Structure

Physi-Chem Properties

Molecular Weight:  272.07
Volume:  273.743
LogP:  2.639
LogD:  2.528
LogS:  -2.993
# Rotatable Bonds:  3
TPSA:  97.99
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.391
Synthetic Accessibility Score:  2.225
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.931
MDCK Permeability:  1.1079420801252127e-05
Pgp-inhibitor:  0.012
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.152
30% Bioavailability (F30%):  0.19

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.029
Plasma Protein Binding (PPB):  99.30765533447266%
Volume Distribution (VD):  0.466
Pgp-substrate:  1.4295717477798462%

ADMET: Metabolism

CYP1A2-inhibitor:  0.89
CYP1A2-substrate:  0.113
CYP2C19-inhibitor:  0.218
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.611
CYP2C9-substrate:  0.825
CYP2D6-inhibitor:  0.449
CYP2D6-substrate:  0.704
CYP3A4-inhibitor:  0.797
CYP3A4-substrate:  0.145

ADMET: Excretion

Clearance (CL):  16.32
Half-life (T1/2):  0.924

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.283
Drug-inuced Liver Injury (DILI):  0.682
AMES Toxicity:  0.826
Rat Oral Acute Toxicity:  0.649
Maximum Recommended Daily Dose:  0.662
Skin Sensitization:  0.959
Carcinogencity:  0.509
Eye Corrosion:  0.031
Eye Irritation:  0.956
Respiratory Toxicity:  0.299

Download Data

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

  Natural Product: NPC26697

Natural Product ID:  NPC26697
Common Name*:   Butein
IUPAC Name:   (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Synonyms:   3,4,2',4'-Tetrahydroxychalone; Butein
Standard InCHIKey:  AYMYWHCQALZEGT-ORCRQEGFSA-N
Standard InCHI:  InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+
SMILES:  Oc1ccc(c(c1)O)C(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL128000
PubChem CID:   5281222
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO28952 Sapium haematospermum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[15104489]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15730237]
NPO23510 Vicia faba Species Fabaceae Eukaryota flowers n.a. n.a. PMID[16180811]
NPO32846 heamatoxylon campechianum Species n.a. n.a. stems XiShuangBanNa, Yunnan Province, China 2005-Sep PMID[18610999]
NPO2188 Dendrobium candidum Species Orchidaceae Eukaryota n.a. stem n.a. PMID[19182417]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO26559 Glycine soja Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21545185]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[23743282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26690274]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9525107]
NPO23510 Vicia faba Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16682 Cirsium chinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16682 Cirsium chinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6361 Turpinia arguta Species Staphyleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2188 Dendrobium candidum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26559 Glycine soja Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4330 Crotalus atrox Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7250 Ventilago vitiensis Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23549 Erysimum siliculosum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9726 Panzeria canescens Species Tachinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8842 Neurymenia fraxinifolia Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15970 Chrysanthemum uliginosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26722 Dorstenia dinklagei Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10786 Trichocereus werdermannianus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10917 Junceella gemmacea Species Ellisellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8308 Bryocaulon pseudosatoanum Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2188 Dendrobium candidum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1973 Conyza japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16682 Cirsium chinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28952 Sapium haematospermum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO131 Euphrasia stricta Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26531 Aeschrion excelsa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6790 Camchaya loloana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26403 Brachymeris montana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8922 Kaempferia rotunda Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26881 Croton zehntneri Species Euphorbiaceae 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
NPO23510 NPC26697 Other (raw) Fruit 0.351 0.002 0.7 mg/100g Database [DUKE]
NPO23510 NPC26697 Raw n.a. 0.075000001 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

