Natural Product: NPC45536

Natural Product IDNPC45536
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Perillaketone
IUPAC Name 1-(furan-3-yl)-4-methylpentan-1-one
Synonyms Perillaketone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL469753
PubChem CID 68381
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:0003671] Aryl alkyl ketones

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 LVHLZMUFIYAEQB-UHFFFAOYSA-N
Standard InCHI InChI=1S/C10H14O2/c1-8(2)3-4-10(11)9-5-6-12-7-9/h5-8H,3-4H2,1-2H3
SMILES CC(CCC(=O)c1cocc1)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   166.1 Volume:   182.631
?
Van der Waals volume.
Dense:   0.909 LogP:   2.696
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.574
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.36
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   6.0
TPSA:   30.21
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   1.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.644 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.327 Fsp3:   0.5
MCE-18:   6.0
?
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:   0.074 Fluc inhibitor:   0.147
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.006
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.014
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.973 Promiscuous compounds:   0.259

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.792 MDCK Permeability:   -4.556
Pgp-inhibitor:   0.607 Pgp-substrate:   0.102
PAMPA:   0.14
?
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):   0.009
20% Bioavailability (F20%):   0.062 30% Bioavailability (F30%):   0.124
50% Bioavailability (F50%):   0.491

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.708 MRP1:   0.734
Plasma Protein Binding (PPB):   66.182% Volume Distribution (VD):   -0.022
Fu: 31.265%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.157
OATP1B3 inhibitor:   0.222 BCRP inhibitor:   0.458
BSEP inhibitor:   0.506

ADMET: Metabolism

CYP1A2-inhibitor:   0.731 CYP1A2-substrate:   0.998
CYP2C19-inhibitor:   0.997 CYP2C19-substrate:   0.981
CYP2C9-inhibitor:   0.966 CYP2C9-substrate:   0.678
CYP2D6-inhibitor:   0.247 CYP2D6-substrate:   0.52
CYP3A4-inhibitor:   0.001 CYP3A4-substrate:   0.945
CYP2B6-substrate:   0.392 CYP2C8-inhibitor:   0.993
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):  9.463 Half-life (T1/2):  0.746

ADMET: Toxicity

hERG Blockers:  0.17 hERG Blockers (10um):  0.566
Human Hepatotoxicity (H-HT):  0.239 Drug-induced Liver Injury (DILI):  0.353
AMES Toxicity:  0.322 Rat Oral Acute Toxicity:  0.549
Maximum Recommended Daily Dose:  0.505 Skin Sensitization:  0.236
Carcinogencity:  0.602 Eye Corrosion:  0.614
Eye Irritation:  0.992 Respiratory Toxicity:  0.912
Drug-induced Neurotoxicity:  0.423 Ototoxicity:  0.111
Hematotoxicity:  0.253 Drug-induced Nephrotoxicity:  0.163
Genotoxicity:  0.214 RPMI-8226 Immunitoxicity:  0.041
A549 Cytotoxicity:  0.075 Hek293 Cytotoxicity:  0.15
BCF:   1.04
?
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:   3.276
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.534
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.121
?
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
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10757731]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. stem n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota fruits n.a. n.a. PMID[16038540]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. PMID[1612412]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. leaf n.a. PMID[18566831]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota roots n.a. n.a. PMID[19128156]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota exudate n.a. n.a. PMID[20028108]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20674349]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21428274]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21428274]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[22272932]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25320841]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. fruit n.a. PMID[26169681]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[32872604]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[36352904]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39679248]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[39680258]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13467 Anarsia lineatella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14057 Apollonias barbujana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10550 Artemisia hanseniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13766 Ceanothus velutinus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12509 Dipterocarpus dyeri Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO205 Lasianthus fordii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11998 Ledebouria socialis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO746 Panax innovans Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5191 Penicillium cinerascens Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4671 Persea mexicana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8892 Sordaria araneosa Species Sordariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650.3 Perilla frutescens (l.) britt. var. crispa (thunb.) hand.-mazz. Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5191 Penicillium cinerascens Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4671 Persea mexicana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8892 Sordaria araneosa Species Sordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13766 Ceanothus velutinus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14057 Apollonias barbujana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11998 Ledebouria socialis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO746 Panax innovans Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10550 Artemisia hanseniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13467 Anarsia lineatella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12509 Dipterocarpus dyeri Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO205 Lasianthus fordii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29463 Pogostemon cablin Species Lamiaceae 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
NPT1534 Individual protein Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus Efficacy = 181.2 % PMID[19162486]
NPT1534 Individual protein Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus EC50 = 40738.03 nM PMID[19162486]
NPT1534 Individual protein Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus EC50 = 19700.0 nM PMID[19162486]
NPT1841 Individual protein Transient receptor potential cation channel subfamily M member 8 Rattus norvegicus Inhibition = 39.3 % PMID[19162486]
NPT346 Individual protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 19700.0 nM PMID[20356305]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell line SN12C Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT367 Cell line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT370 Cell line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT369 Cell line ACHN Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT371 Cell line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT372 Cell line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT116 Cell line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT374 Cell line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT90 Cell line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT373 Cell line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT375 Cell line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT111 Cell line K562 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT377 Cell line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT112 Cell line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT379 Cell line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT378 Cell line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT380 Cell line U-251 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT382 Cell line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT381 Cell line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT82 Cell line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT383 Cell line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT384 Cell line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT385 Cell line SR Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT323 Cell line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT386 Cell line KM12 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT387 Cell line M14 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT389 Cell line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT456 Cell line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT390 Cell line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT147 Cell line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT81 Cell line A549 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT392 Cell line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT391 Cell line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT148 Cell line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT393 Cell line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT395 Cell line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT83 Cell line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT394 Cell line EKVX Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT306 Cell line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT146 Cell line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT396 Cell line T47D Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT397 Cell line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT398 Cell line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT308 Cell line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT400 Cell line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT399 Cell line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT458 Cell line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT402 Cell line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT403 Cell line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT401 Cell line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT404 Cell line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT405 Cell line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT139 Cell line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT170 Cell line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT406 Cell line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT407 Cell line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set

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
- Mus musculus LD50 = 4.822743269 mg/kg TOXRIC

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 NPC45536 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
0.6571 Remote Similarity NPC79557
0.619 Remote Similarity NPC608686
0.5135 Remote Similarity NPC140688

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC45536 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