Natural Product: NPC193949

Natural Product IDNPC193949
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Scoulerine
IUPAC Name (13aS)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
Synonyms Aequaline; Discretamine; Scoulerine
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1235966
PubChem CID 439654
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

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 KNWVMRVOBAFFMH-HNNXBMFYSA-N
Standard InCHI InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
SMILES COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(O)c(cc1)OC

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   327.15 Volume:   333.293
?
Van der Waals volume.
Dense:   0.982 LogP:   1.092
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.24
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.237
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   21.0
TPSA:   62.16
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   4.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.888 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.994 Fsp3:   0.368
MCE-18:   74.462
?
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:   1 PAINS Alert:   1
Colloidal aggregators:   0.29 Fluc inhibitor:   0.025
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.61
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.47
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.002 Promiscuous compounds:   0.103

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.064 MDCK Permeability:   -4.744
Pgp-inhibitor:   0.07 Pgp-substrate:   0.616
PAMPA:   0.004
?
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):   0.02
20% Bioavailability (F20%):   0.689 30% Bioavailability (F30%):   0.651
50% Bioavailability (F50%):   0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.44 MRP1:   0.966
Plasma Protein Binding (PPB):   86.208% Volume Distribution (VD):   -0.303
Fu: 12.795%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.989
OATP1B3 inhibitor:   0.977 BCRP inhibitor:   0.846
BSEP inhibitor:   0.825

ADMET: Metabolism

CYP1A2-inhibitor:   1.0 CYP1A2-substrate:   0.429
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.001
CYP2C9-inhibitor:   1.0 CYP2C9-substrate:   0.999
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   0.022
CYP3A4-inhibitor:   0.999 CYP3A4-substrate:   0.999
CYP2B6-substrate:   0.302 CYP2C8-inhibitor:   0.981
HLM stability:   0.97
?
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):  5.228 Half-life (T1/2):  2.457