☑ 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
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 20000.0 nM PMID[510143]
NPT25 Cell Line MT4 Homo sapiens CC50 = 5300.0 nM PMID[510143]
NPT91 Cell Line KB Homo sapiens CC50 = 9100.0 nM PMID[510143]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 = 4.6 nM PMID[510145]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 19952.62 nM PMID[510146]
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum IC50 = 12500.0 nM PMID[510147]
NPT1573 Individual Protein Enoyl-[acyl-carrier-protein] reductase Escherichia coli K-12 IC50 = 30000.0 nM PMID[510147]
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum Ki = 5500.0 nM PMID[510147]
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum Ki = 2970.0 nM PMID[510147]
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum Ki = 14.0 nM PMID[510147]
NPT202 Individual Protein Protease Human immunodeficiency virus 1 Inhibition = 50.0 % PMID[510148]
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens IC50 = 16000.0 nM PMID[510149]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens IC50 = 65000.0 nM PMID[510149]
NPT1371 Individual Protein Cyclin-dependent kinase 2 Homo sapiens Kd = 100000.0 nM PMID[510149]
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens IC50 = 8000.0 nM PMID[510150]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens IC50 = 65000.0 nM PMID[510150]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens Inhibition = 9.1 % PMID[510151]
NPT1478 Individual Protein Vascular endothelial growth factor receptor 2 Homo sapiens Inhibition = 48.3 % PMID[510151]
NPT1479 Individual Protein Stem cell growth factor receptor Homo sapiens Inhibition = 15.1 % PMID[510151]
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens Inhibition = 3.0 % PMID[510151]
NPT1480 Individual Protein Fibroblast growth factor receptor 1 Homo sapiens Inhibition = 68.5 % PMID[510151]
NPT1481 Individual Protein Fibroblast growth factor receptor 2 Homo sapiens Inhibition = 3.0 % PMID[510151]
NPT1337 Individual Protein Hepatocyte growth factor receptor Homo sapiens Inhibition = 81.7 % PMID[510151]
NPT276 Individual Protein Angiotensin-converting enzyme Oryctolagus cuniculus IC50 = 730.0 nM PMID[510154]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 10000.0 nM PMID[510155]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 17.5 % PMID[510157]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 14.8 % PMID[510157]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -7.3 % PMID[510157]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -80.8 % PMID[510157]
NPT276 Individual Protein Angiotensin-converting enzyme Oryctolagus cuniculus IC50 = 730000.0 nM PMID[510158]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 44668.4 nM PMID[510155]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 21192.3 nM PMID[510155]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 6137.62 nM PMID[510159]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 14521.12 nM PMID[510159]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 18030.18 nM PMID[510159]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 16672.47 nM PMID[510159]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14028.14 nM PMID[510159]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 15739.83 nM PMID[510159]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 3288.52 nM PMID[510159]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 9099.13 nM PMID[510159]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 11194.38 nM PMID[510159]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 11641.26 nM PMID[510159]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 13931.57 nM PMID[510159]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 4265.8 nM PMID[510159]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 17660.38 nM PMID[510159]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 15417.0 nM PMID[510159]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 7638.36 nM PMID[510159]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 17378.01 nM PMID[510159]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 17418.07 nM