Structure

Physi-Chem Properties

Molecular Weight:  244.04
Volume:  233.231
LogP:  2.303
LogD:  2.417
LogS:  -3.433
# Rotatable Bonds:  0
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.526
Synthetic Accessibility Score:  2.315
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:  -4.912
MDCK Permeability:  7.66764787840657e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.433
Human Intestinal Absorption (HIA):  0.023
20% Bioavailability (F20%):  0.908
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  92.8376235961914%
Volume Distribution (VD):  0.726
Pgp-substrate:  9.351752281188965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.336
CYP2C19-inhibitor:  0.147
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.521
CYP2C9-substrate:  0.94
CYP2D6-inhibitor:  0.778
CYP2D6-substrate:  0.667
CYP3A4-inhibitor:  0.662
CYP3A4-substrate:  0.102

ADMET: Excretion

Clearance (CL):  7.606
Half-life (T1/2):  0.886

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.085
Drug-inuced Liver Injury (DILI):  0.927
AMES Toxicity:  0.61
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.865
Skin Sensitization:  0.936
Carcinogencity:  0.073
Eye Corrosion:  0.202
Eye Irritation:  0.967
Respiratory Toxicity:  0.207

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC169479

Natural Product ID:  NPC169479
Common Name*:   1,3,7-Trihydroxyxanthone
IUPAC Name:   1,3,7-trihydroxyxanthen-9-one
Synonyms:   1,3,7-Trihydroxyxanthone
Standard InCHIKey:  JJUNZBRHHGLJQW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H
SMILES:  Oc1cc(O)c2c(c1)oc1c(c2=O)cc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL361025
PubChem CID:   5281635
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
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]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[10705751]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11473425]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11975482]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. seed n.a. PMID[12822897]
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]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[16309313]
NPO22748 Neophaeosphaeria quadriseptata Species Leptosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[16499313]
NPO24232 Boehmeria pannosa Species Urticaceae Eukaryota roots n.a. n.a. PMID[16872154]
NPO26529 Hypericum oblongifolium Species Hypericaceae Eukaryota n.a. whole plant n.a. PMID[16880649]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. PMID[16933891]
NPO12573 Hypericum annulatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[17260692]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. leaf n.a. PMID[17401878]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. stem n.a. PMID[17401878]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. root n.a. PMID[17401878]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. rhizome n.a. PMID[17404979]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[17716892]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[18064621]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[18064621]
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]
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]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO19755 Artemisia anomala Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20000780]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO32798 polygala karensium Species Polygalaceae Eukaryota n.a. n.a. n.a. PMID[22552195]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[24257774]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. root n.a. PMID[26129938]
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]
NPO26234 Annona muricata Species Annonaceae Eukaryota Leaves n.a. n.a. PMID[7494150]
NPO26234 Annona muricata Species Annonaceae Eukaryota Leaves n.a. n.a. PMID[7673926]
NPO26234 Annona muricata Species Annonaceae Eukaryota Leaves n.a. n.a. PMID[7673935]
NPO26234 Annona muricata Species Annonaceae Eukaryota Leaves n.a. n.a. PMID[7673936]
NPO26234 Annona muricata Species Annonaceae Eukaryota leaves n.a. n.a. PMID[8946744]
