Natural Product: NPC146973

Natural Product IDNPC146973
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 FISMJUPMCGKNNX-PCGJYRBUSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 5315898
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins

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 FISMJUPMCGKNNX-PCGJYRBUSA-N
Standard InCHI InChI=1S/C22H22O11/c23-10-15-18(28)19(29)20(32-16(26)7-6-11-4-2-1-3-5-11)22(31-15)33-21(30)12-8-13(24)17(27)14(25)9-12/h1-9,15,18-20,22-25,27-29H,10H2/b7-6+/t15-,18-,19+,20-,22+/m1/s1
SMILES c1ccc(cc1)/C=C/C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1OC(=O)c1cc(c(c(c1)O)O)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   462.12 Volume:   436.363
?
Van der Waals volume.
Dense:   1.059 LogP:   1.237
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.577
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.831
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   8.0 Rigid Bonds:   21.0
TPSA:   183.21
?
Topological Polar Surface Area.
 H-Bond Acceptor:   11.0
H-Bond Donor:   6.0 Rings:   3.0
Heavy Atoms:   11.0

MedChem Properties

QED Drug-Likeness Score:   0.193 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.845 Fsp3:   0.273
MCE-18:   70.5
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.821 Fluc inhibitor:   0.764
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.176
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.634
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.484 Promiscuous compounds:   0.853

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.364 MDCK Permeability:   -5.326
Pgp-inhibitor:   0.007 Pgp-substrate:   0.006
PAMPA:   0.964
?
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):   0.045
20% Bioavailability (F20%):   0.961 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.024 MRP1:   0.975
Plasma Protein Binding (PPB):   75.386% Volume Distribution (VD):   -0.566
Fu: 26.317%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.044
BSEP inhibitor:   0.013

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.006
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.892
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.007
?
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):  3.524 Half-life (T1/2):  2.266

ADMET: Toxicity

hERG Blockers:  0.03 hERG Blockers (10um):  0.51
Human Hepatotoxicity (H-HT):  0.47 Drug-induced Liver Injury (DILI):  0.985
AMES Toxicity:  0.96 Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.235 Skin Sensitization:  1.0
Carcinogencity:  0.249 Eye Corrosion:  0.0
Eye Irritation:  0.576 Respiratory Toxicity:  0.022
Drug-induced Neurotoxicity:  0.019 Ototoxicity:  0.949
Hematotoxicity:  0.035 Drug-induced Nephrotoxicity:  0.414
Genotoxicity:  0.988 RPMI-8226 Immunitoxicity:  0.016
A549 Cytotoxicity:  0.985 Hek293 Cytotoxicity:  0.388
BCF:   0.644
?
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:   3.409
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.952
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.402
?
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
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[10978210]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[19012276]
NPO19996 Caulerpa peltata Species Caulerpaceae Eukaryota n.a. n.a. n.a. PMID[25593390]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[32933154]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10359 Chaiturus marrubiastrum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19818 Jacquemontia paniculata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14248 Mandragora autumnalis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20223 Rosa pomifera Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22675 Helichrysum chionosphaerum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18144 Metrodorea nigra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19037 Senecio praecox Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20422 Albizia myriophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26393.1 Petunia integrifolia subsp. inflata Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20753 Grangea maderaspatana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13454 Amphorogyne spicata Species Amphorogynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16142 Verbascum thapsiforme Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15422 Carduus tenuiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18287 Penicillium bilaiae Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13754 Tanacetum coccineum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2228 Photinia serratifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20947 Tagetes filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12108 Aizopsis selskiana Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21807 Lindera umbellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13754 Tanacetum coccineum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19512 Gleichenia quadripartita Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16572 Rhododendron dahuricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21691 Dillenia indica Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20144 Lespedeza tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21244 Delphinium nuttallianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13454 Amphorogyne spicata Species Amphorogynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20560 Polyporus betulinus Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19818 Jacquemontia paniculata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17018 Salvia greggii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20625 Delphinium virgatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21376 Lupinus corymbosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18867 Stephanitis takeyai Species Tingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14800 Oophaga granulifera Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19037 Senecio praecox Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17856 Anaphalis lactea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18144 Metrodorea nigra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19996 Caulerpa peltata Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14932.1 Dalbergia lanceolaria subsp. paniculata Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21564 Senecio behnii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2228 Photinia serratifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14248 Mandragora autumnalis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13246 Pinalia stricta Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26393.1 Petunia integrifolia subsp. inflata Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20844 Sphaerella rosigena n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17568 Balanophora laxiflora Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19232 Anchusa azurea Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19671 Dipsacus azureus Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22675 Helichrysum chionosphaerum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15422 Carduus tenuiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19395 Nepeta granatensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20223 Rosa pomifera Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20753 Grangea maderaspatana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16142 Verbascum thapsiforme Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24407 Bipolaris heveae Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18287 Penicillium bilaiae Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21112 Chaetomium carinthiacum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10216 Leptocereus quadricostatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20353 Degenia velebitica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10359 Chaiturus marrubiastrum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20422 Albizia myriophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27737 Penicillium shearii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19913 Rhynchophorus ferrugineus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26917 Quercus rubra Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20490 Erythrophleum ivorense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25238 Rheum coreanum Species Polygonaceae 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

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

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 NPC146973 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
0.5652 Remote Similarity NPC253668
0.5652 Remote Similarity NPC57039
0.5652 Remote Similarity NPC83218
0.5652 Remote Similarity NPC479471
0.5652 Remote Similarity NPC126991
0.5652 Remote Similarity NPC479467
0.5652 Remote Similarity NPC201249
0.5652 Remote Similarity NPC479470
0.5652 Remote Similarity NPC479472
0.5316 Remote Similarity NPC479268
0.5122 Remote Similarity NPC479269
0.5122 Remote Similarity NPC479267
0.5075 Remote Similarity NPC232880
0.506 Remote Similarity NPC479271

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC146973 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