Natural Product: NPC233238

Natural Product IDNPC233238
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Dihydrocoumarin
IUPAC Name 3,4-dihydrochromen-2-one
Synonyms Chroman-2-One; Dihydrocoumarin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL89306
PubChem CID 660
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002642] 3,4-dihydrocoumarins

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 VMUXSMXIQBNMGZ-UHFFFAOYSA-N
Standard InCHI InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2
SMILES O=C1CCc2c(O1)cccc2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   148.05 Volume:   154.142
?
Van der Waals volume.
Dense:   0.96 LogP:   1.356
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.24
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.853
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   12.0
TPSA:   26.3
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   2.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.412 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.091 Fsp3:   0.222
MCE-18:   21.273
?
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:   0.055 Fluc inhibitor:   0.185
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.148
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.109
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.966 Promiscuous compounds:   0.496

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.291 MDCK Permeability:   -4.526
Pgp-inhibitor:   0.717 Pgp-substrate:   0.001
PAMPA:   0.134
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.0
20% Bioavailability (F20%):   0.001 30% Bioavailability (F30%):   0.0
50% Bioavailability (F50%):   0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.942 MRP1:   0.468
Plasma Protein Binding (PPB):   89.461% Volume Distribution (VD):   -0.215
Fu: 11.484%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.385
OATP1B3 inhibitor:   0.218 BCRP inhibitor:   0.001
BSEP inhibitor:   0.99

ADMET: Metabolism

CYP1A2-inhibitor:   0.304 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.024 CYP2C19-substrate:   0.987
CYP2C9-inhibitor:   0.464 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.025 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.193 CYP3A4-substrate:   0.003
CYP2B6-substrate:   0.086 CYP2C8-inhibitor:   0.524
HLM stability:   0.999
?
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):  8.265 Half-life (T1/2):  1.128

ADMET: Toxicity

hERG Blockers:  0.087 hERG Blockers (10um):  0.448
Human Hepatotoxicity (H-HT):  0.507 Drug-induced Liver Injury (DILI):  0.425
AMES Toxicity:  0.518 Rat Oral Acute Toxicity:  0.356
Maximum Recommended Daily Dose:  0.245 Skin Sensitization:  0.757
Carcinogencity:  0.723 Eye Corrosion:  0.873
Eye Irritation:  0.987 Respiratory Toxicity:  0.449
Drug-induced Neurotoxicity:  0.713 Ototoxicity:  0.19
Hematotoxicity:  0.402 Drug-induced Nephrotoxicity:  0.291
Genotoxicity:  0.311 RPMI-8226 Immunitoxicity:  0.042
A549 Cytotoxicity:  0.1 Hek293 Cytotoxicity:  0.147
BCF:   0.219
?
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:   2.714
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.857
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.174
?
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
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10843584]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. antarctic n.a. PMID[15270575]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[15497934]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. fruit n.a. PMID[16378372]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. flower n.a. PMID[16378372]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[30407007]
NPO26453 Prunus lusitanica Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[37240175]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3346 Piper sanctum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19849 Melilotus officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26109 Pilocarpus spicatus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25926 Tephrosia pumila Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26903 Plectranthus purpuratus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26213 Tephrosia vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18292 Guarea trichilioides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26952 Cineraria geifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2344 Carlina acanthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26352 Heuchera cylindrica Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26078 Mussaenda parviflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24378 Osmanthus heterophyllus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12524 Teucridium parvifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13991 Iris cristata Species Iridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14810 Araucaria imbricata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26625 Stichopus chloronotus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25793 Gremmeniella abietina Species Helotiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26053 Pluchea suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27377 Diaporthe helianthi Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26884 Helichrysum davenportii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25741 Aster ageratoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26430 Aplysina laevis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2344 Carlina acanthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26213 Tephrosia vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25952 Lastrea thelypteris n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25873 Thaminophyllum multiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26625 Stichopus chloronotus Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26352 Heuchera cylindrica Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26535 Balanus glandula Species Balanidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18292 Guarea trichilioides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26453 Prunus lusitanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26563 Alectoria japonica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26026 Vitis silvestris Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13781 Eremostachys moluccelloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26754 Stevia connata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26244 Panax papyrifer Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO137 Nepeta multifida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25997 Senecio rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19823 Vicia benghalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25926 Tephrosia pumila Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26727 Eremocarpus setiger n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26408 Melanophryniscus moreirae Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3346 Piper sanctum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25849 Streptomyces lomondensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25793 Gremmeniella abietina Species Helotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26377 Amelanchier vulgaris Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26186 Stereocaulon leprocauloides Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7214 Bufotes viridis Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26903 Plectranthus purpuratus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26980 Halocarpus biformis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26109 Pilocarpus spicatus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24378 Osmanthus heterophyllus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26678 Calea pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11845 Petrorhagia dubia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26289 Lecidella chodati Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26952 Cineraria geifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26078 Mussaenda parviflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26135 Walsura tubulata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19849 Melilotus officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14810 Araucaria imbricata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2720 Dactylorhiza hatagirea Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8806 Artemisia marschalliana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12524 Teucridium parvifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13991 Iris cristata Species Iridaceae 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
NPT1652 Individual protein Serum paraoxonase/arylesterase 1 Homo sapiens Activity = 12.99 umol/min/mg PMID[18572410]
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PubChem BioAssay data set
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 74978.0 nM PubChem BioAssay data set
NPT11 Individual protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 5623.4 nM PubChem BioAssay data set
NPT4620 Individual protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c MGC = 0.85 uM PMID[15115404]
NPT4620 Individual protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c IC50 = 122000.0 nM PMID[15115404]
NPT4620 Individual protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c SI = 144.0 n.a. PMID[15115404]
NPT4620 Individual protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c Inhibition = 0.15 uM PMID[15115404]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 8912.5 nM PubChem BioAssay data set
NPT367 Cell line MDA-N Homo sapiens GI50 n.a. 53088.44 nM PubChem BioAssay data set
NPT368 Cell line SN12C 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
NPT116 Cell line HL-60 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
NPT90 Cell line DU-145 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
NPT376 Cell line A498 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
NPT381 Cell line OVCAR-8 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
NPT383 Cell line SNB-19 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
NPT385 Cell line SR 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
NPT323 Cell line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PubChem BioAssay data set
NPT455 Cell line NCI-H522 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
NPT388 Cell line NCI-H322M 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
NPT390 Cell line LOX IMVI 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
NPT147 Cell line SK-MEL-2 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
NPT392 Cell line SNB-75 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
NPT148 Cell line HCT-15 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
NPT394 Cell line EKVX 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
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
NPT458 Cell line IGROV-1 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
NPT402 Cell line Hs-578T 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
NPT403 Cell line UACC-257 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
NPT407 Cell line COLO 205 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
NPT2 Others Unspecified n.a. Potency n.a. 2199.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 695.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 77350.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 195 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 61441.5 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 39114.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 54759.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 68938.5 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
- Rattus norvegicus LD50 = 1460.0 mg/kg ToxVal
- Rattus norvegicus NOEL < 75.0 mg/kg-day ToxVal
- Rattus norvegicus NOAEL = 300.0 mg/kg-day ToxVal
- Rattus norvegicus NOAEL = 150.0 mg/kg-day ToxVal
- Mus musculus LOEL = 10.0 % ToxVal
- Oryctolagus cuniculus LD50 > 5000.0 mg/kg ToxVal
- Cavia porcellus LD50 = 1760.0 mg/kg ToxVal

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 NPC233238 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
NPC

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC233238 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