Natural Product: NPC65741

Natural Product IDNPC65741
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 NQYBQBZOHCACCR-UHFFFAOYSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 6450808
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003670] Aryl ketones
              • [CHEMONTID:0004296] Phenylketones
                • [CHEMONTID:0004298] Alkyl-phenylketones

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 NQYBQBZOHCACCR-UHFFFAOYSA-N
Standard InCHI InChI=1S/C21H30O4/c1-12(2)7-9-15-19(23)16(10-8-13(3)4)21(25)18(20(15)24)17(22)11-14(5)6/h7-8,14,23-25H,9-11H2,1-6H3
SMILES CC(=CCc1c(c(CC=C(C)C)c(c(C(=O)CC(C)C)c1O)O)O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   346.21 Volume:   382.558
?
Van der Waals volume.
Dense:   0.905 LogP:   4.681
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.603
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.248
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   7.0 Rigid Bonds:   9.0
TPSA:   77.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   3.0 Rings:   1.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.477 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.019 Fsp3:   0.476
MCE-18:   13.0
?
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:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.836 Fluc inhibitor:   0.222
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.518
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.129
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.707 Promiscuous compounds:   0.116

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.013 MDCK Permeability:   -4.706
Pgp-inhibitor:   0.992 Pgp-substrate:   0.001
PAMPA:   0.046
?
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):   0.409
20% Bioavailability (F20%):   0.929 30% Bioavailability (F30%):   0.99
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.005 MRP1:   0.924
Plasma Protein Binding (PPB):   91.08% Volume Distribution (VD):   0.363
Fu: 9.419%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   0.998 BCRP inhibitor:   0.329
BSEP inhibitor:   0.995

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   0.003 CYP2C9-substrate:   0.179
CYP2D6-inhibitor:   0.081 CYP2D6-substrate:   0.204
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.919
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   1.0
?
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):  5.93 Half-life (T1/2):  0.658

ADMET: Toxicity

hERG Blockers:  0.044 hERG Blockers (10um):  0.536
Human Hepatotoxicity (H-HT):  0.515 Drug-induced Liver Injury (DILI):  0.259
AMES Toxicity:  0.496 Rat Oral Acute Toxicity:  0.828
Maximum Recommended Daily Dose:  0.319 Skin Sensitization:  0.947
Carcinogencity:  0.312 Eye Corrosion:  0.001
Eye Irritation:  0.598 Respiratory Toxicity:  0.946
Drug-induced Neurotoxicity:  0.528 Ototoxicity:  0.59
Hematotoxicity:  0.402 Drug-induced Nephrotoxicity:  0.816
Genotoxicity:  0.546 RPMI-8226 Immunitoxicity:  0.062
A549 Cytotoxicity:  0.395 Hek293 Cytotoxicity:  0.31
BCF:   2.079
?
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:   4.856
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.411
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.911
?
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
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1007/s11746-010-1670-2]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.foodcont.2016.09.002]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.jfca.2010.08.006]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.06.003]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.12.007]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2016.02.010]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2018.06.017]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.12691/jfnr-2-5-9]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[15217296]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[16499319]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. Mongolian n.a. PMID[17542634]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast 2003-JUN PMID[18298079]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[18942825]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[19628108]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[20405844]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[22538527]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[24811150]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[28274428]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30236698]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[30384263]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds Guangzhou, China PMID[30563201]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30583361]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30599958]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31159190]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31861466]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36613240]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[37631012]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[38354824]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[39199155]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13030 Artemisia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21830 Buddleja cordata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12196 Buphane fischeri n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO5930 Crambe tatarica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12700 Diospyros eriantha Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO252 Hoffmannia strigillosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11848 Lemaireocereus griseus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9934 Mycobacterium leprae Species Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13671 Ononis vaginalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14578 Prorocentrum micans Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8928 Pteris semipinnata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13585 Rapanea lancifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10783 Syncarpia hillii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6360 Xenoacremonium recifei Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8928 Pteris semipinnata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9934 Mycobacterium leprae Species Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10783 Syncarpia hillii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13585 Rapanea lancifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13030 Artemisia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21830 Buddleja cordata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12700 Diospyros eriantha Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6360 Xenoacremonium recifei Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11848 Lemaireocereus griseus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO252 Hoffmannia strigillosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14578 Prorocentrum micans Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5930 Crambe tatarica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12196 Buphane fischeri n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13671 Ononis vaginalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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



  NP Quantity Composition/Concentration

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

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



 Biological Activity

Molecular-level activity

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

In vitro activity

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

In vivo activity

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





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC65741 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
0.6 Remote Similarity NPC285054
0.5676 Remote Similarity NPC218333
0.55 Remote Similarity NPC215392
0.5122 Remote Similarity NPC306288

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC65741 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