Structure

Physi-Chem Properties

Molecular Weight:  228.04
Volume:  224.441
LogP:  2.803
LogD:  2.591
LogS:  -3.417
# Rotatable Bonds:  0
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.579
Synthetic Accessibility Score:  2.149
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.804
MDCK Permeability:  1.1113912478322163e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.301
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.484
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  94.88508605957031%
Volume Distribution (VD):  0.55
Pgp-substrate:  8.714795112609863%

ADMET: Metabolism

CYP1A2-inhibitor:  0.987
CYP1A2-substrate:  0.427
CYP2C19-inhibitor:  0.497
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.551
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.814
CYP2D6-substrate:  0.836
CYP3A4-inhibitor:  0.59
CYP3A4-substrate:  0.158

ADMET: Excretion

Clearance (CL):  4.408
Half-life (T1/2):  0.774

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.111
Drug-inuced Liver Injury (DILI):  0.921
AMES Toxicity:  0.744
Rat Oral Acute Toxicity:  0.135
Maximum Recommended Daily Dose:  0.412
Skin Sensitization:  0.933
Carcinogencity:  0.819
Eye Corrosion:  0.311
Eye Irritation:  0.986
Respiratory Toxicity:  0.192

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC18457

Natural Product ID:  NPC18457
Common Name*:   1,7-Dihydroxyxanthone
IUPAC Name:   1,7-dihydroxyxanthen-9-one
Synonyms:   1,7-Dihydroxyxanthone
Standard InCHIKey:  KDXFPEKLLFWHMN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H
SMILES:  Oc1ccc2c(c1)c(=O)c1c(o2)cccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL389166
PubChem CID:   5281631
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(74)80113-5]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. DOI[10.1246/bcsj.30.618]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10075773]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. whole plant n.a. PMID[10361686]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. root n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. bark n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. xylem n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. leaf n.a. PMID[14727919]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[15568778]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. Uzbekistan n.a. PMID[15568778]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[16309313]
NPO25801 Harungana madagascariensis Species Hypericaceae Eukaryota stem bark n.a. n.a. PMID[16499321]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[16724839]
NPO20815 Lindera fruticosa Species Lauraceae Eukaryota roots n.a. n.a. PMID[16724860]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. PMID[16933891]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota roots n.a. n.a. PMID[16989524]
NPO25801 Harungana madagascariensis Species Hypericaceae Eukaryota Leaves n.a. n.a. PMID[17352491]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[17716892]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18464091]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18558747]
NPO22503 Salix matsudana Species Salicaceae Eukaryota n.a. leaf n.a. PMID[18794770]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19113969]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO20091 Iotrochota baculifera Species Iotrochotidae Eukaryota Chinese n.a. n.a. PMID[20624681]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[21214226]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[21214226]
NPO3648 Pittocaulon velatum Species Asteraceae Eukaryota n.a. root n.a. PMID[21661732]
NPO3648 Pittocaulon velatum Species Asteraceae Eukaryota n.a. stem n.a. PMID[21661732]
NPO32798 polygala karensium Species Polygalaceae Eukaryota n.a. n.a. n.a. PMID[22552195]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. rhizome n.a. PMID[22863942]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota aerial parts n.a. n.a. PMID[24042007]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota leaves Bobai, Guangxi Province, China 2005-Dec PMID[24679044]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota Barks n.a. n.a. PMID[24754786]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
NPO5259 Garcinia buchananii Species Clusiaceae Eukaryota stem bark n.a. n.a. PMID[25625705]
NPO25801 Harungana madagascariensis Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[26727375]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27280968]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. PMID[27466882]
NPO40853 Garcinia tetrandra Species Clusiaceae Eukaryota Stem Bark n.a. n.a. PMID[30978023]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31117521]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31873014]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[7288442]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[7400820]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18656 Iphigenia indica Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7839 Rosa sericea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4992 Goniothalamus griffithii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20091 Iotrochota baculifera Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25801 Harungana madagascariensis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO4992 Goniothalamus griffithii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18656 Iphigenia indica Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22183 Dryobalanops oblongifolia Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20382 Ramalina paludosa Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27363 Gynochthodes officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7839 Rosa sericea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18656 Iphigenia indica Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7839 Rosa sericea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4992 Goniothalamus griffithii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27363 Gynochthodes officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28824 Forsteronia refracta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO95 Streptomyces ambofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29242 Salvia dorrii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29446 Stevia polycephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2812 Lecanora kukunorensis Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29203 Gymnocarpium robertianum Species Cystopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21852 Montanoa karwinskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29510 Aulacocephalus temmincki Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23186 Verbena bonariensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9298 Piper wightii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29225 Oncoba echinata Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3744 Polycephalomyces nipponicus Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2885 Erechtites quadridentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28918 Ophiolepis superba Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29047 Disynaphia halimifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27363 Gynochthodes officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13132 Genista corsica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29363 Aconitum nevadense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9157 Rubrivivax gelatinosus Species n.a. Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29154 Heliotropium floridum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20091 Iotrochota baculifera Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6948 Davidsoniella virescens Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25801 Harungana madagascariensis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26192 Cordylanthus kingii Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15242 Setosphaeria holmii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20458 Strychnos decussata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28971 Bersama yangambiensis Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8927 Poria selecta Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16068 Berberis stolonifera Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21034 0cardia alba Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27687 Peliosanthes sinica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20647 Eugenia myrcianthes Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14855 Vismia laurentii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29292 Teucrium depressum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3340 Fridericia chica Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28937 Heterotheca grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29488 Sophora angustifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4992 Goniothalamus griffithii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20773 Jacobaea persoonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18516 Aplysilla spinifera Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22503 Salix matsudana Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13828 Achillea santolina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13818 Narcissus concolor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10228 Ascochyta viciae Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20382 Ramalina paludosa Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1245 Eunicella cavolinii Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28845 Eragrostis viscosa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21601 Crocus sieberi Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28784 Alseodaphne corneri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22183 Dryobalanops oblongifolia Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5259 Garcinia buchananii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29127 Cystophora scalaris Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17693 Forcipomyia marksae Species Ceratopogonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17772 Piper nepalense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19688 Mangifera odorata Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29189 Castanopsis sclerophylla Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1366 Piptothrix areolare n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20897 Suberites domuncula Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4244 Doodia picta Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7839 Rosa sericea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3707 Chromatium okenii Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29068 Papilio phorcas Species Papilionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25981 Crinipellis scabella Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18656 Iphigenia indica Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28898 Grewia mollis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27269 Annona impressivenia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12600 Trametes cinnabarina Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1154 Neomeris annulata Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29400 Conocephalum japonicum Species Conocephalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26341 Trifolium resupinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29415 Hovenia acerba Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20815 Lindera fruticosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29142 Kaunia saltensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3648 Pittocaulon velatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16833 Nauclea pilosa Species Rubiaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 14500.0 ug.mL-1 PMID[447790]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 19500.0 ug.mL-1 PMID[447790]
NPT1214 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens Inhibition = 31.0 % PMID[447791]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 13.01 ug.mL-1 PMID[447793]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 11.54 ug.mL-1 PMID[447793]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 22.45 ug.mL-1 PMID[447793]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 23.54 ug.mL-1 PMID[447793]
NPT81 Cell Line A549 Homo sapiens IC50 > 200000.0 nM PMID[447796]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 60350.0 nM PMID[447796]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 149900.0 nM PMID[447797]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 0.0 % PMID[447798]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[447799]
NPT91 Cell Line KB Homo sapiens IC50 > 10000.0 nM PMID[447799]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[447799]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000.0 nM PMID[447799]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[447800]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 > 10000.0 nM PMID[447800]
NPT1230 Organism Bacillus megaterium Bacillus megaterium IZ = 9.0 mm PMID[447789]
NPT1230 Organism Bacillus megaterium Bacillus megaterium IZ = 12.0 mm PMID[447789]
NPT1234 Organism Chlorella fusca Chlorella fusca IZ = 10.0 mm PMID[447789]
NPT1231 Organism Microbotryum violaceum Microbotryum violaceum IZ = 12.0 mm PMID[447789]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 386000.0 nM PMID[447791]
NPT2 Others Unspecified Ratio IC50 = 243.0 n.a. PMID[447793]
NPT35 Others n.a. EC50 = 80200.0 nM PMID[447794]
NPT35 Others n.a. Activity = 1.33 mmolequiv/mmol PMID[447794]
NPT35 Others n.a. Activity = 0.4 mmolequiv/mmol PMID[447794]
NPT35 Others n.a. Activity = 2.95 mmolequiv/mmol PMID[447794]
NPT35 Others n.a. Activity = 2.43 mmolequiv/mmol PMID[447794]
NPT29 Organism Rattus norvegicus Rattus norvegicus Retention_time = 40.4 min PMID[447795]
NPT20985 CELL-LINE MCF7-ADR Homo sapiens IC50 > 200000.0 nM PMID[447796]
NPT617 Organism Danio rerio Danio rerio Activity = 0.0 % PMID[447798]
NPT20987 CELL-LINE HeLa S3 Homo sapiens IC50 > 10000.0 nM PMID[447799]
NPT2 Others Unspecified Inhibition = 38.07 % PMID[447801]
NPT2 Others Unspecified Inhibition = 39.1 % PMID[447801]
NPT741 Individual Protein Tyrosinase Homo sapiens IC50 = 4520.0 nM PMID[447801]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 99.59 % PMID[447801]

