Structure

Physi-Chem Properties

Molecular Weight:  126.03
Volume:  122.237
LogP:  0.114
LogD:  0.431
LogS:  -0.979
# Rotatable Bonds:  0
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.555
Synthetic Accessibility Score:  2.706
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.594
MDCK Permeability:  2.428159859846346e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.033
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.261
Plasma Protein Binding (PPB):  83.32140350341797%
Volume Distribution (VD):  0.701
Pgp-substrate:  37.93932342529297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.344
CYP1A2-substrate:  0.733
CYP2C19-inhibitor:  0.092
CYP2C19-substrate:  0.461
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.704
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.531
CYP3A4-inhibitor:  0.014
CYP3A4-substrate:  0.245

ADMET: Excretion

Clearance (CL):  10.211
Half-life (T1/2):  0.848

ADMET: Toxicity

hERG Blockers:  0.054
Human Hepatotoxicity (H-HT):  0.116
Drug-inuced Liver Injury (DILI):  0.236
AMES Toxicity:  0.036
Rat Oral Acute Toxicity:  0.33
Maximum Recommended Daily Dose:  0.027
Skin Sensitization:  0.548
Carcinogencity:  0.788
Eye Corrosion:  0.545
Eye Irritation:  0.943
Respiratory Toxicity:  0.453

