Natural Product: NPC283746

Natural Product IDNPC283746
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 OVKDFILSBMEKLT-JTQLQIEISA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 16059268
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001401] Menthane monoterpenoids

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 OVKDFILSBMEKLT-JTQLQIEISA-N
Standard InCHI InChI=1S/C10H16O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,11H,1,5-7H2,2-3H3/t10-/m0/s1
SMILES C=C(C)[C@@]1(CC=C(C)CC1)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   152.12 Volume:   176.477
?
Van der Waals volume.
Dense:   0.862 LogP:   1.995
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.917
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.052
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   7.0
TPSA:   20.23
?
Topological Polar Surface Area.
 H-Bond Acceptor:   1.0
H-Bond Donor:   1.0 Rings:   1.0
Heavy Atoms:   1.0

MedChem Properties

QED Drug-Likeness Score:   0.572 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.776 Fsp3:   0.6
MCE-18:   20.0
?
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:   Rejected
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.042 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.003
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.037
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.998 Promiscuous compounds:   0.261

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.279 MDCK Permeability:   -4.513
Pgp-inhibitor:   0.072 Pgp-substrate:   0.643
PAMPA:   0.719
?
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):   0.015
20% Bioavailability (F20%):   0.269 30% Bioavailability (F30%):   0.256
50% Bioavailability (F50%):   0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.752 MRP1:   0.877
Plasma Protein Binding (PPB):   86.585% Volume Distribution (VD):   0.428
Fu: 17.1%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.903
OATP1B3 inhibitor:   0.793 BCRP inhibitor:   0.475
BSEP inhibitor:   0.447

ADMET: Metabolism

CYP1A2-inhibitor:   0.364 CYP1A2-substrate:   0.452
CYP2C19-inhibitor:   0.332 CYP2C19-substrate:   0.017
CYP2C9-inhibitor:   0.448 CYP2C9-substrate:   0.009
CYP2D6-inhibitor:   0.547 CYP2D6-substrate:   0.026
CYP3A4-inhibitor:   0.049 CYP3A4-substrate:   0.148
CYP2B6-substrate:   0.02 CYP2C8-inhibitor:   0.604
HLM stability:   0.88
?
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):  12.803 Half-life (T1/2):  1.882

ADMET: Toxicity

hERG Blockers:  0.035 hERG Blockers (10um):  0.247
Human Hepatotoxicity (H-HT):  0.639 Drug-induced Liver Injury (DILI):  0.241
AMES Toxicity:  0.398 Rat Oral Acute Toxicity:  0.34
Maximum Recommended Daily Dose:  0.303 Skin Sensitization:  0.932
Carcinogencity:  0.816 Eye Corrosion:  0.849
Eye Irritation:  0.991 Respiratory Toxicity:  0.483
Drug-induced Neurotoxicity:  0.559 Ototoxicity:  0.187
Hematotoxicity:  0.256 Drug-induced Nephrotoxicity:  0.231
Genotoxicity:  0.214 RPMI-8226 Immunitoxicity:  0.062
A549 Cytotoxicity:  0.24 Hek293 Cytotoxicity:  0.123
BCF:   1.412
?
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:   3.214
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.742
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.344
?
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
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[ 3619437]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/btpr.97]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11738-010-0631-6]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.plaphy.2018.10.015]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/17429145.2017.1293852]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1186/1750-2187-3-9]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO15432 Sarcodon aspratus Species Thelephoraceae Eukaryota n.a. n.a. n.a. PMID[15665489]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. whole plant n.a. PMID[16079548]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. Indonesian n.a. PMID[17311456]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO5489 Cinnamomum tenuifolium Species Lauraceae Eukaryota stems n.a. n.a. PMID[19754130]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota roots and rhizomes n.a. n.a. PMID[21570846]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. leaf n.a. PMID[24024688]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[25522543]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[28841316]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[32260539]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[38194794]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[38195615]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[38681233]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[38731845]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[39553766]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[39723058]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[7798960]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3200 Arthrophytum leptocladum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO4311 Asterolasia squamuligera Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14661 Blepharis sindica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8834 Cellulomonas biazotea Species Cellulomonadaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO5489 Cinnamomum tenuifolium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14035 Cladosporium tenuissimum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6239 Corbicula fluminea Species Corbiculidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14156 Fragaria indica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13289 Frullania brittoniae Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9919 Jaspis stellifera Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11880 Latua pubiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO238 Lobelia st Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9765 Petriella guttulata Species Microascaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15150 Phebalium gracile Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7263 Phyllobates aurotaenia Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27957.1 Pinus densiflora var. densiflora Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17324 Pluchea dioscoridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO890 Remijia pedunculata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12622 Rudbeckia hirta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15240 Saracha viscosa Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15432 Sarcodon aspratus Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15616 Solanum toxicarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14271 Spongia australis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11098 Stelletta inconspicua Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11107 Stevia alpina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29494 Stoeba extensa n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO7003 Streptomyces violaceochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO10402 Strophanthus eminii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9283 Trichia favoginea Species Trichiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15150 Phebalium gracile Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14035 Cladosporium tenuissimum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14156 Fragaria indica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5517 Rhododendron tomentosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9765 Petriella guttulata Species Microascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4311 Asterolasia squamuligera Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15616 Solanum toxicarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11107 Stevia alpina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7263 Phyllobates aurotaenia Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5489 Cinnamomum tenuifolium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8834 Cellulomonas biazotea Species Cellulomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11880 Latua pubiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15240 Saracha viscosa Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29494 Stoeba extensa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3200 Arthrophytum leptocladum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3860 Allium victorialis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6239 Corbicula fluminea Species Corbiculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14271 Spongia australis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11098 Stelletta inconspicua Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7003 Streptomyces violaceochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27957.1 Pinus densiflora var. densiflora Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10402 Strophanthus eminii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9919 Jaspis stellifera Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14661 Blepharis sindica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9283 Trichia favoginea Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15432 Sarcodon aspratus Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO890 Remijia pedunculata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO238 Lobelia st Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4485 Lamellodysidea herbacea Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17324 Pluchea dioscoridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12622 Rudbeckia hirta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13289 Frullania brittoniae Species Frullaniaceae 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 NPC283746 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 NPC71506
0.6 Remote Similarity NPC177112

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC283746 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