☑ 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 NPC18457 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
0.9851 High Similarity NPC145673
0.9706 High Similarity NPC159855
0.9706 High Similarity NPC169479
0.9429 High Similarity NPC46941
0.9394 High Similarity NPC141549
0.9362 High Similarity NPC186397
0.9362 High Similarity NPC37135
0.9318 High Similarity NPC278787
0.9296 High Similarity NPC294502
0.9296 High Similarity NPC200221
0.9296 High Similarity NPC223988
0.9296 High Similarity NPC266499
0.9231 High Similarity NPC120105
0.9231 High Similarity NPC101957
0.9225 High Similarity NPC194856
0.9225 High Similarity NPC276930
0.9214 High Similarity NPC59551
0.9191 High Similarity NPC9985
0.9191 High Similarity NPC239495
0.9167 High Similarity NPC149614
0.9167 High Similarity NPC251110
0.9155 High Similarity NPC207729
0.9149 High Similarity NPC469764
0.9137 High Similarity NPC182421
0.9111 High Similarity NPC128216
0.9104 High Similarity NPC137264
0.9103 High Similarity NPC75069
0.9098 High Similarity NPC197425
0.9097 High Similarity NPC227122
0.9097 High Similarity NPC62042
0.9097 High Similarity NPC179183
0.9097 High Similarity NPC248102
0.9097 High Similarity NPC61620
0.9091 High Similarity NPC118726
0.9091 High Similarity NPC12367
0.9085 High Similarity NPC469758
0.9085 High Similarity NPC209278
0.9041 High Similarity NPC271779
0.9041 High Similarity NPC292214
0.9041 High Similarity NPC88645
0.9041 High Similarity NPC206238
0.9041 High Similarity NPC167091
0.9037 High Similarity NPC113006
0.9034 High Similarity NPC204515
0.9034 High Similarity NPC117579
0.903 High Similarity NPC7569
0.903 High Similarity NPC39753
0.903 High Similarity NPC115998
0.9028 High Similarity NPC70764
0.9021 High Similarity NPC239312
0.9021 High Similarity NPC275772
0.9021 High Similarity NPC71055
0.9021 High Similarity NPC130230
0.9014 High Similarity NPC184649
0.9014 High Similarity NPC98926
0.9014 High Similarity NPC155144
0.9014 High Similarity NPC303185
0.9007 High Similarity NPC1534
0.9007 High Similarity NPC73028
0.9 High Similarity NPC275734
0.8993 High Similarity NPC472460
0.8993 High Similarity NPC329225
0.8993 High Similarity NPC147686
0.8978 High Similarity NPC248872
0.8978 High Similarity NPC172262
0.8973 High Similarity NPC281272
0.8973 High Similarity NPC39007
0.8973 High Similarity NPC180234
0.8973 High Similarity NPC199100
0.8973 High Similarity NPC120537
0.8973 High Similarity NPC474843
0.8973 High Similarity NPC161277
0.8973 High Similarity NPC101996
0.8966 High Similarity NPC45873
0.8966 High Similarity NPC470107
0.8958 High Similarity NPC272721
0.8958 High Similarity NPC5537
0.8958 High Similarity NPC43669
0.8958 High Similarity NPC196277
0.8951 High Similarity NPC196114
0.8951 High Similarity NPC299011
0.8944 High Similarity NPC113770
0.8929 High Similarity NPC261234
0.8929 High Similarity NPC316480
0.8921 High Similarity NPC243083
0.8921 High Similarity NPC287246
0.8921 High Similarity NPC212767
0.8921 High Similarity NPC228661
0.8921 High Similarity NPC107586
0.8921 High Similarity NPC290291
0.8921 High Similarity NPC296490
0.8921 High Similarity NPC32441
0.8921 High Similarity NPC275055
0.8921 High Similarity NPC12296
0.8921 High Similarity NPC13768
0.8921 High Similarity NPC299379
0.8921 High Similarity NPC84585
0.8921 High Similarity NPC79943