PMID[510159]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 9246.98 nM PMID[510159]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 17378.01 nM PMID[510159]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 17906.06 nM PMID[510159]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 10616.96 nM PMID[510159]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18492.69 nM PMID[510159]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 15848.93 nM PMID[510159]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 7095.78 nM PMID[510159]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 19408.86 nM PMID[510159]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 8531.0 nM PMID[510159]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 14028.14 nM PMID[510159]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 2254.24 nM PMID[510159]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10162.49 nM PMID[510159]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 16143.59 nM PMID[510159]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 16255.49 nM PMID[510159]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 12246.16 nM PMID[510159]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 10471.29 nM PMID[510159]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 19054.61 nM PMID[510159]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 8260.38 nM PMID[510159]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 9268.3 nM PMID[510159]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 14859.36 nM PMID[510159]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 17060.82 nM PMID[510159]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 17100.15 nM PMID[510159]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 25003.45 nM PMID[510159]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 11142.95 nM PMID[510159]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 13001.7 nM PMID[510159]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16255.49 nM PMID[510159]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 26853.44 nM PMID[510159]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 14825.18 nM PMID[510159]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 19588.45 nM PMID[510159]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 3981.07 nM PMID[510159]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 15739.83 nM PMID[510159]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 2471.72 nM PMID[510159]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 14354.89 nM PMID[510159]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 15240.53 nM PMID[510159]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 16865.53 nM PMID[510159]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 9078.21 nM PMID[510159]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 10495.42 nM PMID[510159]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 15205.48 nM PMID[510159]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 22335.72 nM PMID[510159]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 11994.99 nM PMID[510159]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 19408.86 nM PMID[510159]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 15559.66 nM PMID[510159]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 20796.97 nM PMID[510159]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 13931.57 nM PMID[510159]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 3749.73 nM PMID[510159]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 17458.22 nM PMID[510159]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 17338.04 nM PMID[510159]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 14454.4 nM PMID[510159]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 12189.9 nM PMID[510159]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 14454.4 nM PMID[510159]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 16557.7 nM PMID[510159]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 10.05 % PMID[510161]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 = 4.6 nM PMID[510165]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 19952.6 nM PMID[510155]
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens Activity = 87.5 % PMID[510166]
