Natural Product: NPC604189

Natural Product IDNPC604189
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 MJHMXBDRUWSJOS-UHFFFAOYSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1466906
PubChem CID n.a.
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]

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 MJHMXBDRUWSJOS-UHFFFAOYSA-N
Standard InCHI InChI=1S/C16H14O6/c1-21-13-7-9(3-5-11(13)17)15(19)16(20)10-4-6-12(18)14(8-10)22-2/h3-8,17-18H,1-2H3
SMILES COc1cc(C(=O)C(=O)c2ccc(O)c(OC)c2)ccc1O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   302.08 Volume:   299.829
?
Van der Waals volume.
Dense:   1.008 LogP:   1.849
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.111
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.807
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   14.0
TPSA:   93.06
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.649 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.039 Fsp3:   0.125
MCE-18:   14.0
?
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:   1
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.137 Fluc inhibitor:   0.339
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.161
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.488
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.667 Promiscuous compounds:   0.854

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.126 MDCK Permeability:   -4.759
Pgp-inhibitor:   0.933 Pgp-substrate:   0.026
PAMPA:   0.017
?
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):   0.015
20% Bioavailability (F20%):   0.219 30% Bioavailability (F30%):   0.246
50% Bioavailability (F50%):   0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.685
Plasma Protein Binding (PPB):   95.923% Volume Distribution (VD):   -0.673
Fu: 3.399%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.989
BSEP inhibitor:   0.943

ADMET: Metabolism

CYP1A2-inhibitor:   0.279 CYP1A2-substrate:   0.03
CYP2C19-inhibitor:   0.305 CYP2C19-substrate:   0.081
CYP2C9-inhibitor:   0.986 CYP2C9-substrate:   0.012
CYP2D6-inhibitor:   0.847 CYP2D6-substrate:   0.985
CYP3A4-inhibitor:   0.018 CYP3A4-substrate:   0.029
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.856
HLM stability:   0.211
?
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):  7.734 Half-life (T1/2):  1.091

ADMET: Toxicity

hERG Blockers:  0.103 hERG Blockers (10um):  0.431
Human Hepatotoxicity (H-HT):  0.443 Drug-induced Liver Injury (DILI):  0.386
AMES Toxicity:  0.527 Rat Oral Acute Toxicity:  0.231
Maximum Recommended Daily Dose:  0.395 Skin Sensitization:  0.735
Carcinogencity:  0.485 Eye Corrosion:  0.174
Eye Irritation:  0.98 Respiratory Toxicity:  0.727
Drug-induced Neurotoxicity:  0.368 Ototoxicity:  0.239
Hematotoxicity:  0.262 Drug-induced Nephrotoxicity:  0.459
Genotoxicity:  0.217 RPMI-8226 Immunitoxicity:  0.096
A549 Cytotoxicity:  0.177 Hek293 Cytotoxicity:  0.346
BCF:   1.012
?
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:   3.455
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.355
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.817
?
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
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/BF00714468]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. DOI[10.1021/jf00055a023]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota Fruits n.a. n.a. PMID[11141122]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[11539687]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[12713418]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[15577254]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15621610]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stems Wulai Hsiang, Taipei County, Taiwan 2005-MAY PMID[17253858]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[18217715]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[21080643]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. husk n.a. PMID[21574561]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. leaf n.a. PMID[21574561]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23025417]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[23292602]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[23327905]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stem bark Laifeng, Hubei Province, China 2012-JUL PMID[26087384]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[28453270]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[29762032]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[36014413]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36838931]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37480748]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. pollen n.a. PMID[8987503]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6956 Citrus limonia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13501 Gynura segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Cob n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Husk Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6956 Citrus limonia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13501 Gynura segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6956 Citrus limonia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13501 Gynura segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13501 Gynura segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6956 Citrus limonia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13501 Gynura segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6956 Citrus limonia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11100 Artemisia capillaris Species Asteraceae 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
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT537 Individual protein Ras-related protein Rab-9A Homo sapiens Potency = 1000.0 nM PubChem BioAssay data set
NPT9 Individual protein DNA polymerase eta Homo sapiens Potency n.a. 39810.7 nM PubChem BioAssay data set
NPT484 Individual protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 37933.0 nM PubChem BioAssay data set
NPT26910 Single protein Myocilin Homo sapiens Kd = 300000.0 nM PMID[28739043]
NPT26910 Single protein Myocilin Homo sapiens Delta Tm = 0.91 degrees C PMID[28739043]
NPT478 Individual protein Ataxin-2 Homo sapiens Potency n.a. 1995.3 nM PubChem BioAssay data set
NPT28644 Nucleic-acid microRNA 21 Homo sapiens Potency = 14689.2 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5858.4 nM PubChem BioAssay data set
NPT28438 Unchecked Unchecked n.a. Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PubChem BioAssay data set
NPT28438 Unchecked Unchecked n.a. Potency = 4.6 nM PubChem BioAssay data set
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 8.6 % CO-ADD screening of NIH NCI Diversity Set V
NPT20 Organism Candida albicans Candida albicans Inhibition = 1.86 % CO-ADD screening of NIH NCI Diversity Set V
NPT28797 Organism Cryptococcus neoformans Cryptococcus neoformans Inhibition = -17.88 % CO-ADD screening of NIH NCI Diversity Set V
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 13.12 % CO-ADD screening of NIH NCI Diversity Set V
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 16.47 % CO-ADD screening of NIH NCI Diversity Set V
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = -3.81 % CO-ADD screening of NIH NCI Diversity Set V
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = -13.36 % CO-ADD screening of NIH NCI Diversity Set V
NPT29533 Protein-protein interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set