0.8921 High Similarity NPC476480
0.8921 High Similarity NPC295261
0.8912 High Similarity NPC472915
0.8912 High Similarity NPC178964
0.8912 High Similarity NPC135522
0.8912 High Similarity NPC95842
0.8912 High Similarity NPC280530
0.8905 High Similarity NPC57601
0.8905 High Similarity NPC274121
0.8905 High Similarity NPC50898
0.8905 High Similarity NPC213216
0.8905 High Similarity NPC78540
0.8904 High Similarity NPC171010
0.8904 High Similarity NPC202157
0.8904 High Similarity NPC39819
0.8904 High Similarity NPC475076
0.8897 High Similarity NPC1612
0.8897 High Similarity NPC195351
0.8897 High Similarity NPC216318
0.8897 High Similarity NPC296197
0.8897 High Similarity NPC183959
0.8897 High Similarity NPC17286
0.8897 High Similarity NPC259713
0.8889 High Similarity NPC77378
0.8881 High Similarity NPC70136
0.8881 High Similarity NPC311144
0.8873 High Similarity NPC144499
0.8873 High Similarity NPC202981
0.8873 High Similarity NPC310340
0.8865 High Similarity NPC69769
0.8859 High Similarity NPC181960
0.8859 High Similarity NPC99597
0.8859 High Similarity NPC210084
0.8857 High Similarity NPC188947
0.8857 High Similarity NPC280284
0.8857 High Similarity NPC99333
0.8857 High Similarity NPC118813
0.8851 High Similarity NPC37392
0.8851 High Similarity NPC472909
0.8851 High Similarity NPC2928
0.8851 High Similarity NPC113906
0.8849 High Similarity NPC193792
0.8849 High Similarity NPC116775
0.8849 High Similarity NPC87545
0.8849 High Similarity NPC256042
0.8849 High Similarity NPC281917
0.8849 High Similarity NPC216361
0.8849 High Similarity NPC187432
0.8849 High Similarity NPC235428
0.8836 High Similarity NPC37348
0.8836 High Similarity NPC77858
0.8836 High Similarity NPC29231
0.8836 High Similarity NPC306821
0.8836 High Similarity NPC184136
0.8828 High Similarity NPC294852
0.8828 High Similarity NPC39195
0.8828 High Similarity NPC321011
0.8828 High Similarity NPC218569
0.8828 High Similarity NPC188679
0.8828 High Similarity NPC218490
0.8819 High Similarity NPC290133
0.8819 High Similarity NPC24136
0.8819 High Similarity NPC187282
0.8819 High Similarity NPC231013
0.8811 High Similarity NPC166138
0.8811 High Similarity NPC18585
0.8811 High Similarity NPC106985
0.8811 High Similarity NPC279121
0.8803 High Similarity NPC3188
0.88 High Similarity NPC172770
0.88 High Similarity NPC185258
0.8794 High Similarity NPC225153
0.8794 High Similarity NPC20709
0.8794 High Similarity NPC150648
0.8794 High Similarity NPC274784
0.8794 High Similarity NPC329203
0.8794 High Similarity NPC265871
0.8794 High Similarity NPC222342
0.8794 High Similarity NPC310135
0.8792 High Similarity NPC255106
0.8792 High Similarity NPC201837
0.8792 High Similarity NPC68093
0.8792 High Similarity NPC472916
0.8792 High Similarity NPC235165
0.8792 High Similarity NPC138243
0.8792 High Similarity NPC191146
0.8786 High Similarity NPC250266
0.8786 High Similarity NPC266597
0.8784 High Similarity NPC280937
0.8784 High Similarity NPC89474
0.8777 High Similarity NPC234560
0.8777 High Similarity NPC39426
0.8776 High Similarity NPC308451
0.8776 High Similarity NPC208043
0.8776 High Similarity NPC225731
0.8776 High Similarity NPC226973
0.8767 High Similarity NPC105512
0.8767 High Similarity NPC10027
0.8767 High Similarity NPC65775
0.8759 High Similarity NPC51443
0.8759 High Similarity NPC74881
0.8759 High Similarity NPC95864