NPT276 Individual Protein Angiotensin-converting enzyme Oryctolagus cuniculus IC50 = 730000000.0 nM PMID[510168]
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 1300.0 nM PMID[510169]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 5300.0 nM PMID[510171]
NPT34 Cell Line BV-2 Mus musculus IC50 = 4300.0 nM PMID[510171]
NPT804 Cell Line HT-22 Mus musculus FC = 1.22 n.a. PMID[510172]
NPT804 Cell Line HT-22 Mus musculus FC = 0.69 n.a. PMID[510172]
NPT804 Cell Line HT-22 Mus musculus Activity = 59.79 % PMID[510172]
NPT34 Cell Line BV-2 Mus musculus IC50 = 10900.0 nM PMID[510173]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens IC50 = 7300.0 nM PMID[510174]
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 67.0 uM PMID[510176]
NPT2219 Cell Line C2C12 Mus musculus IC10 = 3.99 ug ml-1 PMID[510181]
NPT2219 Cell Line C2C12 Mus musculus IC50 = 18.99 ug.mL-1 PMID[510181]
NPT27 Others Unspecified Fold increase = 2.2 n.a. PMID[510143]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 66000.0 nM PMID[510144]
NPT27 Others Unspecified IC50 = 16000.0 nM PMID[510144]
NPT1476 Protein Family Cyclooxygenase Homo sapiens IC50 = 120000.0 nM PMID[510145]
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = 40.0 % PMID[510145]
NPT2 Others Unspecified IC50 > 500000.0 nM PMID[510149]
NPT2 Others Unspecified IC50 > 20000.0 nM PMID[510152]
NPT35 Others n.a. Activity = 2.42 MU PMID[510153]
NPT35 Others n.a. Activity = 2.27 MU PMID[510153]
NPT35 Others n.a. Activity = 119.5 mg/L PMID[510153]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 17782.8 nM PMID[510155]
NPT2 Others Unspecified IC50 > 20000.0 nM PMID[510156]
NPT27 Others Unspecified Activity < 5.0 % PMID[510156]
NPT888 Individual Protein 78 kDa glucose-regulated protein Homo sapiens Potency n.a. 44668.4 nM PMID[510155]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -0.63 % PMID[510161]
NPT32 Organism Mus musculus Mus musculus Inhibition = 14.36 % PMID[510162]
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 450.0 nM PMID[510163]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 35100.0 nM PMID[510164]
NPT1559 Protein Family Cyclooxygenase Rattus norvegicus IC50 = 4.6 nM PMID[510165]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens IC50 = 38000.0 nM PMID[510167]
NPT35 Others n.a. Activity = 90.0 % PMID[510169]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 71.0 % PMID[510169]
NPT35 Others n.a. IC50 = 3.3 ug.mL-1 PMID[510170]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 92.46 % PMID[510172]
NPT21770 PROTEIN FAMILY MAP kinase p38 Mus musculus FC = 0.75 n.a. PMID[510172]
NPT2 Others Unspecified FC = 1.49 n.a. PMID[510172]
NPT2 Others Unspecified FC = 0.73 n.a. PMID[510172]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -4.59 % PMID[510175]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 8.451 % PMID[510177]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.13 % PMID[510178]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[510180]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[510180]
NPT2 Others Unspecified Inhibition = 20.0 % PMID[510182]
NPT2 Others Unspecified IC50 = 43300.0 nM PMID[510182]
NPT27 Others Unspecified Stability = 9.93 % PMID[510182]
NPT27 Others Unspecified Stability = 18.1 % PMID[510182]
NPT27 Others Unspecified Stability = 61.6 % PMID[510182]
NPT35 Others n.a. pKa = 7.96 n.a. PMID[510182]
NPT35 Others n.a. LogP = 0.42 n.a. PMID[510182]
NPT27 Others Unspecified logPapp = -5.35 n.a. PMID[510182]
NPT35 Others n.a. Solubility = 21.0 ug.mL-1 PMID[510182]
NPT27 Others Unspecified Tmax = 0.1 hr PMID[510182]
NPT27 Others Unspecified Tmax = 0.3 hr PMID[510182]
NPT27 Others Unspecified Cmax = 0.041 ug.mL-1 PMID[510182]
NPT27 Others Unspecified Cmax = 0.601 ug.mL-1 PMID[510182]
NPT27 Others Unspecified Cmax = 0.083 ug.mL-1 PMID[510182]
NPT27 Others Unspecified AUC = 6.7 ng.hr.mL-1 PMID[510182]
NPT27 Others Unspecified AUC = 251.0 ng.hr.mL-1 PMID[510182]
NPT27 Others Unspecified AUC = 141.0 ng.hr.mL-1 PMID[510182]
NPT27 Others Unspecified F = 37.0 % PMID[510182]
NPT32 Organism Mus musculus Mus musculus Inhibition = 52.0 % PMID[510182]
NPT27 Others Unspecified F = 15.0 % PMID[510182]

