Natural Product: NPC155025

Natural Product IDNPC155025
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 QNMWLBQJIVQIBA-WNZMXVTFSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL464163
PubChem CID NA
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002456] Germacrane sesquiterpenoids

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 QNMWLBQJIVQIBA-WNZMXVTFSA-N
Standard InCHI InChI=1S/C15H26O2/c1-10(2)14-6-5-11(3)7-13(16)8-12(4)9-15(14)17/h7,9-10,13-17H,5-6,8H2,1-4H3/b11-7+,12-9+/t13-,14-,15-/m0/s1
SMILES C/C/1=C[C@H](O)C/C(=C/[C@@H]([C@@H](CC1)C(C)C)O)/C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   238.19 Volume:   271.747
?
Van der Waals volume.
Dense:   0.877 LogP:   2.211
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.422
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.492
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   10.0
TPSA:   40.46
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   2.0 Rings:   1.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.689 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.425 Fsp3:   0.733
MCE-18:   22.154
?
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:   0.631 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.012
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.0
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.844 Promiscuous compounds:   0.27

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.304 MDCK Permeability:   -5.125
Pgp-inhibitor:   0.526 Pgp-substrate:   0.103
PAMPA:   0.606
?
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):   0.706
20% Bioavailability (F20%):   0.838 30% Bioavailability (F30%):   0.895
50% Bioavailability (F50%):   0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.02 MRP1:   0.454
Plasma Protein Binding (PPB):   76.072% Volume Distribution (VD):   -0.168
Fu: 17.527%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.998
OATP1B3 inhibitor:   0.985 BCRP inhibitor:   0.052
BSEP inhibitor:   0.104

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.006
CYP2C19-inhibitor:   0.12 CYP2C19-substrate:   0.002
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.002
CYP2D6-inhibitor:   0.002 CYP2D6-substrate:   0.069
CYP3A4-inhibitor:   0.909 CYP3A4-substrate:   0.891
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.06
HLM stability:   0.861
?
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):  12.073 Half-life (T1/2):  1.466

ADMET: Toxicity

hERG Blockers:  0.055 hERG Blockers (10um):  0.274
Human Hepatotoxicity (H-HT):  0.498 Drug-induced Liver Injury (DILI):  0.585
AMES Toxicity:  0.503 Rat Oral Acute Toxicity:  0.3
Maximum Recommended Daily Dose:  0.23 Skin Sensitization:  0.983
Carcinogencity:  0.471 Eye Corrosion:  0.858
Eye Irritation:  0.985 Respiratory Toxicity:  0.669
Drug-induced Neurotoxicity:  0.719 Ototoxicity:  0.319
Hematotoxicity:  0.403 Drug-induced Nephrotoxicity:  0.727
Genotoxicity:  0.096 RPMI-8226 Immunitoxicity:  0.097
A549 Cytotoxicity:  0.456 Hek293 Cytotoxicity:  0.327
BCF:   1.543
?
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:   3.326
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.626
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.079
?
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
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/cbdv.200690067]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. DOI[10.1021/ja00388a092]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. PMID[11325216]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. PMID[11809069]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. PMID[12932129]
NPO29822 Santolina insularis Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[15974607]
NPO29822 Santolina insularis Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[15974607]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[16933863]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota roots n.a. n.a. PMID[17253841]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[18640035]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[19193043]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota whole plant n.a. n.a. PMID[19422205]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. South China Sea n.a. PMID[25932671]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. Gulf of Aomori, Japan n.a. PMID[8691208]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. leaf n.a. PMID[8699184]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. PMID[8882431]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO752 Oligonychus bessardi Species Tetranychidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16789 Erythrina sandwicensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16878 Roldana barba-johannis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17447 Agathosma betulina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12087 Amaioua guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8782 Arnica sachalinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16466 Baccharis santelicis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3742 Betula maximowicziana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16713 Choisya arizonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13773 Eriogonum nudum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15194 Euphorbia balsamifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6899 Hepialus hecta Species Hepialidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22394 Hyacinthoides hispanica Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5824 Hygrophila polysperma Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11413 Incarvillea emodi Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13410 Mcneillia graminifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15341 Mucuna sloanei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1354 Myelochroa rhytidodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13130 Notholaena peninsularis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16313 Ochrocarpos odoratus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13296 Pinus sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27425 Pseudotaxus chienii Species Taxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9425 Punctelia microsticta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21773 Rothmannia urcelliformis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29822 Santolina insularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14625 Santolina rosmarinifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15691 Senecio coahuilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15452 Senecio othonniformis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16223 Serratula xeranthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8298 Sphaeria biglobosa n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO1780 Sphaeria doliolum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16553 Theonella cupola Species Theonellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29072 Tritomaria quinquedentata Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27420 Venidium hirsutum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26942 Vicoa vestita n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14625 Santolina rosmarinifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16466 Baccharis santelicis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11413 Incarvillea emodi Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13296 Pinus sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12087 Amaioua guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5824 Hygrophila polysperma Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15691 Senecio coahuilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16878 Roldana barba-johannis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13130 Notholaena peninsularis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16789 Erythrina sandwicensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO752 Oligonychus bessardi Species Tetranychidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21773 Rothmannia urcelliformis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8298 Sphaeria biglobosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29072 Tritomaria quinquedentata Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27420 Venidium hirsutum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16223 Serratula xeranthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15341 Mucuna sloanei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22394 Hyacinthoides hispanica Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1780 Sphaeria doliolum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6899 Hepialus hecta Species Hepialidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15194 Euphorbia balsamifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1354 Myelochroa rhytidodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9425 Punctelia microsticta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17447 Agathosma betulina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3742 Betula maximowicziana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26942 Vicoa vestita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27425 Pseudotaxus chienii Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13410 Mcneillia graminifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16553 Theonella cupola Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16713 Choisya arizonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8782 Arnica sachalinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16313 Ochrocarpos odoratus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13773 Eriogonum nudum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15452 Senecio othonniformis 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
NPT27 Others Unspecified n.a. IC50 >= 10.0 ug.mL-1 PMID[15974607]

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 NPC155025 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
0.7879 Intermediate Similarity NPC99487
0.6286 Remote Similarity NPC473508
0.5946 Remote Similarity NPC311736
0.55 Remote Similarity NPC207811

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC155025 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