  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 NPC18457 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
0.8993 High Similarity NPD1549 Phase 2
0.8921 High Similarity NPD1552 Clinical (unspecified phase)
0.8921 High Similarity NPD1550 Clinical (unspecified phase)
0.8811 High Similarity NPD1511 Approved
0.8777 High Similarity NPD1510 Phase 2
0.869 High Similarity NPD1512 Approved
0.8658 High Similarity NPD2801 Approved
0.8623 High Similarity NPD1240 Approved
0.8621 High Similarity NPD4378 Clinical (unspecified phase)
0.8591 High Similarity NPD1934 Approved
0.8582 High Similarity NPD1551 Phase 2
0.8533 High Similarity NPD2393 Clinical (unspecified phase)
0.85 High Similarity NPD1607 Approved
0.8477 Intermediate Similarity NPD5402 Approved
0.8472 Intermediate Similarity NPD3750 Approved
0.8382 Intermediate Similarity NPD1203 Approved
0.8367 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8345 Intermediate Similarity NPD2313 Discontinued
0.8333 Intermediate Similarity NPD4380 Phase 2
0.8322 Intermediate Similarity NPD2796 Approved
0.8322 Intermediate Similarity NPD2935 Discontinued
0.8289 Intermediate Similarity NPD7819 Suspended
0.8264 Intermediate Similarity NPD2346 Discontinued
0.8247 Intermediate Similarity NPD3749 Approved
0.8247 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD3882 Suspended
0.8158 Intermediate Similarity NPD7411 Suspended
0.8146 Intermediate Similarity NPD3226 Approved
0.8141 Intermediate Similarity NPD5494 Approved
0.8129 Intermediate Similarity NPD7075 Discontinued
0.8125 Intermediate Similarity NPD3748 Approved
0.8117 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD943 Approved
0.8095 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8082 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD3818 Discontinued
0.8052 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD6166 Phase 2
0.805 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD447 Suspended
0.8029 Intermediate Similarity NPD9717 Approved
0.8027 Intermediate Similarity NPD2800 Approved
0.8013 Intermediate Similarity NPD5403 Approved
0.8 Intermediate Similarity NPD5401 Approved
0.7986 Intermediate Similarity NPD1470 Approved
0.7975 Intermediate Similarity NPD6959 Discontinued
0.7973 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD7768 Phase 2
0.7945 Intermediate Similarity NPD6099 Approved
0.7945 Intermediate Similarity NPD6100 Approved
0.7943 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD1465 Phase 2
0.7933 Intermediate Similarity NPD6799 Approved
0.7927 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD2344 Approved
0.7885 Intermediate Similarity NPD3817 Phase 2
0.7877 Intermediate Similarity NPD2799 Discontinued
0.7877 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD6559 Discontinued
0.7853 Intermediate Similarity NPD7074 Phase 3
0.7832 Intermediate Similarity NPD411 Approved
0.7826 Intermediate Similarity NPD1610 Phase 2
0.7826 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD1201 Approved
0.7801 Intermediate Similarity NPD2798 Approved
0.7793 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD7054 Approved
0.7785 Intermediate Similarity NPD1243 Approved
0.7778 Intermediate Similarity NPD920 Approved
0.7763 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6844 Discontinued
0.7756 Intermediate Similarity NPD6801 Discontinued
0.7755 Intermediate Similarity NPD4308 Phase 3
0.775 Intermediate Similarity NPD1247 Approved
0.7744 Intermediate Similarity NPD7472 Approved
0.7742 Intermediate Similarity NPD6599 Discontinued
0.7724 Intermediate Similarity NPD1613 Approved
0.7724 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD6232 Discontinued
0.7697 Intermediate Similarity NPD6797 Phase 2
0.7692 Intermediate Similarity NPD6832 Phase 2
0.7683 Intermediate Similarity NPD5844 Phase 1
0.7683 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD2309 Approved
0.7669 Intermediate Similarity NPD7473 Discontinued
0.7667 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD1548 Phase 1
0.7651 Intermediate Similarity NPD7251 Discontinued
0.7647 Intermediate Similarity NPD2534 Approved
0.7647 Intermediate Similarity NPD2533 Approved
0.7647 Intermediate Similarity NPD2532 Approved
0.7643 Intermediate Similarity NPD1608 Approved
0.7639 Intermediate Similarity NPD4625 Phase 3
0.7632 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD2797 Approved
0.7605 Intermediate Similarity NPD7808 Phase 3