NPO26234 Annona muricata Species Annonaceae Eukaryota seeds n.a. n.a. PMID[8991944]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO26234 Annona muricata Species Annonaceae Eukaryota Leaves n.a. n.a. PMID[9584396]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO26234 Annona muricata Species Annonaceae 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]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7336 Senecio brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15229 Hypericum degenii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17885 Eupatorium sachalinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18911 Piper umbellatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19755 Artemisia anomala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11057 Artocarpus integra Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO28864 Nauclea officinalis Species Rubiaceae 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]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19755 Artemisia anomala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18911 Piper umbellatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae 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]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17885 Eupatorium sachalinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11057 Artocarpus integra Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15229 Hypericum degenii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12573 Hypericum annulatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7336 Senecio brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10429 Gentiana scabra Species Gentianaceae 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]
NPO19755 Artemisia anomala Species Asteraceae 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]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29127 Cystophora scalaris Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26234 Annona muricata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10429 Gentiana scabra Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4244 Doodia picta Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25981 Crinipellis scabella Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26315 Trikentrion flabelliforme Species Raspailiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28898 Grewia mollis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12600 Trametes cinnabarina Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3744 Polycephalomyces nipponicus Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12573 Hypericum annulatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29400 Conocephalum japonicum Species Conocephalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28824 Forsteronia refracta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19755 Artemisia anomala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3707 Chromatium okenii Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18412 Lobophytum microlobulatum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29142 Kaunia saltensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9157 Rubrivivax gelatinosus Species n.a. Bacteria 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]
NPO15229 Hypericum degenii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27269 Annona impressivenia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26529 Hypericum oblongifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29488 Sophora angustifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6714 Securidaca inappendiculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29510 Aulacocephalus temmincki Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7336 Senecio brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28918 Ophiolepis superba Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29415 Hovenia acerba Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28937 Heterotheca grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29242 Salvia dorrii Species Lamiaceae 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]
NPO3170 Piper lanceifolium Species Piperaceae 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]
NPO17885 Eupatorium sachalinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota 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]
NPO29203 Gymnocarpium robertianum Species Cystopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25812 Dipentodon sinicus Species Dipentodontaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18013 Sceletium subvelutinum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25943 Cirsium carolinianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29068 Papilio phorcas Species Papilionidae 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]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1755 Pinus heldreichii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29225 Oncoba echinata Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22748 Neophaeosphaeria quadriseptata Species Leptosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16291 Leptochloa digitata Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29292 Teucrium depressum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11057 Artocarpus