ADMET: Toxicity

hERG Blockers:  0.346 hERG Blockers (10um):  0.611
Human Hepatotoxicity (H-HT):  0.555 Drug-induced Liver Injury (DILI):  0.158
AMES Toxicity:  0.532 Rat Oral Acute Toxicity:  0.726
Maximum Recommended Daily Dose:  0.794 Skin Sensitization:  0.751
Carcinogencity:  0.703 Eye Corrosion:  0.003
Eye Irritation:  0.517 Respiratory Toxicity:  0.965
Drug-induced Neurotoxicity:  0.644 Ototoxicity:  0.379
Hematotoxicity:  0.208 Drug-induced Nephrotoxicity:  0.513
Genotoxicity:  0.798 RPMI-8226 Immunitoxicity:  0.112
A549 Cytotoxicity:  0.383 Hek293 Cytotoxicity:  0.406
BCF:   1.212
?
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:   3.793
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.935
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.382
?
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
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. DOI[10.1042/BA20020118]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. DOI[10.1556/abot.45.2003.3-4.15]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[11141125]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[12398544]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[18419154]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[19296389]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21910504]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. seed n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[22011319]
NPO929 Corydalis scouleri Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Barks n.a. n.a. PMID[2348205]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. rhizome n.a. PMID[25277281]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. tuber n.a. PMID[25670016]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[37685099]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. fruit n.a. PMID[8786370]
NPO2884 Annona squamosa Species Annonaceae Eukaryota bark n.a. n.a. PMID[9214729]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO929 Corydalis scouleri Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2020 Corydalis cava Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO929 Corydalis scouleri Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO929 Corydalis scouleri Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2884 Annona squamosa Species Annonaceae 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
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 4610.9 nM PubChem BioAssay data set
NPT2971 Individual protein DNA dC->dU-editing enzyme APOBEC-3F Homo sapiens Potency n.a. 11155.6 nM PubChem BioAssay data set
NPT2971 Individual protein DNA dC->dU-editing enzyme APOBEC-3F Homo sapiens Potency n.a. 12516.8 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 20596.2 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT242 Individual protein Dopamine D1 receptor Homo sapiens Ki = 22.0 nM PMID[23332346]
NPT243 Individual protein Dopamine D2 receptor Homo sapiens Ki = 214.0 nM PMID[23332346]
NPT242 Individual protein Dopamine D1 receptor Homo sapiens Inhibition = 99.1 % PMID[23332346]
NPT243 Individual protein Dopamine D2 receptor Homo sapiens Inhibition = 93.4 % PMID[23332346]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens Inhibition = 20.9 % PMID[23332346]
NPT204 Individual protein Acetylcholinesterase Homo sapiens IC50 = 143300.0 nM PMID[37615114]
NPT1433 Individual protein Serine/threonine-protein kinase Aurora-B Homo sapiens Inhibition n.a. n.a. % PMID[34406008]
NPT1432 Individual protein Serine/threonine-protein kinase Aurora-A Homo sapiens Inhibition n.a. n.a. % PMID[34406008]
NPT803 Individual protein Flap endonuclease 1 Homo sapiens Potency n.a. 4466.8 nM PubChem BioAssay data set
NPT9 Individual protein DNA polymerase eta Homo sapiens Potency n.a. 89125.1 nM PubChem BioAssay data set
NPT4907 Individual protein Tyrosyl-DNA phosphodiesterase 2 Homo sapiens IC50 > 128332.0 nM PubChem BioAssay data set
NPT477 Individual protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 11220.2 nM PubChem BioAssay data set
NPT477 Individual protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 12516.8 nM PubChem BioAssay data set
NPT444 Individual protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT4674 Individual protein Apoptotic protease-activating factor 1 Homo sapiens IC50 > 100000.0 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT4674 Individual protein Apoptotic protease-activating factor 1 Homo sapiens IC50 = 16300.0 nM PubChem BioAssay data set
NPT861 Individual protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 50118.7 nM PubChem BioAssay data set
NPT478 Individual protein Ataxin-2 Homo sapiens Potency n.a. 44668.4 nM PubChem BioAssay data set
NPT92 Individual protein Serotonin 1a (5-HT1a) receptor Homo sapiens Inhibition = 14.2 % PMID[23332346]
NPT861 Individual protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 2592.9 nM PubChem BioAssay data set
NPT30107 Single protein Amyloid-beta A4 protein Homo sapiens IC50 > 50000.0 nM PMID[37615114]
NPT30107 Single protein Amyloid-beta A4 protein Homo sapiens Inhibition = 3.3 % PMID[37615114]
NPT864 Individual protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 15848.9 nM PubChem BioAssay data set
NPT5 Individual protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT439 Individual protein Butyrylcholinesterase Homo sapiens IC50 = 61300.0 nM PMID[37615114]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2511 Cell line HGC-27 Homo sapiens IC50 = 6100.0 nM PMID[35286954]
NPT3140 Cell line MGC-803 Homo sapiens IC50 = 12600.0 nM PMID[35286954]
NPT397 Cell line NCI-H460 Homo sapiens Activity n.a. n.a. n.a. PMID[34406008]
NPT165 Cell line HeLa Homo sapiens IC50 = 6737.0 nM PMID[34406008]
NPT370 Cell line NCI-H23 Homo sapiens IC50 = 2541.0 nM PMID[34406008]
NPT660 Cell line SW480 Homo sapiens IC50 = 4237.0 nM PMID[34406008]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 = 7324.0 nM PMID[34406008]
NPT81 Cell line A549 Homo sapiens IC50 = 26320.0 nM PMID[34406008]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 6573.3 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PubChem BioAssay data set
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM DOI[10.6019/CHEMBL4651402]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM DOI[10.6019/CHEMBL4651402]
NPT28438 Unchecked Unchecked n.a. Ratio IC50 = 0.4 n.a. PMID[37615114]
NPT28833 No target No relevant target n.a. IC50 = 43800.0 nM PMID[37615114]
NPT28438 Unchecked Unchecked n.a. Activity n.a. n.a. n.a. PMID[34406008]
NPT28438 Unchecked Unchecked n.a. IC50 = 4622.0 nM PMID[34406008]
NPT28438 Unchecked Unchecked n.a. IC50 = 6811.0 nM PMID[34406008]
NPT28438 Unchecked Unchecked n.a. IC50 = 4065.0 nM PMID[34406008]
NPT28438 Unchecked Unchecked n.a. EC50 = 3545.0 nM PMID[34406008]
NPT28438 Unchecked Unchecked n.a. EC50 = 3595.0 nM PMID[34406008]
NPT28438 Unchecked Unchecked n.a. IC50 = 5484.0 nM PMID[34406008]
NPT2 Others Unspecified n.a. Potency n.a. 10322.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 4466.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 4300.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 11220.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 2511.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 2592.9 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 12497.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. IC50 = 7493.0 nM PubChem BioAssay data set
NPT21769 Cell line GES1 Homo sapiens IC50 = 95300.0 nM PMID[35286954]

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
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 NPC193949 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
1.0 High Similarity NPC249797
0.8036 Intermediate Similarity NPC276588
0.8036 Intermediate Similarity NPC127674
0.8036 Intermediate Similarity NPC278799
0.7377 Intermediate Similarity NPC276944
0.7377 Intermediate Similarity NPC238530
0.7167 Intermediate Similarity NPC295691
0.7167 Intermediate Similarity NPC207757
0.7167 Intermediate Similarity NPC54379
0.7143 Intermediate Similarity NPC88249
0.6833 Remote Similarity NPC189266
0.6833 Remote Similarity NPC2413
0.6833 Remote Similarity NPC110416
0.6515 Remote Similarity NPC232514
0.6349 Remote Similarity NPC204828
0.6349 Remote Similarity NPC5238
0.6271 Remote Similarity NPC220858
0.6032 Remote Similarity NPC469817
0.6032 Remote Similarity NPC172765
0.5968 Remote Similarity NPC151895
0.5806 Remote Similarity NPC147390
0.5806 Remote Similarity NPC428
0.5469 Remote Similarity NPC321505
0.5469 Remote Similarity NPC179825
0.5385 Remote Similarity NPC39701
0.5385 Remote Similarity NPC184026
0.5294 Remote Similarity NPC264850
0.5156 Remote Similarity NPC210437
0.5156 Remote Similarity NPC16107
0.5156 Remote Similarity NPC106295
0.5147 Remote Similarity NPC312025
0.5085 Remote Similarity NPC192768
0.5077 Remote Similarity NPC51957

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC193949 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
0.5156 Remote Similarity NPD4584 Phase 2

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