Natural Product: NPC886

Natural Product IDNPC886
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Calceolarioside A
IUPAC Name [(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL481635
PubChem CID 5273566
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey UHIGZYLCYRQESL-VJWFJHQPSA-N
Standard InCHI InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1
SMILES OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   478.15 Volume:   456.296
?
Van der Waals volume.
Dense:   1.048 LogP:   0.929
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.379
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.899
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   9.0 Rigid Bonds:   20.0
TPSA:   186.37
?
Topological Polar Surface Area.
 H-Bond Acceptor:   11.0
H-Bond Donor:   7.0 Rings:   3.0
Heavy Atoms:   11.0

MedChem Properties

QED Drug-Likeness Score:   0.155 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.956 Fsp3:   0.348
MCE-18:   69.774
?
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:   0.68 Fluc inhibitor:   0.858
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.103
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.594
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.231 Promiscuous compounds:   0.466

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.404 MDCK Permeability:   -5.235
Pgp-inhibitor:   0.0 Pgp-substrate:   0.022
PAMPA:   0.983
?
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):   0.904
20% Bioavailability (F20%):   1.0 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.002 MRP1:   0.06
Plasma Protein Binding (PPB):   65.134% Volume Distribution (VD):   -0.263
Fu: 29.747%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.045
BSEP inhibitor:   0.003

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.032
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.951
?
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):  9.036 Half-life (T1/2):  2.288

ADMET: Toxicity

hERG Blockers:  0.065 hERG Blockers (10um):  0.529
Human Hepatotoxicity (H-HT):  0.525 Drug-induced Liver Injury (DILI):  0.813
AMES Toxicity:  0.954 Rat Oral Acute Toxicity:  0.052
Maximum Recommended Daily Dose:  0.19 Skin Sensitization:  1.0
Carcinogencity:  0.172 Eye Corrosion:  0.0
Eye Irritation:  0.445 Respiratory Toxicity:  0.025
Drug-induced Neurotoxicity:  0.003 Ototoxicity:  0.979
Hematotoxicity:  0.093 Drug-induced Nephrotoxicity:  0.176
Genotoxicity:  0.886 RPMI-8226 Immunitoxicity:  0.015
A549 Cytotoxicity:  0.994 Hek293 Cytotoxicity:  0.628
BCF:   0.79
?
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:   3.424
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.024
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.482
?
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
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s00253-012-4489-y]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. DOI[10.1093/oxfordjournals.pcp.a076462]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers bought from a drugstore in Beijing n.a. PMID[10514305]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11858748]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1367520]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flower buds n.a. n.a. PMID[14738377]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15974609]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[19093848]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21381678]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers n.a. n.a. PMID[21524582]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22118684]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[24840014]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26692349]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[31180680]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33089690]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8626236]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO16764 Penstemon linarioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[COCONUT]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15621 Lethasterias fusca Species Asteriidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28240 Notholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13225 Spergula japonica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO255 Solanum pseudopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28240 Notholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2667 Acacia lasiopetala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27134 Euphrasia rubra Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8556 Eucalyptus kitsoniana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10527 Cyathula tomentosa Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26381 Bombus pascuorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15513 Pseudocyphellaria rubella Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15806 Rhododendron campylocarpum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1777 Toddalia aculeata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9299.3 Hordeum vulgare var. distichon Varieties Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15718 Lindera sericea Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13460 Asphodeline damascena Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22101 Himantoglossum hircinum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26951 Gymnopus androsaceus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11243 Exochorda giraldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21851 Chaetomella raphigera Species Chaetomellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29322 Rhodanthe maryonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15621 Lethasterias fusca Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16764 Penstemon linarioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11577 Buddleja officinalis Species Scrophulariaceae 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
NPT182 Individual protein Protein kinase C alpha Homo sapiens IC50 = 600.0 nM PMID[9834166]
NPT183 Individual protein Arachidonate 5-lipoxygenase Rattus norvegicus Inhibition = 0.0 % PMID[10514305]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified n.a. Inhibition = 0.0 % PMID[10514305]

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 NPC886 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
0.7568 Intermediate Similarity NPC483705
0.7162 Intermediate Similarity NPC260425
0.7162 Intermediate Similarity NPC81515
0.6883 Remote Similarity NPC472350
0.6883 Remote Similarity NPC197316
0.6883 Remote Similarity NPC89105
0.6795 Remote Similarity NPC68092
0.679 Remote Similarity NPC269141
0.6627 Remote Similarity NPC296954
0.662 Remote Similarity NPC287597
0.6538 Remote Similarity NPC171134
0.6538 Remote Similarity NPC483706
0.6533 Remote Similarity NPC254398
0.6344 Remote Similarity NPC488390
0.6279 Remote Similarity NPC96795
0.6279 Remote Similarity NPC264632
0.6235 Remote Similarity NPC112
0.6125 Remote Similarity NPC328273
0.6118 Remote Similarity NPC298257
0.6118 Remote Similarity NPC175214
0.6098 Remote Similarity NPC76406
0.6 Remote Similarity NPC34293
0.5976 Remote Similarity NPC321184
0.593 Remote Similarity NPC252292
0.5926 Remote Similarity NPC40305
0.5926 Remote Similarity NPC205195
0.5846 Remote Similarity NPC266045
0.5833 Remote Similarity NPC257847
0.5833 Remote Similarity NPC611289
0.5806 Remote Similarity NPC147654
0.5795 Remote Similarity NPC100998
0.5747 Remote Similarity NPC105005
0.5714 Remote Similarity NPC476384
0.5647 Remote Similarity NPC476377
0.561 Remote Similarity NPC46137
0.5581 Remote Similarity NPC263829
0.5568 Remote Similarity NPC205864
0.5568 Remote Similarity NPC247032
0.5556 Remote Similarity NPC610636
0.5542 Remote Similarity NPC64141
0.5495 Remote Similarity NPC300894
0.5495 Remote Similarity NPC23845
0.5474 Remote Similarity NPC64195
0.5441 Remote Similarity NPC232880
0.5395 Remote Similarity NPC477294
0.5376 Remote Similarity NPC476375
0.5376 Remote Similarity NPC106818
0.5361 Remote Similarity NPC94871
0.5357 Remote Similarity NPC321638
0.5333 Remote Similarity NPC119537
0.5316 Remote Similarity NPC473285
0.5263 Remote Similarity NPC288416
0.5263 Remote Similarity NPC476380
0.5263 Remote Similarity NPC476381
0.5231 Remote Similarity NPC147192
0.5231 Remote Similarity NPC224208
0.5231 Remote Similarity NPC41661
0.5165 Remote Similarity NPC476397
0.5155 Remote Similarity NPC87403
0.5152 Remote Similarity NPC229505
0.5111 Remote Similarity NPC34587
0.5109 Remote Similarity NPC34927
0.5056 Remote Similarity NPC47471

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC886 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
0.6883 Remote Similarity NPD7266 Phase 2

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data