Natural Product: NPC231149

Natural Product IDNPC231149
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Daphnoretin
IUPAC Name 7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-2-one
Synonyms NSC-291852
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL508494
PubChem CID 5281406
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0002908] Hydroxycoumarins
          • [CHEMONTID:0002909] 7-hydroxycoumarins

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 JRHMMVBOTXEHGJ-UHFFFAOYSA-N
Standard InCHI InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3
SMILES COc1cc2cc(c(=O)oc2cc1O)Oc1ccc2ccc(=O)oc2c1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   352.06 Volume:   338.121
?
Van der Waals volume.
Dense:   1.041 LogP:   1.554
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.671
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.922
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   24.0
TPSA:   99.11
?
Topological Polar Surface Area.
 H-Bond Acceptor:   7.0
H-Bond Donor:   1.0 Rings:   4.0
Heavy Atoms:   7.0

MedChem Properties

QED Drug-Likeness Score:   0.564 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.476 Fsp3:   0.053
MCE-18:   22.0
?
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:   0.771 Fluc inhibitor:   0.705
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.999
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.929
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.454 Promiscuous compounds:   0.357

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.762 MDCK Permeability:   -4.688
Pgp-inhibitor:   0.0 Pgp-substrate:   0.0
PAMPA:   0.836
?
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):   0.0
20% Bioavailability (F20%):   0.756 30% Bioavailability (F30%):   0.102
50% Bioavailability (F50%):   0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   1.0
Plasma Protein Binding (PPB):   98.503% Volume Distribution (VD):   -0.478
Fu: 1.351%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.971
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.0
BSEP inhibitor:   0.997

ADMET: Metabolism

CYP1A2-inhibitor:   0.277 CYP1A2-substrate:   0.222
CYP2C19-inhibitor:   0.647 CYP2C19-substrate:   0.785
CYP2C9-inhibitor:   0.999 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.415 CYP2D6-substrate:   0.382
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.632
CYP2B6-substrate:   0.132 CYP2C8-inhibitor:   1.0
HLM stability:   0.971
?
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):  1.575 Half-life (T1/2):  1.268

