Natural Product: NPC110958

Natural Product IDNPC110958
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (-)-Hinokinin
IUPAC Name (3S,4S)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL180970
PubChem CID 11002708
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003424] 9,9'-epoxylignans
            • [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

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 DDWGQGZPYDSYEL-CABCVRRESA-N
Standard InCHI InChI=1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m1/s1
SMILES O=C1OC[C@H]([C@@H]1Cc1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   354.11 Volume:   345.98
?
Van der Waals volume.
Dense:   1.023 LogP:   2.316
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.386
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.256
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   26.0
TPSA:   63.22
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   0.0 Rings:   5.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.787 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.24 Fsp3:   0.35
MCE-18:   80.889
?
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:   0 PAINS Alert:   0
Colloidal aggregators:   0.267 Fluc inhibitor:   0.755
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.028
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.173
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.32 Promiscuous compounds:   0.158

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.882 MDCK Permeability:   -4.609
Pgp-inhibitor:   0.924 Pgp-substrate:   0.006
PAMPA:   0.119
?
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%):   0.216 30% Bioavailability (F30%):   0.001
50% Bioavailability (F50%):   0.512

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.442 MRP1:   0.462
Plasma Protein Binding (PPB):   97.937% Volume Distribution (VD):   -0.386
Fu: 2.003%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.989
OATP1B3 inhibitor:   0.942 BCRP inhibitor:   0.001
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.954 CYP1A2-substrate:   0.998
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.999
CYP2C9-inhibitor:   0.904 CYP2C9-substrate:   1.0
CYP2D6-inhibitor:   0.737 CYP2D6-substrate:   1.0
CYP3A4-inhibitor:   0.986 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.118 CYP2C8-inhibitor:   0.009
HLM stability:   0.941
?
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):  2.538 Half-life (T1/2):  1.068

ADMET: Toxicity

hERG Blockers:  0.342 hERG Blockers (10um):  0.592
Human Hepatotoxicity (H-HT):  0.954 Drug-induced Liver Injury (DILI):  0.995
AMES Toxicity:  0.813 Rat Oral Acute Toxicity:  0.632
Maximum Recommended Daily Dose:  0.73 Skin Sensitization:  0.959
Carcinogencity:  0.912 Eye Corrosion:  0.001
Eye Irritation:  0.83 Respiratory Toxicity:  0.446
Drug-induced Neurotoxicity:  0.943 Ototoxicity:  0.704
Hematotoxicity:  0.818 Drug-induced Nephrotoxicity:  0.958
Genotoxicity:  0.999 RPMI-8226 Immunitoxicity:  0.261
A549 Cytotoxicity:  0.461 Hek293 Cytotoxicity:  0.677
BCF:   1.756
?
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:   4.338
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.124
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.497
?
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
NPO22821 Chamaecyparis obtusa Species Cupressaceae Eukaryota n.a. heartwood n.a. DOI[10.1007/s10086-012-1280-8]
NPO24287 Dalbergia louvelii Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[14640516]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota Leaves and branches Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota leaves Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[15679319]
NPO22821 Chamaecyparis obtusa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[16540181]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota bark n.a. n.a. PMID[18549276]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. twig n.a. PMID[22474975]
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota twigs and leaves n.a. n.a. PMID[24953598]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[25559759]
NPO13468.1 Cryptomeria japonica var. sinensis Varieties Cupressaceae Eukaryota n.a. n.a. n.a. PMID[30485090]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31096694]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[31244143]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[31347365]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota Twigs n.a. n.a. PMID[32786878]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[9014350]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31384 Thuja orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21506 Artemisia xerophytica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24287 Dalbergia louvelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24027 Myxopyrum smilacifolium Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23308 Rhododendron adamsii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13009 Laurencia saitoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13314 Callitropsis funebris Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29982 Cupressus funebris Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22821 Chamaecyparis obtusa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28099 Epimedium cremeum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20173 Aristolochia triangularis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10765 Dracaena concinna Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1787 Agathis lanceolata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27987 Clavelina cylindrica Species Clavelinidae 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]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31384 Thuja orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20173 Aristolochia triangularis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29982 Cupressus funebris Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22821 Chamaecyparis obtusa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20173 Aristolochia triangularis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13468.1 Cryptomeria japonica var. sinensis Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13314 Callitropsis funebris Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22821 Chamaecyparis obtusa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31384 Thuja orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11169 Piper cubeba Species Piperaceae 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]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5082 Cycas revoluta Species Cycadaceae 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]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10765 Dracaena concinna Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21506 Artemisia xerophytica Species Asteraceae 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]
NPO13468.1 Cryptomeria japonica var. sinensis Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1787 Agathis lanceolata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23308 Rhododendron adamsii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13009 Laurencia saitoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28419 Tribolium confusum Species Tenebrionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20173 Aristolochia triangularis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13314 Callitropsis funebris Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28099 Epimedium cremeum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24027 Myxopyrum smilacifolium Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24287 Dalbergia louvelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27987 Clavelina cylindrica Species Clavelinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22821 Chamaecyparis obtusa Species Cupressaceae 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
NPT81 Cell line A549 Homo sapiens IC50 = 7860.0 nM PMID[26916436]
NPT111 Cell line K562 Homo sapiens IC50 = 9070.0 nM PMID[26916436]
NPT2245 Cell line SiHa Homo sapiens IC50 = 68400.0 nM PMID[26916436]
NPT91 Cell line KB Homo sapiens IC50 = 7680.0 nM PMID[26916436]
NPT139 Cell line HT-29 Homo sapiens IC50 = 35700.0 nM PMID[26916436]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 = 72580.0 nM PMID[26916436]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 59.2 % PMID[27955811]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 18.3 % PMID[27955811]
NPT2254 Organism Schistosoma mansoni Schistosoma mansoni Activity > 75.0 % PMID[33479649]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = 63.0 % PMID[15686907]





