Natural Product: NPC54394

Natural Product IDNPC54394
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Tamarixetin
IUPAC Name 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Synonyms 4'-O-methylquercetin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL226034
PubChem CID 5281699
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0001136] Flavonols

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 FPLMIPQZHHQWHN-UHFFFAOYSA-N
Standard InCHI InChI=1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
SMILES COc1ccc(cc1O)c1oc2cc(O)cc(c2c(=O)c1O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   316.06 Volume:   300.063
?
Van der Waals volume.
Dense:   1.053 LogP:   1.773
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.844
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.877
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   18.0
TPSA:   120.36
?
Topological Polar Surface Area.
 H-Bond Acceptor:   7.0
H-Bond Donor:   4.0 Rings:   3.0
Heavy Atoms:   7.0

MedChem Properties

QED Drug-Likeness Score:   0.572 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.47 Fsp3:   0.062
MCE-18:   19.0
?
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:   1 PAINS Alert:   0
Colloidal aggregators:   0.818 Fluc inhibitor:   0.708
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.903
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.624
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.549 Promiscuous compounds:   0.906

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.499 MDCK Permeability:   -4.87
Pgp-inhibitor:   0.362 Pgp-substrate:   0.152
PAMPA:   0.348
?
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):   0.16
20% Bioavailability (F20%):   0.074 30% Bioavailability (F30%):   0.922
50% Bioavailability (F50%):   0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.734
Plasma Protein Binding (PPB):   98.259% Volume Distribution (VD):   -0.757
Fu: 1.38%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.949
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.997
BSEP inhibitor:   0.418

ADMET: Metabolism

CYP1A2-inhibitor:   0.928 CYP1A2-substrate:   0.252
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.882
CYP2C9-inhibitor:   0.948 CYP2C9-substrate:   0.018
CYP2D6-inhibitor:   0.998 CYP2D6-substrate:   0.446
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.003
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.998
?
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):  3.45 Half-life (T1/2):  1.719