ADMET: Toxicity

hERG Blockers:  0.162 hERG Blockers (10um):  0.376
Human Hepatotoxicity (H-HT):  0.474 Drug-induced Liver Injury (DILI):  0.966
AMES Toxicity:  0.606 Rat Oral Acute Toxicity:  0.512
Maximum Recommended Daily Dose:  0.809 Skin Sensitization:  0.105
Carcinogencity:  0.883 Eye Corrosion:  0.069
Eye Irritation:  0.972 Respiratory Toxicity:  0.615
Drug-induced Neurotoxicity:  0.143 Ototoxicity:  0.116
Hematotoxicity:  0.166 Drug-induced Nephrotoxicity:  0.138
Genotoxicity:  0.954 RPMI-8226 Immunitoxicity:  0.071
A549 Cytotoxicity:  0.109 Hek293 Cytotoxicity:  0.567
BCF:   0.872
?
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:   3.769
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.559
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.329
?
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
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[15387673]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[15635251]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[16792421]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21534540]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota whole plants Panshi, Jilin Province, China 2009-JUN PMID[21534540]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. flower n.a. PMID[21916433]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22494026]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota flower buds n.a. n.a. PMID[23558238]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24156713]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[24660446]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25453801]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26702644]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27228307]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[28383891]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota Roots n.a. n.a. PMID[31150241]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[31860304]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32223193]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32997496]
NPO40954 Wikstroemia elliptica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[3783168]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[501363]
NPO40265 Peddiea fischeri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[6875580]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[7320737]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13009 Laurencia saitoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17452 Setaria italica Species Poaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19479 Trametes feei Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10765 Dracaena concinna Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1787 Agathis lanceolata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Leaf Diffusate n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18285 Daphne gnidium Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17452 Setaria italica Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17283 Rhizoma dryopteris crassirhizomae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17452 Setaria italica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18285 Daphne gnidium Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3837 Wikstroemia indica Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17452 Setaria italica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15287 Vernonia megapotamica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10882 Acer caudatifolium Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17558 Cynoglossum formosanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7037 Rumohra adiantiformis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19406 Chrysanthemum leptophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19479 Trametes feei Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14015 Salacia cordata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10705 Marshallia graminifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12376 Baccharis macraei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18285 Daphne gnidium Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3426 Pseudocyphellaria hirsuta Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18247 Globicephala melas Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10765 Dracaena concinna Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13505 Grateloupia livida Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10542 Liparis keitaoensis Species Liparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14335 Ophiorrhiza kuroiwae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1787 Agathis lanceolata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13009 Laurencia saitoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17452 Setaria italica Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3837 Wikstroemia indica Species Thymelaeaceae 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
NPT2216 Individual protein DNA polymerase beta Rattus norvegicus IC50 = 122300.0 nM PMID[15387673]
NPT149 Individual protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PubChem BioAssay data set
NPT150 Individual protein Anthrax lethal factor Bacillus anthracis Potency = 12589.3 nM PubChem BioAssay data set
NPT151 Individual protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT109 Individual protein Cytochrome P450 3A4 Homo sapiens Potency = 501.2 nM PubChem BioAssay data set
NPT199 Individual protein DNA polymerase kappa Homo sapiens Potency n.a. 354.8 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 20596.2 nM PubChem BioAssay data set
NPT105 Individual protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 6309.6 nM PubChem BioAssay data set
NPT1592 Individual protein Dipeptidyl peptidase IV Homo sapiens IC50 = 87100.0 nM DOI[10.1039/C0MD00245C]
NPT50 Individual protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT48 Individual protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set
NPT94 Individual protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 25118.9 nM PubChem BioAssay data set
NPT94 Individual protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 17782.8 nM PubChem BioAssay data set
NPT446 Individual protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 79432.8 nM PubChem BioAssay data set
NPT446 Individual protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 50118.7 nM PubChem BioAssay data set
NPT51 Individual protein Microtubule-associated protein tau Homo sapiens Potency = 44668.4 nM PubChem BioAssay data set
NPT59 Individual protein DNA polymerase beta Homo sapiens Potency = 44668.4 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 63095.7 nM PubChem BioAssay data set
NPT755 Individual protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 79432.8 nM PubChem BioAssay data set
NPT49 Individual protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 44668.4 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell line P388 Mus musculus ED50 = 2.2 ug ml-1 PMID[6875580]
NPT168 Cell line P388 Mus musculus ED50 = 3.4 ug ml-1 PMID[3783168]
NPT83 Cell line MCF7 Homo sapiens Activity = 5.32 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity n.a. n.a. n.a. PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity n.a. n.a. n.a. PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 51.27 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 9.33 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 45.58 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 47.72 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 8.43 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 37.3 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 43.73 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 38.59 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 53.37 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 1.92 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 59.49 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens IC50 = 2000.0 nM PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens IC50 = 1000.0 nM PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 2.2 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 36.99 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 15.29 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 50.95 % PMID[36154031]
NPT82 Cell line MDA-MB-231 Homo sapiens Activity = 46.0 % PMID[36154031]
NPT83 Cell line MCF7 Homo sapiens Activity = 46.53 % PMID[36154031]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PubChem BioAssay data set
NPT28438 Unchecked Unchecked n.a. Activity n.a. n.a. n.a. PMID[36154031]
NPT28438 Unchecked Unchecked n.a. Inhibition n.a. n.a. % PMID[36154031]
NPT28438 Unchecked Unchecked n.a. IC50 = 90.0 ug.mL-1 PMID[29032032]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 97.0 % PMID[7320737]
NPT2 Others Unspecified n.a. Potency = 35481.3 nM PubChem BioAssay data set
NPT28736 Protein family Alpha-glucosidase Saccharomyces cerevisiae S288c IC50 = 86.0 ug.mL-1 PMID[29032032]

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 NPC231149 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
0.7377 Intermediate Similarity NPC281558
0.7213 Intermediate Similarity NPC185127
0.6429 Remote Similarity NPC76336
0.5696 Remote Similarity NPC284810
0.5082 Remote Similarity NPC139548

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC231149 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