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC158853

Natural Product ID:  NPC158853
Common Name*:   Maltol
IUPAC Name:   3-hydroxy-2-methylpyran-4-one
Synonyms:   E636; Maltol
Standard InCHIKey:  XPCTZQVDEJYUGT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3
SMILES:  Cc1c(c(=O)cco1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL31422
PubChem CID:   8369
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[10423860]
NPO15672 Clavularia koellikeri Species Clavulariidae Eukaryota n.a. Okinawan soft coral n.a. PMID[11141107]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO15672 Clavularia koellikeri Species Clavulariidae Eukaryota n.a. Okinawan soft coral n.a. PMID[12398540]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Flower buds n.a. n.a. PMID[12880307]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO15672 Clavularia koellikeri Species Clavulariidae Eukaryota n.a. Okinawan n.a. PMID[15104486]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[15863936]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. PMID[16499326]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Stems n.a. n.a. PMID[17663584]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Roots n.a. n.a. PMID[18186611]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota roots n.a. n.a. PMID[20346658]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO24893 Polyalthia nemoralis Species Annonaceae Eukaryota n.a. branch n.a. PMID[21809577]
NPO24893 Polyalthia nemoralis Species Annonaceae Eukaryota n.a. leaf n.a. PMID[21809577]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21848266]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[21848266]
NPO14429 0cardiopsis dassonvillei Species 0cardiopsaceae Bacteria isolated from marine sediments The estuary of Yellow River, Dongying, Shandong Province, China n.a. PMID[21958359]
NPO14429 0cardiopsis dassonvillei Species 0cardiopsaceae Bacteria n.a. spore n.a. PMID[21958359]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[23439553]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota leaves and stems n.a. n.a. PMID[25442304]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. PMID[26035239]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Steamed Roots n.a. n.a. PMID[26200131]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO15672 Clavularia koellikeri Species Clavulariidae Eukaryota n.a. n.a. n.a. PMID[30994348]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. tuber n.a. Database[Article]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Leaf Diffusate n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO13979 Tilia argentea Species Malvaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24893 Polyalthia nemoralis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8338 Macrothelypteris oligophlebia Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18797 Hemibarbus labeo Species Cyprinidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3011 Rubia wallichiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5087 Daphne oleoides Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO15365 Maytenus heterophylla Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15459 Bolbostemma paniculatum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8111 Rhizoma bolbostemmae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO7686 Semen phaseoli n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO18797 Hemibarbus labeo Species Cyprinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24893 Polyalthia nemoralis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3011 Rubia wallichiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12407 Herba cichorii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5087 Daphne oleoides Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8338 Macrothelypteris oligophlebia Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3734 Vigna umbellata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15459 Bolbostemma paniculatum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18224 Vigna umbeuata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9261 Ophiopogon japonicus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15672 Clavularia koellikeri Species Clavulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16130 Streptomyces longwoodensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14429 0cardiopsis dassonvillei Species 0cardiopsaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15365 Maytenus heterophylla Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5275 Liriope muscari Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3011 Rubia wallichiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18525 Diosma prama Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5087 Daphne oleoides Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18797 Hemibarbus labeo Species Cyprinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13979 Tilia argentea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19193 Chrysanthemum monspeliense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8338 Macrothelypteris oligophlebia Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24893 Polyalthia nemoralis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9768 Matricaria globifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18380 Marsdenia tinctoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3734 Vigna umbellata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17075 Relicina sydneyensis Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16849 Melaleuca linariifolia Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4335 Anthracocystis flocculosa Species Ustilaginaceae 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1566 Individual Protein Glyoxalase I Homo sapiens Ki = 223872.11 nM PMID[496592]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 7943.3 nM PMID[496594]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 15848.9 nM PMID[496595]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 35481.3 nM PMID[496594]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 11220.2 nM PMID[496595]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = -319.0 % PMID[496596]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = 19.0 % PMID[496596]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 34.0 % PMID[496596]
NPT270 Individual Protein Nitric oxide synthase, inducible Mus musculus Inhibition = 6.0 % PMID[496596]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = -6.0 % PMID[496596]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = 38.0 % PMID[496596]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 19.0 % PMID[496596]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = 32.0 % PMID[496596]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 25118.9 nM PMID[496594]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 1778.3 nM PMID[496594]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 79432.8 nM PMID[496594]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 5000.35 nM PMID[496598]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 3837.07 nM PMID[496598]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4246.2 nM PMID[496598]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[496598]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 7079.5 nM PMID[496594]