☑ 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 NPC26697 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
0.9919 High Similarity NPC469526
0.9919 High Similarity NPC34070
0.984 High Similarity NPC135801
0.9839 High Similarity NPC233056
0.9535 High Similarity NPC264112
0.9535 High Similarity NPC194764
0.9535 High Similarity NPC65005
0.9524 High Similarity NPC244441
0.9512 High Similarity NPC13238
0.9462 High Similarity NPC290030
0.944 High Similarity NPC107672
0.9389 High Similarity NPC175552
0.936 High Similarity NPC8745
0.9318 High Similarity NPC472903
0.928 High Similarity NPC10926
0.9268 High Similarity NPC224273
0.9268 High Similarity NPC115159
0.9268 High Similarity NPC19174
0.9268 High Similarity NPC73532
0.9268 High Similarity NPC45438
0.9268 High Similarity NPC143427
0.9268 High Similarity NPC267552
0.9248 High Similarity NPC203063
0.9194 High Similarity NPC32032
0.9194 High Similarity NPC133909
0.9187 High Similarity NPC297186
0.9179 High Similarity NPC472904
0.9167 High Similarity NPC170742
0.9113 High Similarity NPC242895
0.9113 High Similarity NPC156139
0.9111 High Similarity NPC301178
0.9111 High Similarity NPC284556
0.9091 High Similarity NPC223836
0.9044 High Similarity NPC238629
0.9044 High Similarity NPC287722
0.9044 High Similarity NPC254659
0.9044 High Similarity NPC471417
0.9032 High Similarity NPC248363
0.9024 High Similarity NPC158222
0.8984 High Similarity NPC156539
0.8984 High Similarity NPC214620
0.8978 High Similarity NPC142165
0.8978 High Similarity NPC242893
0.8978 High Similarity NPC38065
0.8952 High Similarity NPC159525
0.8913 High Similarity NPC70136
0.8872 High Similarity NPC72918
0.8871 High Similarity NPC161617
0.8846 High Similarity NPC474998
0.8846 High Similarity NPC109123
0.8846 High Similarity NPC92624
0.8841 High Similarity NPC279121
0.8837 High Similarity NPC98254
0.8837 High Similarity NPC105157
0.8837 High Similarity NPC30501
0.8837 High Similarity NPC23126
0.8837 High Similarity NPC103356
0.8837 High Similarity NPC162612
0.8837 High Similarity NPC72158
0.8837 High Similarity NPC266689
0.8837 High Similarity NPC100067
0.8837 High Similarity NPC190043
0.8837 High Similarity NPC169250
0.881 High Similarity NPC196976
0.8797 High Similarity NPC282780
0.8797 High Similarity NPC166480
0.8797 High Similarity NPC44437
0.879 High Similarity NPC40649
0.879 High Similarity NPC209486
0.8786 High Similarity NPC95864
0.8786 High Similarity NPC140840
0.8786 High Similarity NPC168803
0.8786 High Similarity NPC125449
0.8786 High Similarity NPC86847
0.8786 High Similarity NPC188074
0.8786 High Similarity NPC51443
0.8786 High Similarity NPC74881
0.8779 High Similarity NPC259942
0.8769 High Similarity NPC473017
0.8769 High Similarity NPC221777
0.8769 High Similarity NPC21305
0.8768 High Similarity NPC175013
0.8768 High Similarity NPC119663
0.876 High Similarity NPC267846
0.876 High Similarity NPC62952
0.8759 High Similarity NPC110419
0.8731 High Similarity NPC129752
0.873 High Similarity NPC146642
0.8723 High Similarity NPC203747
0.8723 High Similarity NPC19545
0.8723 High Similarity NPC196277
0.8723 High Similarity NPC287395
0.8723 High Similarity NPC183655
0.8723 High Similarity NPC194653
0.8723 High Similarity NPC118726
0.8723 High Similarity NPC43669
0.8723 High Similarity NPC218490
0.8723 High Similarity NPC12367