0.759 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD4749 Approved
0.7586 Intermediate Similarity NPD3268 Approved
0.7586 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD422 Phase 1
0.7569 Intermediate Similarity NPD4908 Phase 1
0.7551 Intermediate Similarity NPD1933 Approved
0.7535 Intermediate Similarity NPD3225 Approved
0.7518 Intermediate Similarity NPD1481 Phase 2
0.7518 Intermediate Similarity NPD9493 Approved
0.7518 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3751 Discontinued
0.75 Intermediate Similarity NPD2861 Phase 2
0.7485 Intermediate Similarity NPD5953 Discontinued
0.7483 Intermediate Similarity NPD4307 Phase 2
0.747 Intermediate Similarity NPD7286 Phase 2
0.7466 Intermediate Similarity NPD3764 Approved
0.7466 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD8313 Approved
0.7456 Intermediate Similarity NPD8312 Approved
0.7452 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1535 Discovery
0.7445 Intermediate Similarity NPD6671 Approved
0.7439 Intermediate Similarity NPD3926 Phase 2
0.7438 Intermediate Similarity NPD4288 Approved
0.7432 Intermediate Similarity NPD230 Phase 1
0.7431 Intermediate Similarity NPD1019 Discontinued
0.7429 Intermediate Similarity NPD17 Approved
0.7419 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD919 Approved
0.7383 Intermediate Similarity NPD6651 Approved
0.7361 Intermediate Similarity NPD3267 Approved
0.7361 Intermediate Similarity NPD3266 Approved
0.7356 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD7390 Discontinued
0.7347 Intermediate Similarity NPD1296 Phase 2
0.7303 Intermediate Similarity NPD1471 Phase 3
0.7303 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD7033 Discontinued
0.7278 Intermediate Similarity NPD1653 Approved
0.7273 Intermediate Similarity NPD3787 Discontinued
0.7273 Intermediate Similarity NPD4628 Phase 3
0.725 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4287 Approved
0.7241 Intermediate Similarity NPD1164 Approved
0.7237 Intermediate Similarity NPD5404 Approved
0.7237 Intermediate Similarity NPD5405 Approved
0.7237 Intermediate Similarity NPD5406 Approved
0.7237 Intermediate Similarity NPD5408 Approved
0.723 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD9266 Approved
0.7185 Intermediate Similarity NPD74 Approved
0.7174 Intermediate Similarity NPD1241 Discontinued
0.7169 Intermediate Similarity NPD5710 Approved
0.7169 Intermediate Similarity NPD5711 Approved
0.7164 Intermediate Similarity NPD968 Approved
0.7133 Intermediate Similarity NPD3496 Discontinued
0.7117 Intermediate Similarity NPD2296 Approved
0.7111 Intermediate Similarity NPD9267 Approved
0.7111 Intermediate Similarity NPD9264 Approved
0.7111 Intermediate Similarity NPD9263 Approved
0.7101 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4360 Phase 2
0.7079 Intermediate Similarity NPD4363 Phase 3
0.7072 Intermediate Similarity NPD6777 Approved
0.7072 Intermediate Similarity NPD6782 Approved
0.7072 Intermediate Similarity NPD6779 Approved
0.7072 Intermediate Similarity NPD6778 Approved
0.7072 Intermediate Similarity NPD6781 Approved
0.7072 Intermediate Similarity NPD6780 Approved
0.7072 Intermediate Similarity NPD6776 Approved
0.7072 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD3027 Phase 3
0.7045 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD9545 Approved
0.7034 Intermediate Similarity NPD9269 Phase 2
0.703 Intermediate Similarity NPD6971 Discontinued
0.7 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.6995 Remote Similarity NPD6823 Phase 2
0.6993 Remote Similarity NPD9268 Approved
0.6987 Remote Similarity NPD2654 Approved
0.6982 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6981 Remote Similarity NPD4662 Approved
0.6981 Remote Similarity NPD4661 Approved
0.6977 Remote Similarity NPD1252 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6585 Discontinued
0.6974 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6974 Remote Similarity NPD5124 Phase 1
0.6966 Remote Similarity NPD1611 Approved
0.6964 Remote Similarity NPD7229 Phase 3
0.6957 Remote Similarity NPD7698 Approved
0.6957 Remote Similarity NPD7435 Discontinued
0.6957 Remote Similarity NPD7697 Approved
0.6957 Remote Similarity NPD2370 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7696 Phase 3
0.6954 Remote Similarity NPD6233 Phase 2
0.6944 Remote Similarity NPD1778 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