integra Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28845 Eragrostis viscosa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29363 Aconitum nevadense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29189 Castanopsis sclerophylla Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3340 Fridericia chica Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24232 Boehmeria pannosa Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4308 Pericome caudata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26192 Cordylanthus kingii Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13818 Narcissus concolor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19563 Gyrophora hyperborea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1245 Eunicella cavolinii Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18911 Piper umbellatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28784 Alseodaphne corneri Species Lauraceae 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
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 8000.0 nM PMID[486076]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100000.0 nM PMID[486079]
NPT15 Cell Line Jurkat Homo sapiens IC50 > 100000.0 nM PMID[486079]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 13.41 ug.mL-1 PMID[486080]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 24.77 ug.mL-1 PMID[486080]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 26.81 ug.mL-1 PMID[486080]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 9.14 ug.mL-1 PMID[486080]
NPT81 Cell Line A549 Homo sapiens IC50 = 146350.0 nM PMID[486082]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 38520.0 nM PMID[486082]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 25100.0 nM PMID[486083]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 31200.0 nM PMID[486083]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 200000.0 nM PMID[486083]
NPT111 Cell Line K562 Homo sapiens IC50 = 105600.0 nM PMID[486083]
NPT2641 Cell Line COLO 320 Homo sapiens IC50 > 200000.0 nM PMID[486083]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 200000.0 nM PMID[486084]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 200000.0 nM PMID[486084]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 200000.0 nM PMID[486084]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 18300.0 nM PMID[486085]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[486086]
NPT91 Cell Line KB Homo sapiens IC50 > 10000.0 nM PMID[486086]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[486086]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000.0 nM PMID[486086]
NPT2 Others Unspecified IC50 = 14700.0 nM PMID[486077]
NPT2 Others Unspecified IC50 = 67608297.54 nM PMID[486077]
NPT865 Individual Protein Fatty acid synthase Homo sapiens IC50 = 40980.0 nM PMID[486078]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 128.0 ug.mL-1 PMID[486079]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC > 128.0 ug.mL-1 PMID[486079]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 128.0 ug.mL-1 PMID[486079]
NPT1121 Organism Moraxella catarrhalis Moraxella catarrhalis MIC = 128.0 ug.mL-1 PMID[486079]
NPT1122 Organism Haemophilus influenzae Haemophilus influenzae MIC > 128.0 ug.mL-1 PMID[486079]
NPT19 Organism Escherichia coli Escherichia coli MIC > 128.0 ug.mL-1 PMID[486079]
NPT2 Others Unspecified Ratio IC50 = 243.0 n.a. PMID[486080]
NPT20985 CELL-LINE MCF7-ADR Homo sapiens IC50 = 192660.0 nM PMID[486082]
NPT20987 CELL-LINE HeLa S3 Homo sapiens IC50 > 10000.0 nM PMID[486086]

☑ 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 NPC169479 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
1.0 High Similarity NPC159855
0.9706 High Similarity NPC18457
0.9645 High Similarity NPC186397
0.9645 High Similarity NPC37135
0.9577 High Similarity NPC266499
0.9577 High Similarity NPC223988
0.9565 High Similarity NPC145673
0.951 High Similarity NPC101957
0.951 High Similarity NPC120105
0.9507 High Similarity NPC194856
0.9507 High Similarity NPC276930
0.9485 High Similarity NPC9985
0.9485 High Similarity NPC239495
0.9444 High Similarity NPC251110
0.9444 High Similarity NPC149614
0.9437 High Similarity NPC207729
0.9424 High Similarity NPC182421
0.9375 High Similarity NPC61620
0.9375 High Similarity NPC248102
0.9375 High Similarity NPC179183
0.9375 High Similarity NPC227122
0.9375 High Similarity NPC62042
0.9371 High Similarity NPC12367
0.9371 High Similarity NPC118726
0.9315 High Similarity NPC271779
0.9315 High Similarity NPC167091
0.9315 High Similarity NPC206238
0.9315 High Similarity NPC88645
0.9315 High Similarity NPC292214
0.931 High Similarity NPC204515
0.931 High Similarity NPC117579
0.9301 High Similarity NPC130230
0.9301 High Similarity NPC275772
