Natural Product: NPC299706

Natural Product IDNPC299706
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Matairesinoside
IUPAC Name (3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
Synonyms Matairesinoside
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL459834
PubChem CID 486612
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan glycosides

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 AAGCATAPYOEULE-LHHMAMHXSA-N
Standard InCHI InChI=1S/C26H32O11/c1-33-19-9-13(3-5-17(19)28)7-15-12-35-25(32)16(15)8-14-4-6-18(20(10-14)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21+,22+,23-,24+,26+/m0/s1
SMILES OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C[C@H]2C(=O)OC[C@@H]2Cc2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   520.19 Volume:   502.264
?
Van der Waals volume.
Dense:   1.036 LogP:   -0.163
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   0.493
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.28
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   9.0 Rigid Bonds:   24.0
TPSA:   164.37
?
Topological Polar Surface Area.
 H-Bond Acceptor:   11.0
H-Bond Donor:   5.0 Rings:   4.0
Heavy Atoms:   11.0

MedChem Properties

QED Drug-Likeness Score:   0.286 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.166 Fsp3:   0.5
MCE-18:   88.667
?
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:   Accepted BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.592 Fluc inhibitor:   0.052
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.042
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.354
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.085 Promiscuous compounds:   0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.99 MDCK Permeability:   -5.109
Pgp-inhibitor:   0.005 Pgp-substrate:   0.275
PAMPA:   0.382
?
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):   0.317
20% Bioavailability (F20%):   0.729 30% Bioavailability (F30%):   0.996
50% Bioavailability (F50%):   0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.168
Plasma Protein Binding (PPB):   75.311% Volume Distribution (VD):   -0.393
Fu: 22.5%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.016
BSEP inhibitor:   0.324

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.606
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.056
CYP3A4-inhibitor:   0.865 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.648
?
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):  3.004 Half-life (T1/2):  3.645

ADMET: Toxicity

hERG Blockers:  0.065 hERG Blockers (10um):  0.198
Human Hepatotoxicity (H-HT):  0.966 Drug-induced Liver Injury (DILI):  0.996
AMES Toxicity:  0.938 Rat Oral Acute Toxicity:  0.084
Maximum Recommended Daily Dose:  0.099 Skin Sensitization:  1.0
Carcinogencity:  0.34 Eye Corrosion:  0.0
Eye Irritation:  0.119 Respiratory Toxicity:  0.027
Drug-induced Neurotoxicity:  0.22 Ototoxicity:  0.984
Hematotoxicity:  0.755 Drug-induced Nephrotoxicity:  0.985
Genotoxicity:  0.995 RPMI-8226 Immunitoxicity:  0.314
A549 Cytotoxicity:  0.694 Hek293 Cytotoxicity:  0.551
BCF:   0.725
?
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:   3.425
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.008
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.216
?
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
NPO30753 Symplocos setchuensis Species Symplocaceae Eukaryota stems n.a. n.a. PMID[11473435]
NPO30753 Symplocos setchuensis Species Symplocaceae Eukaryota n.a. stem n.a. PMID[11473435]
NPO1766 Hymenaea courbaril Species Fabaceae Eukaryota n.a. Suriname rain forest n.a. PMID[11809056]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[12880322]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. flower n.a. PMID[15481244]
NPO30866 Styrax japonica Species Styracaceae Eukaryota n.a. bark n.a. PMID[15577246]
NPO30866 Styrax japonica Species Styracaceae Eukaryota stem bark n.a. n.a. PMID[15620237]
NPO31354 Cupressus duclouxiana Species Cupressaceae Eukaryota n.a. branch n.a. PMID[16753802]
NPO31354 Cupressus duclouxiana Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[16753802]
NPO20266 Plectocephalus americanus Species Asteraceae Eukaryota n.a. seed n.a. PMID[16996096]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[17156960]
NPO2689 Symplocos caudata Species Symplocaceae Eukaryota n.a. root n.a. PMID[17905350]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18057725]
NPO6779 Sutherlandia frutescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18808182]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota stem bark Kunming, Yunnan Province, China n.a. PMID[18986199]
NPO13275 Centaurea scabiosa Species Asteraceae Eukaryota n.a. fruit n.a. PMID[22396124]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. fruit n.a. PMID[22396124]
NPO9064 Cirsium arvense Species Asteraceae Eukaryota n.a. fruit n.a. PMID[22396124]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO5985 Klebsiella pneumoniae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24572278]
NPO7267 Glycosmis chlorosperma Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24798019]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26422318]
NPO6381 Dendrobium crepidatum Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[26710212]
NPO16601 Styrax perkinsiae Species Styracaceae Eukaryota n.a. bark n.a. PMID[26762060]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota Fruits n.a. n.a. PMID[28218000]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota Roots n.a. n.a. PMID[30676026]
NPO13275 Centaurea scabiosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[36501307]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[36903911]
NPO8340 Stachys sylvatica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38769997]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5039 Cryptomonas ovata Species Cryptomonadaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7267 Glycosmis chlorosperma Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8175 Acacia kempeana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9064 Cirsium arvense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5235 Laburnum watereri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30866 Styrax japonica Species Styracaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO850 Metatrichia vesparium Species Trichiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8340 Stachys sylvatica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2366 Diospyros buxifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7812 Alhagi persarum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1766 Hymenaea courbaril Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13275 Centaurea scabiosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2689 Symplocos caudata Species Symplocaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6979 Baillonella toxisperma Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31354 Cupressus duclouxiana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19459 Dictyota kunthii Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5985 Klebsiella pneumoniae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO20266 Plectocephalus americanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10449 Arctium lappa Species Asteraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10449 Arctium lappa Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO10449 Arctium lappa Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO10449 Arctium lappa Species Asteraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2689 Symplocos caudata Species Symplocaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30866 Styrax japonica Species Styracaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4271 Dendrobium thyrsiflorum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8340 Stachys sylvatica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7267 Glycosmis chlorosperma Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4271 Dendrobium thyrsiflorum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2689 Symplocos caudata Species Symplocaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4271 Dendrobium thyrsiflorum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7812 Alhagi persarum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12235 Trachelospermum jasminoides Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8175 Acacia kempeana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2525 Castanopsis cuspidata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10398 Myrica gale Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8476 Teucrium lanigerum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19459 Dictyota kunthii Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6381 Dendrobium crepidatum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5039 Cryptomonas ovata Species Cryptomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4271 Dendrobium thyrsiflorum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5235 Laburnum watereri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6979 Baillonella toxisperma Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4644 Pteris pacifica Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4096 Acanthias vulgaris n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3672 Montanoa guatemalensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1766 Hymenaea courbaril Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO720 Badilloa salicina n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6779 Sutherlandia frutescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2011 Decaisnea fargesii Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9064 Cirsium arvense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8312 Polygonatum stenophyllum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5985 Klebsiella pneumoniae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2366 Diospyros buxifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14834 Trachelospermum asiaticum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO850 Metatrichia vesparium Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2218 Aframomum sulcatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10449 Arctium lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6760 Saussurea conica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO683 Rosa canina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8340 Stachys sylvatica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16601 Styrax perkinsiae Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3944 Senecio variabilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7601 Centaurea cana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22995 Oophaga histrionica Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26373.1 Microbispora rosea subsp. aerata Subspecies Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7267 Glycosmis chlorosperma Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13275 Centaurea scabiosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20266 Plectocephalus americanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