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 NPC604189 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
0.8065 Intermediate Similarity NPC32163
0.7879 Intermediate Similarity NPC139519
0.7353 Intermediate Similarity NPC16651
0.7222 Intermediate Similarity NPC50763
0.7222 Intermediate Similarity NPC325625
0.6667 Remote Similarity NPC239608
0.6667 Remote Similarity NPC46161
0.6471 Remote Similarity NPC309203
0.6341 Remote Similarity NPC474903
0.625 Remote Similarity NPC7097
0.6176 Remote Similarity NPC203719
0.5714 Remote Similarity NPC246358
0.5714 Remote Similarity NPC156840
0.5714 Remote Similarity NPC293619
0.5682 Remote Similarity NPC908
0.5676 Remote Similarity NPC159418
0.5676 Remote Similarity NPC320987
0.5676 Remote Similarity NPC221049
0.5556 Remote Similarity NPC469539
0.5556 Remote Similarity NPC296874
0.5455 Remote Similarity NPC66905
0.5405 Remote Similarity NPC257124
0.5385 Remote Similarity NPC255675
0.5319 Remote Similarity NPC469540
0.5294 Remote Similarity NPC208760
0.5263 Remote Similarity NPC160380
0.5263 Remote Similarity NPC38996
0.5263 Remote Similarity NPC8547
0.5263 Remote Similarity NPC36108
0.5263 Remote Similarity NPC140359
0.5263 Remote Similarity NPC233731
0.5263 Remote Similarity NPC610203
0.525 Remote Similarity NPC35071
0.525 Remote Similarity NPC177475
0.525 Remote Similarity NPC78918
0.525 Remote Similarity NPC39793
0.525 Remote Similarity NPC85488
0.525 Remote Similarity NPC148615
0.525 Remote Similarity NPC476343
0.525 Remote Similarity NPC139617
0.525 Remote Similarity NPC603326
0.5128 Remote Similarity NPC326599
0.5128 Remote Similarity NPC165133
0.5128 Remote Similarity NPC242885
0.5128 Remote Similarity NPC95614
0.5128 Remote Similarity NPC471693
0.5128 Remote Similarity NPC181969
0.5128 Remote Similarity NPC193544
0.5128 Remote Similarity NPC232316
0.5128 Remote Similarity NPC329595
0.5122 Remote Similarity NPC224814
0.5122 Remote Similarity NPC299406
0.5122 Remote Similarity NPC606519
0.5102 Remote Similarity NPC480702
0.5102 Remote Similarity NPC27139

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC604189 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
0.6944 Remote Similarity NPD824 Phase 4
0.5405 Remote Similarity NPD228 Phase 0

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