 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 NPC110958 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 NPC19890
0.9111 High Similarity NPC205915
0.8723 High Similarity NPC176586
0.8723 High Similarity NPC210354
0.8542 High Similarity NPC191158
0.8542 High Similarity NPC177644
0.7885 Intermediate Similarity NPC145569
0.7727 Intermediate Similarity NPC476748
0.7593 Intermediate Similarity NPC282291
0.7593 Intermediate Similarity NPC166137
0.7556 Intermediate Similarity NPC223807
0.7292 Intermediate Similarity NPC92693
0.7143 Intermediate Similarity NPC40237
0.6939 Remote Similarity NPC211386
0.6889 Remote Similarity NPC600801
0.68 Remote Similarity NPC143895
0.6667 Remote Similarity NPC3982
0.6383 Remote Similarity NPC72796
0.6271 Remote Similarity NPC216223
0.625 Remote Similarity NPC293757
0.625 Remote Similarity NPC668
0.6207 Remote Similarity NPC56184
0.6154 Remote Similarity NPC158737
0.6078 Remote Similarity NPC192255
0.6078 Remote Similarity NPC474288
0.6071 Remote Similarity NPC5310
0.6071 Remote Similarity NPC300776
0.6071 Remote Similarity NPC176814
0.6071 Remote Similarity NPC4982
0.6071 Remote Similarity NPC606629
0.5962 Remote Similarity NPC171550
0.5962 Remote Similarity NPC134764
0.5778 Remote Similarity NPC80241
0.5778 Remote Similarity NPC301641
0.5778 Remote Similarity NPC485483
0.5738 Remote Similarity NPC174512
0.5686 Remote Similarity NPC11453
0.5667 Remote Similarity NPC487679
0.5667 Remote Similarity NPC487678
0.5614 Remote Similarity NPC230968
0.5614 Remote Similarity NPC102260
0.5556 Remote Similarity NPC68779
0.5556 Remote Similarity NPC108598
0.5517 Remote Similarity NPC218092
0.5517 Remote Similarity NPC106920
0.5517 Remote Similarity NPC15811
0.5517 Remote Similarity NPC246474
0.5517 Remote Similarity NPC162851
0.5439 Remote Similarity NPC18576
0.5417 Remote Similarity NPC40352
0.5417 Remote Similarity NPC213711
0.5345 Remote Similarity NPC47181
0.5345 Remote Similarity NPC185908
0.5345 Remote Similarity NPC482891
0.5312 Remote Similarity NPC478705
0.5306 Remote Similarity NPC344161
0.5231 Remote Similarity NPC478703
0.5231 Remote Similarity NPC478704
0.5172 Remote Similarity NPC273657
0.5161 Remote Similarity NPC482889
0.5075 Remote Similarity NPC158635
0.5075 Remote Similarity NPC229882

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC110958 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