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

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT759 Cell line H9 Homo sapiens IC50 > 192000.0 nM PMID[11473435]
NPT113 Cell line RAW264.7 Mus musculus IC50 > 300000.0 nM PMID[18986199]
NPT71 Cell line HEK293 Homo sapiens Inhibition = 9.3 % PMID[24018191]

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 NPC299706 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
1.0 High Similarity NPC115466
1.0 High Similarity NPC61604
0.863 High Similarity NPC245615
0.8551 High Similarity NPC158635
0.8551 High Similarity NPC229882
0.7821 Intermediate Similarity NPC486549
0.7821 Intermediate Similarity NPC486548
0.7722 Intermediate Similarity NPC486546
0.725 Intermediate Similarity NPC163635
0.6957 Remote Similarity NPC300776
0.6957 Remote Similarity NPC176814
0.6957 Remote Similarity NPC4982
0.6957 Remote Similarity NPC606629
0.6951 Remote Similarity NPC486547
0.6829 Remote Similarity NPC185307
0.6829 Remote Similarity NPC470950
0.6353 Remote Similarity NPC283995
0.6351 Remote Similarity NPC278961
0.6351 Remote Similarity NPC113680
0.6324 Remote Similarity NPC68779
0.6324 Remote Similarity NPC108598
0.6267 Remote Similarity NPC282291
0.6267 Remote Similarity NPC166137
0.625 Remote Similarity NPC106920
0.625 Remote Similarity NPC15811
0.619 Remote Similarity NPC486545
0.619 Remote Similarity NPC39657
0.6154 Remote Similarity NPC478703
0.6154 Remote Similarity NPC478704
0.5977 Remote Similarity NPC129417
0.5977 Remote Similarity NPC470235
0.5976 Remote Similarity NPC471063
0.5972 Remote Similarity NPC273657
0.5854 Remote Similarity NPC38041
0.5854 Remote Similarity NPC22150
0.5769 Remote Similarity NPC216223
0.5753 Remote Similarity NPC472024
0.5753 Remote Similarity NPC270849
0.5682 Remote Similarity NPC46092
0.5682 Remote Similarity NPC478055
0.5676 Remote Similarity NPC26653
0.5676 Remote Similarity NPC80600
0.56 Remote Similarity NPC5310
0.5529 Remote Similarity NPC38699
0.5476 Remote Similarity NPC18979
0.5467 Remote Similarity NPC210015
0.5362 Remote Similarity NPC223807
0.5294 Remote Similarity NPC227902
0.5294 Remote Similarity NPC279298
0.5294 Remote Similarity NPC147596
0.5275 Remote Similarity NPC112861
0.527 Remote Similarity NPC9912
0.519 Remote Similarity NPC145569
0.5176 Remote Similarity NPC61594
0.5176 Remote Similarity NPC286235
0.5135 Remote Similarity NPC166040
0.5128 Remote Similarity NPC100675
0.5128 Remote Similarity NPC601691
0.5125 Remote Similarity NPC276753
0.5125 Remote Similarity NPC205796
0.5125 Remote Similarity NPC469661
0.5116 Remote Similarity NPC56735
0.5068 Remote Similarity NPC211386
0.5063 Remote Similarity NPC302378
0.5062 Remote Similarity NPC246947
0.5062 Remote Similarity NPC604095
0.506 Remote Similarity NPC478705
0.5056 Remote Similarity NPC44452

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC299706 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