0.9301 High Similarity NPC239312
0.9296 High Similarity NPC155144
0.9296 High Similarity NPC184649
0.9296 High Similarity NPC303185
0.9291 High Similarity NPC73028
0.9286 High Similarity NPC275734
0.9281 High Similarity NPC329225
0.9281 High Similarity NPC472460
0.9281 High Similarity NPC147686
0.927 High Similarity NPC172262
0.9247 High Similarity NPC39007
0.9247 High Similarity NPC161277
0.9247 High Similarity NPC474843
0.9247 High Similarity NPC101996
0.9247 High Similarity NPC199100
0.9247 High Similarity NPC180234
0.9247 High Similarity NPC120537
0.9241 High Similarity NPC45873
0.9241 High Similarity NPC470107
0.9236 High Similarity NPC196277
0.9236 High Similarity NPC43669
0.9236 High Similarity NPC272721
0.9231 High Similarity NPC299011
0.9231 High Similarity NPC196114
0.9225 High Similarity NPC113770
0.9214 High Similarity NPC316480
0.9214 High Similarity NPC261234
0.9209 High Similarity NPC13768
0.9209 High Similarity NPC32441
0.9209 High Similarity NPC107586
0.9209 High Similarity NPC287246
0.9209 High Similarity NPC212767
0.9209 High Similarity NPC275055
0.9209 High Similarity NPC290291
0.9209 High Similarity NPC299379
0.9209 High Similarity NPC84585
0.9209 High Similarity NPC296490
0.9209 High Similarity NPC228661
0.9209 High Similarity NPC12296
0.9209 High Similarity NPC476480
0.9209 High Similarity NPC243083
0.9209 High Similarity NPC79943
0.9209 High Similarity NPC295261
0.9197 High Similarity NPC213216
0.9197 High Similarity NPC78540
0.9197 High Similarity NPC57601
0.9197 High Similarity NPC50898
0.9197 High Similarity NPC274121
0.9184 High Similarity NPC178964
0.9184 High Similarity NPC95842
0.9184 High Similarity NPC472915
0.9184 High Similarity NPC280530
0.9178 High Similarity NPC171010
0.9178 High Similarity NPC202157
0.9172 High Similarity NPC183959
0.9172 High Similarity NPC195351
0.9172 High Similarity NPC216318
0.9172 High Similarity NPC1612
0.9172 High Similarity NPC296197
0.9172 High Similarity NPC17286
0.9172 High Similarity NPC259713
0.9167 High Similarity NPC77378
0.9167 High Similarity NPC46941
0.9161 High Similarity NPC70136
0.9161 High Similarity NPC469764
0.9161 High Similarity NPC311144
0.9155 High Similarity NPC310340
0.9155 High Similarity NPC202981
0.9155 High Similarity NPC144499
0.9149 High Similarity NPC69769
0.9143 High Similarity NPC188947
0.9143 High Similarity NPC99333
0.9143 High Similarity NPC118813
0.9143 High Similarity NPC280284
0.9137 High Similarity NPC216361
0.9137 High Similarity NPC281917
0.9137 High Similarity NPC256042
0.9137 High Similarity NPC187432
0.9137 High Similarity NPC193792
0.9137 High Similarity NPC116775
0.9137 High Similarity NPC87545
0.9137 High Similarity NPC235428
0.9128 High Similarity NPC181960
0.9128 High Similarity NPC99597
0.9128 High Similarity NPC210084
0.9122 High Similarity NPC37392
0.9122 High Similarity NPC2928
0.9122 High Similarity NPC113906
0.9122 High Similarity NPC472909
0.9118 High Similarity NPC141549
0.911 High Similarity NPC29231
0.911 High Similarity NPC184136
0.911 High Similarity NPC77858
0.911 High Similarity NPC37348
0.911 High Similarity NPC306821
0.9103 High Similarity NPC294852
0.9103 High Similarity NPC321011
0.9103 High Similarity NPC218490
0.9103 High Similarity NPC218569
0.9103 High Similarity NPC188679
0.9103 High Similarity NPC39195
0.9097 High Similarity NPC469758
0.9097 High Similarity NPC187282
0.9097 High Similarity NPC290133
0.9097 High Similarity NPC24136
0.9097 High Similarity NPC231013
0.9091 High Similarity NPC18585
0.9091 High Similarity NPC106985
0.9091 High Similarity NPC166138
0.9091 High Similarity NPC279121
0.9085 High Similarity NPC3188
0.9078 High Similarity NPC265871
0.9078 High Similarity NPC225153
0.9078 High Similarity NPC329203
0.9078 High Similarity NPC274784
0.9078 High Similarity NPC20709
0.9078 High Similarity NPC222342
0.9078 High Similarity NPC150648
0.9078 High Similarity NPC310135
0.9071 High Similarity NPC250266
0.9071 High Similarity NPC266597
0.9067 High Similarity NPC185258
0.9067 High Similarity NPC172770
0.9065 High Similarity NPC234560
0.9065 High Similarity NPC39426
0.906 High Similarity NPC472916
0.906 High Similarity NPC235165
0.906 High Similarity NPC201837
0.906 High Similarity NPC255106
0.906 High Similarity NPC191146
0.906 High Similarity NPC138243
0.906 High Similarity NPC68093
0.9054 High Similarity NPC280937
0.9054 High Similarity NPC89474
0.9051 High Similarity NPC113006
0.9048 High Similarity NPC226973
0.9048 High Similarity NPC308451
0.9048 High Similarity NPC208043
0.9048 High Similarity NPC225731
0.9044 High Similarity NPC278787
0.9041 High Similarity NPC294502
0.9041 High Similarity NPC200221
0.9041 High Similarity NPC65775
0.9041 High Similarity NPC105512
0.9041 High Similarity NPC10027