ADMET: Toxicity

hERG Blockers:  0.065 hERG Blockers (10um):  0.465
Human Hepatotoxicity (H-HT):  0.393 Drug-induced Liver Injury (DILI):  0.743
AMES Toxicity:  0.581 Rat Oral Acute Toxicity:  0.459
Maximum Recommended Daily Dose:  0.732 Skin Sensitization:  0.619
Carcinogencity:  0.704 Eye Corrosion:  0.617
Eye Irritation:  0.998 Respiratory Toxicity:  0.786
Drug-induced Neurotoxicity:  0.038 Ototoxicity:  0.095
Hematotoxicity:  0.082 Drug-induced Nephrotoxicity:  0.039
Genotoxicity:  0.885 RPMI-8226 Immunitoxicity:  0.068
A549 Cytotoxicity:  0.269 Hek293 Cytotoxicity:  0.575
BCF:   1.023
?
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:   3.668
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.473
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.96
?
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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[ 21030913]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. North Sea n.a. PMID[14640534]
NPO17398 Cyperus teneriffae Species Cyperaceae Eukaryota n.a. root n.a. PMID[21504148]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. PMID[7853008]
NPO1391 Zanthoxylum rubescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17398 Cyperus teneriffae Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO5473 Streptomyces orinoci Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO15972 Quercus gilva Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16526 Papularia sphaerosperma n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15151 Syringa vulgaris Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15027 Helianthus divaricatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15762 Eucalyptus sieberiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14896 Reaumuria mucronata Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9827 Indigofera linnaei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16439 Alphitonia macrocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13005 Aplophyllum telephioides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11241 Arisarum vulgare Species Araceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13257 Euphorbia officinarum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3488 Glossocalyx brevipes Species Siparunaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. DOI[DOI: 10.1111/j.1574-6968.1992.tb05311.x]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15151 Syringa vulgaris Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1391 Zanthoxylum rubescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16439 Alphitonia macrocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1391 Zanthoxylum rubescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15151 Syringa vulgaris Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15762 Eucalyptus sieberiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15972 Quercus gilva Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14896 Reaumuria mucronata Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11241 Arisarum vulgare Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3488 Glossocalyx brevipes Species Siparunaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13257 Euphorbia officinarum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1556 Gundelia tournefortii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15027 Helianthus divaricatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9827 Indigofera linnaei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16526 Papularia sphaerosperma n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17398 Cyperus teneriffae Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13005 Aplophyllum telephioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5473 Streptomyces orinoci Species Streptomycetaceae Bacteria 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
NPT208 Individual protein Cytochrome P450 1A2 Homo sapiens IC50 = 1215.0 nM PMID[20696580]
NPT1603 Individual protein Cytochrome P450 1A1 Homo sapiens IC50 = 120.0 nM PMID[20696580]
NPT1604 Individual protein Cytochrome P450 1B1 Homo sapiens IC50 = 20.0 nM PMID[20696580]
NPT1628 Individual protein Thrombin Oryctolagus cuniculus TT = 16.6 s PMID[22647223]
NPT1628 Individual protein Thrombin Oryctolagus cuniculus PT = 6.9 s PMID[22647223]
NPT1628 Individual protein Thrombin Oryctolagus cuniculus APTT = 49.8 s PMID[22647223]
NPT1628 Individual protein Thrombin Oryctolagus cuniculus Activity = 7.5 g/L PMID[22647223]
NPT1380 Individual protein Avian myoblastosis virus polyprotein II Avian myeloblastosis virus Inhibition = 59.7 % DOI[10.1007/s00044-011-9570-z]
NPT1426 Individual protein c-Jun N-terminal kinase 1 Homo sapiens K = 4.9 10'5/M PMID[29851490]
NPT281 Individual protein MAP kinase ERK1 Homo sapiens K = 6.31 10'4/M PMID[26974691]
NPT67 Individual protein Cholinesterase Equus caballus Inhibition = 3.18 % PMID[23062825]
NPT66 Individual protein Acetylcholinesterase Electrophorus electricus Inhibition = 25.93 % PMID[23062825]
NPT21852 Single protein Dihydroorotate dehydrogenase Homo sapiens Inhibition = 29.0 % PMID[30145372]
NPT21851 Single protein Dihydroorotate dehydrogenase (fumarate) Leishmania major IC50 = 93700.0 nM PMID[30145372]
NPT21851 Single protein Dihydroorotate dehydrogenase (fumarate) Leishmania major IC50 = 100000.0 nM PMID[30145372]
NPT21851 Single protein Dihydroorotate dehydrogenase (fumarate) Leishmania major Inhibition = 46.0 % PMID[30145372]
NPT207 Protein family MAP kinase p38 Homo sapiens K = 4.64 10'4/M PMID[26974691]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT189 Cell line Vero Chlorocebus aethiops IC50 = 170.3 ug.mL-1 PMID[18855442]
NPT1668 Cell line NCI-H157 Homo sapiens IC50 = 3040.0 nM PMID[25139569]
NPT81 Cell line A549 Homo sapiens IC50 = 2630.0 nM PMID[25139569]
NPT1669 Cell line NCI-H1792 Homo sapiens IC50 = 4060.0 nM PMID[25139569]
NPT455 Cell line NCI-H522 Homo sapiens IC50 > 50000.0 nM PMID[25139569]
NPT379 Cell line HOP-62 Homo sapiens IC50 = 9930.0 nM PMID[25139569]
NPT387 Cell line M14 Homo sapiens IC50 = 14850.0 nM PMID[25139569]
NPT165 Cell line HeLa Homo sapiens IC50 = 1810.0 nM PMID[25139569]
NPT81 Cell line A549 Homo sapiens Activity n.a. n.a. n.a. PMID[35833867]
NPT2615 Cell line HEK-293T Homo sapiens Activity n.a. n.a. n.a. PMID[35833867]
NPT65 Cell line HepG2 Homo sapiens Activity n.a. n.a. n.a. PMID[35833867]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1.1 ug.mL-1 PMID[18855442]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 46830.0 nM PMID[30145372]
NPT28438 Unchecked Unchecked n.a. IC50 = 49730.0 nM PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Kdiss = 4.26 10^-3/s PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Inhibition n.a. n.a. % PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Activity n.a. n.a. n.a. PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Kd = 2520.0 nM PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Inhibition = 2.5 % PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Inhibition = 83.89 % PMID[35833867]
NPT28438 Unchecked Unchecked n.a. Delta Tm > 2.0 degrees C PMID[35833867]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 4450.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 3860.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 7570.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 21970.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 12540.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 24950.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 19910.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[25139569]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 7970.0 nM PMID[25139569]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 53150.0 nM PMID[30145372]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 20250.0 nM PMID[30145372]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC90 = 632000.0 nM PMID[26974691]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC90 > 632000.0 nM PMID[26974691]
NPT1 Others Radical scavenging activity n.a. EC50 > 100.0 ug PMID[21821414]
NPT22995 Cell line B16-F0 Mus musculus Activity = 95.1 % PMID[24853321]
NPT22995 Cell line B16-F0 Mus musculus Activity = 97.5 % PMID[24853321]
NPT22995 Cell line B16-F0 Mus musculus Activity = 133.5 % PMID[24853321]
NPT22995 Cell line B16-F0 Mus musculus Activity = 125.6 % PMID[24853321]
NPT22995 Cell line B16-F0 Mus musculus Activity = 106.9 % PMID[24853321]
NPT22995 Cell line B16-F0 Mus musculus Activity = 97.9 % PMID[24853321]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity = 7.03 log10CFU/g PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity n.a. n.a. n.a. PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition > 55.0 % PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity = 70.0 % PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity = 20.0 % PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 512.0 ug.mL-1 PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 16.0 ug.mL-1 PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus FICI = 0.375 n.a. PMID[35833867]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 85.81 % PMID[35833867]
NPT2 Others Unspecified n.a. IC50 = 4600.0 nM PMID[8882428]
NPT2 Others Unspecified n.a. IC50 > 100000.0 nM PMID[19296652]
NPT2 Others Unspecified n.a. IC50 = 16400.0 nM PMID[19296652]
NPT2 Others Unspecified n.a. FC = 1.52 n.a. PMID[26517554]
NPT2 Others Unspecified n.a. FC = 1.32 n.a. PMID[26517554]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Activity = 80.0 % PMID[29851490]
NPT32 Organism Mus musculus Mus musculus Activity = 60.0 % PMID[29851490]





