency n.a. 4610.9 nM PubChem BioAssay data set
NPT83 Cell line MCF7 Homo sapiens IC50 = 7230.0 nM PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens IC50 = 4620.0 nM PMID[29903663]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 = 9010.0 nM PMID[29903663]
NPT83 Cell line MCF7 Homo sapiens Activity = 12.08 % PMID[29903663]
NPT83 Cell line MCF7 Homo sapiens Activity = 21.63 % PMID[29903663]
NPT83 Cell line MCF7 Homo sapiens Activity = 39.52 % PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens Activity = 28.16 % PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens Activity = 45.35 % PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens Activity = 63.29 % PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens Activity = 0.19 n.a. PMID[29903663]
NPT378 Cell line NCI/ADR-RES Homo sapiens Activity = 6.4 n.a. PMID[29903663]
NPT83 Cell line MCF7 Homo sapiens Activity = 0.02 n.a. PMID[29903663]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 7375.3 nM PubChem BioAssay data set
NPT28438 Unchecked Unchecked n.a. IC50 = 3160.0 nM PMID[33158578]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 0.0 % PMID[11575945]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 15.2 % PMID[11575945]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 70.7 % PMID[11575945]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 80.6 % PMID[11575945]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 88.9 % PMID[11575945]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 74900.0 nM PMID[18950230]
NPT852 Organism Phomopsis obscurans Phomopsis obscurans GI = 100.0 % PMID[12568545]
NPT852 Organism Phomopsis obscurans Phomopsis obscurans GI = 80.0 % PMID[12568545]
NPT2 Others Unspecified n.a. IC50 = 61800.0 nM PMID[18950230]
NPT2 Others Unspecified n.a. Potency = 82.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 50.0 % PMID[12568545]

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
- Artemia salina LC50 = 367.0 ppm DOI[10.1021/np50087a020]

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
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 NPC217176 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
NPC

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC217176 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  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