0.8723 High Similarity NPC80710
0.8723 High Similarity NPC272721
0.8723 High Similarity NPC254702
0.8723 High Similarity NPC139364
0.8722 High Similarity NPC294226
0.8714 High Similarity NPC20791
0.8714 High Similarity NPC179271
0.8705 High Similarity NPC257025
0.8702 High Similarity NPC102829
0.8702 High Similarity NPC120488
0.8696 High Similarity NPC312256
0.8692 High Similarity NPC116513
0.8686 High Similarity NPC50823
0.8676 High Similarity NPC61398
0.8676 High Similarity NPC416
0.8662 High Similarity NPC333691
0.8662 High Similarity NPC183959
0.8662 High Similarity NPC102003
0.8662 High Similarity NPC92722
0.8662 High Similarity NPC1612
0.8662 High Similarity NPC40290
0.8662 High Similarity NPC105512
0.8662 High Similarity NPC264550
0.8662 High Similarity NPC200060
0.8662 High Similarity NPC139293
0.8662 High Similarity NPC195763
0.8662 High Similarity NPC38545
0.8662 High Similarity NPC142876
0.8662 High Similarity NPC69430
0.8662 High Similarity NPC171916
0.8662 High Similarity NPC264289
0.8652 High Similarity NPC239312
0.8652 High Similarity NPC77378
0.8652 High Similarity NPC108406
0.8652 High Similarity NPC275772
0.8652 High Similarity NPC130230
0.8651 High Similarity NPC294037
0.8636 High Similarity NPC117609
0.8636 High Similarity NPC147757
0.8626 High Similarity NPC179898
0.8603 High Similarity NPC473391
0.8603 High Similarity NPC53414
0.8603 High Similarity NPC147418
0.8603 High Similarity NPC472364
0.8603 High Similarity NPC53206
0.8601 High Similarity NPC29231
0.8601 High Similarity NPC85131
0.8601 High Similarity NPC472279
0.8601 High Similarity NPC45873
0.8601 High Similarity NPC260582
0.8601 High Similarity NPC10467
0.8594 High Similarity NPC225710
0.8594 High Similarity NPC309765
0.8592 High Similarity NPC119059
0.8592 High Similarity NPC166036
0.8592 High Similarity NPC203077
0.8592 High Similarity NPC15329
0.8592 High Similarity NPC294852
0.8592 High Similarity NPC194856
0.8592 High Similarity NPC471907
0.8592 High Similarity NPC131451
0.8592 High Similarity NPC3036
0.8592 High Similarity NPC238279
0.8592 High Similarity NPC321011
0.8592 High Similarity NPC188679
0.8592 High Similarity NPC276930
0.8583 High Similarity NPC149246
0.8582 High Similarity NPC40524
0.8582 High Similarity NPC213485
0.8582 High Similarity NPC267205
0.8582 High Similarity NPC139074
0.8582 High Similarity NPC12377
0.8582 High Similarity NPC169749
0.8571 High Similarity NPC188814
0.8571 High Similarity NPC207732
0.8571 High Similarity NPC105213
0.8571 High Similarity NPC195262
0.8571 High Similarity NPC475042
0.8561 High Similarity NPC291078
0.8561 High Similarity NPC476119
0.856 High Similarity NPC150919
0.8542 High Similarity NPC154345
0.8542 High Similarity NPC35
0.8542 High Similarity NPC251110
0.8542 High Similarity NPC260895
0.8542 High Similarity NPC256406
0.8542 High Similarity NPC227485
0.8542 High Similarity NPC31363
0.854 High Similarity NPC212767
0.854 High Similarity NPC123714
0.8538 High Similarity NPC477454
0.8538 High Similarity NPC262671
0.8538 High Similarity NPC201728
0.8531 High Similarity NPC287101
0.8531 High Similarity NPC223579
0.8531 High Similarity NPC183950
0.8531 High Similarity NPC270465
0.8531 High Similarity NPC216318
0.8531 High Similarity NPC17286
0.8531 High Similarity NPC195351
0.8531 High Similarity NPC52005
0.8531 High Similarity NPC87125