0.9034 High Similarity NPC21835
0.9034 High Similarity NPC308200
0.9034 High Similarity NPC17816
0.9034 High Similarity NPC51443
0.9034 High Similarity NPC74881
0.9034 High Similarity NPC168803
0.9034 High Similarity NPC95864
0.9028 High Similarity NPC311741
0.9028 High Similarity NPC131766
0.9028 High Similarity NPC234629
0.9028 High Similarity NPC98926
0.9021 High Similarity NPC1534
0.9021 High Similarity NPC175013
0.9021 High Similarity NPC473042
0.9014 High Similarity NPC270883
0.9014 High Similarity NPC110228
0.9014 High Similarity NPC284550
0.9014 High Similarity NPC281207
0.9014 High Similarity NPC261227
0.9014 High Similarity NPC76445
0.9014 High Similarity NPC188243
0.9014 High Similarity NPC129853

  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 NPC169479 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
0.9281 High Similarity NPD1549 Phase 2
0.9209 High Similarity NPD1550 Clinical (unspecified phase)
0.9209 High Similarity NPD1552 Clinical (unspecified phase)
0.9091 High Similarity NPD1511 Approved
0.9065 High Similarity NPD1510 Phase 2
0.8966 High Similarity NPD1512 Approved
0.8926 High Similarity NPD2801 Approved
0.8913 High Similarity NPD1240 Approved
0.8897 High Similarity NPD4378 Clinical (unspecified phase)
0.8859 High Similarity NPD1934 Approved
0.88 High Similarity NPD2393 Clinical (unspecified phase)
0.8786 High Similarity NPD1607 Approved
0.8639 High Similarity NPD7410 Clinical (unspecified phase)
0.8601 High Similarity NPD2796 Approved
0.86 High Similarity NPD4380 Phase 2
0.8553 High Similarity NPD7819 Suspended
0.8506 High Similarity NPD3749 Approved
0.8506 High Similarity NPD4381 Clinical (unspecified phase)
0.8493 Intermediate Similarity NPD3750 Approved
0.8442 Intermediate Similarity NPD3882 Suspended
0.8421 Intermediate Similarity NPD7411 Suspended
0.8397 Intermediate Similarity NPD5494 Approved
0.8387 Intermediate Similarity NPD7075 Discontinued
0.838 Intermediate Similarity NPD943 Approved
0.8377 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8345 Intermediate Similarity NPD1551 Phase 2
0.8345 Intermediate Similarity NPD2935 Discontinued
0.8323 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD3818 Discontinued
0.8312 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD6166 Phase 2
0.8302 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD2800 Approved
0.8258 Intermediate Similarity NPD5402 Approved
0.8228 Intermediate Similarity NPD6959 Discontinued
0.82 Intermediate Similarity NPD6799 Approved
0.8194 Intermediate Similarity NPD1465 Phase 2
0.8171 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD2344 Approved
0.8151 Intermediate Similarity NPD3748 Approved
0.8151 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD1203 Approved
0.8141 Intermediate Similarity NPD3817 Phase 2
0.8112 Intermediate Similarity NPD2313 Discontinued
0.8098 Intermediate Similarity NPD7074 Phase 3
0.8075 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD1243 Approved
0.8052 Intermediate Similarity NPD3226 Approved
0.8041 Intermediate Similarity NPD2346 Discontinued
0.8039 Intermediate Similarity NPD920 Approved
0.8037 Intermediate Similarity NPD7054 Approved
0.8026 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6801 Discontinued
0.8 Intermediate Similarity NPD6599 Discontinued
0.8 Intermediate Similarity NPD1247 Approved
0.7988 Intermediate Similarity NPD7472 Approved
0.7986 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7768 Phase 2
0.7973 Intermediate Similarity NPD6100 Approved
0.7973 Intermediate Similarity NPD6099 Approved
0.7972 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD6232 Discontinued
0.7947 Intermediate Similarity NPD2309 Approved
0.7939 Intermediate Similarity NPD6797 Phase 2
0.7933 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD5844 Phase 1
0.7927 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD7473 Discontinued
0.7908 Intermediate Similarity NPD2532 Approved
0.7908 Intermediate Similarity NPD2534 Approved
0.7908 Intermediate Similarity NPD2533 Approved
0.7905 Intermediate Similarity NPD2799 Discontinued
0.7902 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD7251 Discontinued
0.7892 Intermediate Similarity NPD6559 Discontinued
0.7881 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1610 Phase 2
0.7844 Intermediate Similarity NPD7808 Phase 3
0.7831 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD447 Suspended
0.7806 Intermediate Similarity NPD5403 Approved
0.7801 Intermediate Similarity NPD9717 Approved
0.7792 Intermediate Similarity NPD5401 Approved
0.7785 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD1470 Approved
0.7755 Intermediate Similarity NPD1613 Approved
0.7755 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD5953 Discontinued