NPT1346 Individual Protein Polymerase acidic protein Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 > 200000.0 nM PMID[496600]
NPT1346 Individual Protein Polymerase acidic protein Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Inhibition > 80.0 % PMID[496600]
NPT1346 Individual Protein Polymerase acidic protein Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Inhibition > 50.0 % PMID[496600]
NPT1346 Individual Protein Polymerase acidic protein Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 > 199526.23 nM PMID[496600]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 19510.5 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 77037.1 nM PubChem BioAssay data set
NPT27 Others Unspecified mean log D = 0.05 n.a. PMID[496591]
NPT27 Others Unspecified mean log D = -0.59 n.a. PMID[496591]
NPT27 Others Unspecified mean log D = -0.81 n.a. PMID[496591]
NPT27 Others Unspecified mean log D = -0.09 n.a. PMID[496591]
NPT938 Organism Cavia porcellus Cavia porcellus Relaxation = 16.0 % PMID[496593]
NPT938 Organism Cavia porcellus Cavia porcellus pD2 = 5.25 n.a. PMID[496593]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 41.0 % PMID[496596]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7.03 ug.mL-1 PMID[496597]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5.59 ug.mL-1 PMID[496597]
NPT2 Others Unspecified Potency n.a. 3548.1 nM PMID[496594]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 79.28 % PMID[496599]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 74.61 % PMID[496599]
NPT2 Others Unspecified Potency n.a. 4466.8 nM PMID[496594]
NPT20 Organism Candida albicans Candida albicans Inhibition = 4.42 % PMID[496601]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -2.15 % PMID[496601]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 4.13 % PMID[496601]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 10.28 % PMID[496601]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 10.89 % PMID[496601]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 26.74 % PMID[496601]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 14.12 % PMID[496601]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[496602]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[496602]
NPT2 Others Unspecified Potency n.a. 24562.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61697.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 64613 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27333.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 50887.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12892 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 36025.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54538.1 nM PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC158853 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.881 High Similarity NPC2741
0.7843 Intermediate Similarity NPC116366
0.766 Intermediate Similarity NPC106547
0.766 Intermediate Similarity NPC75134
0.75 Intermediate Similarity NPC110396
0.7037 Intermediate Similarity NPC135537
0.6923 Remote Similarity NPC107703
0.6923 Remote Similarity NPC220191
0.6792 Remote Similarity NPC22329
0.6744 Remote Similarity NPC304788
0.6731 Remote Similarity NPC313553
0.6667 Remote Similarity NPC46565
0.6667 Remote Similarity NPC137396
0.6667 Remote Similarity NPC229046
0.6545 Remote Similarity NPC474805
0.6545 Remote Similarity NPC168521
0.6491 Remote Similarity NPC51846
0.6429 Remote Similarity NPC129710
0.6349 Remote Similarity NPC475555
0.6349 Remote Similarity NPC475675
0.6316 Remote Similarity NPC317548
0.6296 Remote Similarity NPC275316
0.625 Remote Similarity NPC251429
0.6167 Remote Similarity NPC302564
0.614 Remote Similarity NPC317796
0.6087 Remote Similarity NPC72258
0.6061 Remote Similarity NPC262673
0.6061 Remote Similarity NPC94488
0.6034 Remote Similarity NPC297280
0.6 Remote Similarity NPC320421
0.6 Remote Similarity NPC243272
0.6 Remote Similarity NPC197356
0.6 Remote Similarity NPC139056
0.6 Remote Similarity NPC281195
0.6 Remote Similarity NPC63121
0.597 Remote Similarity NPC291062
0.597 Remote Similarity NPC94743
0.5957 Remote Similarity NPC75204
0.5938 Remote Similarity NPC7940
0.5932 Remote Similarity NPC150717
0.5932 Remote Similarity NPC230296
0.5909 Remote Similarity NPC146376
0.5909 Remote Similarity NPC263382
0.5909 Remote Similarity NPC125578
0.5902 Remote Similarity NPC473494
0.5862 Remote Similarity NPC300121
0.5849 Remote Similarity NPC474202
0.5849 Remote Similarity NPC474362
0.5833 Remote Similarity NPC299369
0.5833 Remote Similarity NPC224103
0.5833 Remote Similarity NPC200831
0.5833 Remote Similarity NPC8416
0.5833 Remote Similarity NPC279300
0.5833 Remote Similarity NPC71755
0.5818 Remote Similarity NPC477778
0.5806 Remote Similarity NPC130953
0.58 Remote Similarity NPC8270
0.58 Remote Similarity NPC111474
0.5781 Remote Similarity NPC475618
0.5758 Remote Similarity NPC122627
0.5745 Remote Similarity NPC269641
0.5714 Remote Similarity NPC130923
0.5714 Remote Similarity NPC288381
0.5714 Remote Similarity NPC226511
0.5714 Remote Similarity NPC225974
0.5714 Remote Similarity NPC94980
0.5714 Remote Similarity NPC264178
0.5714 Remote Similarity NPC263732
0.5714 Remote Similarity NPC20934
0.5692 Remote Similarity NPC96414
0.5692 Remote Similarity NPC273600
0.5686 Remote Similarity NPC221250
0.5667 Remote Similarity NPC221763
0.5652 Remote Similarity NPC266979
0.5645 Remote Similarity NPC86789
0.5636 Remote Similarity NPC324812
0.5625 Remote Similarity NPC53109
0.5625 Remote Similarity NPC477830
0.5625 Remote Similarity NPC57463
0.5625 Remote Similarity NPC2328
0.5625 Remote Similarity NPC151728
0.5625 Remote Similarity NPC143168
0.5606 Remote Similarity NPC470033
0.5606 Remote Similarity NPC201356
0.5606 Remote Similarity NPC16119
0.56 Remote Similarity NPC33761
0.56 Remote Similarity NPC200147
0.56 Remote Similarity NPC217923

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC158853 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD9090 Phase 3
0.9286 High Similarity NPD9297 Discontinued
0.9286 High Similarity NPD9091 Suspended
0.6552 Remote Similarity NPD9306 Approved
0.6207 Remote Similarity NPD9286 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8779 Phase 3
0.5833 Remote Similarity NPD9287 Clinical (unspecified phase)
0.5625 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5606 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5606 Remote Similarity NPD3704 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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