  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 NPC26697 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
0.984 High Similarity NPD943 Approved
0.9091 High Similarity NPD651 Clinical (unspecified phase)
0.8841 High Similarity NPD1511 Approved
0.8714 High Similarity NPD1512 Approved
0.8594 High Similarity NPD9269 Phase 2
0.8529 High Similarity NPD1509 Clinical (unspecified phase)
0.8394 Intermediate Similarity NPD1510 Phase 2
0.837 Intermediate Similarity NPD1240 Approved
0.8356 Intermediate Similarity NPD1934 Approved
0.8311 Intermediate Similarity NPD3882 Suspended
0.8299 Intermediate Similarity NPD2801 Approved
0.8299 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8281 Intermediate Similarity NPD9268 Approved
0.8248 Intermediate Similarity NPD1607 Approved
0.8175 Intermediate Similarity NPD230 Phase 1
0.812 Intermediate Similarity NPD1470 Approved
0.8092 Intermediate Similarity NPD1201 Approved
0.8085 Intermediate Similarity NPD1549 Phase 2
0.8014 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD7390 Discontinued
0.7907 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD4380 Phase 2
0.7852 Intermediate Similarity NPD1164 Approved
0.7834 Intermediate Similarity NPD3818 Discontinued
0.7832 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6166 Phase 2
0.7821 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD3817 Phase 2
0.7755 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD74 Approved
0.7698 Intermediate Similarity NPD9266 Approved
0.7692 Intermediate Similarity NPD5408 Approved
0.7692 Intermediate Similarity NPD5405 Approved
0.7692 Intermediate Similarity NPD5406 Approved
0.7692 Intermediate Similarity NPD5404 Approved
0.7687 Intermediate Similarity NPD6799 Approved
0.7673 Intermediate Similarity NPD7054 Approved
0.7635 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD7074 Phase 3
0.7625 Intermediate Similarity NPD7472 Approved
0.7619 Intermediate Similarity NPD9264 Approved
0.7619 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD9263 Approved
0.7619 Intermediate Similarity NPD9267 Approved
0.7582 Intermediate Similarity NPD1465 Phase 2
0.758 Intermediate Similarity NPD6232 Discontinued
0.7578 Intermediate Similarity NPD6797 Phase 2
0.7569 Intermediate Similarity NPD2935 Discontinued
0.7569 Intermediate Similarity NPD1551 Phase 2
0.7569 Intermediate Similarity NPD2796 Approved
0.7561 Intermediate Similarity NPD1242 Phase 1
0.7548 Intermediate Similarity NPD7075 Discontinued
0.7548 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD7473 Discontinued
0.7531 Intermediate Similarity NPD7251 Discontinued
0.7517 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9493 Approved
0.7485 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3750 Approved
0.7482 Intermediate Similarity NPD9494 Approved
0.7468 Intermediate Similarity NPD7819 Suspended
0.7468 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD1203 Approved
0.7432 Intermediate Similarity NPD6190 Approved
0.7429 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD447 Suspended
0.7386 Intermediate Similarity NPD6599 Discontinued
0.7378 Intermediate Similarity NPD7808 Phase 3
0.7365 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD3022 Approved
0.7364 Intermediate Similarity NPD3021 Approved
0.7357 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD9281 Approved
0.7342 Intermediate Similarity NPD5494 Approved
0.7338 Intermediate Similarity NPD7411 Suspended
0.7325 Intermediate Similarity NPD3749 Approved
0.7319 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD9261 Approved
0.729 Intermediate Similarity NPD6801 Discontinued
0.7279 Intermediate Similarity NPD2344 Approved
0.7278 Intermediate Similarity NPD919 Approved
0.7267 Intermediate Similarity NPD3300 Phase 2
0.7259 Intermediate Similarity NPD9545 Approved
0.7256 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1613 Approved
0.7222 Intermediate Similarity NPD846 Approved
0.7222 Intermediate Similarity NPD940 Approved
0.7222 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3926 Phase 2
0.7197 Intermediate Similarity NPD5402 Approved
0.719 Intermediate Similarity NPD5403 Approved
0.7188 Intermediate Similarity NPD1247 Approved
0.7181 Intermediate Similarity NPD1243 Approved
0.7181 Intermediate Similarity NPD2800 Approved