0.7711 Intermediate Similarity NPD7286 Phase 2
0.7703 Intermediate Similarity NPD230 Phase 1
0.7698 Intermediate Similarity NPD1548 Phase 1
0.7683 Intermediate Similarity NPD3926 Phase 2
0.7676 Intermediate Similarity NPD1608 Approved
0.7654 Intermediate Similarity NPD919 Approved
0.7651 Intermediate Similarity NPD3751 Discontinued
0.7651 Intermediate Similarity NPD6651 Approved
0.7619 Intermediate Similarity NPD411 Approved
0.7613 Intermediate Similarity NPD7390 Discontinued
0.7606 Intermediate Similarity NPD422 Phase 1
0.7606 Intermediate Similarity NPD1201 Approved
0.7603 Intermediate Similarity NPD4908 Phase 1
0.7586 Intermediate Similarity NPD2798 Approved
0.7584 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6844 Discontinued
0.7552 Intermediate Similarity NPD1481 Phase 2
0.755 Intermediate Similarity NPD4308 Phase 3
0.7534 Intermediate Similarity NPD2861 Phase 2
0.7532 Intermediate Similarity NPD4628 Phase 3
0.7529 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3764 Approved
0.75 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3268 Approved
0.7486 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1535 Discovery
0.7483 Intermediate Similarity NPD6832 Phase 2
0.7471 Intermediate Similarity NPD4287 Approved
0.7469 Intermediate Similarity NPD4288 Approved
0.7468 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD17 Approved
0.7452 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD1471 Phase 3
0.7448 Intermediate Similarity NPD3225 Approved
0.7432 Intermediate Similarity NPD4625 Phase 3
0.741 Intermediate Similarity NPD5710 Approved
0.741 Intermediate Similarity NPD3787 Discontinued
0.741 Intermediate Similarity NPD5711 Approved
0.7397 Intermediate Similarity NPD2797 Approved
0.7383 Intermediate Similarity NPD1296 Phase 2
0.7379 Intermediate Similarity NPD4749 Approved
0.7362 Intermediate Similarity NPD2296 Approved
0.7351 Intermediate Similarity NPD1933 Approved
0.7324 Intermediate Similarity NPD9545 Approved
0.732 Intermediate Similarity NPD7033 Discontinued
0.7312 Intermediate Similarity NPD1653 Approved
0.731 Intermediate Similarity NPD9269 Phase 2
0.7305 Intermediate Similarity NPD9493 Approved
0.7305 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD4363 Phase 3
0.7303 Intermediate Similarity NPD4360 Phase 2
0.7293 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4307 Phase 2
0.7284 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD8313 Approved
0.7283 Intermediate Similarity NPD8312 Approved
0.7279 Intermediate Similarity NPD3267 Approved
0.7279 Intermediate Similarity NPD3266 Approved
0.7279 Intermediate Similarity NPD1164 Approved
0.7273 Intermediate Similarity NPD5408 Approved
0.7273 Intermediate Similarity NPD5404 Approved
0.7273 Intermediate Similarity NPD5405 Approved
0.7273 Intermediate Similarity NPD9268 Approved
0.7273 Intermediate Similarity NPD5406 Approved
0.7267 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2654 Approved
0.7234 Intermediate Similarity NPD6671 Approved
0.723 Intermediate Similarity NPD1019 Discontinued
0.7214 Intermediate Similarity NPD1241 Discontinued
0.7202 Intermediate Similarity NPD7229 Phase 3
0.7198 Intermediate Similarity NPD6778 Approved
0.7198 Intermediate Similarity NPD6779 Approved
0.7198 Intermediate Similarity NPD6777 Approved
0.7198 Intermediate Similarity NPD6782 Approved
0.7198 Intermediate Similarity NPD6780 Approved
0.7198 Intermediate Similarity NPD6781 Approved
0.7198 Intermediate Similarity NPD6776 Approved
0.7192 Intermediate Similarity NPD3972 Approved
0.7181 Intermediate Similarity NPD9494 Approved
0.7175 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6190 Approved
0.7151 Intermediate Similarity NPD1729 Discontinued
0.7115 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3027 Phase 3
0.7081 Intermediate Similarity NPD7696 Phase 3
0.7081 Intermediate Similarity NPD7698 Approved
0.7081 Intermediate Similarity NPD7435 Discontinued
0.7081 Intermediate Similarity NPD7697 Approved
0.7072 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD4361 Phase 2
0.7069 Intermediate Similarity NPD6104 Discontinued
0.7066 Intermediate Similarity NPD6971 Discontinued
0.7062 Intermediate Similarity NPD8434 Phase 2
0.7044 Intermediate Similarity NPD2354 Approved
0.7043 Intermediate Similarity NPD7871 Phase 2
0.7043 Intermediate Similarity NPD7870 Phase 2
0.7041 Intermediate Similarity NPD7199 Phase 2
0.7039 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2403 Approved
0.7013 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD5124 Phase 1
0.7011 Intermediate Similarity NPD1252 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2370 Clinical (unspecified phase)
0.6993 Remote Similarity NPD6233 Phase 2

  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