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference
Staphylococcus aureus n.a. Ka = 1.69 10^3/M/s PMID[35833867]





 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 NPC54394 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
0.8077 Intermediate Similarity NPC50403
0.8077 Intermediate Similarity NPC241838
0.7778 Intermediate Similarity NPC159103
0.7636 Intermediate Similarity NPC609179
0.75 Intermediate Similarity NPC125062
0.7455 Intermediate Similarity NPC200740
0.7455 Intermediate Similarity NPC82325
0.7407 Intermediate Similarity NPC28274
0.7321 Intermediate Similarity NPC52005
0.7222 Intermediate Similarity NPC219330
0.7193 Intermediate Similarity NPC133953
0.6981 Remote Similarity NPC179271
0.6842 Remote Similarity NPC55205
0.6792 Remote Similarity NPC20791
0.6724 Remote Similarity NPC93376
0.6716 Remote Similarity NPC254306
0.6613 Remote Similarity NPC130955
0.6604 Remote Similarity NPC116775
0.6604 Remote Similarity NPC187432
0.6481 Remote Similarity NPC169749
0.6441 Remote Similarity NPC189179
0.6429 Remote Similarity NPC21100
0.6207 Remote Similarity NPC59951
0.6167 Remote Similarity NPC75215
0.6167 Remote Similarity NPC603596
0.6167 Remote Similarity NPC606638
0.6034 Remote Similarity NPC44079
0.6034 Remote Similarity NPC123886
0.5946 Remote Similarity NPC606270
0.5932 Remote Similarity NPC201451
0.5932 Remote Similarity NPC231772
0.5932 Remote Similarity NPC601901
0.5902 Remote Similarity NPC162351
0.5902 Remote Similarity NPC12200
0.5806 Remote Similarity NPC279989
0.5806 Remote Similarity NPC194653
0.5797 Remote Similarity NPC171821
0.5789 Remote Similarity NPC216361
0.5763 Remote Similarity NPC98661
0.5763 Remote Similarity NPC184536
0.5763 Remote Similarity NPC103342
0.5738 Remote Similarity NPC166753
0.569 Remote Similarity NPC256042
0.5667 Remote Similarity NPC286342
0.5667 Remote Similarity NPC87125
0.5667 Remote Similarity NPC143799
0.5667 Remote Similarity NPC610359
0.5614 Remote Similarity NPC601197
0.5593 Remote Similarity NPC26227
0.5574 Remote Similarity NPC9609
0.5574 Remote Similarity NPC256283
0.5556 Remote Similarity NPC183950
0.5556 Remote Similarity NPC252933
0.5556 Remote Similarity NPC482982
0.55 Remote Similarity NPC152042
0.5484 Remote Similarity NPC270620
0.5467 Remote Similarity NPC219904
0.5455 Remote Similarity NPC205046
0.541 Remote Similarity NPC62536
0.541 Remote Similarity NPC281207
0.541 Remote Similarity NPC120464
0.541 Remote Similarity NPC605755
0.5397 Remote Similarity NPC287101
0.5397 Remote Similarity NPC223579
0.5397 Remote Similarity NPC607642
0.5397 Remote Similarity NPC610401
0.5395 Remote Similarity NPC120099
0.5373 Remote Similarity NPC200694
0.5323 Remote Similarity NPC49824
0.5238 Remote Similarity NPC50728
0.5231 Remote Similarity NPC142876
0.5231 Remote Similarity NPC483775
0.5195 Remote Similarity NPC197285
0.5195 Remote Similarity NPC486578
0.5195 Remote Similarity NPC609478
0.5161 Remote Similarity NPC270465
0.5161 Remote Similarity NPC483773
0.5156 Remote Similarity NPC602125
0.5152 Remote Similarity NPC605634
0.5152 Remote Similarity NPC607815
0.5128 Remote Similarity NPC136761
0.5079 Remote Similarity NPC32420
0.5079 Remote Similarity NPC86485
0.5077 Remote Similarity NPC604021

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC54394 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
0.6792 Remote Similarity NPD1512 Phase 3

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