0.7171 Intermediate Similarity NPD5401 Approved
0.7143 Intermediate Similarity NPD3748 Approved
0.7133 Intermediate Similarity NPD3027 Phase 3
0.7123 Intermediate Similarity NPD6651 Approved
0.7122 Intermediate Similarity NPD9717 Approved
0.7086 Intermediate Similarity NPD2309 Approved
0.7083 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3764 Approved
0.7081 Intermediate Similarity NPD6959 Discontinued
0.7059 Intermediate Similarity NPD2532 Approved
0.7059 Intermediate Similarity NPD2534 Approved
0.7059 Intermediate Similarity NPD2533 Approved
0.7055 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7768 Phase 2
0.7042 Intermediate Similarity NPD2798 Approved
0.7039 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5844 Phase 1
0.7027 Intermediate Similarity NPD2799 Discontinued
0.7006 Intermediate Similarity NPD6559 Discontinued
0.698 Remote Similarity NPD9570 Approved
0.697 Remote Similarity NPD4750 Phase 3
0.6968 Remote Similarity NPD920 Approved
0.6966 Remote Similarity NPD2313 Discontinued
0.6966 Remote Similarity NPD411 Approved
0.6954 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6948 Remote Similarity NPD642 Clinical (unspecified phase)
0.6939 Remote Similarity NPD1933 Approved
0.6929 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6923 Remote Similarity NPD258 Approved
0.6923 Remote Similarity NPD257 Approved
0.6918 Remote Similarity NPD520 Approved
0.6908 Remote Similarity NPD8166 Discontinued
0.6908 Remote Similarity NPD4628 Phase 3
0.6883 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6879 Remote Similarity NPD3226 Approved
0.6879 Remote Similarity NPD3455 Phase 2
0.6875 Remote Similarity NPD9569 Approved
0.6867 Remote Similarity NPD6099 Approved
0.6867 Remote Similarity NPD6100 Approved
0.6846 Remote Similarity NPD1237 Approved
0.6845 Remote Similarity NPD5953 Discontinued
0.6842 Remote Similarity NPD2654 Approved
0.6828 Remote Similarity NPD6832 Phase 2
0.6824 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2346 Discontinued
0.6821 Remote Similarity NPD7266 Discontinued
0.6812 Remote Similarity NPD5536 Phase 2
0.6809 Remote Similarity NPD422 Phase 1
0.6791 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6786 Remote Similarity NPD2932 Approved
0.6786 Remote Similarity NPD3019 Approved
0.6766 Remote Similarity NPD3751 Discontinued
0.6763 Remote Similarity NPD1548 Phase 1
0.6761 Remote Similarity NPD1608 Approved
0.6761 Remote Similarity NPD3972 Approved
0.676 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2934 Approved
0.6746 Remote Similarity NPD2933 Approved
0.6741 Remote Similarity NPD228 Approved
0.6726 Remote Similarity NPD6020 Phase 2
0.6726 Remote Similarity NPD7286 Phase 2
0.6724 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6709 Remote Similarity NPD1653 Approved
0.6693 Remote Similarity NPD2860 Approved
0.6693 Remote Similarity NPD2859 Approved
0.6691 Remote Similarity NPD9377 Approved
0.6691 Remote Similarity NPD9379 Approved
0.669 Remote Similarity NPD1610 Phase 2
0.6689 Remote Similarity NPD4308 Phase 3
0.6689 Remote Similarity NPD259 Phase 1
0.6689 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1196 Approved
0.6688 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4357 Discontinued
0.6667 Remote Similarity NPD3020 Approved
0.6667 Remote Similarity NPD9537 Phase 1
0.6667 Remote Similarity NPD1543 Discontinued
0.6667 Remote Similarity NPD7199 Phase 2
0.6667 Remote Similarity NPD9536 Phase 1
0.6667 Remote Similarity NPD9094 Approved
0.6647 Remote Similarity NPD1220 Phase 1
0.6646 Remote Similarity NPD6234 Discontinued
0.6644 Remote Similarity NPD825 Approved
0.6644 Remote Similarity NPD3018 Phase 2
0.6644 Remote Similarity NPD826 Approved
0.6623 Remote Similarity NPD1195 Approved
0.6622 Remote Similarity NPD3268 Approved
0.6609 Remote Similarity NPD8150 Discontinued
0.6601 Remote Similarity NPD1471 Phase 3
0.66 Remote Similarity NPD275 Approved
0.66 Remote Similarity NPD274 Approved
0.66 Remote Similarity NPD555 Phase 2
0.6597 Remote Similarity NPD1755 Approved
0.6587 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6587 Remote Similarity NPD5242 Approved
0.6564 Remote Similarity NPD2296 Approved
0.6564 Remote Similarity NPD4288 Approved
0.6562 Remote Similarity NPD844 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